32789 Zip Code FL Real Estate, Homes with Open Floorplan for Sale

5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

2525 Temple Drive, Winter Park

$1,419,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1546 Miller Avenue, Winter Park

$795,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

This well-cared-for immaculate home features quality workmanship inside and out! In addition to the three bedroom two bath, there is an 'office-bonus' room. The mature tropical oasis landscaping, cozy seating areas, and winding pathways make you feel right at home and at the same time on vacation! Open Kitchen, dining room, living room and bonus room. Located on a quaint street nestled among custom built homes. Have the best of both worlds, family life with upscale restaurants and shopping, and the annual Art and Holiday Festivals, movies in the park, parades, Rollins College, Boat Tours, kayaking and paddleboarding on the Winter Park Chain of Lakes all linked together and easily accessed via an Italian-inspired canal system. Only a mile away from famous ‘Park Avenue’ where visitors travel from all over the world to experience and celebrate our romantic sidewalk cafés and festivities.

1850 Bryan Avenue, Winter Park

$3,275,000

5 Beds ⋅ 6 Baths ⋅ Flora Park 2nd Add SubDv. ⋅ 32789 Zip Code

1811 Oneco Avenue — an architectural presence unlike anything around it. A canopy of mature pines and oaks lines the approach, and the home reveals itself at the end of a quiet dead-end street. Step inside — more than 4,500 square feet across three levels. The foyer sets the tone — twin chandeliers above, white oak floors below. The eye is pulled past the curved staircase, straight into the gathering room, where French-pane glass opens the wall to a full-length lanai. The gathering room is the center the rest of the home answers to. A floor-to-ceiling fireplace anchors the space, framed by twin illuminated arches with chevron oak detailing and custom built-ins. The kitchen is a destination. Custom floor-to-ceiling white oak cabinetry. A statement fluted island wrapped in stone commands the center beneath brass pendants. A Viking gas range, double ovens, and custom hood complete a space designed to be lived around as much as admired. Coffee becomes conversation. Ordinary evenings become occasions. Behind the kitchen, a scullery reveals one of the most thoughtful luxuries — rich custom wood detailing, wine refrigeration, and dedicated prep space. The dining room sits beneath a vaulted ceiling with exposed beams, warm wood detailing, and a statement fixture above the table, a full wall of glass drawing a picturesque setting into every gathering. The primary suite is the most personal expression of luxury. A tray ceiling crowns the room while an alabaster chandelier casts a warm glow across the space. Beyond frosted glass doors, the bath unfolds in marble, warm brass, designer lighting, and custom cabinetry — a freestanding soaking tub anchoring the room, an oversized walk-in shower beyond. Dual custom walk-in closets complete the suite, the dressing room anchored by a center island beneath floor-to-ceiling cabinetry. Off the foyer, a steel-and-glass door reveals one of the home's most unforgettable spaces, walls of windows flooding the interior with natural light. With its own bath and walk-in closet, it serves just as easily as a fifth bedroom. Then the powder bath — scenic mural wallpaper climbs above elegant paneling, a sculptural fluted marble vanity beneath wall-mounted brass fixtures. Unforgettable. Beyond the glass, the home extends into its finest space. A full-length covered lanai runs beneath wood-clad ceilings, opening to a fully equipped outdoor kitchen with grill, beverage refrigeration, and storage. Beyond it, the pool stretches long and clear, framed in natural stone, a fire feature anchoring the lounge. Mature greenery closes the yard on every side — neighbors behind, never beside. A third of an acre of privacy this close to Park Avenue is its own kind of rare. This is the heart of Winter Park's 32789 — minutes from Park Avenue, in one of the area's most sought-after school zones: Lakemont Elementary, Maitland Middle, Winter Park High. Five bedrooms. Five and a half baths. More than 4,500 square feet. A three-car tandem garage. New construction, complete and ready. You can find another new-construction home. You will not find this lot, this design, and this floor plan together again at this number. Come see it. You will not forget it. Schedule your showing today.

1811 Oneco Avenue, Winter Park

$2,275,000

4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park

$6,700,000

4 Beds ⋅ 3 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Stunning Custom Estate on the Shores of Lake Osceola

405 Lakewood Drive, Winter Park

$1,800,000

5 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 02 SubDv. ⋅ 32789 Zip Code

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park

$624,900

4 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Completely updated and move-in ready, this stunning Winter Park home offers the perfect blend of timeless charm and modern comfort! Located in the desirable Shores of Lake Killarney, this 4-bedroom, 2-bath home features 1,933 square feet of thoughtfully updated living space, deeded access to Lake Killarney, and NO HOA! As you step inside, an open layout creates a seamless flow between the kitchen, dining, and living area. The updated kitchen features quartz countertops, stainless steel appliances, generous cabinetry, an island with breakfast bar, and dining area. Sliding doors off the living area open to a private, fully fenced backyard! Whether you're enjoying a quiet morning coffee or hosting outdoor gatherings, this large, inviting space provides the perfect extension of the home's living space! Enjoy peace of mind knowing the major updates have already been completed, including a new roof (2023), new A/C and hot water heater (2025), new windows (2024), complete re-pipe (2021), new electrical panel (2021), and many additional improvements throughout the home. Conveniently located near Winter Park Village, Park Avenue, Rollins College, top-rated dining, shopping, entertainment, and major roadways, this location puts the best of Winter Park and Greater Orlando within easy reach. This is the perfect opportunity to own a move-in-ready Winter Park home that offers the character of an established neighborhood with the peace of mind and convenience of modern updates. Call to set up a private showing today!

216 Blossom Lane, Winter Park

$409,900

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational living, rental income, a guest suite, or added privacy. Situated on a beautiful, tree-lined dead-end street, the property offers a peaceful setting while remaining close to shopping, dining, and entertainment. Inside, you'll find contemporary fixtures, stylish finishes, updated appliances, and an abundance of natural light throughout. The spacious backyard and inviting seating area provide the perfect space to relax or entertain family and friends. Major updates include a recently replaced roof, HVAC system, and electrical panel, offering added peace of mind. Some photos have been virtually staged to help showcase the home's layout and potential.

