32789 Zip Code FL Real Estate, Homes with Pool for Sale

5 Beds ⋅ 4 Baths ⋅ Lugano Terrace SubDv. ⋅ 32789 Zip Code

Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park

$2,232,000

3 Beds ⋅ 4 Baths ⋅ Perle Du Lac SubDv. ⋅ 32789 Zip Code

Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered lakefront patio, where you can enjoy al fresco meals and admire your boat in its personal covered slip with electric lift. The spacious kitchen offers new cabinetry, under-cabinet lighting, hardwood countertops, and a farmhouse sink. Built-in appliances include a Sub-Zero® Refrigerator, a Wolfe® Gas Cooktop, Dacor® Ovens, and a Bosch® Dishwasher. From the kitchen, you have access to the sizable adjacent library, with its wall-to-wall bookcases. Configure it as your office or a family room if you wish. A wall of glass doors and windows makes the lake a focal point in your primary bedroom suite. The en-suite bathroom features a jacuzzi bathtub, walk-in shower, two separate vanities, and a secluded Toto®-equipped water closet. A large walk-in closet completes the suite. Two more spacious bedrooms are on the opposite end of the residence. One includes its own en-suite full bathroom. Both share an outdoor patio space. Additionally, you’ll find a third full bathroom and a powder bathroom. The laundry room includes a Miele® washing machine and dryer set. In the secured garage, you have two assigned parking spaces and a sizeable storage room. Perle du Lac residents enjoy exclusive community amenities, including a heated swimming pool, hot tub, beautifully maintained grounds, and double-gated security for peace of mind. All of this is minutes from Park Avenue, Rollins College, and everything that makes downtown Winter Park famous.

660 Osceola Avenue Unit 101, Winter Park

$6,111,000

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

Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.

1860 Summerland Avenue, 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

$1,589,000

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

Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history of Winter Park, and within true walking distance of Rollins College, Park Avenue, and all the lively bustle of downtown Winter Park. Better yet, enjoy deeded lake access from the neighborhood lakefront park just a 3-minute walk from your front door, where neighbors gather for social events, holiday parties, and relaxing lake views. With a sprawling green lawn, dock, kayak/canoe storage racks, and picnic tables, the perfect daily retreat is just steps away. The home is move-in ready and bursting with charm, with over 2800 SF of thoughtfully designed space for everyday living and entertaining. The ideal, split-bedroom floorplan includes 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace (piped for gas), dining room with a built-in lighted bar, large family room, and over 400 SF of covered lanai space overlooking the pool & backyard paradise. The oversized primary suite is truly special, with room for a sitting area, tons of built-in storage, and a mirrored barn door that opens to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large zero-entry marble shower, custom mahogany-topped vanity, maple board-and-batten walls, brass fixtures, and cypress vaulted ceilings, plus 2 walk-in closets and a third storage closet at the bedroom entrance. The sunny family room extends to the rear of the home, where French doors are equipped with retractable screen doors for enjoying the breeze indoors and out, in true Key-West style. Past the French doors, a travertine lanai stretches across the back of the home and overlooks a lagoon-style pool and travertine deck, with surrounding palms and lush tropical landscaping to create the perfect backyard oasis. The kitchen features Thermador appliances, with a gas cooktop and a brand new vent hood framed by a new marble backsplash, and new pendant lighting over the breakfast bar. Both secondary bedrooms have French doors that open to the covered lanai, and en-suite bathrooms. Other conveniences include a whole-house sound system with interior and exterior speakers, custom laundry room (renovated in 2021), and 2-car garage with built-in storage. Move-in ready, the home was completely replumbed in July 2025, with a new gas water heater, partial roof replacement (all new flat roof in Aug 2025), up-to-date electrical, and (2) recently serviced 2019 HVAC units with UV lights. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$3,390,000

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

Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen is a work of art, showcasing quartz countertops, exquisite custom cabinetry, integrated LED lighting, a Wolf appliance suite, and a charming breakfast nook. The formal dining room captivates, with stunning coffered ceilings floor to ceiling windows, and an atmosphere perfectly suited for elegant entertainment. The primary suite is a private sanctuary, offering dual vanities with floating mirrors, a freestanding soaking tub, a walk-in rain shower, and a spacious custom closet. Each additional bedroom has been thoughtfully designed with generous proportions and its own en-suite bath, blending comfort with sophistication. Upstairs, a loft and secondary laundry area provide convenience and versatility, while the main level includes a full mudroom and butler’s pantry with an additional washer and dryer, tailored for effortless living. The outdoor living space rivals the most luxurious resorts. A covered lanai with retractable screens seamlessly extends the interior’s sophistication outdoors, offering a year-round retreat for dining or lounging. The expansive pool deck unfolds around a sparkling pool and integrated spa, complemented by a dedicated pool bath connected to the detached garage. From the curved archways to the meticulous millwork and layered LED lighting throughout, every inch of this home reflects the builder’s attention to detail and commitment to craftsmanship. It is more than a home, it is a statement of style, presence, and precision in the heart of Winter Park’s most coveted location.

1751 Glencoe 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

$2,150,000

4 Beds ⋅ 4 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

2299 Via Tuscany, Winter Park

$2,175,000

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

This stunning LunDev-built pool home has been meticulously maintained and thoughtfully updated, blending timeless craftsmanship with modern style. The ideal floorplan features a first-floor primary suite, a private office, and an open kitchen and family room that flow effortlessly to the home’s exceptional outdoor living space. Outside, the spacious backyard is a private retreat complete with an oversized covered patio, gas firepit, and a fully equipped summer kitchen with a pizza oven, all surrounding a sparkling pool and heated spa. In 2022, the kitchen received a major renovation, showcasing a new island, updated countertops and backsplash, fresh fixtures and cabinet hardware, and elegant lighting that elevate the space. The primary bath renovation mirrors the same level of quality, with new custom vanities topped with quartz countertops, all-new tile, a glass-enclosed shower, a relaxing soaking tub, and classic lighting and mirrors. Additional improvements include a new roof (2021), newer hardwood floors throughout the 2nd floor, updated brick paver driveway, newer pool equipment, and fresh interior and exterior paint, each reflecting consistent care and attention to detail. Designed for both everyday comfort and effortless entertaining, this home is truly move-in ready and radiates pride of ownership inside and out.

2030 Versailles Avenue, Winter Park

$2,295,000

4 Beds ⋅ 6 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood. This residence combines timeless elegance with modern luxury, showcasing exceptional design and craftsmanship throughout. The thoughtfully designed home features a marble front façade and professional landscaping. Inside, you’ll find an open, bright layout with high ceilings, wide-plank white oak floors, oversized picture windows, and refined crown molding. A welcoming flex space—perfect as a sitting room or den—greets you at the entry, across from another room ideal for a private office. The great room, at the center of the home, offers 12-foot ceilings, a sleek fireplace, and a full wall of sliding glass doors that open to the resort-style backyard. Designed for both entertaining and daily living, the open-concept kitchen, dining, and living areas flow seamlessly together. The chef’s kitchen impresses with a striking waterfall island, premium Thermador appliances, a dual-fuel range with a 6-burner gas cooktop, a third oven plus convection microwave, and an expansive custom pantry. A stylish mudroom and decorative laundry room complete the main level’s amenities. The primary suite on the first floor features direct access to the pool, a spa-inspired bath with a soaking tub, multi-spray shower, dual sinks with a large vanity, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room connects to three additional bedroom suites, each with custom closets and ample storage. Outdoor living includes a saltwater pool with an elegant fountain feature, marble pavers, a summer kitchen with a built-in grill, sink, and beverage fridge, an outdoor bathroom, and a lush grassy area perfect for play or pets. Additional highlights include a two-car garage and zoning for top-rated schools—Lakemont Elementary, Maitland Middle, and Winter Park High. Walk to the Winter Park YMCA and Phelps Park, and enjoy being just minutes from vibrant downtown Winter Park. Elegant design, modern luxury, and a prime location—this exceptional new home offers the very best of Winter Park living.

1661 Palm Avenue, Winter Park

$1,050,000

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

Incredible opportunity to rebuild on this 95’ x 125’ prime Winter Park corner lot in Timberlane Shores. Surrounded by multi-million dollar homes, and across the street from Lake Virginia! This property will have lake views from the second story of your future new home! A+ location that will not last long!

620 Virginia Drive, Winter Park

$266,000

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

Beautifully updated and meticulously maintained. Improvements done in late 2020. Kitchen Ceiling raised and recessed lights installed, new Cabinets, Quart Counters, Stainless Steel Samsung Appliances including Counter-depth Refrigerator. Wall opened into Living Room and Breakfast Bar Installed. Updated Master Bath includes new Vanity, Mirror and Lights, Commode and beautiful new Shower, Barn Door installed for Privacy. Guest Bath also updated. Luxury Vinyl and Bathroom Tiles replaced throughout. New Double Paned Windows and Sliding Door, 6" Floor Moldings, Knock-down Ceilings and Decorator Paint. A/C and water Heater done with rest of updates. This 2 Bedroom 2 bath End Unit is centrally located in Lakefront Community with covered Patio in private Courtyard! Enjoy Sunsets on Lakefront Deck, Private Lakefront Ramp Access to skiable Lake Killarney, Heated Pool, Saunas and walking access to Shops, Restaurants, Movies and short distance to Park Avenue, Farmers Market and Downtown Art Festivals. Don't miss seeing this "little bit of heaven"! Call today for private viewing!

1500 Gay Road Unit 9B, Winter Park

$5,700,000

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

374 Henkel Circle, Winter Park

$1,100,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this two-bedroom, two-bath residence now reflects a highly customized living experience. Every surface, system and layout choice has been elevated, beginning with level 5 smooth drywall, Emtek polished nickel hardware, custom millwork, full-height solid-core doors and Panaget engineered hardwood flooring. Lutron lighting systems control dimmable LED lighting throughout. Bedrooms, as well as the family room, include prewiring for additional fixtures, and the primary suite features dedicated pendants over each nightstand, independently controlled bedside. The kitchen is anchored by a full suite of smart Thermador appliances, including an induction range, range hood and a full-height refrigerator with a convertible Flex drawer for additional refrigeration or freezer storage, an internal water dispenser, built-in compartment cameras and Thermador’s signature Diamond ice maker. Calacatta Laza quartz surfaces and full-height backsplash accentuate custom oak cabinetry featuring soft-close drawers, an integrated appliance station with interior outlets, and an oversized pantry for seamless storage. A breakfast bar opens to the dining and living areas, which comfortably accommodate full-size furnishings and create defined spaces for formal dining, casual living and media use. The primary suite offers two built-in closets and a spa-inspired bath with Fantasy Brown quartz countertops on a wall-to-wall vanity. A lighted medicine cabinet mirror with integrated speakers sits above the vanity, with interior power outlets for charging accessories. A fully tiled frameless shower features a lighted accent wall, overhead rain shower and wall-mounted handheld options. Additional built-in cabinetry provides deep storage for linens and supplies, as well as a dedicated laundry storage closet. The second bedroom functions as a guest suite, supported by a beautifully appointed bath in matching design. Additional highlights include custom-trimmed window casings throughout, ready for shades or shutters, and an entry closet that can double as storage or pantry overflow. The residence includes assigned covered parking and private storage. Residents of The Cloisters enjoy an amenity-rich lifestyle with on-site management, access to a heated pool, two fitness rooms with saunas, a clubhouse and manicured lakefront park space. This turnkey optional offering places you at the heart of Winter Park’s cultural, dining and retail corridor, where enduring architectural character meets elevated, modern living.

