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$1,450,000
2 Beds ⋅ 1 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code
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141 W Lake Sue Avenue, Winter Park
$1,550,000
Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
This is your chance to create the home of your dreams in one of Winter Park’s most sought-after neighborhoods. Situated on an oversized 80 x 180 lot (0.30 acres), this property offers ample space and endless potential. The existing structure has already been removed, making way for a seamless building process.Enjoy a walkable lifestyle with the Winter Park Racquet Club just steps away and the renowned Interlachen Country Club a short drive down the road. Take a leisurely stroll to Park Avenue, home to some of the area’s best restaurants, boutiques, and cultural attractions.Don’t miss this rare opportunity to build your custom home in the pristine and highly desirable Via neighborhood of Winter Park.

1181 Via Capri, Winter Park
$1,450,000
6 Beds ⋅ 5 Baths ⋅ J Kronenberger SubDv. ⋅ 32789 Zip Code
Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-à-terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Maitland, and walking distance to the renowned boutiques and dining of Park Avenue. Positioned on a beautiful 0.30-acre lot, this residence is enveloped with manicured landscaping, meandering brick pathways, and outdoor living spaces designed for effortless entertaining. This home captivates with exceptional curb appeal—complete with vibrant florals, a stately new blue front door, and architectural charm. The total square footage is 3784sf with the main home 5 bedrooms/4 bathrooms and 3304sf; the guest retreat is 1 bedroom/1 bathroom with 480sf. Recent updates include new flooring, fresh interior and exterior paint, a renovated kitchen, three new bathroom renovations, almost all new windows, and numerous decorative touches like new crown molding and plantation shutters. The heart of the home features a spacious open-concept layout ideal for entertaining. The living room with an updated gas fireplace flows into the kitchen, which boasts new Bosch appliances, bar seating, a walk-in pantry, and a charming picture window with garden views. The elegant dining space, with 11-foot ceilings and a wall of windows, frames the picturesque backyard. The first floor offers three bedrooms and two full bathrooms, including an en-suite, as well as an office. The second floor includes two large bedroom suites with high ceilings and a laundry room. The upstairs luxurious primary suite impresses with a tray ceiling, cozy fireplace, dual walk-in closets, and a renovated bathroom with granite dual vanities, a freestanding soaking tub, and an oversized walk-in shower. The secondary suite includes its own walk-in closet, spacious bath with double vanities, and a large climate-controlled storage area for ultimate flexibility. Features include French doors, hardwood floors, custom built-ins, crown molding, and plantation shutters throughout. But the crown jewel of the property is the brand-new 2024 detached pied-à-terre—a versatile studio suite with a full bedroom and bathroom, a refreshment area, and a private balcony with tranquil views, ideal as a guest house, executive office, fitness studio, or artist’s retreat. Outdoor living is a dream with a screened brick patio beneath a beamed ceiling, a charming open-air terrace, an enchanting fountain, and complete privacy thanks to a 6-foot concrete wall surrounding the grounds. With ample space to add a custom pool, the possibilities are endless. Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves.

1299 Harding Street, Winter Park
$1,335,000
4 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 32789 Zip Code
Under Construction. New Construction in the Heart of Winter Park by Nautilus Homes - Introducing an exceptional opportunity to own a brand-new luxury residence by award-winning builder Nautilus Homes, ideally situated between Orlando Avenue and Orange Avenue—just moments from Winter Park’s renowned shops, dining, and cultural attractions. This thoughtfully designed 4-bedroom, 4-bath estate with a private office/den seamlessly blends timeless elegance with elevated modern living. Spanning over 4,000 square feet under roof, every inch of this custom home showcases the finest craftsmanship and luxury finishes. Step inside to be greeted by Creme Brûlée wide-plank wood flooring throughout, setting a warm and inviting tone. The heart of the home is the chef’s kitchen, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and a stunning Kit-Kat tile backsplash in the adjoining butler’s pantry, perfectly positioned between the kitchen and formal dining room. Entertain effortlessly with a built-in wine and coffee bar just off the expansive living room. The floor plan offers versatility and privacy with one en-suite bedroom and a dedicated office on the main level, while upstairs you'll find three generously sized bedroom suites, each with walk-in closets and refined finishes. Retreat to the primary suite's spa-inspired bathroom, a true sanctuary with a soaking tub, an oversized 9-foot walk-in shower featuring dual sprayers, a frameless glass enclosure, and linear drainage for a sleek, seamless look. Luxury new construction in this coveted Winter Park location at $337 per square foot is virtually unheard of. Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment.