2568 Lotafun Avenue, Winter Park

$775,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes - not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

$1,339,000

3 Beds ⋅ 4 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Luxury waterfront living in Winter Park. Perfectly positioned on a premium corner homesite overlooking beautiful Lake Killarney, this exceptional contemporary townhome offers 3 bedrooms, 3.5 bathrooms, and nearly 2,400 square feet of thoughtfully designed living space with spectacular water views, abundant natural light, and the low-maintenance lifestyle today’s buyers desire.A dramatic 17-foot foyer welcomes you into an expansive open-concept living area where soaring 11-foot ceilings and walls of floor-to-ceiling glass showcase breathtaking lake vistas and create an effortless connection between the indoor and outdoor living spaces. The spacious great room flows seamlessly into the dining area and kitchen, creating an ideal setting for both everyday living and entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, stone countertops, a large center island with seating, a generous walk-in pantry, new designer RH lighting throughout, and motorized window shades. Just beyond, the covered rear lanai provides the perfect place to enjoy morning coffee, evening cocktails, or simply relax while overlooking the peaceful shoreline. Upstairs, the luxurious primary suite serves as a private retreat featuring expansive waterfront windows, dual walk-in closets, and a spa-inspired bath with an oversized frameless glass shower, a long single vanity with dual sinks, ample storage, and a private water closet. A spacious loft provides the perfect flex space for a home office, media room, or reading lounge. Step outside to the second-floor balcony complete with an outdoor kitchen, where elevated views of Lake Killarney create an unforgettable backdrop for entertaining. Two additional bedrooms, including one with an en-suite bath, provide comfort and privacy for family and guests, while the upstairs laundry room is thoughtfully positioned between the primary and secondary bedrooms. Additional features include engineered hardwood flooring, porcelain tile, high-end contemporary finishes throughout, abundant storage, a two-car attached garage with an epoxy floor, EV charging station, garage door opener, and a tankless gas water heater. Residents of Mondrian at Winter Park enjoy beautifully maintained grounds, private roads, reclaimed irrigation, a community dock, and lake access to one of Central Florida’s most desirable ski lakes. The HOA also includes cable television, high-speed internet, exterior grounds maintenance, and pest control, making for truly effortless ownership. Combining exceptional waterfront views, sophisticated contemporary design, premium finishes, an ideal floor plan, and one of Winter Park’s most convenient locations, this is a rare opportunity to own one of the community’s most desirable lakefront residences. Just minutes from Park Avenue, Winter Park Village, AdventHealth, Rollins College, Interstate 4, and Downtown Orlando, this home offers the perfect balance of luxury, convenience, and low-maintenance living. Schedule your private showing today and discover everything this exceptional Lake Killarney residence has to offer.

1778 Mondrian Circle, Winter Park

$1,595,000

3 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park

$4,250,000

4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$719,900

4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

436 W Swoope Avenue, Winter Park

$625,000

3 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE FAMILY TOWNHOME with NO HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!

786 Mcintyre Avenue, Winter Park

$2,195,000

4 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. The second floor features two additional guest bedrooms, each with access to a full bathroom, along with a spacious loft that serves as the perfect media room, playroom, or secondary living area. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.

1750 Walnut Avenue, Winter Park

$569,000

3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$3,395,000

6 Beds ⋅ 8 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Come tour this brand new, elaborately finished luxury home in Winter Park! Designed and constructed by a well-established, award-winning custom home builder, no expense has been spared. This home is truly a leader in its class! Located just a short walk to the esteemed Audobon K-8 school, East End market, restaurants, shopping, Blue Jacket Park, Baldwin Park. Just a short drive to Park Avenue restaurants and shopping. As you pull up to this vast estate home, the dimensional architectural detail on the home on a huge lot boasts a commanding presence. The 12 foot ceilings on the first floor and 10 foot ceilings on the second floor give the home a voluminous feel throughout. The first floor features a huge master suite with an accessible washer and dryer off the giant walk-in closet, plus an additional full guest suite and separate office. The gourmet kitchen features luxury custom cabinets, an accent island with exotic granite counter tops. Thermador appliances outfit the main kitchen as follows: Large 30” refrigerator and 30” freezer towers, 48” dual oven gas range with ornamental hood, dishwasher and microwave drawer. Flanking the main kitchen is a spacious Butler’s pantry with its own sink, refrigerator and dishwasher. Just off the Butler’s pantry is both a mudroom just inside the garage, and additional air-conditioned storage room. Over the garage is a separate bonus/flex room with its own full bath and closet. Upstairs is a huge loft living area plus three full bedroom suites and laundry room. The home is ornamented with expensive fit and finishes as follows: extensive architectural ceiling detail with cove lighting, lighting fixtures, plumbing fixtures, hardware, tile, level 5 smooth drywall finishes, designer wallpaper, and more! Designed with energy efficiency in mind, Natural gas fuels two tankless water heaters, the kitchen range, summer kitchen grill and pool/spa heater. Elaborate landscaping provides beautiful accents and plenty of privacy in the rear outdoor living area. Outdoor living includes a huge covered lanai with retractable screens, summer kitchen, and heated salt-water swimming pool with integrated spa and pool deck, plus outdoor shower and separate pool bath. 10' tall pocket sliding glass doors can open the great-room wall completely to integrate your indoor and outdoor entertaining. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself! Come tour your magnificent new luxury home today!

2905 Parkland Drive, Winter Park

$2,569,999

5 Beds ⋅ 5 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

1754 Taylor Avenue, Winter Park

$849,000

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

439 N Capen Avenue, Winter Park

$4,900,000

5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park

$2,549,000

5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

1823 Sunset Drive, Winter Park

$275,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!

1500 Gay Road Unit 18D, Winter Park

$695,000

3 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.

1622 Arbor Park Drive, Winter Park

$300,000

2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

1960 Biscayne Drive, Winter Park

$1,625,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park

$1,025,000

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park

$1,189,000

4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character with the ease of all-new finishes and systems. Four bedrooms and three full bathrooms are arranged around an open living, dining, and kitchen core that opens to a light-filled sitting area. White oak floors run throughout, while designer lighting and ceiling fans, clean horizontal lines, and warm natural finishes carry the home's MCM soul. The kitchen anchors the home with Taj Mahal quartzite counters and brand new KitchenAid stainless steel appliances. Step out to an expanded rear patio overlooking a private fenced backyard, ideal for entertaining or quiet evenings at home. Move in with confidence: new roof, all-new windows, new 200-amp electrical service, all-new plumbing with new water heater, new HVAC ductwork, and a new Nest thermostat. The attached garage and dedicated interior laundry complete the layout. The location is the rare kind you can live on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and the sought-after Audubon Park K-8 School. Winter Park High and the shops and dining of Park Avenue are just minutes away. A thoughtfully rebuilt classic in one of the area's most established and connected neighborhoods.

3006 Northwood Boulevard, Winter Park

$459,900

3 Beds ⋅ 2 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Extensively updated throughout, this move-in-ready home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a stunning renovated kitchen with an open pass-through breakfast bar and seating, ideal for entertaining and everyday living, a large stainless sink beneath a window and plenty of stunning quartz countertop space. Both baths have been tastefully remodeled, and nearly every aspect of the home has been thoughtfully updated to create a fresh, contemporary feel. Major improvements provide added peace of mind, including a new roof in October 2023, an HVAC system in 2023 and a water heater in 2024. Enjoy the convenience of a large covered carport with built-in storage, plus a huge backyard with endless possibilities for gardening, pets, play or future expansion. An additional storage shed, added in 2018, offers even more space for tools, hobbies and outdoor equipment. Ideally located with quick access to Interstate 4 and 17-92 and just minutes from Park Avenue, Winter Park Village, College Park and Downtown Orlando, you'll enjoy some of Central Florida's finest shopping, dining, entertainment and cultural attractions right at your fingertips. Best of all, no HOA. Combining extensive renovations, major system updates, an oversized backyard and an unbeatable location, this exceptional Winter Park home is truly move-in ready and waiting for its next owner. Call to schedule your appointment today!