100 S Interlachen Avenue Unit 415, Winter Park

$162,000

1 Beds ⋅ 1 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Come take a lovely stroll to Mead Gardens(47 acres), located just around the corner from this adorable condo in one of Winter Park’s most popular communities! The pool is located directly behind this condo! This cozy first-floor unit features brand-new luxury vinyl flooring that gives it a fresh, welcoming feel. The spacious living room has sliders that open up to a nice-sized screened-in Florida room—perfect for sipping your morning coffee or relaxing at the end of the day and the best part the pool is located directly behind your Florida room! With the large Florida palm tree as a reference point you can see how close to the pool this condo is! After you enjoy taking a hike around Mead Gardens- then come home to a nice swim in the pool! And here’s some exciting news: the seller is offering seller financing! That means the deed will be in your name, and with just 20% down and flexible terms, it’s an incredible chance for first-time buyers, or to add to your rental portfolio, or anyone looking for a sweet second home. If you've been dreaming of having a Winter Park address, this is your moment! You’ll absolutely love the fantastic location of this condo, and let’s not forget this condo is located less than 2 miles to Advent Health hospital, the Orlando Science center, shopping, restaurants and all that Winter Park has to offer! Don’t miss out on this wonderful investment opportunity. Show and Sell!!

1250 S Denning #122 Street Unit 00122, Winter Park

$1,500,000

4 Beds ⋅ 5 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code

Just Reduced $100,000 below appraised value!!!!! Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy luxury living in this impeccably maintained home. This beauty offers three spacious bedrooms and three beautifully appointed baths in the main house and a 1bed/1bth studio apt above the garage. Enter the spacious floorplan featuring open living and dining areas separated by a gorgeous double sided fireplace. The kitchen is a chef's dream with updated appliances and stunning marble countertops complete with lots of storage and work space. The living room features a panel of french doors overlooking the professionally landscaped and pavered back yard complete with a large resort style pool and soothing heated spa. Enjoy your morning coffee and your favorite afternoon beverage on the pavered lanai featuring remote control exterior shades. A half pool bath is part of this amazing landscape. The 2+car detached garage features an upstairs studio apartment perfect for guests, a home office or rental income. It is complete with a kitchenette, large bathroom and washer/dryer. The large master bedroom boasts two walk in closets, open step in shower, a double vanitiy and water closet . Lots of natural light, too!! Enjoy the guest room complete with an en-suite bath and, of course, the 3rd bedroom is perfect for family. Your paradise is only 2 miles from Park Avenue known and loved by so many for it's art galleries, restaurants, upscale shopping and parks. Top rated medical facilities within a short distance. This is lifestyle living at it's finest !

132 Burks Circle, Winter Park

$6,495,000

5 Beds ⋅ 7 Baths ⋅ Osceola Place SubDv. ⋅ 32789 Zip Code

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, 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

$1,399,500

4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

NEW PRICE — NOW $1,399,500 — THE BEST DEAL IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

607 Ellen Drive, Winter Park

$4,720,000

5 Beds ⋅ 6 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code

*Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

1302 Raintree Place, Winter Park

$586,000

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

RARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS – FULLY FURNISHED AND IN THE HEART OF WINTER PARK! Discover the perfect blend of comfort, style, and unbeatable location! This beautifully maintained 2-bedroom, 2-bath corner unit sits on the top floor of the desirable Villages of Winterset, offering expansive views and abundant natural light throughout. Enjoy the convenience of two elevators, a private storage unit on the same floor, and on-site laundry just steps from your door. Your assigned covered parking keeps your car cool and protected, and the secured mid-rise building features key access, a call box for guests, and a welcoming lobby lounge. Step outside and you’re just a short walk to everything that makes Winter Park special — Park Avenue’s boutique shops and restaurants, Rollins College, the Morse Museum, Winter Park Golf Course, and the SunRail station. Central Park is right there for art festivals, concerts, and weekend strolls! Relax at home by the sparkling community pool, enjoy the sun deck or BBQ area, and soak in the charm of one of Winter Park’s most beloved communities. Winterset is owner-occupied only, where rentals and pets are not permitted ensuring peace, privacy, and pride of ownership all around. Come see why homes at Winterset rarely hit the market — and fall in love with your new Winter Park lifestyle!

265 E Canton Avenue Unit GE, Winter Park

$105,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park lifestyle.

1695 Lee Road Unit C214, Winter Park

$1,850,000

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

Welcome home to 1612 Magnolia Avenue. Built by the renowned custom home builder Lundev, this beautifully crafted transitional residence blends thoughtful design with luxurious comfort. From its striking exterior to the serene backyard oasis, every detail is designed to impress even the most discerning buyer. Upon entry, a dedicated office sits just off the foyer with custom floor-to-ceiling cabinetry and dual workstations, perfect for working from home. Across the hall, the formal dining room offers an elegant setting for entertaining and connects to the kitchen through a temperature-controlled wine cellar with storage for more than 400 bottles. The chef’s kitchen is a culinary dream featuring top-of-the-line appliances, a spacious island ideal for food preparation and presentation, and an open concept that flows seamlessly into the family room. A cozy gas fireplace anchors the family room, which opens through French doors to the covered lanai. Enjoy year-round outdoor living with a fully equipped summer kitchen that includes a grill, Green Egg BBQ, refrigerator, and wraparound counter space for hosting while overlooking the sparkling pool. The backyard is a private sanctuary complete with a luxurious pool and a large cabana with a wood-burning fireplace. The first-floor primary suite offers peaceful views of the backyard and a spa-like bath with dual sinks, a soaking tub, and a separate shower leading to an oversized walk-in closet with built-in storage. A mudroom, laundry room, powder bath, and convenient pool bath complete the well-planned first floor. Upstairs, three additional bedrooms provide ample space for family or guests. Two bedrooms share a Jack and Jill bath, while the third enjoys its own private en suite. This home has been extensively upgraded, combining comfort, sophistication, and modern convenience. Ideally located on a tree-lined street in one of Winter Park’s most desirable neighborhoods, it is minutes from the Winter Park Racquet Club, Park Avenue’s shopping and dining, YMCA, top-rated hospitals, and excellent public and private schools. Do not miss this rare opportunity to own a home that truly has it all. Welcome to the best of Winter Park living.

1612 Magnolia Avenue, Winter Park

$1,650,000

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

Nestled on a magnificent oversized lot in the heart of Winter Park, this 4-bedroom, 3-bath home offers plenty of space and opportunity. The backyard is a true highlight, featuring a large swimming pool and additional green space tucked just beyond the back hedges, adding a sense of privacy and flexibility for the outdoor area. Inside, the home showcases hardwood floors that flow throughout the living room, dining room, kitchen, family room, and bedrooms, creating a warm and inviting feel. A spacious family room with a cozy fireplace serves as the centerpiece of the home, while French doors open onto a vaulted screened porch, perfect for unwinding or entertaining with a view of the backyard. The kitchen offers stone countertops, and recent updates to the electrical, plumbing, and roof provide peace of mind for the next owner. This property is ideal for someone looking to renovate or update to their personal taste, or even to build a new home on this generous lot. Its location is hard to beat, set on a nice and quiet Winter Park street close to Park Avenue’s shops and dining, Rollins College, top-rated schools, and the area’s many lakes and parks. It’s a wonderful investment in both lifestyle and location.

1915 Stonehurst Road, Winter Park

$1,599,900

5 Beds ⋅ 5 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

1510 Miller Avenue, Winter Park

$195,000

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

Located in the historic Winter Park Gardens community, this condo has been meticulously maintained and updated. Featuring an open and inviting layout that flows seamlessly into a spacious living room, ideal for entertaining or relaxing.The kitchen boasts modern appliances, ample cabinetry, and plenty of counter space. The expansive sunroom serves as your personal oasis, overlooking the courtyard pond and lush gardens—perfect for morning coffee or evening unwinding with stunning floor-to-ceiling views. The spacious primary bedroom serves as a tranquil retreat, complemented by a full bathroom. Move-in ready with a renovated kitchen, bathroom, and new air conditioner. As part of the vibrant 55+ Winter Park Gardens community, you'll enjoy resort-like amenities including a community pool, walking paths, a courtyard with a pond and beautifully landscaped grounds. This condominium embodies refined, low-maintenance living with the HOA covering essentials like water, trash, pool upkeep, and common areas, allowing you to focus on what matters most—enjoying life. Just a short walk to the iconic Park Avenue with its world-class restaurants, boutique shops, and entertainment; Rollins College; Mead Botanical Garden for nature lovers; and downtown Winter Park. Easy access to I-4, and Orlando International Airport (13.7 miles).

700 Melrose Avenue Unit D21, Winter Park

$8,950,000

7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$1,900,000

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

Nestled in coveted Winter Park’s Sevilla neighborhood, this 4-bed, 4.5-bath pool home delivers 3,500+ SF of refined living including 500 SF upstairs flex suite with its own full bath. A traditional foyer introduces formal living and dining rooms before the home unfolds into a spectacular 2022-renovated chef’s kitchen—an airy showpiece anchored by a 10-ft quartz island with bar seating, custom cabinetry, designer appliances, including a Thermidor side-by-side paneled refrigerator, Thermidor gas range & hood, and a Scotsman ice maker. The main hallway leads to the re-imagined primary retreat: spa-inspired bath with double vanities, oversized walk-in shower, soaking tub, dressing table, and custom closet. Two additional guest bedrooms share a refreshed full shower bath, while a separate en-suite—ideal for in-laws or overnight guests—enjoys direct access to the pool off the kitchen hall. Upstairs, a large bonus room with full bath adapts effortlessly to a 5th bedroom, media space, or private office. A utility-minded laundry/mud room links the interior to an oversized side-entry garage. Out back, entertain year-round beneath a covered lanai overlooking the expansive pool and sun deck. Mature oak canopy, manicured shrubs, and full privacy fencing create a park-like sanctuary just blocks from Park Avenue dining and the back gate to Mead Botanical Garden. Audubon K-8 and Winter Park High School District.

319 Santiago 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

$259,500

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

Under contract-accepting backup offers. ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS! Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door for Privacy. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Private Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!

1500 Gay Road Unit 24B, Winter Park

$220,000

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

Beautiful 1-Bedroom Condo in the Heart of Winter Park Located on the second floor close to ELEVATORS. Please click on virtual tour to get an over view of this exceptional community. This is stunning one-bedroom condo featuring beautiful wood floors, an updated kitchen with wood cabinetry, solid surface counter tops, and a tankless water heater. The remodeled bathroom boasts a spacious walk-in shower, offering both comfort and style. Located in a prime Winter Park location, this home right by Rollins College, Park Avenue, and scenic parks—offering true walkability to all to shopping, dining, and recreation Winter Park has. Nestled in a gorgeous, well-maintained complex spanning over 8 acres of lush, manicured gardens, residents enjoy serene lighted walking paths and a tranquil pool—perfect for relaxation and outdoor enjoyment. Don’t miss this opportunity to live in one of Winter Park’s most desirable communities! This is a 55+ community with room for younger owners.

700 Melrose Avenue Unit J 23, Winter Park

$2,835,000

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

An incredible Winter Park Chain-of-Lakes opportunity on Lake Virginia with clear views of Rollins College. This transitionally designed home, situated in the highly coveted Virginia Heights, offers an opportunity like no other with proximity to Park Avenue coupled with the lakefront amenities through a Venetian canal system that uniquely connects five lakes and captures the quintessential Winter Park lifestyle. This four-bedroom three-and-a-half-bath home invites you into a two-story foyer surrounded by windows and natural light. The spacious kitchen features a mid-century tile backsplash, light cabinetry and a window out to the pool and lake. The main living space features a beautiful fireplace and back atrium that invites the stars and twinkling sunsets from the water. The separate dining room is spacious and there is an additional den or office space to round out the first floor. All bedrooms are upstairs and generously sized providing flexibility and the primary bedroom has the most incredible lakefront views. A clear water canal runs alongside the home and spills into lake Virginia adding to the ambiance of the backyard where nature abounds. Continue the existing renovation with your own style or build a house of your dreams. Impeccably located with shopping and dining at your fingertips as well as Rollins College. Fantastic schools with Audubon K-8 and Winter Park High. Don’t miss this one – call for your private tour.

