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$2,390,000
4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy 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
$5,600,000
5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, 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
$2,150,000
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
$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
$625,000
3 Beds ⋅ 2 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Welcome to this BEAUTIFULLY MAINTAINED and thoughtfully upgraded 3-bedroom, 2-bath townhome in the exclusive Seville Park community of Winter Park, where timeless elegance, privacy, and exceptional craftsmanship come together in one truly special residence. Offering over 1,600 SQUARE FEET and originally built as the BUILDER'S OWN upgraded showcase unit, this home is nestled within an intimate enclave of just four townhomes and features the LARGEST ENCLOSED BACKYARD of the four. From the moment you arrive, the home makes a memorable impression with its GAS LANTERN LAMPPOST, charming walkway, and ELEGANT GLASS-PANEL FRONT DOOR. Step inside to discover soaring ceilings, crown molding, and rich wood flooring throughout, creating a warm yet elegant atmosphere filled with character and style. The Living Room is both inviting and dramatic, featuring a GAS FIREPLACE, oversized windows that flood the space with natural light, and French doors that open to the private outdoor patio and backyard retreat. The yard is enclosed by a IRON FENCE with GATED ENTRY, while MATURE BAMBOO lining the perimeter provides shade, privacy, and a tranquil ambiance rarely found in townhome living. The spacious Kitchen is a standout with 42-inch cabinetry, granite countertops, a HIGH-END THOR GAS RANGE, NEW WHIRLPOOL REFRIGERATOR, breakfast bar seating, and a closet pantry, combining luxury with functionality. The CHARMING DINING AREA adjacent to the Kitchen, is perfect for everyday dining and special occasions. A rare and highly desirable feature, the home offers a PRIMARY SUITE on the first floor, ideal for guests or multi-generational living, complete with its own en suite bath. Ascend the beautiful staircase accented with BRASS AND IRON RAILINGS to the impressive SECOND PRIMARY SUITE. This elegant retreat features a DRAMATIC BALCONY overlooking the Living Room below, a walk-in closet, and a spacious EN SUITE BATH with dual sinks, a garden tub, and a step-in shower. A third bedroom on the second floor offers its own unique charm with French doors opening to a PRIVATE ROOFTOP BALCONY—the perfect place to unwind and enjoy the peaceful surroundings. Additional upgrades include a NEW TILE ROOF (2022), touchscreen water heater, and RECENT REPIPING and REPLUMBING, offering both luxury and peace of mind. The 2-car garage includes BUILT-IN STORAGE CABINETS, and the driveway even features an extra dedicated parking space, an uncommon bonus in Winter Park. Located in one of Central Florida’s most sought-after areas, this home is zoned for TOP-RATED SCHOOLS and is JUST MINUTES from the boutiques, fine dining, and cultural attractions of Park Avenue and Hannibal Square. You’ll also enjoy CLOSE PROXIMITY to Rollins College, scenic parks, museums, farmers markets, and the renowned chain of lakes. With its designer upgrades, rare private outdoor space, elegant architectural details, and UNBEATABLE WINTER PARK LOCATION, this exceptional Seville Park townhome offers a lifestyle that is both refined and effortlessly inviting. Call and schedule your showing today!

962 Aragon Avenue, Winter Park
$892,500
3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!

1960 Winter Park 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
$475,000
3 Beds ⋅ 2 Baths ⋅ Town Of Winter Park SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated Winter Park bungalow, just steps from Hannibal Square and Park Avenue! This charming 3-bedroom, 2-bath home offers just over 1,100 square feet of thoughtfully renovated living space. The kitchen has been tastefully renovated and upgraded with modern appliances, while tile flooring runs throughout the entire home. Major updates include newer roof, fully replumbed system (completed this month), and a brand-new water heater—giving you true peace of mind. Inside, you’ll love the high ceilings in the living, dining, and kitchen areas, creating a bright and open feel. Large windows flood the home with natural Florida sunlight, and the private rear deck is perfect for relaxing or entertaining. This is a true move-in-ready home in one of Winter Park’s most desirable locations—schedule your showing today before it’s gone!