1077 Minnesota Avenue, Winter Park
$1,942,000
5 Beds ⋅ 5 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Five-bedroom, 3900+ sq ft pool home with 3 car garage on a large corner lot in the sought -after Park Grove neighborhood near Lake Maitland and Park Avenue. Great Room consists of a Family Room area with a wood-burning fireplace and tray ceilings and a Sun Room area with bay windows and french doors overlooking the pool deck. Kitchen bordering the spacious Great Room Area, features a cooking island and custom teak counters with a closet pantry and an extra 7’ x 5’ storage area/dry bar and is adjacent to a butler pantry and laundry room. The luxurious Primary Suite, that opens to its own deck over the back yard and pool deck, features a coffered ceiling, a very large walk-in closet as well as additional closet space. The large Primary Bath contains dual vanities, whirlpool tub, and separate shower. The Second Bedroom Suite includes an en-suite bathroom, built in shelves and a corner window niche for make-up or a reading/work area. Bonus Room with bay windows, built in shelves/entertainment center and dual closets has been utilized as an extra bedroom or as a gaming area. The Living Room, with a wood burning fireplace, is adjacent to the entry foyer and opens to the Dining Room featuring bay windows that could also serve as a sizable and elegant office area. The entire home features recently finished wood floors. 3-zone central HVAC system and dual pane – energy efficient windows and updated, blown-in insulation in attic will keep you comfortable all year round. Recent roof update. Near the Park Avenue Downtown District - Imagine a downtown where history, art, and nature blend seamlessly, creating a vibrant and welcoming community. Here, the past meets the present in every shop, event, and stroll down the Avenue. Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town.

1394 Stewart Street, Winter Park
$1,375,000
4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

1633 Pine Avenue, Winter Park
$2,935,000
5 Beds ⋅ 6 Baths ⋅ Gibbs Sub SubDv. ⋅ 32789 Zip Code
One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.

266 Chase Avenue, Winter Park
$1,250,000
5 Beds ⋅ 6 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code
Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfect blend of sophisticated main residence and private guest cottage. Just minutes from Park Avenue's renowned shopping and dining, this property provides coveted access to Lake Osceola, creating an ideal setting for the Florida lifestyle. The main residence showcases elegant living spaces, including a grand room with hardwood floors and a welcoming fireplace. The gourmet kitchen is a chef's dream, featuring premium Wolf and Sub-Zero appliances, gleaming granite countertops, and a distinctive bead-board center island that opens to a spacious family room. A wall of French doors in the formal dining room creates seamless indoor-outdoor flow to the screened pool and spa area. The thoughtful floor plan includes a downstairs master suite with custom walk-in closet, dual-sink bathroom, and versatile 13x12 flex space. Two additional en-suite bedrooms upstairs provide comfortable accommodations for family or guests. The separate guest cottage adds tremendous value with two bedrooms, a full kitchen, and bathroom – perfect for long-term guests or home office. Recent updates ensure peace of mind: new roof (2025), two new AC units (2023), complete replumbing (2015), and updated electrical. The property offers abundant parking with a two-car garage plus an additional one-car garage with full bath. Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value.

1370 Alberta Drive, Winter Park
$3,845,000
4 Beds ⋅ 4 Baths ⋅ Venetian SubDv. ⋅ 32789 Zip Code
Lake Maitland Custom built home.

2020 Venetian Way, Winter Park
$1,885,000
4 Beds ⋅ 5 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Stunning new Winter Park residence.