259 Orange Terrace Drive, Winter Park

$2,800,000

3 Beds ⋅ 4 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park

$2,499,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

426 Worthington Drive, Winter Park

$244,900

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park

$1,399,000

3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code

Vilasa Homes — Winter Park’s Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this architecturally stunning residence blends refined design with the effortless elegance of Winter Park living. Crafted by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, this home showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two-story block construction for enduring quality. Interiors exude sophistication: soaring 13' ceilings on the main level, 10' upstairs, level-four wall finishes, all-wood flooring, Pella double pain windows and curated designer lighting. The chef’s kitchen is a showpiece— high-end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in-unit elevator provides effortless access to the second-floor, enhancing both convenience and sophistication. The second-floor primary retreat offers a serene escape with a loft for office or wellness space, a spa-caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms provide versatile accommodation for guests, a private office, or fitness space, complemented by a thoughtfully designed shared bath. Outdoor living is exceptional with an expansive 40' x 20' private fenced-in backyard, including a covered patio which extends from the sliding glass doors. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square and Rollins College. Vilasa Homes offers a rare opportunity to live at the center of it all—wrapped in luxury, design, and timeless style.

512 W Swoope Avenue, Winter Park

$5,500,000

4 Beds ⋅ 5 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

313 Sylvan Drive, Winter Park

$849,000

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park

$3,500,000

5 Beds ⋅ 7 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

1836 Whitehall Drive, Winter Park

$1,450,000

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

1421 Chapman Circle, Winter Park

$2,250,000

5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park

$622,000

3 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the kitchen also featuring upgraded granite countertops, stainless steel appliances including a gas range, and plenty of storage space with 42 cabinets. Oversized laundry room with extra storage space. Downstairs also features a spacious half bath with a new countertop.All 3 bedrooms are Upstairs. Bathrooms all have new Quartz counters from recent renovations. All bedrooms come with large closets. 2nd and 3rd bedrooms are connected with "Jack and Jill' bathroom with 2 separate sinks. Master Bathroom has large walk-in shower and separate Jetted Tub.Long driveway provides access to detached oversized garage in the back. Wrought iron fencing in backyard adds to a wonderfully landscaped yard.Nearby is Rollins College, the Charles Hosmer Morse Museum of American Art, Mead Botanical Garden, Albin Polasek Museum and Sculpture Gardens, the Enzian Theater, and so much more.Winter Park is also home to over 70 parks, all home to various events, festivals and celebrations throughout the year.A quick ride to almost anywhere in central Florida, minutes to Downtown Orlando, Winter Park Village, College Park, and Park Ave, 20 min to Disney World, and plenty of shopping and award-winning restaurants just minutes away! Pictures taken January 2024

685 Overspin Drive, Winter Park

$4,950,000

4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park

$254,900

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a light granite sink, and carefully selected high-end finishes, including antique brass hardware and faucet. Vinyl flooring creates a clean, cohesive look across the residence. Additional recent improvements include: Renovated primary shower featuring Italian porcelain tile and added storage shelving (2026) , Dining room chandelier and bedroom ceiling fans (2026), Fresh paint throughout (2026) Tankless water heater (2025) , New A/C system (2024), professionally serviced in June 2026, Renovated hallway bathroom and added storage shelving (2024). The floor plan offers a bright, open living space with two points of entry and an easy flow between the kitchen, dining, and living areas. Beyond the unit itself, residents enjoy an exceptional list of community amenities. The HOA includes water, trash, Spectrum high-speed internet, cable television with 150+ channels, and access to popular streaming services including Disney+, HBO Max, Peacock, and more. Set along scenic Lake Killarney, the community features a private dock, water access for boating and kayaking, a peaceful courtyard, abundant guest parking, and newly completed landscaping enhancements. The association has also recently completed significant infrastructure improvements to the community's incoming water system, with paving improvements and painting coming soon. A great opportunity to purchase a truly turnkey residence.

2500 Lee Road Unit 104, Winter Park

$5,125,000

5 Beds ⋅ 6 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.

1221 Richmond Road, Winter Park

$2,875,000

3 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.

1724 Pine Avenue, Winter Park

$215,000

1 Beds ⋅ 1 Baths ⋅ Winter Park Gdns Condo SubDv. ⋅ 32789 Zip Code

Click on virtual tour link. Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park. This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of live oaks draped in Spanish moss, mature manicured gardens, and lighted walkways- perfect for evening strolls. The unit itself has been thoughtfully renovated with brand-new luxury vinyl plank flooring, an open kitchen, updated granite countertops, and a fully renovated bathroom — all combining to deliver exceptional value in one of Central Florida's most coveted zip codes. This is a 55+ community with room for younger owners.

700 Melrose Avenue Unit F 21, Winter Park

$2,150,000

5 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

JUST LISTED! Located in the highly sought-after Winter Park Lake Sue area, this exceptional contemporary residence offers a rare opportunity to enjoy luxury living among some of the most architecturally significant and beautifully designed homes in Central Florida. Positioned within one of the region's most desirable neighborhoods, the property combines modern design, exceptional functionality, and an outstanding lifestyle location. From its prominent presence to its thoughtfully executed interior spaces, the home offers a seamless blend of modern esthetics and comfort. The open-concept floor plan is designed for both everyday living and entertaining, with expansive living areas that transition effortlessly into the covered outdoor living space, summer kitchen, resort-style pool, and heated spa. A highly desirable layout places both the luxurious primary suite and an additional bedroom/flex room on the main level, providing exceptional flexibility for guests, a home office, fitness space, or multi-purpose living. Upstairs, additional bedrooms and a large bonus room create ample space for family and entertaining. The private first-floor primary suite serves as a true retreat, featuring direct access to the outdoor living areas and a beautifully appointed spa-inspired bath. Throughout the home, quality finishes, extensive wood flooring, designer lighting, custom window treatments, and carefully curated details create an elevated living experience. The kitchen serves as the centerpiece of the home, featuring premium appliances, generous workspace, and a large entertaining island that connects seamlessly to the main gathering spaces. Perhaps most compelling is the location. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, the home enjoys convenient access to Park Avenue, Rollins College, East End Market, Winter Park Village, Downtown Winter Park, and Downtown Orlando. Residents enjoy the unique advantage of being positioned between the charm and sophistication of Winter Park and the energy of Orlando's most vibrant dining, cultural, and lifestyle destinations. Opportunities to secure a fantastic residence at this price point in the Winter Park Lake Sue area are increasingly rare. This is a unique opportunity to enjoy a wonderful lifestyle and home in one of Central Florida's most desirable neighborhoods.

230 E Rockwood Way, Winter Park

$560,000

3 Beds ⋅ 4 Baths ⋅ Urban Green 12 SubDv. ⋅ 32789 Zip Code

Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!