665 Lyman Avenue, Winter Park
$3,978,550
4 Beds ⋅ 5 Baths ⋅ Tuscania SubDv. ⋅ 32789 Zip Code
PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

2020 Via Tuscany, Winter Park
$625,090
3 Beds ⋅ 2 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart of Winter Park—lovingly cared for by the same owner for over 30 years. This home reflects true pride of ownership with thoughtful updates and improvements that provide both comfort and peace of mind. Enjoy entertaining in the spacious eat in kitchen with full Stainless appliance package. Outdoor living shines with an extended paver driveway and rear patio, screened lanai, and lush, mature landscaping—creating a private, relaxing retreat perfect for entertaining or everyday enjoyment. Major upgrades include energy-efficient double-pane windows and patio door (2014), HVAC system (2020), redesigned Primary Bath Shower, updated electrical panel with new breakers including surge protection (2024), Water Heater (2024), Roof (2022). The home has also been repiped features a replaced drain field and a recently serviced septic system (2025). Additional improvements include gutters with mesh guards (2019), vinyl fencing and garage door hardware updates (2025). Designed for worry-free living, this home includes a long-standing transferable termite bond and resilient fiber cement siding for enhanced durability and protection. Ideally situated in a desirable Winter Park corridor, this home offers effortless access to both downtown Winter Park and Orlando, as well as the vibrant amenities of Baldwin Park. Surrounded by properties ranging from $600,000 to multi-million-dollar estates, the location presents an exceptional opportunity to enjoy a premier lifestyle with strong long-term value. Residents benefit from zoning to highly regarded schools and proximity to Park Avenue, Rollins College, and an array of fine dining, shopping, and cultural destinations. With convenient access to major roadways, daily commuting and connectivity are seamless. Set within an established neighborhood characterized by a blend of long-time ownership and thoughtfully updated homes, the area continues to experience ongoing growth and enhancement. A rare opportunity to own a beautifully maintained home in one of Central Florida’s most desirable communities.

2713 Eastern Parkway, Winter Park
$2,699,000
4 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 02 43/71 SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

1529 Holts Grove Circle, Winter Park
$3,675,000
5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

150 Dana Way, Winter Park
$1,900,000
4 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Move-in ready and tucked into a desirable Winter Park setting, this home offers a rare blend of privacy, functionality, and elevated everyday living. For buyers relocating or purchasing a second home, this property eliminates the typical friction points of contractor timelines, uncertain updates, and drawn-out closings. Instead new homeowner gets a clean, turnkey experience in one of Winter Park’s most desirable areas. Inside, the heart of the home is a beautifully designed chef’s kitchen, built for both serious cooking and effortless entertaining, with high-end appliances, generous prep space, and seamless flow into the main living areas. The primary suite serves as a true retreat, featuring a spacious ensuite bath and a layout designed for comfort and quiet. Natural light, clean finishes, and intentional design choices throughout create a calm, polished environment that supports both relaxation and hosting. With both front and rear driveway access, the property provides a unique sense of separation and ease—ideal for discreet entry, guest flow, and a more flexible approach to daily life. Outdoor spaces are designed for privacy and ease, offering a more intimate setting without the demands of a larger property. Well-maintained and thoughtfully updated, the home allows for immediate enjoyment while still offering flexibility to personalize over time. Located just minutes from Winter Park’s dining, shopping, and top-rated schools, this property delivers a refined lifestyle with practical advantages of privacy, flexibility, and a layout that simply works. Easy to show, easy to love, easy to make your own!