2144 Sycamore Drive, Winter Park
$1,295,000
4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Nestled in one of the most sought-after locations, the “Tree Streets” of Winter Park. 1601 Chestnut Avenue is a stunning Modern European Cottage-style home, built in 2017, that masterfully blends classic charm with modern finishes. Offering over 2,800 square feet, this pool home includes: four bedrooms, three full baths, and an over-sized loft. Step inside to hard wood flooring, complemented by upgraded baseboards and crown molding throughout. The formal dining room, also functional as a formal seating area, or office space, is complete with a pass-through bar, flows seamlessly into a chef’s kitchen—featuring a Viking appliance package, a 48” gas range, quartz countertops, an extended bar-top island, and floor-to-ceiling cabinetry. The white cabinetry is solid wood, soft-closing and includes custom pull-outs. The island comfortably seats 5 barstools, and flows seamlessly into the breakfast nook. The great room is a true showpiece, with a stone gas fireplace and a stunning 12 foot tongue-and-groove wood ceiling. Natural light floods the space from the large sliding glass door, and windows to the vaulted ceiling, adding to the open concept floor plan and how spacious it feels. The first-floor primary suite, is situated at the back right of the home, with direct lanai access, and large picture windows overlooking the private pool. The hallway to the en-suite includes dual walk-in closets, with solid wood built-ins. The en-suite features a water closet, an oversized two-sided walk-in shower, and a vanity with dual sinks and quartz countertops. Step outside to the lanai, where a beach-entry pool and spacious covered lanai, complete with the same vaulted tongue and groove ceiling as seen inside. This continuous feature is a statement in the home. The lanai is finished with a travertine deck and gas line hookup. Rock landscaped beds, lush landscaping and a fully fenced yard, complete the back yard, making the perfect space to entertain. The main level also features a guest bedroom and full bathroom, with a frameless glass shower. Next to this bedroom is also access to the two-car garage and a conveniently positioned laundry room. Upstairs, a bonus room with vaulted ceilings (22’ x 14’) provides endless possibilities—ideal for a home theater, office, or playroom. Two additional bedrooms and a full bath complete the second level. Both bedrooms offer walk-in closets. The full bathroom includes a large vanity with quartz countertops, and a tub and shower combination. Additional features of this home, include: newly installed lighting fixtures throughout, a paver driveway, covered front porch, and a two-car garage. The two-car garage was recently finished with custom flooring and custom built-ins to maximize the functionality and storage space in the garage. This exceptional home is just moments from Park Avenue, Winter Park Village, Whole Foods, and beautiful neighborhood parks and lakes. A location like no other, call today to schedule your private tour.

1601 Chestnut Avenue, Winter Park
$1,025,000
4 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to your Winter Park dream home—a modern farmhouse masterpiece blending timeless design with contemporary comforts. Built in 2019, this single-family home offers four spacious bedrooms, two and a half baths, and luxurious finishes you'll cherish for years. Nestled between the highly coveted areas and school zones of College Park and Winter Park, this property is an opportunity you can't miss. Step into the foyer, leading to a bright, open-concept living space and a kitchen that’s designed to impress. Featuring quartz countertops, sleek stainless appliances, shaker cabinetry, and a wine fridge, this kitchen is perfect for both everyday living and entertaining. The living area transitions smoothly into the expansive fenced backyard, complete with ample space for a future pool. Upstairs, you'll find all four bedrooms, including the stunning primary suite with hardwood floors, a custom walk-in closet, and a spa-like bathroom with dual sinks. A versatile loft, laundry room, and additional full bathroom complete the second floor. Enhancing its charm are plantation shutters throughout and proximity to the serene Dubsdread Golf Course—a perfect spot for morning jogs or evening strolls. Enjoy the ease of accessing all that College Park and Winter Park have to offer, as well as convenient commuting via Interstate-4. There is no HOA in this community. This home is available immediately.