255 Stirling Avenue, Winter Park

$3,650,000

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

Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

207 E Kings Way, Winter Park

$2,155,000

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

Sold New Construction -- Data entry

2915 Parkland Drive, Winter Park

$1,860,000

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

Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of upgrades completed in 2025. The home sits on a 1/3-acre lot with 5 bedrooms and 3 ½ baths plus an office and features a 4-way split plan with privacy for all. Upon entering, you're greeted by an open floor plan with marble foyer and white oak engineered wood flooring. The Owners' Retreat is a true sanctuary, featuring newly sanded and smoothed walls with luxe finish, automatic Hunter Douglas shades and an artful chandelier. The brand-new spa-inspired bathroom (2025) showcases the best in design and function which includes Kohler Bask heated surface tub, private toilet room with heated seat, auto lid and integrated bidet. The primary bath also has a new expanded shower, a new double sink vanity and Kohler champagne brass fixtures. The Family/Gathering space with an open chef's kitchen includes a stainless gas range, French door refrigerator, waterfall Quartzite counters and touchless kitchen and bar champagne faucets. The great room has a modern electric fireplace and leads to a screened porch and overlooks the salt water pool and large fenced backyard. Black metal remote controlled gate leads to the large 2 car detached garage with a side entry for grocery and package drop off. Home has updated cameras and security with touch screen keypad. Smart home technology Lutron lighting to schedule and control lights with mobile or Google home. Redesigned Laundry and 1/2 bath with beautiful designer wallpaper and tile and Samsung washer/dryer integrated single unit. Ideally located in one of Winter Park's coveted neighborhoods, with easy access to Park Av, Phelps Park, YMCA and Rollins College. Excellent schools, Lakemont Elem, Maitland Middle and Winter Park High. This is a rare offering of a newer one-story home, that is move in ready in the heart of Winter Park. A Must See!

1540 Palm Avenue, Winter Park

$1,300,000

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

For data entry only.

857 Brock Street, Winter Park

$3,235,000

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

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

1821 Englewood Road, 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

$260,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Fully renovated two-bedroom, two-bath residence in the sought-after Mead Garden Condominium community. Spanning 908 square feet, this second-floor home offers a move-in-ready interior with a contemporary open-concept layout and elevated finishes throughout. The kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, a touchless faucet, and a peninsula island with a breakfast bar. Additional cabinetry beneath the bar provides thoughtful storage. A designated dining space sits between the kitchen and living area, ideal for everyday meals or entertaining. The living room opens to an enclosed sunroom overlooking one of the community’s landscaped courtyards, offering a quiet, natural view. Both bedrooms include ceiling fans and mirrored closet doors, and the second bedroom provides direct access to the front porch through sliding glass doors. The primary suite features a courtyard-facing window and an en-suite bath with a glass-enclosed shower. The second full bath, accessible from the hallway, includes a soaking tub with a shower surround. Both baths are outfitted with anti-fog, lighted vanity mirrors and modern tile finishes. Other upgrades include all-new flooring, recessed lighting, updated plumbing fixtures, and fresh interior paint. Ideally located just blocks from Azalea Park, the new Seven Oaks Park, Mead Botanical Garden, and the Orange Avenue district’s dining and retail. Close proximity to Rollins College and Park Avenue.

1250 S Denning Drive Unit 213, Winter Park

$3,200,000

5 Beds ⋅ 7 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

This stunning modern farmhouse residence, custom-built in 2021 with meticulous attention to detail offers a bright open living design, luxurious finishes, and an ideal floor plan for everyday living and grand-scale entertaining. This home includes five en-suite bedrooms (owner’s suite and potential guest suite on first level) and three bedrooms, plus lounge/flex area upstairs… or a fourth bedroom, office plus lounge/flex area and five full baths plus 2 1/2 baths. The entire property has been maintained in better than new condition featuring gorgeous light wood flooring that transcends the entire home with elegant herringbone design throughout the entry foyer. The open-concept layout is flooded with natural light thanks to walls of sliding glass doors, including a disappearing wall that seamlessly connects the indoor living spaces with the incredible outdoor transitional lanai that is really cool to enjoy outdoor living and has its mini-split air conditioning system. The chef’s kitchen is a showstopper, featuring top-of-the-line appliances, a large island with seating, integrated refrigeration, wine refrigerator and a hidden butler’s pantry with an additional refrigerator—all open to the spacious dining and living areas. The living room showcases floor-to-ceiling windows, a striking fireplace with built-ins, and tranquil views of the beautifully landscaped yard and pool. The private first-floor primary suite features direct access to the backyard and a spa-like bath with a soaking tub and oversized glass shower. A second first-floor bedroom suite, used as an office, provides versatility for guests or multi-generational living. Upstairs, there is a spacious lounge area and three additional bedrooms with en suites, all featuring walk-in closets. The outdoor lanai offers a summer kitchen, gas fireplace and remote-controlled screens under soaring wood ceilings, creating a year-round gathering space. Complemented by a resort-style pool and heated spa surrounded by lush tropical landscaping and manicured bamboo for total privacy. Additional highlights include a drop off/mudroom zone off the two-car garage, a generous laundry room, and an ideal location on a charming brick street just minutes from Park Avenue’s shops and restaurants. Zoned for top-rated public schools and near elite private schools, with easy access to Phelps Park, YMCA, ICC, WPRC and Park Avenue—this exceptional home checks every box!

1610 Oakhurst Avenue, Winter Park

$1,030,000

4 Beds ⋅ 2 Baths ⋅ Hills SubDv. ⋅ 32789 Zip Code

Built by Charles Clayton a renowned builder in Winter Park, this beautifully updated 4-bedroom, 2-bath home is nestled in a peaceful, secluded neighborhood on a spacious corner lot, offering the perfect blend of quality craftsmanship, comfort, and location. Inside, you'll find an open floor plan filled with natural light — ideal for everyday living and entertaining. The modern kitchen flows seamlessly into generous living and dining spaces, creating a warm, inviting atmosphere for family and guests alike. Elegant French doors open to the expansive screened-in patio and pool area, extending your living space into the outdoors. Step outside to your own private tropical retreat. The expansive 84-foot screened-in pool and patio area features over 700 Sq Ft of covered outdoor dining area, a covered outdoor living area, and an additional open-air dining space under the screened enclosure — perfect for everything from morning coffee to evening gatherings. Surrounded by tropical lush landscaping, the pool and patio offer a peaceful, private escape designed for relaxation and entertaining. Additional highlights include: • Close to Park Avenue’s shopping, dining, and culture • Zoned for top-rated, excellent schools • Quiet, walkable neighborhood with a strong sense of privacy This exceptional Clayton Builders home offers timeless design, modern updates, and a tranquil outdoor setting — all in one of the area's most desirable locations. Don’t miss your chance to make it yours.

1611 Tioga Trail, Winter Park

$5,250,000

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

Welcome to Via Palma. This exceptional estate in the heart of the Winter Park Vias has been completely transformed, boasting over $800,000 in luxurious upgrades. A gracious entry foyer sets the tone with marble floors, custom trim work and direct views of the resort-style backyard. The first floor offers elegant formal living and dining spaces, a private study with fireplace, and a spectacular chef’s kitchen featuring an oversized marble island, custom cabinetry, Miele and Sub-Zero appliances, dual dishwashers, a built-in coffee bar, and an adjacent serving bar. The great room showcases custom built-ins, designer lighting, and seamless indoor-outdoor flow to the covered lanai, summer kitchen, lounge space, and saltwater pool. The luxurious first-floor primary suite is a serene retreat with dual dressing rooms and a lavish marble bath featuring a zero-entry double shower, freestanding soaking tub, private laundry room and designer lighting. Upstairs, additional bedrooms each feature en-suite baths and walk-in closets, complemented by a large family room, media lounge and gym with professional flooring. Every detail has been elevated, from European oak and Italian marble floors to Lutron lighting, Sonos audio, Control4 automation, Emtek smart hardware, Nest thermostats, high-efficiency HVAC systems and a backup generator. Outdoor spaces are fully reimagined with a lush landscape design, travertine decking, a putting green and privacy hedging. Near the Winter Park Racquet Club, Kraft Azalea Park, Interlachen Country Club, Phelps Park and YMCA, this home offers a rare opportunity to own a better-than-new custom estate in one of Central Florida’s desirable neighborhoods.

1155 Woodmere Drive, Winter Park

$840,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

100 S Interlachen Avenue Unit 503, Winter Park

$5,125,000

5 Beds ⋅ 6 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

1240 Harding Street, Winter Park

$1,095,000

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

Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers three bedrooms, three and a half bathrooms, and just under 2,000 square feet of beautifully finished living space framed by mature magnolias and manicured hedges. A brick driveway leads to a two-car garage with carriage-style doors, while a covered entry showcases a solid arched wood front door with classic peep hole, setting the tone for the craftsmanship inside. Step through the entry and discover a hidden laundry room with dark wood cabinetry, marble countertops, subway tile backsplash, and front-loading washer and dryer, along with a sophisticated powder bath featuring a floating marble-topped sink, wall-mounted chrome faucet, integrated mirror lighting, and detailed molding. Just beyond is a flexible room that functions as a dining room or formal living space, and through the next doorway the home opens to a large kitchen and great room designed for everyday living and entertaining. The kitchen combines dark wood perimeter cabinetry with accent glass fronts, a creamy white island with storage on both sides, marble countertops, and stainless appliances including a GE Monogram gas cooktop with vent hood, convection oven, refrigerator, dishwasher, and LG under-counter microwave, all anchored by a deep single-barrel undermount sink with extendable faucet. The great room features a gas fireplace with mosaic tile surround, clerestory windows, extensive crown molding, and hardwood floors, with new Anderson French doors that open to the private backyard where brick decking frames a cocktail pool with water features by Signature Landscape, surrounded by mature greenery and magnolias. The primary suite, tucked on the back right wing, also enjoys French doors to the pool terrace and includes new carpet, a customized floor-to-ceiling walk-in closet, and a bath with travertine floors, sunken glass-enclosed shower with built-in shelving, creamy white vanity topped with marble, satin nickel fixtures, dual Kohler undermount sinks, and mirrored walls with crown molding. Upstairs, two spacious bedrooms each feature ensuite baths and customized closets—the front with a built-in desk, marble chicklet tile flooring, creamy cabinetry, and tub/shower combo, the second with a walk-in closet and a bath finished with travertine flooring, a slightly larger vanity with consistent cream cabinetry, marble top, and glass-enclosed shower. Additional highlights include hidden storage under the stairs, unique iron stair railing, 8’ solid wood interior doors, 10’ ceilings, and block construction, while recent updates such as an Italian tile roof (2020), newer garage door and opener, and new HVAC air handler provide peace of mind. Just a short walk to the YMCA, Phelps Park, and Interlachen Country Club, 1450 Chestnut Avenue combines Mediterranean charm, thoughtful updates, and a sought-after Winter Park location for a lock and leave lifestyle with ease.

1450 Chestnut Avenue, Winter Park

$1,600,000

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

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded with natural light from strategically placed skylights. Rich hardwood floors flow throughout, while French doors create seamless indoor-outdoor living. The dramatic great room captivates with distinctive brick flooring, copper-coated ceiling tiles, and an old-fashioned built-in bar—perfect for entertaining. The generously proportioned primary suite features an en suite with double sink vanity and walk-in shower. Two additional well-appointed bedrooms, each with full baths, provide comfort and privacy for the family and guests. The heart of the home centers on an expansive gourmet kitchen boasting dual sinks, premium stainless-steel appliances, solid wood cabinetry, and distinctive decorative tile countertops. A dedicated home office provides the perfect work-from-home sanctuary. Two inviting fireplaces create cozy gathering spaces throughout. The covered patio with ceiling fans extends living space outdoors, while the screened pool area offers private resort-style relaxation. The tile roof crowns this impressive estate with both beauty and durability. Whether you envision a stunning renovation showcasing the home's exceptional bones or a complete rebuild taking advantage of the prime waterfront location, this property represents a once-in-a-lifetime opportunity to create your Winter Park masterpiece.