1760 Alabama Drive, Winter Park
$669,000
4 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and upgraded flooring throughout. The gourmet open kitchen features solid cabinetry, a tile backsplash, NEW French Door Refrigerator and an oversized island that flows seamlessly into the inviting family room, highlighted by a stunning gas fireplace. Architectural details abound, including framed windows, 8-foot solid core doors, custom crown molding, and a triple set of French doors that enhance the home’s character and charm. The oversized primary suite is a true retreat, featuring a spa-like bath with an extra-large double vanity, walk-in closet, jetted tub, spacious shower with steamer, and a private covered Juliet balcony. A large downstairs office/study/den with French doors offers flexibility for work or additional living space. The pavered driveway leads to a detached, oversized 2-car garage with air conditioning and an insulated garage door. Outdoors, the backyard is a private oasis with brand-new vinyl fencing and a generous covered patio—perfect for relaxing or entertaining. Ideally located near Dubsdread Golf Course and just minutes from I-4, Winter Park, and College Park shopping, dining, and professional services, this home offers luxury, comfort, and convenience in one exceptional package. Fireplace has never been operated nor is a propane tank on site.

681 Overspin Drive, Winter Park
$13,000,000
6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code
Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park
$2,010,000
5 Beds ⋅ 3 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code
Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

1711 Barcelona Way, Winter Park
$369,900
3 Beds ⋅ 2 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code
MULTIPLE OFFER SITUATION - Welcome to this classic ranch home offering 3 bedrooms, 2 baths, and a wonderfully livable floor plan designed for everyday comfort, work-from-home flexibility, and easy entertaining. With 1,584 sqft of living space this home lives large and offers generous room sizes, plenty of storage, and a layout that simply makes sense. From the big front patio, step inside to a bright living area with cathedral ceilings and natural light, leading into an updated kitchen featuring granite countertops and newer cabinetry. Stacked bedroom layout, and the bathrooms feature tile finishes and oak cabinetry. Flooring includes tile throughout most of the home, wood laminate in the primary bedroom, and carpet in two bedrooms. The home also features updated double-pane insulated windows. Some of the highlights of this home are the expansive screened-in Florida room, perfect for relaxing, dining outdoors, or hosting friends —while enjoying fresh air. Outside, you'll find a huge, fully fenced backyard with mature oaks, palms, bananas, flowering cactus, and an aloe garden. There’s ample room for a pool, future expansion, and RV / trailer storage. A storage shed with electric adds even more convenience. The location truly can’t be beat — centrally located near downtown Winter Park, Maitland, Casselberry, restaurants, theaters, lakes, bike paths, museums, five golf courses, and endless shopping and recreation. Zoned for highly regarded schools including Dommerich Elementary, Maitland Middle, and Winter Park High, this is a setting many buyers specifically seek out. The neighborhood is on city utilities; this home currently uses septic which may not function properly and may need to be connected to city sewer which is already on the street. This is a conventional and cash-only sale and is being offered As-Is, with buyers responsible for their due diligence including verifying fees, taxes, and property details.

1816 Azalea Avenue, Winter Park
$1,150,000
4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Prime Location! Step into the charm of Old Winter Park in this uniquely designed one story, four bedroom, three bath home located off the Via’s in Lake Knowles Terrace. Built in 1951 and thoughtfully renovated in 1998, this home offers soaring ceilings, generous light from skylights, and a layout that embraces both privacy and togetherness. Enjoy two spacious en-suite bedrooms, ideal for multi-generational living or hosting guests. The open-concept living area flows into a large lanai with a cathedral ceiling and a screened-in lush garden courtyard featuring a fish pond, creating a seamless indoor-outdoor experience perfect for year-round entertaining. The lanai brings the total square footage of living space to over 3000 sf. Take in tranquil views of Lk Wilbar, nestled in a quiet, established neighborhood just a mile away from everything: Park Avenue shopping and dining, top-rated hospitals, the YMCA and two well known country clubs. This property of 9, 787 sf has endless opportunities to make it the perfect home for you and your family. Call to schedule a tour today!