2680 Oglesby Avenue, Winter Park
$2,625,000
4 Beds ⋅ 6 Baths ⋅ Virginia & Morse Brownstones SubDv. ⋅ 32789 Zip Code
Step into luxury with this stunning three-story townhouse featuring an elevator and abundant natural light. A breathtaking staircase elegantly wraps around a magnificent chandelier, creating a striking focal point from the first floor to the third. The first floor boasts a chef's kitchen with high-end cabinets, top-of-the-line appliances, and premium flooring. The second floor offers four elegant main suites, each designed for comfort and privacy. The third floor is home to the impressive main suite, located next to the rooftop terrace, which includes a gazebo and jacuzzi. This home is equipped with an internal vacuum system and a state-of-the-art Pelican water filtration system for ultimate convenience and water quality. A charming backyard garden, a two-car garage, and a prime location within walking distance to top restaurants, parks, and farmer's market complete this exquisite property- ideal for stylish buyers seeking a vibrant lifestyle.

141 N Virginia Avenue, Winter Park
$2,300,000
4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
PRESENTING THE NEWEST WINTER PARK RESIDENCE BUILT BY M. LAHR HOMES! Just completed, this stunning custom level home has come together perfectly with design and finish features that have to be seen in person to be truly appreciated. The combination of a fantastic floor plan that integrates perfectly with the expansive covered outdoor patio/pool/spa/outdoor space makes this house feel nothing less than a resort. This entire outdoor area is an incredible natural four (4) season extension of the interior living space! The home boasts an unparalleled combination of function, elegance and aesthetics. Simply....more detailed, functional, and higher quality than typical Winter Park new construction. The prominent, timeless, and elegant features of this home's exterior are the first taste of the professional design and the experience continues once entering and touring this home and property. Please see floor plans included in photos and CLICK ON TOUR LINK FOR A COMPREHENSIVE VIDEO WALK THROUGH TOUR. Located in a great Winter Park location in the highly desirable Audubon K-8/Winter Park High School District. Minutes to DT Orlando, Baldwin Park, DT Winter Park, WP Park Ave. Shopping, Winter Park Village, Advent Health Village, Orlando Regional Medical Center, Lake Highland Prep., and more. One of Central Florida's most dynamic areas! You will not find a better opportunity to secure a recently completed, highly detailed, unique luxury home in the WP area that offers the feel, presentation, and function of 2814 Parkland Drive.

2814 Parkland Drive, Winter Park
$2,220,000
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Contemporary Lakefront Estate in Winter Park! Nestled along the serene shores of Lake Berry, this spacious single-story, 4-bedroom, 3-bathroom home offers a perfect blend of comfort and natural beauty. With expansive living spaces bathed in natural light, this home invites you to experience relaxed lakefront living at its finest. Offering over 2,600 sf of luxurious living space, the open-concept layout allows for an expansive great room with large sliding doors that frame breathtaking lake views and create an airy and inviting atmosphere. Recently updated to include enhanced finishes that compliment the homes modern aesthetic, the neutral tile floors, vaulted ceilings and glass tile fireplace reflect the home’s cool tones. A sophisticated kitchen with white cabinetry and granite counters is a chef’s dream with its large island and high-end Viking appliances and gas-range. An oversized primary suite overlooks the water and has a private en suite with a double-sink vanity, step-in shower, and walk-in closet. With a coveted split-bedroom layout, 3 guest bedrooms, each comfortably sized, and with ample closet space, and two full baths are located at the opposite side of the home. Step outside to your private oasis, where a sparkling pool awaits. The backyard is well-suited for enjoying Florida’s sunny weather year-round and for hosting gatherings with friends and family. The fenced yard keeps the backyard nice and private, while also providing unobstructed views of Lake Berry. A docks with covered boathouse and lift is perfect for storing a boat or wave runner or jet skis. Located within one of Winter Park’s quiet and charming neighborhoods, this home offers an incredible opportunity to live on one of Winter Park’s pristine waterways and is just a short distance to Park Avenue, Baldwin Park, Advent Health, Rollins College, and many other nearby businesses. Zoned for the Brookshire/Glendridge/WPHS school district and within 15 mins of Orlando’s top private schools. Don’t miss the opportunity to tour this home – schedule your showing today.