1250 Formosa Avenue, Winter Park

$3,500,000

3 Beds ⋅ 5 Baths ⋅ Park Hill SubDv. ⋅ 32789 Zip Code

Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

649 N Park Avenue, Winter Park

$1,549,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

New Construction!!! Escape the hassle of searching endlessly for your dream home in today's competitive market. Embrace the allure of new construction – Nestled in the vibrant Winter Park Grove neighborhood, this modern masterpiece awaits, promising a lifestyle of unparalleled comfort and convenience. Prime Location - Situated just minutes away from the bustling energy of Park Avenue this exceptional residence offers the ultimate in urban living. Explore local cafes, boutique shops, and entertainment venues with ease, all within walking or biking distance from your doorstep. Step inside to discover a world of contemporary elegance, where every detail has been meticulously crafted to perfection. The open floor plan seamlessly blends style and functionality, creating an inviting atmosphere that's perfect for both relaxation and entertainment. Boasting four spacious suites, including a lavish primary retreat on the main level, this home provides unparalleled comfort for you and your guests. Upstairs, two additional suites await, along with a versatile bonus room that can be transformed to suit your lifestyle – whether as a home office, gym, second living room, or fifth bedroom. Indulge your culinary passions in the gourmet kitchen, equipped with top-of-the-line Bosch appliances, including a 36" gas cooktop, built-in microwave, wall oven, French door refrigerator, and a wine fridge. With its sleek design and premium finishes, this kitchen is sure to inspire your inner chef. Step outside to your own private oasis, where a spacious lanai beckons you to unwind in style. Fire up the grill in the fully equipped outdoor kitchen, complete with a grill, sink, and refrigerator, and take a refreshing dip in the sparkling pool – the perfect setting for al fresco gatherings with family and friends. Pictures are of a previous model of the same plan- finishes and specifications are subject to change

1516 Miller Avenue, Winter Park

$1,669,000

3 Beds ⋅ 5 Baths ⋅ Winter Park Oasis SubDv. ⋅ 32789 Zip Code

Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.

641 Northwood Circle, Winter Park

$699,900

3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code

**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.

860 N Denning Drive, Winter Park

$1,150,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

1404 Border Drive, Winter Park

$1,995,000

4 Beds ⋅ 3 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living, unforgettable entertaining and seamless indoor-outdoor enjoyment. Offering 3,696 square feet, the flexible floor plan features four bedrooms, three full baths, a loft and a bonus room with a coffee/cocktail bar adjacent to accommodate a variety of lifestyles. The expansive first-floor primary suite is a true retreat, featuring a spa-inspired bath with heated floors, a soothing tub, an oversized walk-in shower and two large walk-in closets. The downstairs office with an en suite bath can easily function as a private guest suite or fourth bedroom. Quality craftsmanship shines throughout with detailed ceilings, engineered oak hardwood flooring, crown molding and baseboards, designer doors and hardware and plantation shutters throughout, creating a sophisticated yet inviting atmosphere. A rare combination of warmth and sophistication, this home beautifully balances luxury and functionality for modern living. The exceptional chef’s kitchen features a 60-inch Wolf gas range with a large griddle and double ovens, an expansive center island, a Sub-Zero refrigerator, a dining area and an adjacent butler’s pantry with an additional dishwasher and sink and a laundry room. Spacious gathering areas flow effortlessly into the spectacular outdoor retreat, complete with a covered lanai with remote screens, summer kitchen, outdoor fireplace, sparkling saltwater pool, separate heated spa and incredible privacy. Additional highlights include a Sonos sound system, high-definition security cameras, natural gas, a full-house generator, a separate air-conditioned workshop and a two-car garage. This exceptional Winter Park home offers the rare opportunity to enjoy newer construction elevated far beyond builder standards. Check out the 3D walk through home tour! The separate hobby garage and the 2 car garage are not included in the video tour. Call today to schedule your private showing!

2261 Mulbry Drive, Winter Park

$6,000,000

5 Beds ⋅ 8 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

1571 Woodland Avenue, Winter Park

$1,465,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Perfectly situated along a picturesque brick lined street with sidewalks in the heart of Winter Park, this beautifully refined residence offers timeless elegance, exceptional craftsmanship and a warm, inviting atmosphere just moments from the area's renowned parks, boutiques and dining. Bathed in natural light, the thoughtfully designed two story floor plan features four bedrooms, four full baths and rich maple wood flooring throughout the main living areas. At the heart of the home, the stunning chef's kitchen is designed for both everyday living and effortless entertaining, showcasing an expansive center island with a beverage refrigerator, granite countertops, a beautiful backsplash, abundant custom wood cabinetry, a pantry and a five burner gas range with double ovens. The kitchen flows seamlessly into the spacious family room, where a gas fireplace creates a welcoming focal point and French doors open to the covered patio and private backyard, extending the living space outdoors. The elegant dining room, accented with custom wainscoting, provides a sophisticated yet comfortable setting for intimate dinners and larger family gatherings alike. Just beyond, the thoughtfully designed laundry room with a butcher block countertop, custom shelving and storage. A versatile first floor room, currently serving as a playroom, is adjacent to a beautifully appointed marble floored full bath and is equally suited as a guest suite, executive office, fitness room or flex space. Upstairs, a cozy loft landing provides an additional sitting area or workspace, while the luxurious primary suite serves as a peaceful retreat featuring a beautifully new spa inspired bath with dual vanities, granite countertops, a soaking tub, an oversized walk in shower and an impressive custom walk in closet. Two additional bedrooms are connected by a beautifully renovated Jack and Jill bath, each with its own private vanity area for added comfort and functionality. Thoughtful details including higher ceilings, generous storage, plantation shutters, crown molding and baseboards enhance the home's refined character throughout. Adding exceptional versatility, the detached guest house features a full bath and a spacious walk in closet, creating the ideal space for guests, a private home office, studio or multigenerational living. The front paver area along with a long, deep driveway provides abundant parking while complementing the home's exceptional curb appeal. Ideally zoned for highly regarded Dommerich Elementary, Maitland Middle and Winter Park High School, this exceptional property also offers a 2021 roof, three HVAC systems (one approximately three years old and two approximately six years old), a Rinnai gas tankless water heater, newly added insulation and a storage shed not within site yet easily accessed just behind the guest house and the added benefit of no HOA. This is more than a home, it is a place to gather, entertain, relax and create lasting memories in one of Winter Park's most sought after neighborhoods and a most desirable lifestyle. Welcome Home!

1581 Magnolia Ave, Winter Park

$1,695,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

1420 Magnolia Avenue, Winter Park

$1,800,000

4 Beds ⋅ 4 Baths ⋅ Horton Aaron SubDv. ⋅ 32789 Zip Code

Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.

723 Symonds Avenue, Winter Park

$659,998

3 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Park 32789 zip code, just moments from scenic Lake Killarney. Situated on an oversized 0.27-acre lot with no HOA, this exceptional property offers endless possibilities, including ample space to add a pool, guest house/ADU, or create the custom outdoor living space of your dreams. Full of charm and warmth, the home features bright and spacious living areas designed for both everyday comfort and entertaining, highlighted by a cozy wood-burning fireplace. The recently renovated kitchen showcases updated cabinetry, new countertops, newer appliances, and stylish tile flooring throughout the entire first floor. The kitchen flows seamlessly into the breakfast area overlooking the expansive fenced backyard, creating the perfect indoor-outdoor lifestyle. Upstairs, you’ll find wood flooring throughout the staircase and second floor, along with three light-filled bedrooms, two full bathrooms, and a versatile flex space ideal for a home office, playroom, or study area. Additional upgrades include a renovated downstairs half bath, updated secondary bathroom, professionally cleaned and sanitized AC ducts, new ceiling fans in all bedrooms, a newly installed garage door, a new garage roof, new irrigation system and a main roof replacement completed in 2018. Relax on the inviting front porch swing and enjoy peaceful lake breezes with your morning coffee or evening glass of wine. Ideally located near Park Avenue, Winter Park Village, premier dining, shopping, entertainment, and major highways with easy access to Downtown Winter Park and Orlando. Move-in ready and filled with modern updates, timeless character, and unbeatable potential, this property also presents an incredible opportunity to live in while your custom dream home is being built.