825 Palmer Avenue, Winter Park

$1,475,000

5 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Welcome to this updated and architecturally unique 5-bedroom, 3.5-bathroom custom home, offering 3,292 square feet of luxury living in the heart of Winter Park. Step inside and you’re immediately greeted by gleaming porcelain tile floors, smooth modern non-textured walls, and soaring ceilings that create a light and airy feel. The spacious living room features custom wall details, crown molding, an elegant wine cellar with glass wall, and expansive high windows that flood the home with natural light. Glass accents continue throughout with an updated staircase and second-level glass wall, adding a sleek, modern touch. To the left, discover a rare double-primary suite layout. A converted study now serves as a second primary bedroom, connected by a hallway with two walk-in closets. The shared spa-style primary bath includes dual vanities, a hot tub, and a glass shower. The suite on the west side enjoys private access to the pool area. Both bedrooms have tray ceilings with crown molding. The open dining area flows seamlessly into the kitchen, which showcases a natural gas range with pot filler, a large island with seating, pendant lights, granite counters, stainless steel appliances, and a unique indoor-outdoor service window that opens to the summer kitchen. The first floor is completed with a third bedroom (currently used as a home office), a full bath, and a laundry room. Ascend the glass-accented staircase to the second floor, where you’ll find a versatile dining/bonus room with porcelain tile flooring and tray ceiling, a kitchenette and a balcony overlooking the pool. Two additional bedrooms, a full bathroom, and a spacious storage closet complete the upstairs. The outdoor space has been completely reimagined for entertainment and relaxation. Enjoy a heated pool and spa with water features and stonework, outdoor shower, summer kitchen with bar seating, pergola, artificial turf, and plenty of yard space. The backyard is fully fenced and includes a storage building with a half bath. A whole-home 24kW Generac generator provides peace of mind. Additional highlights include a two-car garage, a carport for extra parking, and a prime location just minutes from Park Avenue’s upscale shopping and dining, Whole Foods, and easy access to major highways. This exceptional Winter Park home blends custom design, modern updates, and outdoor luxury. Schedule your private tour today.

1453 Lyndale Boulevard, Winter Park

$4,150,000

4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Coffered ceilings and recessed WAC lighting create a gallery-like ambiance, enhanced by natural light from insulated casement windows. The central living space integrates with the dining area and designer kitchen, which features custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite surfaces, and chef-grade appliances: a La Cornue 43-inch gas range with McGurken hood, Thermador 30-inch refrigerator and freezer columns, and Bosch dishwasher. The kitchen transitions into a walk-in pantry with cabinetry, quartzite, dual refrigeration drawers, and a dedicated ice maker. An oversized mudroom, finished with hardwood built-ins, offers expanded storage and functionality. The first-floor primary suite is privately positioned in its own wing and finished with wide-plank European white oak flooring by Forrest Accents, a walk-in closet with textured built-in systems, and a spa bath with natural stone countertops, Rohl polished nickel fixtures, a marble-tiled floor and shower, and a frameless glass enclosure. All doors are solid core with Emtek hardware. The library, near the front of the home, offers a quiet retreat with matching oak floors and custom casements. A solid wood staircase leads to the second level living areas including a lounge flex space. There are three additional bedroom suites, each with en-suite baths, which offer porcelain flooring, frameless glass shower doors, brushed quartz and dolomite vanities, decorative lighting, and built-in closet systems. Additional features include CAT-5/6 wiring, Sonos-integrated speakers, lighting automation via the Lutron RA-3 smart system, and pre-wired home security with digital camera ports at key access points. Thoughtfully placed access points from the primary suite and kitchen wing lead to a fully enclosed backyard retreat, where mature landscape design by Signature Landscape frames a private outdoor living sanctuary. A Roman-inspired cabana with grand ceilings and exposed beams anchors the outdoor entertaining space, flanked by a fully tiled ($50,000 upgrade) saltwater pool featuring therapy jets, LED-lit bubblers, a dual-skimmer system, automated controls via a Jandy heat pump, and a Paramount self-cleaning system. Clay brick pavers and landscape lighting define the walkways as well as front entry driveway. This home was constructed with stem wall foundation, concrete block first-floor exterior walls, and 2-by-6 second-floor framing for structural performance along with spray foam and sound mat insulation between floors ensure comfort and acoustic separation. Finished in a palette of clay brick and hand-troweled stucco, the home is crowned with architectural tile shingles and custom metal accents. Eight-inch half-round gutters, aluminum downspouts and engineered drainage ensure long-term performance.

702 Via Bella, Winter Park

$837,500

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

A unique opportunity to own this Winter Park luxury corner condominium unit in the gated Park West community. Resting on the corner of New York Avenue and Carolina, with direct second-floor balcony views of Central Park and Park Avenue, and proximity to the quintessential Winter Park experience. Designed by nationally renowned Soco Interiors, a turnkey opportunity that adds ease to the lock-and-go lifestyle. Designer touches and quiet elegance blend to create this California casual interior that was meticulously designed and appointed with function and comfort at the forefront. Open dining and living spaces with balconies on each side make hosting a breeze. A marble-framed fireplace and beautiful wide-plank white oak floors add warmth and charm to this special place. The modern gourmet kitchen is highly functioning for family dinner or entertaining guests. White clean-lined custom cabinetry, gold accent hardware, quartz surfaces and solid quartz backsplash add to the seamless design. A fabulously designed scullery with designer tile floor includes a dedicated laundry/pantry, ample storage and additional counter space for a morning bar. The primary bedroom has ample space and beautiful light with access to one of the two balconies, custom-organized closet and a bath that is appointed with modern finishes such as marble floors/shower and fantastic tropical palm wallpaper that is so chic and fun. An additional large private bedroom suite is inviting and makes it easy to entertain guests for the weekend. Fresh striped wallpaper and organic selections finish out the custom second bath. This pristine unit is in a great building in Park West overlooking Central Park. On a prime corner, with one balcony facing the park and the other overlooking the tennis courts and pool. Elevators throughout and meticulously maintained, all in security of a gated community, Park West has always delivered for decades. Call us for a private showing.

200 Carolina Avenue Unit 201, Winter Park

$1,250,000

3 Beds ⋅ 3 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

Amazing opportunity in the heart of Historic Winter Park! This charming home is full of potential and ready for your personal touch. Whether you're looking to renovate, restore, or re-imagine, this property offers a rare chance to create your dream home in one of Central Florida’s most sought-after neighborhoods. Enjoy tree-lined streets, top-rated schools, and close proximity to Park Avenue, Rollins College, and all that Winter Park has to offer. Don’t miss this unique opportunity to invest in a premier location!

1621 Hillcrest Avenue, Winter Park

$1,100,000

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

Welcome home! Nestled in the heart of Winter Park this 3-bedroom, 2.5 bathroom residence offers a perfect blend of convenience, energy efficiency, and refined comfort. From the moment you enter, you'll be captivated by high ceilings and crown molding for a spacious and refined feel. The kitchen is a chef's dream featuring granite countertops, stainless steel appliances, a gas range and upgraded plumbing fixtures. Enjoy cozy evenings in the living room by the new gas fireplace or relax outside by the cocktail pool, perfect for entertaining and enjoying the Florida sunshine in a tropical setting. The primary suite includes a private balcony with serene views of Lake Midget park. The spacious master bathroom is a true oasis with a soaking tub and rainfall shower. Powered blackout roller shades in the primary suite and downstairs living area ensure restful sleep and complete privacy. Closet systems throughout the home add a layer of organization and luxury. Recent upgrades to the home include a new roof with architectural shingles (2023), energy efficient Pella Impervia windows (2024), an updated air conditioning/heat pump system (2022) and full flake epoxy garage floors with ultra quiet garage door openers. Enjoy low utility bills and energy efficiency with dual-zone A/C, tankless hot water system, R40 attic insulation & foamed block walls. Easy access to I-4 and just minutes from iconic Park Avenue, Downtown Orlando, Rollins College and Baldwin Park. Shopping, numerous restaurants and bars, tennis facilities, multiple parks and city facilities are just a short walk or drive away. Whether you're looking for the perfect place to call home or a stunning Winter Park retreat, this home delivers unmatched quality, location, and lifestyle.

930 S Kentucky Avenue, Winter Park

$1,000,000

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

Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the gorgeous Sevilla neighborhood of Winter Park! Tucked off a charming brick road lined with mature oak trees, this .40-acre property combines privacy and convenience in the heart of Winter Park. Just a 7-minute drive to Park Avenue and moments from Mead Botanical Gardens and scenic Lake Sue, it's perfectly situated for the lifestyle you love. Inside, you’ll find timeless details such as marble and parquet flooring, crown molding and plantation shutters throughout. The heart of the home is the kitchen and family room — both overlooking the pool and anchored by a cozy wood-burning brick fireplace with built-in shelving. Two bedrooms share a Jack-and-Jill bath, while another offers custom shelving — perfect for a home office or study. The primary suite features a spacious walk-in closet and an en-suite bath framed by elegant architectural columns, with private access directly to the pool area. Step outside to your own tropical retreat — an expansive screened, heated pool that lights up in the evenings, surrounded by lush landscaping, multiple seating areas, a covered brick patio, and a charming brick outdoor kitchen waiting for your personal touch. This well-built concrete block home also features a double-door entry and an extended covered front patio — ideal for welcoming guests, relaxing in rocking chairs, or adding seasonal décor throughout the year. Additional highlights include a circular driveway, oversized side-entry garage, fenced yard, spacious laundry room, low HOA, Blink security system, and a roof replaced in 2007. Close proximity to Rollins College, top-rated Winter Park schools, and private schools, this home has been lovingly cared for by the same owner for 33 years. With your personal updates, it has the potential to become a true showpiece in one of Winter Park’s most desirable neighborhoods. Enjoy all that Winter Park living has to give — fine dining, boutiques, museums, art festivals, lakes, and cultural events — just minutes from your front door.

215 Salvador Square, Winter Park

$475,000

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

PROPERTY AS-IS - Perfect for a fix-and-flip or new construction. Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s most coveted neighborhoods. The current structure is being approved for demolition, and the 30-day public notice has been completed. This Prime Location is perfect for Investment or dream-home Lifestyle Potential. Buyer to verify all facts independently.

1740 Anzle Avenue, Winter Park

$1,980,000

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

Situated in the heart of Park Grove, one of Winter Park’s most coveted neighborhoods known for its oversized lots and graceful single-story homes, this residence offers more than 3,500 square feet of beautifully updated living. The thoughtfully remodeled kitchen (2023) features Bosch and KitchenAid appliances, double oven, a warming drawer, and a limestone fireplace, seamlessly blending modern convenience with timeless design. The primary suite is a private retreat with a Carrera marble outfitted bath; showcasing dual vanities, a jetted tub, and an oversized shower with bench. Guest baths have been updated in the same timeless style. Recent improvements include full house replumbing (2023), refinished hardwood floors (2024), HVAC (2022), and roof (2017). Set on a .34-acre lot, the home’s backyard is designed for both relaxation and entertaining with an oversized lap pool, baby pool/swim out, salt/chlorine generator, dry cedar sauna, outdoor shower, and lush landscaping that includes a mature (and blooming!) avocado tree. This is a rare opportunity to own a move-in ready home in Park Grove, offering a blend of elegance, thoughtful updates, and resort-style outdoor living in one of Winter Park’s most distinguished settings.