1611 Walnut Avenue, Winter Park
$540,000
3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an inviting entrance courtyard that creates a sheltered transition into the home. Inside, the floor plan offers generous room sizes and excellent flow, beginning with a large foyer that opens to both the formal living room and the formal dining room. The 17’ x 12’ living room features a vaulted ceiling and large-format windows. The formal dining room is spacious and opens through sliding glass doors to a private side courtyard ideal for container gardening or quiet outdoor seating. The kitchen is sizable and well designed, with extensive counter space and abundant cabinetry, and offers convenient access to the side courtyard. The kitchen opens to the family room, allowing easy interaction between the two spaces, and extends into the Florida room beyond. The Florida room is one of the most charming areas of the home, with a brick façade along one wall, sliding glass doors, and views of the brick-covered and maturely landscaped backyard. This light-filled space is perfect for casual dining, a reading nook, or year-round indoor–outdoor living. The bedroom wing is thoughtfully spaced away from the main living areas. The primary suite is generously proportioned at roughly 21’ x 17’, with a vaulted ceiling, walk-in closet, and a spacious bathroom that includes a standalone tub, separate shower, long vanity with significant counter space, and a dedicated makeup area. Two additional bedrooms are comfortable in size with reach-in closets and share a full hallway bath with a long vanity and a tub-shower combination. Closet space and storage are abundant throughout the home, including hall storage, bedroom closets, built-ins, and a deep garage with workshop potential. Outdoor living is a highlight of the property. In addition to the front entrance courtyard and the private dining courtyard, the home features a lovely brick-paved backyard framed by mature landscaping, planting beds, and established greenery. The space is low-maintenance and provides multiple areas for seating, gardening, and relaxation. Recent updates include replacement of the electrical panels, which is set for final permit closing inspection; a 2017 HVAC; and a 2018 full home replumb. A current four-point inspection is available and will be updated to reflect the electrical panel replacement once the permit is closed. With its cul-de-sac location, elevated lot, multiple courtyards, flexible living areas, and desirable proximity to Park Avenue, Baldwin Park, the Cady Way Trail, the nearby dog park, and Downtown Orlando, the home enjoys an exceptional setting within a highly regarded Winter Park school zone. Meticulously maintained and built on excellent bones, it offers the uncommon opportunity to move right in or renovate with vision and create something extraordinary.

1817 Jessica Court, Winter Park
$2,000,000
3 Beds ⋅ 3 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code
Once closed, call LA for Effective sales price. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

1624 Barcelona Way, Winter Park
$2,500,000
3 Beds ⋅ 7 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code
Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private guest casita and a fully finished basement. Total area including outdoor spaces: 6,821 sq ft. The exterior showcases a stone façade, barrel-tile roof, wrought-iron detailing, and lush courtyards. A gated entry with outdoor fireplace leads to the guest casita with full bath, ideal for extended family, live-in support, or private office use. Inside, arched walkways, travertine floors, and soaring ceilings define the main level. The formal dining room, executive office, and great room flow seamlessly to the resort-style pool and lanai. The chef’s kitchen features dual Sub-Zero refrigerators, separate freezer, hidden walk-in pantry, Dacor 6-burner gas range, double ovens, Sharp drawer microwave, and built-in Miele coffee station. A butler’s hallway, half bath, and custom laundry suite add function and refinement. The primary suite on the main level features marble flooring, French doors to a private courtyard, a spa bath with soaking tub, dual-entry shower, and boutique-style custom closet. Upstairs offers two bedrooms, each with en-suite bath and custom closets, plus two open seating areas/lofts and a half bath. One suite opens to arched French doors overlooking the courtyard, stone architecture, and partial Lake Maitland views. The finished basement completes the 7 bonus rooms, providing flexible space for a home theater, gym, game room, or recreation lounge. Outdoor living includes a heated pool and spa, summer kitchen (installed 2021) with gas grill, beer tap, coolers, hibachi station, and a full cabana bath with accent shower on astro turf. Roof 2024. Three SEER 22 high-efficiency HVAC units (2020). Perfectly positioned on the Winter Park side of Lake Maitland within the renowned Chain of Lakes, Villa Toscana offers exceptional privacy and timeless appeal. This exclusive address places you just five minutes from Park Avenue’s fine dining, boutiques, and cultural attractions, while surrounded by some of Central Florida’s most distinguished waterfront estates. With access to the Winter Park Chain of Lakes, top-rated schools, and the charm of the city’s historic brick streets, Villa Toscana embodies the essence of refined Winter Park living.