2418 Euston Road, Winter Park

$1,595,000

3 Beds ⋅ 4 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!

1841 Lake Spier Drive, Winter Park

$1,084,000

3 Beds ⋅ 4 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

1120 Wisconsin Avenue, Winter Park

$380,000

1 Beds ⋅ 1 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fixtures, bathroom, appliances, new wood cabinets, new stone counters. All NEW The desirable condo community of Winter Park Gardens is nestled between Mead Gardens, Azalea Tennis Center and upcoming Winter Park's Progress Point. Unit is located on the second floor but there is an elevator and stairs to help to the location. Spacious 2 bedroom , 2 bath unit has large open floor plan. Main living area has an additional glass sunroom which provides additional space and breath-taking views of the beautifully landscaped and private courtyard. With its prime location in Winter Park, you'll have easy access to a many of the dining opportunities, shopping, and entertainment options. This is a 55+ community Whether you're strolling through the charming downtown area of Park Avenue or Hannibal Square or immersing yourself in the thriving arts and culture scene, with the Orlando Museum of Art right around the corner This property is centrally located to Downtown Orlando and Downtown Winter Park… no need to use the expressways! !THIS UNIT DOES NOT REQUIRE OWNER TO BE OVER 55+ furniture can convey with purchase.

700 Melrose Avenue Unit J24, Winter Park

$998,000

3 Beds ⋅ 2 Baths ⋅ Lake Monte Sub SubDv. ⋅ 32789 Zip Code

Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage and no HOA. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes both style and comfort. The well-equipped kitchen features granite countertops, a pantry, and a charming breakfast area, flowing effortlessly into the expansive family and dining rooms. French doors open to a generous screened lanai and a private fenced backyard, creating the perfect setting for seamless indoor-outdoor entertaining. Designed with a desirable split floor plan, the luxurious primary suite offers private backyard access, dual walk-in closets plus an additional storage closet and a private bath with a spacious walk-in shower. Two additional guest bedrooms share a beautifully appointed bath with shower/tub, while one bedroom enjoys direct access to a dedicated office space, ideal for guests or working from home. Winter Park is celebrated for its distinctive blend of arts and culture, charming sidewalk cafés, acclaimed museums, upscale accessible neighborhoods, scenic lakes, outdoor recreation and year-round festivals. Surrounded by top-rated schools and picturesque tree-lined streets, this exceptional location offers premier conveniences. Near AdventHealth, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and UCF. Whether you're seeking outdoor adventure, cultural enrichment, or everyday convenience, this location delivers it all. Schedule your private showing today and discover the best of Winter Park living. Roof - 2018, AC - 2015.

1741 Mizell Avenue, Winter Park

$750,000

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park

$211,000

1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to Lake Killarney Living — where Winter Park charm meets everyday convenience. Discover this beautifully appointed condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, premier dining, boutique shopping, and the peaceful waters of Lake Killarney. This is low-maintenance, lock-and-leave living in one of Central Florida's most desirable lakefront communities. Inside, the condo is thoughtfully updated for modern comfort. A brand-new kitchen shines with sleek quartz countertops, while polished terrazzo floors flow throughout — a timeless, low-maintenance finish that's as durable as it is beautiful. Efficient mini-split air conditioning serves both the living room and bedroom, delivering precise, zoned cooling through even the warmest Florida summers, and a generous walk-in closet offers the kind of storage that's rare in condo living. Step outside to your private screened-in patio, the perfect spot for morning coffee, quiet evenings, or creating your own cozy outdoor retreat to unwind and enjoy the waterfront Florida sunset. Residents enjoy an impressive list of community amenities, including a sparkling private pool, a fitness center, lush green spaces, and beautifully maintained grounds. Best of all, the community offers optional private access to Lake Killarney, ideal for launching boats, kayaks, and paddleboards, fishing, or simply taking in serene lakefront views and some of Central Florida's most stunning sunsets. Enjoy evening sunset strolls, a weekend on the water, a relaxing afternoon by the pool, or sunsets around the firepit on the lake. Best of all boat slip is available for only $75 per month. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #259 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in a true lakefront community. month. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit 259, Winter Park

$3,300,000

5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms plus a generous flex space, the perfect office, home gym or playroom and 4.5 baths with designer fixtures and finishes. A separate casita with a full bath provides additional space for multigenerational living or as a private guesthouse. Upon entering, you are greeted by an expansive open-plan living area with soaring ceilings that effortlessly blends sophisticated style with indulging comfort. The kitchen is a culinary dream, equipped with Le Cornue and Monogram appliances, marble and quartzite countertops and a separate scullery with plenty of storage and ample prep space. The kitchen opens to one of the main living areas, featuring a precast concrete fireplace surround with exquisite millwork details, forming a focal point leading up to the angular ceiling and overhead beams. Engineered hardwood floors throughout and curated specialty tiles in wet spaces ensure the home maintains a clean, classic and modern feel. Floor-to-ceiling French doors and oversized sliders invite natural light and offer views of the beautifully landscaped grounds, including a sparkling heated saltwater pool and fully equipped outdoor kitchen. This wellness home incorporates advanced features to ensure a healthy living environment, from air and water purification systems to specialty lighting, all designed to promote a balanced lifestyle. Just moments from charming parks, highly rated restaurants and boutique shopping, 1627 Mizell Avenue is more than just a home, it’s a sanctuary. With excellent accessibility and a vibrant community, this is an ideal setting for those seeking a blend of suburban tranquility and urban convenience.