673 Balmoral Road, Winter Park
$1,810,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Experience modern luxury in this stunning custom-built residence by LunDev Custom Homes, positioned in the heart of Winter Park. Built in 2015, this contemporary home offers four bedrooms, 3.5 baths and 3,440 heated square feet, seamlessly blending elegant design with state-of-the-art smart home technology. The first-floor primary suite is a serene retreat featuring a spacious walk-in closet and a spa-like en-suite bath with dual sinks, a glass-enclosed shower, a separate soaking tub and a private water closet. The formal living room is highlighted by French doors opening to a beautifully designed side yard with low-maintenance artificial turf, creating an indoor-outdoor flow. At the heart of the home, the open-concept kitchen is a chef’s dream, boasting a large island that overlooks the dining and family rooms, ideal for everyday living and entertaining. A dramatic wall of glass doors seamlessly extends the living space to the covered lanai, complete with motorized screens for year-round enjoyment. Recent upgrades, including fresh interior and exterior paint, Philips Hue smart lighting, smart wall switches and new smart locks, enhance style and convenience. Step outside to your private resort-style oasis, where a sparkling pool, built-in gas grill, ceramic Coyote Asado smoker and pergola-covered seating area set the stage for unforgettable gatherings. An outdoor shower and a lush Vistafolia artificial green wall system, illuminated by Philips Hue backlighting, add to the ambiance. A covered walkway connects the home to a detached two-car garage, offering functionality and architectural charm. Upstairs, a versatile bonus room/loft with gym flooring provides endless possibilities, accompanied by three additional bedrooms, two featuring walk-in closets and one with dual closets and an en-suite bath. Additional enhancements include a Ring security system, a new pool filter and skimmer, and upgraded front yard landscaping, ensuring this home is move-in ready. Just minutes from downtown Winter Park’s Park Avenue, Baldwin Park Village Center, and premier dining and shopping, with easy access to downtown Orlando and Orlando International Airport, this residence offers the ideal balance of luxury, comfort and convenience. Don’t miss this opportunity and schedule your private showing today!

1970 Laurel Road, Winter Park
$3,600,000
4 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

851 Georgia Avenue, Winter Park
$2,594,550
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

254 Sylvan Boulevard, Winter Park
$2,910,000
4 Beds ⋅ 6 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code
Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

1911 Stonehurst Road, Winter Park
$1,395,000
Comstock Park SubDv. ⋅ 32789 Zip Code
AMAZING opportunity to build your new home in this phenomenal neighborhood! The existing home is a tear-down and the value of the property lies in the expansive 13,441 sf (.31 Acre) lot. With this tremendous 100 ft wide lot, the property affords any new buyer ample space to build their dream home. Plus, the locale is ideal...Tucked away on a charming, quiet brick street, the property is an easy stroll to Phelps Park and the Y. Plus, you are a short ride to Downtown Park Avenue's shops and restaurants. This is an opportunity not to be missed! SOLD AS-IS.

1560 Lakehurst Avenue, Winter Park
$3,200,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code
Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

1833 Loch Berry Road, Winter Park
$1,305,000
4 Beds ⋅ 4 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code
Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

1600 Barcelona Way, Winter Park
$1,850,000
5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code
This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

1627 Elizabeths Walk, Winter Park
$1,500,000
4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

1741 Pine Avenue, Winter Park
$1,800,000
4 Beds ⋅ 4 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

1682 Arbor Park Drive, Winter Park
$3,550,000
3 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code
This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

443 Lakewood Drive, Winter Park
$4,100,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park.  Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers.  The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out.  The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door.  Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges.  The landscaping is mature for a brand-new home!  Privacy abounds everywhere in this home.  Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel.  Disguised between the refrigerator and freezer is a secret hidden door to the scullery.  Exotic countertops abound throughout the house.  Quartzite like you have never seen before is evident in the kitchen and bar.  Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

1691 Chestnut Avenue, Winter Park
$4,500,000
6 Beds ⋅ 6 Baths ⋅ Killarney Point SubDv. ⋅ 32789 Zip Code
"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset.

2118 Lake Drive, Winter Park
$2,800,000
3 Beds ⋅ 4 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code
Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

315 E New England Avenue Unit 30, Winter Park
$5,400,000
5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park