1401 Green Cove Road, Winter Park
$1,475,000
4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code
Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane upstairs (2025) and fresh exterior and interior paint in the kitchen and bathroom. The updated kitchen features a butcher block island and new cabinetry hardware. Beautiful wine storage room to showcase your finest wines. The newly redesigned powder bath includes hidden storage and a full shower. The living areas are open and welcoming, highlighted by recessed ceilings in the informal living room with distinctive wood beams in the family room giving the home character. The primary suite features dual closets plus a linen closet, fresh paint, new mirrors, tv, lighting, and UV film on doors to keep the suite very cool and save on electrical. The nursery showcases new paint, custom wallpaper, drapes, and remote shades, basically every detail thoughtfully considered. Upstairs, a generous loft serves perfectly as a playroom, exercise room or home office, along with two ensuite bedrooms and a large AC storage room. Outdoor living is private and inviting, with a newly refinished PebbleTec pool finish, new pool coping, gas fireplace, new screen enclosure and professionally updated landscaping (2024). The backyard feels like a personal retreat -quiet, enclosed, and perfect for both relaxing and entertaining. Other features include new insulation (2024), custom aluminum privacy gates with locks, Wi-Fi-enabled Schlage front door lock, touchscreen garage access, Ring cameras, and new thermostats. Living in Windsong offers a sense of community, exclusivity with access to the Winter Park Chain of Lakes, pools, a kids water park area, and playgrounds. Pontoon boat available for residents use. Just minutes from Park Avenue’s shops and restaurants, Baldwin Park, and top-rated schools including Brookshire Elementary, Glenridge Middle, Winter Park High. Great location for private schools- Lake Highland Prep and Trinity Prep.

1408 Chapman Circle, Winter Park
$720,000
4 Beds ⋅ 3 Baths ⋅ Howell Forest SubDv. ⋅ 32789 Zip Code
Discover The Hills of Winter Park, a quiet, tree-lined community just minutes from Park Avenue. This beautifully updated single-family home offers 3,902 square feet of living space on a 0.20-acre lot. It features two spacious primary suites—one located upstairs with a vaulted shiplap ceiling, three walk-in closets, and a private balcony overlooking the pool and spa. The remodeled kitchen includes a 5’x10’ stone island, stainless steel appliances, a 42” Kenmore range, and opens to generous living and dining areas with a wood-burning fireplace. Additional highlights include a large recreation room with French doors leading to a screened lanai and private fenced backyard oasis, perfect for entertaining. Enjoy plenty of driveway and street parking, plus a dedicated area on the lot ideal for recreational storage—perfect for boats, trailers, or extra gear. While there is no garage, the home offers ample storage space throughout, including multiple walk-in closets and flexible indoor utility areas. Recent upgrades include a 2023 roof, indoor laundry room, and an American Home Shield warranty. A rare opportunity to live, work, and relax in the heart of Winter Park.

2955 Lolissa Lane, Winter Park
$2,250,000
4 Beds ⋅ 4 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
This spectacular Winter Park lakefront home is a very rare find indeed - exquisite inside and out! This home has been meticulously renovated and offers all the allure of fine lakefront living and is just minutes from Park Avenue’s shopping, dining and cultural gems. Situated on an oversized .39 acre lot this residence enjoys a picture-perfect setting with long views of Lake Killarney. Superior craftsmanship and attention to architectural detail emanate throughout the 3,749 SqFt of living space. This impressive property features an inspired layout starting with the exquisitely designed public spaces and continues throughout the rest of the home. The spacious owner’s retreat offers large windows overlooking the lake, customized walk-in closets, and just completed $60K bath renovation with a large walk-in shower, luxurious fixtures & finishes. There are 3 additional bedrooms: one with an ensuite bath and two with a shared bath. Additional amenities include a great room with floor to ceiling windows overlooking the lake, stacked stone gas fireplace, 26’ vaulted ceiling; gourmet kitchen with custom cabinetry, top-of-the-line stainless appliances, walk-in pantry. Other features include: built-in cabinetry, stone and hardwood flooring; whole house generator, solar panels pay for all the current electrical usage, 2 new HVAC systems, 4 wine cooler towers (600 Bottles) and an oversized two-car garage with EV charger, epoxy floor and storage cabinetry. Enjoy lakefront living under a 450 SqFt covered porch with a chef-inspired summer kitchen, electric shades, stacked stone wood burning fireplace, wet bar, epoxy flooring, tongue & groove ceiling and just steps away is a 275’ SqFt (Not Included in SqFt) air-conditioned boathouse with a coffered wood ceiling, covered boat dock, and deck.