1627 Mizell Avenue, Winter Park

$377,880

3 Beds ⋅ 2 Baths ⋅ Howell Heights SubDv. ⋅ 32789 Zip Code

Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

2973 Sanbina Street, Winter Park

$1,395,000

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing elegant finishes, designer touches, and a fresh, elevated aesthetic throughout. Recently fully repainted and enhanced with gorgeous new quartz countertops and a crisp white pearl subway tile backsplash, the home now feels both current and timeless while maintaining the charm and character buyers love about Winter Park living. At the heart of the home is a spectacular chef’s kitchen featuring top-of-the-line Viking and Bosch stainless steel appliances, including a Viking gas range with griddle, a large center island with counter seating, stunning cabinetry, and a dramatic 10-foot coffered ceiling. The kitchen flows seamlessly into the inviting family room with gas fireplace and custom window seating, creating the perfect setting for both everyday living and upscale entertaining. Triple French doors open to a generous covered lanai complete with a summer kitchen, built-in grilling station, and beautifully designed outdoor spaces beaming with old-world charm rarely found in newer construction homes. The turf backyard offers easy maintenance while creating a warm and private atmosphere for gatherings year-round. The formal dining room is equally impressive with crown molding, wainscoting, abundant natural light from the oversized bay window, and direct access to a convenient butler’s pantry and dry bar, making hosting effortless. Upstairs, the magnificent owner’s retreat offers oversized walk-in closets and a luxurious spa-inspired bathroom adorned with glorious marble tile work and elegant designer finishes. Two additional generously sized bedrooms share a marble bath and the 4th bedroom is currently shown as an office, with adjacent hall full bath. A downstairs powder room outfitted in new england blue theme is great for guests. Additional luxury features include hardwood flooring, plantation shutters, surround sound, tankless gas water heaters, an electric vehicle charger, oversized two-car garage with high ceilings and level 5 drywall finish, and countless thoughtful upgrades throughout. Located within the highly desirable Windsong community, residents enjoy access to incredible amenities including two resort-style pools, lakefront clubhouse, water park, playground, fishing pier, kayaks, paddleboards, and even a residents-only pontoon boat to explore the Winter Park Chain of Lakes. Just minutes from Park Avenue, Baldwin Park, and top-rated Winter Park schools, this is your opportunity to step directly into the Winter Park home of your dreams—fully upgraded, impeccably styled, and ready now.

1347 Chapman Circle, Winter Park

$875,000

3 Beds ⋅ 3 Baths ⋅ H Vanwies Sub SubDv. ⋅ 32789 Zip Code

Experience refined luxury and effortless living at 1407 Miller Avenue, ideally situated in one of Winter Park’s most desirable and walkable enclaves near the NEW Minnesota Row. Built by SGC Homes, this exceptional Modern Mediterranean detached townhome combines timeless architecture with sophisticated contemporary finishes along a charming, tree-lined brick street. Offering 3 bedrooms, 2.5 bathrooms, and 1,884 square feet of thoughtfully designed living space, the residence features a highly sought-after first-floor primary suite and the privacy of only one shared wall at the garage—no shared interior living walls!! Interior highlights include Level 4 drywall finishes, wide-plank engineered oak flooring, Bosch appliances, LED mirrors, and an impressive Hunter Douglas automated shade system. The open-concept floor plan is both functional and inviting, filled with natural light and seamlessly extending to a private paved patio and fenced backyard—ideal for entertaining, quiet outdoor living, or the future addition of a pool or spa. Set within an exclusive four-residence enclave, this low-maintenance property offers a true lock-and-leave lifestyle just minutes from Park Avenue’s premier dining, boutique shopping, Publix, AdventHealth, and everyday conveniences. Additional features include a private two-car garage with EV charging capability and dedicated guest parking. A rare opportunity to own a design-forward residence in the heart of Winter Park.

1407 Miller Avenue, Winter Park

$615,000

3 Beds ⋅ 2 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

Virtually Staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

1780 Goodrich Avenue, Winter Park

$1,599,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

2430 Chantilly Avenue, Winter Park

$2,460,000

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.

2228 Howard Drive, Winter Park

$1,249,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Enjoy seamless outdoor living on the covered lanai with a fully equipped summer kitchen—ideal for gatherings and enjoying the Florida sunshine. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with similar features- you can still customize to suit your needs!

Winter Park

$1,395,000

5 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park farmers market and by sunset, enjoy Park Avenue or Winter Park Village. Back home, feel comfortable, extremely comfortable in this casual-chic custom designed home. After a welcoming foyer, a kitchen-bar opens to a large and bright great room fitting dining and living areas. It continues to the back covered veranda and back yard. Still on the first floor, you have a guest suite and an office, conveniently located by the entry door. Up the stairs, a large family room, capable of gathering all the family. In the large master suite balcony, you may have your first coffee in the morning, listening to the early birds. The two other rooms also have balconies to the front of the house. All rooms have closets with shelves, to accommodate your needs. Enjoy finishes like wood floors, large mirrors in bathrooms, quartz counters, crown molding, wide windows and more. This beautiful and modern home is ready for its new residents. It is absolutely gorgeous! Come and visit us. Welcome Home!

433 Carolina Avenue, Winter Park

$1,375,000

3 Beds ⋅ 3 Baths ⋅ Lyman Ave Villas 1 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow from the kitchen into the main living areas. The kitchen features high-end appliances, including a Wolf refrigerator and GE Monogram suite, along with dedicated wine and beverage refrigeration—perfect for hosting or everyday use. A new A/C unit has also been installed, providing added peace of mind. That same attention to entertaining continues outdoors, where a screened-in kitchen, hot tub, and professionally installed turf create a private, low-maintenance space ideal for hosting or relaxing. Inside, the home offers a very spacious primary suite complete with a walk-in closet. A full bathroom is conveniently located downstairs adjacent to the study, which can also function as a third bedroom, adding flexibility to the layout. The two car garage has been upgraded with a durable epoxy-coated floor for a clean, finished look. Located just minutes from Winter Park Village and only a short drive to major roadways including Interstate 4 and State Road 436, this home offers unmatched access to shopping, dining, and downtown. Enjoy the charm of tree-lined streets and historic surroundings, all just steps from the shops and restaurants of Park Avenue. This is a rare opportunity to own a turnkey property in one of Winter Park’s most desirable locations.

266 W Lyman Avenue, Winter Park

$380,000

2 Beds ⋅ 1 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

440 Cambridge Boulevard, Winter Park

$1,201,000

3 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to this thoughtfully expanded one-story home in Winter Park’s coveted “Tree Streets” neighborhood. A paved double drive and circular driveway create a gracious arrival with ample guest parking. Originally built in 1962 and expanded over time, this home offers a flexible floor plan designed for comfortable everyday living and effortless entertaining. Spacious living areas and the primary suite open to a stunning garden-like backyard, seamlessly connected by a full-length covered portico perfect for enjoying Florida’s indoor-outdoor lifestyle. The main hallway leads to the primary and guest bedrooms, along with a quiet sitting room overlooking the charming front porch. Expanded in the early 2000s, the private primary suite includes a generous bath with an oversized whirlpool tub, dual vanities, separate shower, dressing table, private water closet, and a spacious walk-in closet. At the heart of the home, the kitchen features solid wood cabinetry and solid-surface countertops, opening to the central family room with a traditional fireplace and casual dining area, all adjacent to the formal dining room. Just off the kitchen, a large flex space offers extensive built-ins, a desk area, dry bar, wine refrigerator, and integrated washer and dryer ideal for a home office, hobby room, or additional entertaining space. Located just minutes from Park Avenue, enjoy easy access to fine dining, boutique shopping, cafés, museums, and year-round community events. This one-story home offers abundant living space, exceptional entertaining areas, and a beautifully landscaped backyard complete with pool and outdoor living spaces all situated on a generous 77 x 150 lot.