1535 Williams Drive, Winter Park

$299,000

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park

$382,575

2 Beds ⋅ 1 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to 1001 Early Ave—a beautifully updated 2-bedroom, 1-bath home that perfectly balances timeless character with contemporary style. Nestled on a spacious 7,405 sq ft lot, this 1,222 sq ft gem invites you in with parquet floors, decorator tile, and abundant natural light. The expanded kitchen is a showstopper, featuring stainless steel appliances, granite countertops, a wine cooler, and sleek wood and glass accents—ideal for both everyday cooking and weekend entertaining. The renovated bathroom offers spa-like serenity with a glass bowl sink and modern finishes. Step outside to your private oasis: a sparkling pool with a tranquil water feature, a tiki-style cabana, and a paver patio designed for unforgettable gatherings. The circular driveway and garage with a service door add convenience and curb appeal. The septic system was replaced in 2019, serviced in 2024 and roof replaced 2021. Located minutes from Whole Foods, Winter Park Village, the Enzian Theater, and the vibrant 17-92 corridor, this home offers unbeatable access to shopping, dining, and entertainment. With easy access to I-4 and College Park, your commute and weekend plans just got easier. Whether you're a first-time buyer, downsizer, or investor, this home is a rare find in one of Central Florida’s most desirable neighborhoods. Don’t miss your chance to own a slice of Winter Park paradise.

1001 Early Avenue, Winter Park

$2,078,500

5 Beds ⋅ 4 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, the Winter Park 9 Golf Course, and the Racquet Club, this address puts you at the center of the city’s most coveted amenities. A deeded greenbelt easement to Lake Osceola—just 100 yards from the front door—provides effortless access for boating, kayaking, or paddle boarding on the Winter Park Chain of Lakes. The two-story brick home spans 4,328sf with 4 bedrooms, 4 baths, and a 2-car garage. Inside, character and craftsmanship shine with brick archways, custom millwork, tongue-and-groove ceilings, and two wood-burning fireplaces. The gourmet kitchen features Thermador appliances, marble counters, and a walnut-topped island, while the expansive primary suite boasts a private screened patio, a fully built-out oversized walk-in closet, and a spa-like bath. Two bonus rooms upstairs provide flexible space for work or play, while updated systems—including a 2018 roof, three HVAC units, dual-pane windows, updated drainage, whole house generator, mosquito misting system, whole house alarm, and smart home upgrades—ensure comfort and peace of mind. Equally impressive are the grounds. The front garden is graced with jasmine, mature oaks, and manicured plantings, while a Chicago brick horseshoe driveway easily accommodates six or more cars. Out back, a private retreat unfolds with a lagoon-style saltwater pool and spa surrounded by flagstone decking, a summer kitchen, covered patio with fans and lighting, and a dedicated pool bath. Living here is about more than a home—it’s about lifestyle. With gardens and stunning architecture at every turn, culture, shopping, and dining just minutes away, and lake access at your fingertips, this property offers a rare opportunity to experience the very best of Winter Park.

715 Via Bella, Winter Park

$750,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience refined Winter Park living in this stunning 2-bedroom, 2-bath pied-a-terre in the Cloisters condominium. Perfectly situated in the heart of town, this residence offers serene lake and pool views, a deeded parking space, and effortless access to the upscale boutiques and renowned dining of Park Avenue. Thoughtfully designed interiors feature luxe furnishings and accessories curated by SMRS Design, blending timeless elegance with modern comfort. Whether enjoying your morning coffee by the water or entertaining in style, this home captures the best of Winter Park’s coveted lifestyle.

100 S Interlachen Avenue Unit 203D, Winter Park

$3,965,000

4 Beds ⋅ 5 Baths ⋅ Valencia Terrace SubDv. ⋅ 32789 Zip Code

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

1161 Valencia Avenue, Winter Park

$1,040,000

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

Welcome home to this beautifully maintained property on more than a third of an acre in one of Winter Park's favorite neighborhoods -- affectionately known as the Tree Streets! 1711 Chestnut Ave blends classic Florida design with intentional, modern systems. In both the front and back of the home, you'll appreciate the attention to detail in the landscape design, which will be in full bloom each Spring. The irrigation system for the lawn is on it's own well system. Enter the home to enjoy two separate living spaces, a split plan that offers a spacious primary suite and three secondary bedrooms, and three full bathrooms. The kitchen has been renovated to include custom cabinetry, granite countertops, and stainless steel appliances. It is open to the Family Room with an incredible view of the oversized backyard and pool. The mature landscaping out back offers privacy to enjoy this retreat, complete with ample space for outdoor living and entertaining! Some notable upgrades to this property include brand new HVAC systems (2) in 2021 and 2022, water heater in 2019, hurricane-rated windows between 2015-2017, home security in 2015, engineered hardwood flooring in 2015, custom wood shutters in 2017, new pool pump in 2016, and a re-plumb in 2005. Zoned for highly rated Orange County Public Schools (Lakemont, Maitland, and Winter Park), you're also central to some of the best shopping and dining in Winter Park: 2 miles from Park Avenue, 0.4 miles from the Winter Park YMCA, 0.3 miles from Phelps Park (playground, pickleball, tennis), 1.5 miles from the nearest Publix, 1.1 miles from Interlachen Country Club, and 14 miles from Orlando International Airport.

1711 Chestnut Avenue, Winter Park

$2,700,000

5 Beds ⋅ 5 Baths ⋅ Windsong Lakeside SubDv. ⋅ 32789 Zip Code

Experience Mediterranean charm in this fabulous five-bedroom, five-bath pool home built by Cahill Builders. On the north side of Windsong, this home features an open floor plan with spacious living areas that flow seamlessly and provide warm natural light. The living room with cozy gas fireplace overlooks the spacious and open dining room while the light-filled family room with French doors has wonderful views of the covered lanai and pool. You will love entertaining in the chef’s eat-in kitchen with many updates and upgrades completed in 2024. Kitchen features include stainless appliances, natural gas cooktop, double ovens, large center prep island and large walk-in pantry. The first-floor luxurious owner’s retreat features vaulted and hand-crafted wood beam ceilings, wide plank wood floors and bath with dual vanities, walk-in shower and spa tub. Bedroom Suite 2, which is also on the main level is ideal for guests, home office or nursery. As you go upstairs, the second floor offers a thoughtfully designed retreat for both relaxation and entertainment. There are three spacious bedrooms each with their private baths. This layout offers comfort and privacy for family or guests. The media room provides the ideal setting for movie nights or immersive gaming and includes an additional room for a playroom, library or large air-conditioned storage space. Whether you are entertaining or unwinding, this upper-level layout delivers functionality and privacy. Go outside to enjoy the covered lanai which overlooks the private and expansive yard filled with a vibrant mix of citrus trees, tropical plants and year-round flowering garden. The fabulous landscape was designed by a landscape architect with the concept to provide continuous blooms and inviting sitting areas under the sun. The sparkling pool and spa, large surrounding patio and firepit area invite year-round enjoyment. Additional amenities include custom molding and trim work, an entry fountain and three-car garage (one with split air conditioning). Windsong, one of Winter Park's sought-after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy Winter Park Chain of Lakes, two community pools, a splash park, playground, a lakefront clubhouse and a scenic pier for fishing. Ideal location is minutes from hospitals, schools, golf courses, and Park Avenue’s amazing dining and shopping.

1445 Holts Grove, Winter Park

$130,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Welcome to a delightfully bright and inviting 2-bedroom, 1-bathroom condo nestled in the peaceful Waterfall Cove community at 1695 Lee Rd, Unit C206, Winter Park, FL 32789. Thoughtfully designed, this home features a covered balcony that invites relaxing mornings or cozy evenings outdoors, while the spacious primary bedroom offers the convenience of a walk-in closet—perfectly blending comfort and efficient use of space. Waterfall Cove elevates everyday living with community amenities including a pool, playground, and covered picnic area, making it ideal for both relaxation and active enjoyment. Plus, high-speed internet and cable are included in the HOA fees, offering modern convenience and simplified budgeting. The location is outstanding. You’re minutes from Rollins College—a short 2½-mile drive—making it perfect for students, faculty, renters, or families alike . Stroll or drive to Park Avenue for galleries, boutiques, and cafes. Winter Park Village, recently refreshed by a major renovation, offers a vibrant array of tenants and experiences—from Arhaus and Brighton Collectibles to coworking at Spaces and upscale dining under one beautifully redesigned streetscape—now fully leased and thriving. With downtown Winter Park just minutes away and I-4 under one mile from your doorstep, getting around town is effortless and efficient . This condo is perfectly balanced for homeowners seeking cozy elegance as well as investors looking for a turnkey residence in a high-demand location of Winter Park. Whether you seek a relaxed retreat or a smart, energy-efficient investment anchored by community and convenience, this property captures it all. Schedule your private showing today—the next chapter of refined Winter Park living starts here.

1695 Lee Road Unit C206, Winter Park

$1,770,000

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

Welcome to this picturesque 3 bedroom, 4 bath pool home nestled in the highly sought-after neighborhood of Park Grove. Overflowing with charm and character, this naturally light-filled home features white oak hardwood floors and plantation shutters throughout. Upon entry, a formal living room with a cozy wood-burning fireplace greets you, offering serene views of the sparkling heated pool and lush backyard oasis. The elegant formal dining room leads to a chef's kitchen adorned with marble countertops, wood cabinetry, a spacious island with seating, and top-of-the-line appliances. A well-appointed wet bar adds to the home's entertainment appeal, while an informal dining space flows seamlessly into the expansive family room, where floor-to-ceiling windows invite the beauty of the outdoors in. Step outside to a covered porch and summer kitchen- perfect for hosting. Enjoy al fresco dining under the shade of a covered pergola or relax by the glistening pool in complete privacy. The home features two secondary bedrooms, each with its own en-suite bath, and a full guest bath off the hallway. The primary suite is a true retreat, offering a private sitting area, his-and-hers closets, and a luxurious bath with dual vanities and a large walk-in shower. Located just minutes from the vibrant shops and fine dining of Park Avenue in downtown Winter Park, and zoned for top-rated schools- this home is an exceptional opportunity you won't want to miss!

690 Williams Drive, Winter Park

$380,000

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Seller financing and lease to own options for qualified buyers. HOA fee covers full time building engineer, spectrum cable tv, phone and internet, water and sewer and amenities. Beautifully updated 2-bedroom, 2-bathroom lakefront condo (Lake Virginia Condo) in the heart of Winter Park, FL. Enjoy a prime location just steps from Park Avenue's charming shops, restaurants, Rollins College, scenic parks, and cultural museums. Freshly painted with new, water-resistant LVP flooring throughout. The refreshed kitchen features energy-efficient appliances, solid wood cabinetry, and ample storage. Expansive wall-to-wall sliding glass windows in the living room and primary bedroom brightens the space with natural light. Convenient in-unit washer/dryer closet and a screened-in back porch overlooking the serene canal connecting Lake Virginia and Lake Osceola. Building has guest suite, pool and spa, boat docks, lake access, common lounges, open patio and grilling area and much more. Some photos are virtually staged with furniture. Vacant and easy to show—contact your realtor to schedule a viewing today!

690 Osceola Avenue Unit 209, Winter Park

$1,150,000

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

One or more photo(s) has been virtually staged. This beautiful 4-bedroom, 3-bathroom home in Winter Park's sought-after Virginia Heights neighborhood offers 3,204 square feet of comfortable living space on a private 0.21-acre lot. The property underwent extensive addition and renovation in 2020, featuring stunning wood floors throughout and a spacious kitchen complete with a bar, center island, and wine fridge. The home's character shines through unique details like authentic New Orleans 100-year-old ironwork on the staircase, adding historical charm to this modern residence. The main floor flows seamlessly, while upstairs you'll find three bedrooms. A large game room provides flexible space that could easily serve as an in-law suite. Recent updates ensure worry-free living with new drywall, insulation, electrical, and plumbing systems installed. The roof was replaced in 2021, and the home features three newer air conditioning units plus water heaters that are just 2-4 years old. A new sewer line to the street was installed in 2009. Outside, you'll discover a well-designed courtyard leading to an amazing pool and backyard perfect for entertaining or relaxing. The property includes a gas line and plenty of parking space. The location offers the best of Winter Park living. You're just steps from Lake Virginia with exclusive access to College Point, a secluded deeded lakefront area reserved for Virginia Heights residents only. This beautiful lakefront spot overlooks Rollins College and includes a dock for launching kayaks or canoes. Daily conveniences are nearby with Park Avenue's shops and restaurants within walking distance. The home provides quick access to downtown Winter Park, Winter Park Village, US 17-92, and Mead Botanical Garden. Families will appreciate the proximity to highly-rated Audubon K-8 and Winter Park High School, both just moments away. This property perfectly combines privacy, luxury, and convenience in one of Winter Park's most desirable neighborhoods.