600 Ololu Drive, Winter Park
$2,325,000
4 Beds ⋅ 4 Baths ⋅ Windsong Lookout Landing 43/79 SubDv. ⋅ 32789 Zip Code
Stunning custom residence in the highly sought-after Windsong community, built by Hal George of Parkland Homes and designed by architect Steve Feller. This one-owner home blends timeless architecture with exceptional craftsmanship and thoughtful design. From the moment you arrive, the storybook curb appeal is undeniable—brick exterior and driveway, lush landscaping, and charming gardens create a warm welcome. Inside, luxury finishes abound: herringbone wood floors, crown molding, cased openings with arched doorways, custom built-ins, and plantation shutters. The highly functional floor plan offers a downstairs owners’ suite plus a secondary bedroom (currently used as an office) with adjacent full bath. Upstairs, a spacious bonus room anchors two private bedroom suites. Soaring 10’ ceilings enhance the sense of space, with lots of natural light. The gourmet kitchen is a chef’s dream, featuring wood custom cabinetry, stainless steel appliances including a six-burner gas cooktop and Dacor double ovens, and an oversized island with sink. The kitchen flows seamlessly into the sunlit dining room with a dramatic vaulted 14’ beamed ceiling, comfortably seating 15. Set on a generous 0.38-acre lot, the outdoor living is equally impressive. The resort-style backyard showcases a covered patio with Pennsylvania Bluestone pavers, tongue-and-groove ceiling, and a charming detached garden house for storage. A serpentine wall winds gracefully through the landscaped grounds, offering privacy and charm. Additional highlights include an oversized two-car garage, indoor laundry with sink, and abundant storage throughout. A rare opportunity to own a meticulously maintained, beautifully appointed home in one of Winter Park’s most desirable communities.

1268 Preserve Point Drive, Winter Park
$312,500
1 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code
This beautifully updated 1-bedroom, 1-bath condo offers 823 sq. ft. of stylish living space in one of Central Florida’s most desirable neighborhoods. Located just steps from Park Avenue, you’ll be able to stroll to Winter Park’s best restaurants, boutique shops, and cafés—your new lifestyle is right outside your door. Inside, the open floor plan and soaring ceilings create a bright, spacious feel. Durable hard flooring throughout keeps things modern and low-maintenance, while the granite countertops and chic tile backsplash make the kitchen as functional as it is eye-catching. Step outside to your expansive private deck—perfect for entertaining, dining al fresco, or enjoying Florida sunshine in your own outdoor oasis. Since the unit is move-in ready, you can start living the Winter Park dream right away. Whether you’re a first-time buyer, an investor looking for a prime rental opportunity, someone seeking a low-maintenance lifestyle, or a snowbird wanting a lock-and-leave retreat, this condo checks every box. It is also just minutes from Rollins College, about 35 minutes to Disney, and only 30 minutes to Orlando International Airport (MCO). Convenience does not get much better. Homes this close to Park Avenue do not last long—schedule your showing today.