1723 Chestnut Avenue, Winter Park

$2,755,000

5 Beds ⋅ 5 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Graceful and timeless, this classic Southern-inspired residence by esteemed builder Charles Clayton sits on a generous lot in Winter Park’s coveted Park Grove neighborhood and makes a striking first impression with beautifully composed architecture, charming dormer windows, a sweeping front porch with historic reclaimed Detroit brick flooring, and curated landscaping. Inside, the foyer unfolds with rich wood floors, raised-panel wainscoting, layered crown molding and detailed millwork which sets the tone for depth and quiet sophistication throughout the home. Just off the entry, a beautifully appointed office with finely crafted built-in shelving thoughtfully designed for both display and function. The same refined trim details carry through, while generous windows introduce soft natural light—an ideal setting for work or a quiet reading. Across, the dining room is both elegant and inviting—bathed in natural light from large windows and enhanced by more detailed millwork that adds character and creates a polished backdrop for dining and entertaining. Continue through wide detailed trim opening to an expansive great room anchored by a classic fireplace with custom built-ins, while a wall of French doors invites in natural light and extends the living space seamlessly to the covered verandah with more reclaimed Detroit brick flooring and the pool, creating perfect space to gather, lounge or entertain. Open to the Great room, the beautifully designed kitchen stands out with a coffered ceiling, marble countertops, and crisp white cabinetry, featuring illuminated upper cabinets and open shelving for thoughtful displays. A central island is complimented by an integrated breakfast table—perfect for casual dining or morning coffee. Professional-grade appliances, including a Wolf gas range and Sub-Zero refrigerator, are paired with a thoughtfully tucked-away walk-in pantry offering abundant storage and effortless organization—bringing both refined style and everyday function to the kitchen. Positioned between the kitchen and living area, this adaptable space creates a natural gathering point—ideal for casual dining, relaxed conversation, or a cozy sitting area thoughtfully suited to your lifestyle. The 1st floor primary suite offers a true retreat, with an elegant, coffered ceiling, private verandah access and dual walk-in closets. The marble bath includes a generous glass-enclosed shower with double shower heads, pedestal soaking tub, a pair of vanities, and water closet. Completing the 1st floor is a large mud room with custom built-in bench seating and integrated storage, an oversized laundry room that blends utility and style with generous storage and marble counters, and a well-appointed guest bath accented with herringbone wainscoting. Upstairs, a versatile loft area is laid out to easily accommodate multiple uses—lounge area, work-from-home space, or media retreat. The 2nd floor split-bedroom plan features a separate guest suite, with vaulted tongue & groove ceilings, a private living area and en-suite bath, a 3rd bedroom with an en-suite bath and walk-in closet, and two additional bedrooms are connected by a bath, plus an air-conditioned storage room. Outdoor living is elevated, with a covered veranda and built-in gas grill, overlooking a sleek, resort-style pool, marble decking, and a beautifully landscaped backyard. Every element of this home reflects livable elegance, all just a stone’s throw from renowned downtown Park Avenue.

670 Williams Drive, Winter Park

$3,150,000

4 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of arrival and sets the tone for what lies within. A grand set of double doors opens to a breathtaking two-story entry, where a dramatic marble mosaic feature establishes the home’s elevated design from the moment you step inside. The main living space is nothing short of stunning, anchored by a sleek electric fireplace and custom built-ins with integrated LED underlighting. At the heart of the home, the chef’s kitchen is a true showpiece, outfitted with Dekton Cosentino countertops, a paneled refrigerator, a full suite of Thermador appliances, and a hidden walk-in pantry. The kitchen flows effortlessly into the dining room which is bathed in natural light from an oversized statement window, making it perfect for hosting at any scale. Designed with versatility and luxury in mind, the home features two primary suites, one on each level. The downstairs primary offers soaring 12-foot ceilings and a serene, spa-like bath wrapped in marble mosaic tile. Upstairs, the main primary suite is a true showstopper, defined by its scale and attention to detail. Dual custom closet systems include an expansive hers closet complete with a dedicated makeup vanity, while the bathroom delivers a resort-caliber experience with stunning marble floors, a freestanding soaking tub, and dual vanities. The upper level continues to impress with a spacious loft designed for both relaxation and entertaining, complete with a custom entertainment center, wet bar, wine fridge, and a full bath. Each additional bedroom is ensuite, offering privacy and comfort for family and guests alike. Outdoor living rivals that of a private resort. A massive covered lanai features a fully equipped summer kitchen with tile backsplash, overlooking an expansive lounging area framed by a wall of glass. The heated pool and spa create the ultimate setting for year-round enjoyment, while the oversized front yard (an incredibly rare find in Winter Park), adds an unmatched sense of space and setting rarely found in this market. Additional features further elevate the home, including a sleek metal roof, striking hex LED lighting in the garage, and curated designer lighting fixtures throughout. Perfectly positioned just moments from Lake Chelton and Virginia Heights Park, with easy access to the boutiques and dining of Park Avenue and the charm of Hannibal Square, this residence offers a lifestyle that is as elevated as the home itself.

1910 Glencoe Road, Winter Park

$2,750,000

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.

1630 Lasbury Avenue, Winter Park

$1,150,000

4 Beds ⋅ 2 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

1981 Blue Ridge Road, Winter Park

$2,500,000

5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park

$7,164,000

5 Beds ⋅ 7 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code

Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

1821 Pinetree Road, Winter Park

$1,755,000

4 Beds ⋅ 4 Baths ⋅ Windsong - Knowles Place SubDv. ⋅ 32789 Zip Code

Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

1813 Harland Park Drive, Winter Park

$495,900

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location, and a home that is ready to be enjoyed from day one while maintaining long term upside.

525 Ololu Drive, Winter Park

$680,000

3 Beds ⋅ 2 Baths ⋅ Sylvan Hgts SubDv. ⋅ 32789 Zip Code

Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system updates have been completed, including a 2024 metal roof and 2025 HVAC system, providing peace of mind for the next owner. Additional exterior improvements include new soffits and gutters, fresh exterior paint in 2025, a whole-home surge protector, and updated breezeway or office door and windows installed in 2024. Inside, you will find a well-equipped kitchen with Samsung appliances, including a range, microwave, dishwasher and a 2023 refrigerator, along with a 2020 Samsung washer and dryer. Comfort and efficiency have also been enhanced with replaced air ducts in 2016, an Ecobee smart thermostat and updated ceiling fans. Smart home features include a Logitech Circle View wired doorbell, smart blinds and updated smoke detectors, providing modern convenience throughout the home. The property sits toward the rear of the lot, creating a private, fenced yard space ideal for pets, outdoor enjoyment or entertaining. An irrigation system is also in place to help maintain the landscaping. In the desirable Winter Park area and zoned for highly regarded Winter Park schools, this home offers a combination of location, updates and flexibility. With major systems addressed, this home presents a move-in-ready opportunity and being sold as is.