1213 Richmond Road, Winter Park

$164,000

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!

2500 Lee Rd Unit 219, Winter Park

$1,875,000

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

Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style. At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings. Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat. Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space. Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis. Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets. The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality. Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park. A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.

1752 Chestnut Avenue, Winter Park

$4,500,000

6 Beds ⋅ 6 Baths ⋅ Dyer Susan Resub SubDv. ⋅ 32789 Zip Code

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

887 Georgia Avenue, Winter Park

$1,110,000

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

Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and maximize the value of the property. Whether updating or building new, you will revel in the ambiance and privacy of this sought after neighborhood among an eclectic blend of classical and modern homes built by premier custom homebuilders. Walk or bicycle to Rollins College and downtown Winter Park's fine restaurants, boutique shops, and farmers market, or enjoy exclusive deeded lake access to the beautiful Winter Park Chain of Lakes, Lake Virginia with kayaks, paddle boards, canoes and fishing from College Point, a private lakefront park. This property could be your ideal family retreat for generations to come.

233 Hampden Place, Winter Park

$465,000

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

SUPERB LOCATION! Don’t miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon entering, you immediately notice the charm and character of this impeccably maintained condo. Recent updates include a fully renovated screened porch including floor, screen enclosure and roof, new sliding doors and windows, new refrigerator, new dishwasher, newly painted interior and recently installed closet organization systems. The kitchen with solid wood cabinets, stainless steel appliances, granite countertops and counter seating is open to the dining/family room combo featuring a cozy corner fireplace. The flex space in the front of the condo can serve as a formal dining room, home office or art studio with generous shelves that span an entire wall of the room. Convenient downstairs laundry room with storage and half bath with access to additional storage under the stairs. Wood tile floors, plantation shutters, ceiling fans and vaulted ceilings in the upstairs bedrooms. Wood plank flooring on the staircase. Generous upstairs hall closet! Two master suites both with spacious walk-in closets and en suite bathrooms. The front bedroom features a balcony with a sitting area and alcove for a tv or desk and the back bedroom presents as a quiet, private retreat with extra closet space. The recently renovated screened porch overlooking the manicured landscape is the perfect place to relax and unwind. Two assigned parking spaces, one covered and located in front of the condo. Outdoor closet located on screened porch. Community pool and dock and view of Lake Killarney. Kayaks and paddleboard storage available. Walkable to Winter Park Village, Trader Joes and a variety of restaurants and shopping along the 17-92 corridor. Easy access to I.4 via Fairbanks or Lee Rds. You simply cannot beat this location! Call today to schedule your showing!

130 Killarney Bay Court Unit 5-3, Winter Park

$1,250,000

4 Beds ⋅ 2 Baths ⋅ Tuscany Place First Add SubDv. ⋅ 32789 Zip Code

This is a rare opportunity to own a ONE STORY LARKEFRONT home on a HALF-ACRE lot in the highly desirable Via’s of Winter Park. Nestled on a quiet cul-de-sac in Tuscany Place and zoned for top A-rated schools, this beautifully maintained 4-bedroom, 2-bath home offers breathtaking views of Lake Temple from nearly every room. The spacious and light-filled interior features a split bedroom floor plan with a formal living room, dining room, and a comfortable family room—an ideal layout for any family. The kitchen is equipped with solid wood cabinets, granite countertops, and opens to the family room, which includes custom built-ins and a wood-burning fireplace with granite surround. Hardwood floors run throughout the home, and large windows flood the space with natural light. The primary suite overlooks the lake and includes a walk-in closet, dual sinks, a separate shower, and direct access to the screened-in rear porch. Three additional guest bedrooms are privately situated on the opposite side of the home. A spacious indoor laundry room leads to a side-entry two-car garage. Outside, the screened patio offers the perfect place to entertain while enjoying the pool, spa, and serene lakefront setting. Located just minutes from Park Avenue and the Winter Park Racquet Club, this unique property offers endless potential to live in as-is, renovate, or build new on one of the Via’s most coveted lakefront lots.

1049 Tuscany Place, Winter Park

$510,000

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

Off market Sale

2804 Mulford Avenue, Winter Park

$2,650,000

6 Beds ⋅ 5 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a wall of glass folding doors that reveal a private backyard retreat—featuring a heated pool and spa, lush landscaping, and an expansive lanai with summer kitchen. The home is serviced by natural gas, seamlessly supporting modern comfort and efficiency. The kitchen is truly the heart of the home, boasting dual oversized islands, WOLF appliances, fully custom cabinetry, two dishwashers, a double oven and a massive walk-in pantry. A nearby sunken bar offers the perfect spot for entertaining. Downstairs includes two well-appointed bedrooms, one with its own en suite—ideal for guests or multigenerational living. The detached casita includes a full bath and is pre-plumbed for a kitchenette and washer/dryer, offering endless potential as a guest suite, gym, or studio. Upstairs, the primary suite is a sanctuary: a double-sided fireplace, private balcony overlooking the pool, two generous walk-in closets (one with a secondary laundry hookup), and a spa-worthy bath complete with a sauna and a massive multi-head shower. A bonus loft with wet bar and two additional bedrooms round out the second floor. Located just minutes from Park Avenue and zoned for top-rated public schools including Winter Park High, a community known for both academic and extracurricular excellence (some say there’s championship energy in the air), this home offers a rare blend of luxury, lifestyle, and location.

575 Palmer Avenue, Winter Park

$1,565,000

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

Experience the charm and comfort of this one-story, Key West-style pool home, nestled on a brick-lined street and canopied by majestic oaks in the highly sought-after Virginia Heights neighborhood. Within true walking distance of Rollins College and Park Avenue, and in the Audubon K-8 school district, this home was thoughtfully designed for everyday living and entertaining. The 2,662 SF home features a split-bedroom floorplan with 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace piped for gas, dining room with a built-in lighted bar, a large family room, and a 400 SF covered lanai overlooking the pool & backyard paradise. The oversized primary suite is truly a retreat, with a sitting area plus a cozy window bench spanning a wall of windows with built-in cabinetry and shelves for ample storage. A mirrored barn door slides open to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large, zero-entry marble shower, mahogany-topped custom-crafted vanity, maple board-and-batten walls, brass fixtures, cypress vaulted ceilings, and windows overlooking the sparkling pool, with convenient top-down bottom-up privacy shades. Enjoy 2 walk-in closets, plus a third closet at the primary suite entrance that offers easy-access housing for the home’s AV equipment. The sunny family room, lined with built-ins and a custom-designed “wall of books,” extends to the back of the home. French doors with hidden screens open to the private backyard oasis, showcasing a travertine lanai, lagoon-style pool, and travertine deck surrounded by palms and lush tropical landscaping. At the heart of the home sits the kitchen with Thermador appliances— gas cooktop, built-in oven, convection oven/microwave, and dishwasher— and a breakfast bar, plus a brand new vent hood framed by a new marble backsplash, and new under-cabinet and pendant lighting. Both secondary bedrooms have French doors that open to the covered lanai, while the rear left bedroom offers a private, en-suite bathroom renovated in 2021, wrapped in marble and brass with coil-heated floors and a custom Kohler air-jet soaking tub. Other conveniences include a whole-house sound system with speakers in every room as well as the rear lanai, and a custom laundry room (renovated in 2021) that leads to a 2-car garage with built-in storage. Virginia Heights is truly a special neighborhood, offering residents deeded access to a private lakefront park that's just a 3-minute walk from this home. This hidden park was deeded to the property owners of Virginia Heights in 1922, and includes a dock on College Point directly across from Rollins College, canoe/kayak racks, tables for airy picnics in the lake breeze, and a sprawling green lawn where neighbors gather for social events, holiday parties, or just to enjoy the lake view. A part of the beloved culture and history of Winter Park, this unique property is just minutes from Rollins, the shops and restaurants of Park Avenue, and all the lively bustle of downtown Winter Park. Recent upgrades include a complete replumb and new gas water heater (July 2025), a partial roof replacement (all new flat roof), landscape clean-up/refresh, fresh paint inside and out, and all new lighting and ceiling fans throughout. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$245,900

3 Beds ⋅ 4 Baths ⋅ Sandalwood Creek Condo Ph 13 SubDv. ⋅ 32789 Zip Code

Your Dream Home Awaits in Winter Park! 3 Beds 3.5 baths! Discover the perfect blend of comfort and convenience in the heart of Winter Park at Sandlewood Creek! This charming townhome-style condo offers a rare opportunity to own a piece of paradise with no neighbors above or below, ensuring a peaceful living environment. Plus, enjoy a very low HOA! Key Features: Financing Made Easy: FHA, VA, and DPA approved, welcoming a wide range of buyers. Spacious Living: OVER 1,100 sq. ft. with an open floorplan, tile flooring, a large kitchen, and a convenient half-bath. Full sized washer dryer located inside. Private Retreat: A patio perfect for relaxation or entertaining. Community Perks: A sparkling pool and well-maintained grounds for a low-maintenance lifestyle. Prime Location: Minutes from Park Avenue, Downtown Maitland, and top shopping and dining spots. Zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. This move-in ready home is a rare find in Winter Park, offering unbeatable value. Don’t miss your chance to make your dreams a reality!

195 Sandlewood Trail Unit 2, Winter Park

$4,772,500

4 Beds ⋅ 5 Baths ⋅ Sicilian Shores Rep 02 SubDv. ⋅ 32789 Zip Code

An architectural gem in the heart of the Vias, this one-of-a-kind modern, custom residence masterfully crafted in 2019 by renowned builder Z Properties, Inc. Rarely does a single-story home of this caliber and scale become available combined with being on one of the best addresses in all of Winter Park! Offering nearly 4,900 square feet of refined living space under air (which includes a noteworthy 551-square-foot lanai, fully finished and separate zone air-conditioning) encompassing over 5,400 square feet total under roof, all tastefully designed with an emphasis on clean lines, organic textures and exceptional indoor-outdoor flow. Beyond its striking curb appeal, the home opens to reveal expansive living spaces grounded by wide-plank hardwood floors and bathed in natural light from soaring cathedral ceilings and oversized windows. A seamless open layout connects the living and dining areas with a central gathering area anchored by a sleek linear gas fireplace. Award-winning chef-designed kitchen is framed by a dramatic wall of glass and features premium Wolf and Sub-Zero appliances, including an eight-burner gas cooktop, integrated refrigerator, double built-in ovens, Miele coffee system, warming drawer, Scotsman ice maker, high-level custom cabinetry and more, flanked by dual wine columns. The primary retreat is in its wing, complete with a 20-by-10-foot custom walk-in closet and a spa-inspired bath with a soaking tub and oversized walk-in shower featuring multiple shower heads. The home's most captivating element is the fully enclosed, air-conditioned 29-by-17-foot lanai, accessible through disappearing glass doors that create a seamless transition from indoors to out. This sophisticated outdoor living space includes a full summer kitchen, alfresco dining area, lounge with gas fireplace and motorized screens for further flexible utilization. Just beyond, a heated lap pool is framed by lush bamboo landscaping, creating a serene and secluded outdoor living environment. Another special feature is a secluded casita, which offers an ideal space for guests or multigenerational living. Two additional bedrooms with en suites, each with walk-in closets, complete the three-way split flexible bedroom layout along with a well-appointed utility/mud room entry off the oversized two-car garage. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary blend of modern design, luxurious functionality and premier location. Winter Park living at its finest!