1308 S Pennsylvania Avenue Unit 3, Winter Park
$750,000
3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park’s Virginia Heights neighborhood, just steps from Park Avenue and Seven Oaks Park, this Mediterranean-inspired townhome-style condominium offers refined living with exceptional walkability. Featuring three bedrooms, two and a half baths, and nearly 2,000 square feet under air, this residence combines architectural elegance and everyday functionality. Inside, soaring ceilings and dramatic design elements, including arched hallways, column-lined corridors, and a custom wrought-iron spiral staircase, create a grand yet welcoming ambiance. The second-floor primary suite impresses with cathedral ceilings, dual walk-in closets and a luxurious spa bath with a jetted tub, multi-head rain shower, dual vanities, a makeup area and a private water closet. Two additional bedrooms, one with Juliet balcony, share a full bath and are thoughtfully separated from the primary. The main living area features travertine and luxury vinyl plank floors, coffered ceilings, designer lighting and an open-concept layout. The chef’s kitchen includes solid wood cabinetry, granite counters, a walk-in pantry and a central island with seating. French doors from the living and dining areas lead to a screened, private courtyard ideal for alfresco entertaining. Additional features include a powder bath, a two-car garage with mudroom entry, plantation shutters and ceiling fans throughout. A third-floor rooftop terrace offers a secluded outdoor escape, while an adjacent walk-in attic presents a flexible bonus room or future conditioned space. Casa Jardin recently completed a full exterior refresh, including a new roof and new paint. Residents enjoy exclusive access to Lake Virginia and the Winter Park Chain-of-Lakes via College Point, featuring a lakefront area along with kayak and paddleboard storage. Enjoy walkability to Azalea Park, the Winter Park Tennis Center, Orange Avenue’s restaurants and boutiques and top-rated schools. This is Winter Park lifestyle at its finest.

1278 S Pennsylvania Avenue Unit 13, Winter Park
$1,700,000
4 Beds ⋅ 3 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Don’t miss the opportunity to live in one of Winter Park’s most desirable neighborhoods. Nestled on a charming, tree-lined brick street, this meticulously updated 4-bedroom, 3-bath home exudes elegance and style, offering ample space for family comfort as well as areas to relax and entertain. This impressive property has been fully renovated and is truly move-in ready. From the moment you arrive, you'll be captivated by the charming exterior and lush landscaping on a spacious .32acre lot. Inside, you'll find a bright, sophisticated home featuring beautiful hardwood floors throughout, tons of windows accented with plantation shutters, and exquisite handcrafted details. The front family room features a wood-burning fireplace, creating a comfortable space for binge-watching Netflix or Sunday NFL games, unwinding with a good book, sharing wine with friends, or hosting elegant dinner parties in the dining area. The light and bright chef’s kitchen is a culinary dream that offers a generous layout with abundant wood cabinetry, gleaming granite and gorgeous wood countertops, a large prep island with seating for four, state-of-the-art Thermador stainless steel appliances including a 6-burner professional oven, and an inviting sitting nook, capped off by a dramatic cathedral ceiling and windows that overlook the lush back yard. On one side of the home are three generously sized bedrooms with ample closet space and two full bathrooms with gorgeous custom tile and flooring. On the other side of the home awaits a true retreat: the private Primary Suite, a sanctuary equipped with a spacious bedroom, sitting area, walk-in custom closet, and a luxurious spa-inspired bath with stunning porcelain tile flooring, a large dual sink vanity, an oversized walk-in shower, and a separate water closet. Step outside to experience the quintessential Florida lifestyle in the private backyard oasis, complete with a beautiful sparkling saltwater pool, a spacious patio, and professionally landscaped grounds — ideal for entertaining year-round. Additional features include a convenient laundry/mudroom with storage for backpacks and gear, abundant closet space, a water softener, and a two-car garage with storage cabinets and shelves. Improvements include updated electrical, plumbing, and ductwork, plus a brand new tile roof (2023). This remarkable property is located close to Winter Park’s renowned Park Avenue shopping, premier restaurants, the area’s top-rated schools, and also close to Interlachen Country Club and the Winter Park Racquet Club. This exceptional property won’t last. See for yourself why this gorgeous house should be the place you call home. Schedule your showing today.

1571 Lasbury Avenue, Winter Park