1701 Goodrich Avenue, Winter Park

$1,625,000

4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

$1,569,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still accommodating entertaining with ease. Clean lines, curated finishes, and natural light define the main living spaces, where the kitchen, dining, and living areas flow seamlessly together. The kitchen serves as a true focal point, featuring Calacatta Gioia quartz countertops, custom cabinetry with ample storage, a paneled refrigerator, and a full suite of Thermador appliances. The space transitions naturally into the dining area and living room, where a built-in wet bar with a wine fridge adds an elevated layer of functionality and style. The living room is designed to feel both open and connected, anchored by expansive pocketing sliders that completely open to the outdoor living area. The primary suite is thoughtfully positioned on the main level, serving as a calming retreat, featuring a spa-inspired bathroom with dual vanities, a freestanding soaking tub, and a spacious walk-in shower. Upstairs, three additional bedrooms are generously sized and well laid out, providing flexibility for guests, family, or a secondary living setup. The outdoor living experience is equally impressive, centered around a large covered lanai that offers ample space for al fresco dining and lounging. The spacious pool area is designed to complement the home’s indoor-outdoor lifestyle, creating a private setting that feels both relaxed and elevated. Beyond the home itself, the location is what truly sets this home apart. Situated in the heart of the Tree Streets, you are just a short walk to Phelps Park and the YMCA, minutes from Interlachen Country Club, and only a quick golf cart ride to the shops, dining, and energy of Park Avenue. Homes of this caliber and location are few and far between, making this a standout opportunity in today’s market.

1660 Walnut Avenue, Winter Park

$345,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code

Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

2889 Rouen Avenue, Winter Park

$1,295,000

4 Beds ⋅ 4 Baths ⋅ Hamilton Place SubDv. ⋅ 32789 Zip Code

Now offered out an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest – seller is actively moving. This remarkable home represents one of the best opportunities in today’s Winter Park luxury market, featuring exquisite finishes, modern design, and an unmatched lifestyle just moments from Park Avenue. Built in 2018, this custom-designed 4-bedroom, 3.5-bath residence offers 2,843 square feet of thoughtfully crafted living space, just a short walk from Park Avenue and the historic Winter Park Golf Course. Distinctive architectural details—including shiplap ceilings in the living room and kitchen, decorative ceiling treatments, and a dramatic tile staircase feature illuminated by natural light—create a home that is both elegant and inviting. At the heart of the home is a chef-inspired kitchen featuring Wolf and Sub-Zero appliances, custom cabinetry, Kohler fixtures, and an open-concept layout that flows effortlessly into the living and dining spaces, making it ideal for everyday living and entertaining alike. The primary suite serves as a peaceful retreat with a spa-inspired marble bathroom, while the upstairs bonus room offers flexible space for a media room, home office, or playroom. Outside, enjoy your own backyard oasis complete with a sparkling pool and spa combo—perfect for relaxing or hosting family and friends. Located just minutes from Park Avenue’s renowned restaurants, boutiques, and year-round events, this home delivers one of Central Florida’s most sought-after lifestyles. Schedule your private showing today.

802 Hamilton Place Court, Winter Park

$4,550,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Under Construction. Stunning Winter Park new build by Vimaro Homes in Park Grove.

1701 Summerland Avenue, Winter Park

$569,900

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

1398 Grove Terrace, Winter Park

$2,249,000

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first impression. Step inside and you're immediately greeted by soaring ceilings, exposed oak beams, wide-plank white oak flooring, and expansive walls of glass that fill the home with natural light. The great room serves as the heart of the residence, anchored by a floor-to-ceiling natural stone fireplace with illuminated built-ins and expansive sliders that seamlessly connect indoor and outdoor living. At the center of the home, you'll find a beautifully executed kitchen designed for both entertaining and everyday living, featuring floor-to-ceiling custom white oak cabinetry, designer stone surfaces, a substantial center island, illuminated wine display, a 48-inch gas range, and abundant storage. Nearby, a walk-in pantry, fully built-out laundry room, and mudroom enhance functionality while maintaining the home's refined design language. Privately positioned on the main level, the dedicated office provides an inspiring setting for work, study, or creativity, while the primary suite serves as a true retreat. The spa-inspired bath is finished with floating oak vanities, rich stone surfaces, a freestanding soaking tub, and an expansive wet room that feels more like a luxurious resort. It's the kind of retreat you'll appreciate every morning and look forward to returning to at the end of each day. Upstairs, a versatile loft creates the perfect setting for a media room, playroom, study space, or secondary gathering area. One bedroom enjoys the privacy of its own ensuite bath and walk-in closet, while two additional bedrooms are connected by a beautifully appointed Jack-and-Jill bath. Step outside and you'll find yourself lingering a little longer than planned. A custom PebbleTec pool, covered tongue-and-groove lanai, fully integrated outdoor kitchen, and private backyard setting create an environment designed for effortless entertaining and low-maintenance enjoyment. Built by Structure Redevelopment, a boutique builder known for delivering thoughtfully crafted custom residences throughout Central Florida. Just minutes from Park Avenue, Rollins College, East End Market, Audubon Park, and Downtown Orlando, Casa Noir brings together exceptional architecture, thoughtful design, and everyday livability in one of Winter Park's most desirable locations - Schedule your tour today.

2361 Mulbry Drive, Winter Park

$1,300,000

3 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Beauifully rennovated property on coveted brick street in PRIME Winter Park Location! This exceptional 3-bedroom, 3.5-bath home sits on a generously sized, fenced, private lot—perfect for entertaining or family living. Every inch of this residence has been thoughtfully updated, featuring 3-zone AC, updated plumbing, electrical, windows, foam insulation, and 2022 roof. Inside, luxurious designer touches abound. You're welcomed by an elegant foyer with Calacatta gold marble flooring and designer sphere lighting. The open-concept living space features rich eucalyptus flooring and soaring vaulted ceilings, seamlessly connecting to the outdoors through french doors that open to a bricked patio with tongue-and-groove wood ceiling, summer kitchen, and expansive yard. At the heart of the home is a gourmet kitchen that will delight any chef, complete with a Viking 6-burner natural gas range including griddle and double oven, an oversized entertaining island and a stylish wet bar with wine fridge. The thoughtfully designed floor plan includes two downstairs bedrooms, one makes a perfect home office, the other is a mother-in-law suite with a private entrance—ideal for guests or teens. Both secondary full bathrooms boast rainfall shower heads, dual flush toilets, and designer fixtures and tile. Upstairs, the expansive master suite offers vaulted ceilings, a custom walk-in closet, and french doors leading to a private balcony. The luxurious master bath features a 7-spray shower system, an aromatic Jacuzzi tub, and a ceiling-mounted waterfall spout for the ultimate spa-like experience. This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living!

1661 Woodland Avenue, Winter Park

$4,285,000

4 Beds ⋅ 6 Baths ⋅ Winflor Court Pt Rep SubDv. ⋅ 32789 Zip Code

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

1441 Cardinal Court, Winter Park

$460,000

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge 1st Add SubDv. ⋅ 32789 Zip Code

Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.

950 Hanover Avenue, Winter Park

$1,395,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.

2408 Lafayette Avenue, Winter Park

$2,050,000

4 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.

1636 Elizabeths Walk, Winter Park

$920,000

3 Beds ⋅ 2 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

250 Cortland Avenue, Winter Park

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

1870 Staunton Avenue, Winter Park

$1,699,000

3 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Come home to this gorgeous 3 Bed/3 Bath Winter Park masterpiece on a premier corner lot at the intersection of the coveted Alabama Drive and Palmer Avenue. FULLY RENOVATED DOWN TO THE STUDS IN 2020. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.

1110 Alabama Drive, Winter Park

32789 Zip Code Real Estate & Homes with Open Floorplan

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