765 Via Lugano, Winter Park

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Ardmore SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand over time, or build new. This 4-bedroom, 3-bathroom block and brick home has been fully renovated with wide plank flooring and tile, a stunning light-filled kitchen with Café appliances and quartz countertops, Carrara marble bathrooms, and a primary suite featuring a walk-in shower built with a Schluter system. Bathed in natural light, the sunroom serves as an additional living or flex space, with a row of French doors opening to the pool and patio. A screened-in lanai overlooks a remarkable backyard, sparkling pool and spa surrounded by lush landscaping, creating a perfect setting for entertaining, relaxing, or letting pets play. All new ductwork, interior and exterior paint, and a clean, natural aesthetic throughout make the home move-in ready. Sidewalks invite morning strolls to Lake Mizell and scenic walks or bike rides through the neighboring Windsong community and winding shaded brick streets. Zoned for great schools including Brookshire Elementary, Glenridge Middle, and Winter Park High, and close to wonderful private schools such as Park Maitland, Trinity Prep, Lake Highland Prep, and more. Just minutes from Park Avenue’s shops and dining and close to Baldwin Park. Whether you love it as it is or envision building a custom estate on this .31-acre lot, 1500 Mizell Ave offers a rare chance to own a legacy property in one of Winter Park’s most coveted neighborhoods. The location is superb.

1500 Mizell Avenue, Winter Park

$1,277,000

3 Beds ⋅ 4 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance created by the centerpiece of the home: a screened-in courtyard with a heated saltwater pool and spa, perfect for relaxing or entertaining year-round. Adjacent to this serene space is a private guest casita complete with a full bath and separate entrance, ideal for in-laws, visitors, or an independent-minded teen. Step into the main house, and you will be immediately captivated by the 15-foot Frank Lloyd Wright-inspired rock wall in the stunning Living Room. The 12-foot ceilings give the space a seemingly endless light and airy feel. Overlooking the great room is a fully equipped chef-inspired kitchen where creating meals will be a breeze with an abundance of cabinets, gleaming quartz counter tops, a large prep island,14 foot breakfast bar and newer top-of-the-line LG SS appliances, and a GE Profile cook top — ensuring that entertaining and meal prep are effortless. There is also a large dining room that can fit more than a large dinner party or family holiday gathering. Also, tucked away on the opposite side of the first floor is a guest suite, featuring a spa-inspired bath with beautiful cabinetry, exquisite tile work, and a large walk-in shower. Plus, the large laundry room with an abundance of storage and a utility sink to round out the main floor of this stunning home. Upstairs is the elegant private owner’s retreat, which also enjoys a quiet sitting area and an expansive custom walk-in closet. The spa-like bath will not disappoint with its large soaking tub, separate stall shower, and dual sinks with contemporary cabinetry and elegant tile throughout. Additional amenities include a large 2-car garage with an EV 30 amp outlet, plus an oversized over 300 square foot separate flex space that would make an excellent home office, home gym, or craft/hobby space. The home features tons of storage space, custom automated blinds with remotes, blackout blinds, a new AC unit, new lighting, new exterior paint, and a tankless water heater. This remarkable home is flooded with natural light and ambiance, with many floor-to-ceiling windows, while exuding a warm and cozy atmosphere. Zoned for some of the best public schools in the area, including Audubon K-8 and Winter Park HS, and conveniently located near Audubon Park/Corrine Drive shopping and restaurants, and of course easy access to Winter Park's Park Ave with its fine restaurants and shopping, and also close proximity to Blue Jacket Park/Baldwin Park, Downtown Orlando, Leu Gardens, the Mills 50 District and Rollins College. Don't miss your opportunity to own this exquisite Winter Park retreat, a perfect blend of luxury, privacy, and location. Florida living at its finest!

2728 Eastern Parkway, Winter Park

$5,225,000

3 Beds ⋅ 4 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors flood the interiors with natural light and deliver unobstructed panoramic lake views from nearly every room. Enter through a dramatic 12-foot glass pivot door into a 21-foot-long art gallery foyer adorned with a sculptural linear chandelier and Venetian plaster walls and ceilings that lend a soft, refined texture. The open-concept living spaces are accentuated by terrazzo floors, 12-foot ceilings, and thoughtful spatial design—including a great room with a sitting area and dining space, a separate media room concealed behind custom 12-foot decorative doors, and a sleek galley-style kitchen outfitted with fully integrated Miele appliances and a secondary glass pivot door for seamless indoor-outdoor flow. Ascending one of two custom staircases, the second floor features warm hardwood floors and a showstopping primary suite that feels suspended above the lake, backyard and pool. This serene retreat offers an all-glass shower, spa-inspired soaking tub, beautifully finished bath cabinetry, and an upholstered wall that subtly conceals a walk-in closet and built-in storage. A second bedroom suite offers an inspired use of space with clever screen walls for privacy and flexibility. Detached from the main home, a third bedroom suite doubles as a guest house, home office, or gym, complete with an en-suite bath, custom built-ins and a wet bar. Outside, the terraced backyard is a tranquil oasis with a saltwater pool and spa, turf lawn for year-round perfection, dual staircases leading to a sundeck and a private, covered boat dock crowned by a glass-enclosed studio mirroring the home’s signature design. Bamboo privacy walls, soaring palms, and a Banyan tree imported from South Florida create a lush and artful landscape. The two-car garage includes epoxy flooring and dual EV charging stations. A singular residence in every sense, this home blends innovative architecture, luxurious finishes and thoughtful design into a rare offering unlike anything else in Winter Park. Built by Z Properties, celebrated in Florida Design and numerous design publications, this is a home for those who appreciate beauty, intention and the art of living well.

1333 Alberta Drive, Winter Park

$980,000

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue. Inside, you'll find an open floor plan with engineered hardwood flooring, high ceilings, crown molding, and abundant natural light. The kitchen is a chef’s dream, featuring a convection oven, cooktop, range hood, and brand-new appliances—ideal for both daily living and entertaining. A wet bar with wine fridge, cozy sunroom, and custom closets in all three bedrooms elevate the home’s comfort and convenience. The primary suite is located upstairs, offering privacy and retreat. The backyard is a true Florida oasis, complete with a newly resurfaced saltwater pool, expansive artificial turf, a custom putting green, and a deck with a retractable awning—all within a fully fenced yard designed for privacy and year-round enjoyment. Additional upgrades include a new roof (2020), updated A/C system (2021), garage storage solutions, and lush front landscaping. With no HOA, a 2-car garage, and extended driveway parking for 4+ vehicles, this home offers both style and flexibility in one of Winter Park’s most coveted neighborhoods. A rare opportunity to own a turnkey home in a prime location—schedule your private showing today.

1610 Chestnut Avenue, Winter Park

$775,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$1,575,000

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

Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

1394 Grove Terrace, Winter Park

$4,195,000

4 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

$1,607,160

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

An extraordinary home, built in 2018 by Lazarus, is on a quaint cobblestone street in the exclusive Tree Streets of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A four-bedroom, three-bath pool home stretches over 2,800 square feet with natural light filling the spaces through expansive windows. The home offers open concept living in the main gathering room as well as dedicated dining and office/or guest rooms. Fantastic kitchen with custom double cabinetry to the ceiling features an abundance of storage and generous workspace, a large center island with quartz counters, with a stylish waterfall edge and subway glass tile backsplash. Top of the line appliances include Kitchen Aid and Bosch and a Viking 48-inch gas range, microwave drawer and kitchen are rounded out with a butler's pantry/bar area with built-in wine refrigerator that blends the kitchen to dining. Kitchen is open to the living room with a gas fireplace finished with sleek tile extending to ceiling and vaulted ceiling with wood detail all opens to outdoor living under a covered porch with tongue and groove ceiling and sparkling pool. The main level owner’s retreat has two large walk-in closets, and serene bath with double sinks, soaking tub and custom tiled walk-in shower with seamless glass. An additional guest room/study on the first floor has a private bath while upstairs you’ll find two oversized bedrooms and a second bonus/family room. Other details include frosted glass garage door, hardwood pre-engineered wood floors, home recently painted, Phillip Jeffries Wallpaper in dining, designer Restoration Hardware and Pottery Barn Fixtures, professional designed landscaping with architectural outdoor lighting, recessed lighting package, upgraded insulation and energy-efficient tankless water heaters contribute to lower energy bills, 10-foot ceilings, 8-foot doors, custom tile work and beautiful crown moldings. In walking distance to Phelps Park and YMCA, close to hospital, Park Avenue, great shops and restaurants as well as Rollins College. Schools are the best with Lakemont Elementary, Maitland Middle and Winter Park high schools.

1541 Chestnut Avenue, Winter Park

$1,725,000

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

WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an entertainer’s dream. Inside, soaring ceilings, gleaming wood floors, expansive picture windows, and an abundance of natural light create an inviting and sophisticated atmosphere. The gourmet kitchen is a chef’s paradise, with white maple cabinetry, Quartz countertops, a breakfast island, and stainless-steel gas appliances. The open floor plan seamlessly connects the kitchen, great room, and outdoor living spaces, perfect for hosting friends and family. Located on the first-floor, the spacious primary suite includes a spa-inspired bathroom, while a dedicated home office and guest suite offer comfort and versatility. Upstairs, discover three additional bedrooms, two full bathrooms, and a versatile loft space. Step outside to the wrap-around porch overlooking meticulously landscaped gardens, creating a serene and private outdoor retreat. Located just minutes from Park Avenue, Rollins College, and Advent Health Winter Park, this exceptional residence offers convenient access to top shopping, dining, and cultural attractions. Zoned for the highly sought-after Brookshire School District, this is your chance to experience elevated living in one of Winter Park’s most coveted neighborhoods. Schedule your private showing today and make this exquisite property your new home.

617 Worthington Drive, Winter Park

$2,575,000

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter Park location. This residence boasts a sought-after open floor plan with 12-foot ceilings, wide plank wood flooring and truly exceptional detailed finishes throughout. You will feel instantly at home as you pass through the fully enclosed front yard and enter through the double door entrance from the covered wrap-around front porch. The open-concept design seamlessly connect the dining room and family rooms as you make your way to the kitchen area complete with Wolf & Sub-Zero stainless-steel appliances, double islands, Wellborn custom cabinetry, and private Butler's Pantry with new washer/dryer. The gourmet kitchen opens to the spacious family room where you will find a built-in fireplace with custom millwork, recessed lighting, and beautiful French doors that open fully to the outside entertainment/living area. The split floor plan is perfect for the family and as you find your way throughout the remainder of the home, you will be impressed by the designer window treatments, plantation shutters, built-in speaker system, high-quality upgraded light fixtures, and private pool bath. The main floor includes a spacious primary retreat with a large walk-in closet and private French doors leading to the pool area. The spa-like bathroom includes a stand-along soaking tub, dual sink with stone counters and generous walk-in shower. The formal dining room and en-suite guest bedroom complete the first level. Upstairs are 3 spacious bedroom suites with full baths, a generous bonus/media room with built-in desk, and a second upstairs laundry room with hook ups. You will enjoy Florida living while relaxing on your covered lanai complete with retractable screens and summer kitchen overlooking the saltwater sparkling pool/spa with new pool heater and fully enclosed kid friendly yard. Upgrades include: Control 4, new electronic driveway entry gate, whole house interior and exterior painting, Jeld Wen solid core interior doors, hardwood floors throughout the first floor & bonus room, custom closet systems in all closets, rare 3-car garage, vinyl insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in frame walls, Carrier 15-Seer AC dual systems with UV filtration, and two Rinnai gas tankless water heaters, whole house water filtration. This pristine residence is situated on an oversized corner lot and it truly timeless, move-in ready, and only ½ mile to the Winter Park Raquet Club and 2 miles to famed Park Avenue to enjoy incredible dining and boutique shopping. Call now for your private tour!

1341 Place Picardy, Winter Park

$1,785,000

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

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

1640 Mayfield Avenue, Winter Park

$3,600,000

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

Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter Park pool home features 5 bedrooms, 5 full bathrooms, 2 half baths, and a private home office. A grand entryway opens to a bright, open-concept interior with expansive Andersen windows that enhance indoor-outdoor flow—an essential feature for Florida homes. The chef’s kitchen is a standout, equipped with Wolf and Sub-Zero appliances, custom cabinetry, quartz countertops, and an oversized island ideal for entertaining. The great room offers seamless living with a wet bar, wine column, and elegant tiled electric fireplace. The first-floor primary suite serves as a private retreat with a spa-style bathroom that includes dual vanities, a soaking tub, glass-enclosed walk-in shower, towel warmer, and custom walk-in closet. A guest suite with a walk-in closet and en-suite bathroom, dining area, and main laundry room complete the first level. Upstairs, you’ll find a dedicated office, activity room, powder bath, secondary stackable laundry, and 3 spacious ensuite bedrooms—each with generous walk-in closets and ceiling fans. Designed for year-round indoor-outdoor living, the transitional room features a full summer kitchen with grill, hood vent, refrigerator, retractable screen, mini-split A/C, and an additional powder bath. Step into your private backyard oasis with a resort-style pool, spa, fire pit, outdoor shower, Travertine pool deck, and lush tropical landscaping—perfect for relaxing or entertaining. Additional features include security cameras, surround sound, an oversized 2-car garage with EV charging port, epoxy floors, LED lighting, a paver driveway with extra parking, standing seam metal roof, privacy fencing, and professional landscaping. Located in one of Winter Park’s most desirable neighborhoods and zoned for Audubon K-8 / Winter Park High School. Schedule your private tour today. **Builder is offering up to $30,000 in buyer incentives toward window treatments with an acceptable offer.**

1820 Glencoe Road, Winter Park

$425,000

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

Welcome to this newly updated 2-bedroom, 2-bath condo ideally situated just steps down from shops, dining, and cultural attractions of Park Ave and Rollins College. Freshly painted and featuring brand-new flooring throughout, this home offers a perfect blend of comfort, convenience, and modern style. The spacious open layout includes a bright living area that opens to a lovely screened-in lanai—perfect for enjoying your morning coffee or relaxing after a day on the lake. The primary suite boasts a generous walk-in closet and an en suite bath, providing a private and relaxing retreat. Located in the highly sought after Lake Virginia Condominiums, residents enjoy resort style amenities, including a lakefront pool and hot tub, boat dock, fitness center, kayak storage, fire pit, bike storage, elevator access, and reserved covered parking. Don’t miss this rare opportunity to own a modernized lakefront unit in one of Winter Park’s most desirable locations! Residents also have the option to reserve the clubhouse, which features a kitchen, comfortable seating, and direct access to the pool area—making it the perfect venue for gatherings, celebrations, or special events. A poolside guest suite is available to rent for additional visitors. Whether you're looking for a permanent residence, a seasonal getaway, or a smart investment opportunity, this move-in-ready condo offers the very best of Florida living.

690 Osceola Ave Unit 410, Winter Park

$1,800,000

5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and excellent public and private schools, it offers the best of Winter Park living. A charming front porch leads into a thoughtfully designed interior that blends classic style with modern functionality. To the right of the foyer is a private office with built-in shelving and glass pocket door, while the left opens to a formal dining room with a tray ceiling, chandelier, and ambient lighting. The spacious living room features a gas fireplace, beamed ceiling, crown molding, and built-in shelving, with French doors that open to the screened lanai for seamless indoor-outdoor living. The chef’s kitchen offers ample cabinetry, expansive countertops, a center island with secondary sink, walk-in pantry, and a breakfast nook with more French doors to the lanai. On the main floor, the primary suite includes a spa-inspired bath with double vanities, garden tub, and multiple closets. A guest suite also on the first floor includes a private bath, beverage fridge, and coffee station. A full laundry room and butler’s pantry with wine fridge complete the first level. Upstairs features a large loft with built-in cabinetry, under-cabinet lighting, and a beverage fridge. A built-in desk and cabinets line the hallway for study or work space. Two bedrooms share a Jack and Jill bath, and a third has access to a nearby full bath. A second laundry room, currently used as an office, adds flexibility. Step outside to a private backyard oasis with a screened lanai, sparkling pool, outdoor kitchen, mature landscaping, and full pool bathroom. With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities.

1355 Hibiscus Avenue, Winter Park

$2,585,000

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

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815 Bonita Drive, Winter Park

$699,000

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

Rare find in Winter Park! This charming one-story pool home offers three bedrooms, two full baths, high ceilings, and an open floor plan—all at an incredible price point. The updated kitchen features gas appliances, a center island, breakfast bar, and a separate beverage fridge. Wood-look tile flooring runs throughout the home for a cohesive, modern feel. The spacious primary suite features French doors that open to a private patio with pool access. The en suite bathroom is oversized, with a large walk-in shower and double vanities. The garage has been temporarily enclosed and is air-conditioned, offering flexible bonus space that can easily be converted back. The home’s nearly 1,700 square feet do not include this additional area. Located just minutes from top-rated Winter Park schools, shopping, and dining. Don’t miss this opportunity!

1891 Bryan Avenue, Winter Park

$675,000

3 Beds ⋅ 2 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

LOCATION! LOCATION! LOCATION! EXPECT TO BE IMPRESSED IN THIS CHARMER LOCATED IN THE HEART OF WINTER PARK! Welcoming you and guests is an attractive curb appeal with walkways and pretty landscaping located on a nicely sized lot all fenced in for privacy. Sit back and relax in this easy, carefree, low maintenance home, desirably located in a peaceful & established community close to major highways. Breathe in some fresh air and walk to Park Avenue known for lots of shopping and delicious restaurants or open your front door & you’re invited into plenty of space to enjoy everyday living & entertaining in this generously sized 3 bedroom, 2 bath pool home offering 1,442 sq. ft. The charming kitchen delivers good looks with an eat in kitchen nook, plenty of storage and access to your outdoor patio made easy for grilling or relaxing. The family room open to the kitchen is light and bright allowing natural light in and creating a cozy atmosphere. Indoor and outdoor space combine perfectly, inviting you to enjoy delightful views and savor Florida living at its very best. Walk through the doors, sit on your enclosed porch, have a glass of wine and listen to the birds. Set on a generously sized homesite, this private backyard is bigger than most, offering a sparkling pool and plenty of room to throw a football & build a swing set. Thoughtfully set far from the busy family area, you'll find a nicely sized master suite with a walk in closet. Extra features include; a newer roof (2022) including new soffits and gutters! A thoughtful layout ensures that everyone will have their own personal space. COME SEE THIS CHARMING HOME LOVINGLY MAINTAINED AND MAKE IT YOURS TODAY!

2190 Temple Drive, Winter Park

$355,000

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

Charming One-Story Townhome in Prime Winter Park Location! Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience. Step inside to find a bright, open layout and peace of mind with recent updates, including a new roof (2021), re-piping (2023), and AC system (2016). The single-story design offers ease and comfort, whether you’re looking for a primary residence or a winter retreat. The community features a refreshing pool and clubhouse, and the HOA covers cable and internet—making day-to-day living even easier. Don’t miss this rare opportunity to enjoy the charm and convenience of Winter Park in a move-in-ready home!

1117 Park Green Place, Winter Park

$420,000

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

Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers plenty of room to relax or entertain, and the enclosed porch provides a versatile space. The kitchen is a chef's delight with GRANITE countertops and ample cabinet space. Outside, enjoy a large FENCED yard, ideal for pets, play, or gardening. Located in a highly sought after Winter Park neighborhood, this home is just minutes from top-rated schools, shopping, dining, parks, and more. Don't miss this incredible opportunity, schedule your showing today!

2809 Sanbina Street, Winter Park

$2,037,500

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

Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience. The chef’s kitchen showcases waterfall quartz countertops, Sub-Zero & Wolf appliances, a large island, walk-in pantry, and opens to the living area with phantom screens and views of the resort-style gas-heated pool, fire pit, and a brand-new outdoor kitchen, perfect for entertaining. A first-floor owner’s suite offers pool views, private terrace, motorized shades, spa bath with soaking tub, and expansive shower. Upstairs you'll find 4 en-suite bedrooms, a bonus room with wet bar, wine fridge, 2nd laundry, and balcony overlooking the backyard. Additional upgrades include Summer Kitchen, surround sound, gas fireplace, upstairs & downstairs laundry, private well for irrigation, generator, new HVAC system for downstairs (2025), new water heater (2025), and air-conditioned garage with tiled floors (not included in living SF). This home has been impeccably maintained and is in pristine condition, aluminum roof is a plus. — it truly feels like new. From the moment you step inside, you’ll fall in love with its elegance and charm.

1781 Pine Avenue, Winter Park

$1,595,000

5 Beds ⋅ 5 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3,267 square feet of thoughtfully crafted space. This residence combines timeless architectural character with modern functionality, From the moment you enter, you’re welcomed by warm natural light, the first floor features an office with an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious kitchen and a generous living and dining area, perfect for entertaining and relaxing, creating a warm and inviting atmosphere. The sliding glass door leads to the refreshing Swimming Pool, Summer Kitchen, a serene retreat for relaxation and entertaining. Following the wooden staircase to the second floor, this home features a spacious primary master suite, offering privacy, convenience, and ease of living. The Pool, the detached two-car garage, and the charming private flex suite are the perfect balance of elegance and comfort. Located just minutes from the heart of Park Avenue Winter Park, downtown Orlando, and fine dining, boutique shopping, museums, and local cafés.

1733 Harmon Avenue, Winter Park

$145,000

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. You'll find the bedroom spacious with a large double closet. Ceiling fans in living and bedroom. Location in the community is handy, with assigned parking space just steps away and easy access to the quiet courtyard. You'll love the lakefront outdoor space including pool, club house, tons of manicured green space, over-water covered seating on the new dock, boat launch and slips. Close to shopping and dining in Winter Park, easy access to highways. This community is everything people come to Florida to find!

2500 Lee Road Unit 243, Winter Park

$199,000

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated second-floor corner unit nestled within the sought-after Aragon Condominium community in the heart of Winter Park. This bright and airy two-bedroom, one-bath home offers a perfect blend of comfort, style, and convenience. Step inside to discover freshly painted interiors and elegant laminate flooring that flows seamlessly throughout the space. The galley-style kitchen offers a functional layout and opens to a spacious living and dining area—ideal for both relaxed evenings at home and entertaining guests. Natural light fills the open-concept living space, while the cozy front patio invites you to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are generously sized with pool view and feature built-in closets for easy organization, while a hallway closet adds extra storage for linens or household essentials. The bathroom features modern finishes and thoughtful design, with a shower and tub. The Aragon community offers a host of amenities designed for easy living, including a tranquil central courtyard, a sparkling community pool, on-site laundry facilities, and ample parking with both assigned and guest spaces. Located in one of Winter Park’s most vibrant neighborhoods, this condo is just steps from shopping centers, grocery stores, restaurants, and retail boutiques. With quick access to I-4 and nearby parks, it offers both a peaceful retreat and a connected urban lifestyle. Whether you’re a first-time buyer, downsizing, or searching for an ideal investment opportunity, this delightful home provides the perfect combination of charm, location, and livability.

851 Miles Avenue Unit 8, Winter Park

$2,288,215

3 Beds ⋅ 4 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

1602 Alabama Drive Unit PH404, Winter Park

32789 Zip Code Real Estate & Homes with Pool

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