Location: Winter Park, Winter Park
Do Not Show Listings
2412 CHANTILLY AVE, WINTER PARK, FL 32789
$2,395,00054 Days on yellowkey MLS ID: O6381552
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4506 Built: 2026 Tax: $4,779 (2025)Community: Winter Park VillageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,779
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Tab Bish Llc (855-450-0442)
781 NORTHWOOD CIR, WINTER PARK, FL 32789
$775,0005 Days on yellowkey MLS ID: O6394119
0 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1566 Built: 1971 Tax: $6,931 (2025)Community: Winter Park OasisSingle Family
Taxes:$6,931
Elementary School: Lakemont Elem
Remarks: Under contract-accepting backup offers. Amazing location near Park Ave! Completely reimagined and rebuilt from the studs, this exceptional one-story 3-bedroom, 2-bath residence offers the perfect blend of modern luxury and timeless charm in one of Winter Park’s most coveted locations—just a short stroll to the boutiques, dining, and cultural attractions of Park Avenue. Every inch of this home has been thoughtfully renovated in 2026 with no detail overlooked. Enjoy peace of mind with all-new electrical, plumbing, HVAC, windows, and garage door, ensuring efficiency and reliability for years to come. Roof 2021. A beautifully designed paver driveway enhances the home's curb appeal, creating a warm and welcoming first impression. Inside, the open and inviting floor plan is enhanced by premium tile flooring, designer finishes, and an abundance of natural light. The stunning, fully updated kitchen serves as the heart of the home, featuring sleek cabinetry, quartz counters, high-end finishes, and center island with bar seating. The kitchen flows seamlessly into the living and dining spaces—perfect for both everyday living and entertaining. Both bathrooms have been beautifully redesigned with modern fixtures and elegant touches. The spacious first floor primary suite offers a serene retreat with en-suite bath featuring a stunning walk in shower. Enjoy the convenience of the indoor laundry room with extra storage space. Step outside to the screened in back porch to enjoy the Florida lifestyle. Situated in a highly desirable Winter Park neighborhood, this turnkey home combines walkability, luxury upgrades, and an unbeatable location. A rare opportunity to own a like-new home just moments from the very best of Park Avenue living.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ingrid Livingston (407-595-5972)
1134 WASHINGTON AVE #13, WINTER PARK, FL 32789
$625,000133 Days on yellowkey MLS ID: O6362206
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2083 Built: 1981 Tax: $7,472 (2025)Community: Quarters At Winter Park CondoCondo
Taxes:$7,472
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Discover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of flexible living space in one of Winter Park's most coveted locations. This two-story residence features a semi-attached 2-car garage and thoughtful room layouts perfect for today's lifestyle. The main level welcomes you with formal living and dining rooms, ideal for entertaining. The separate family room showcases a wood-burning fireplace and flows seamlessly to the heart of the home—the kitchen. French doors open from the family room to a vaulted screened lanai, creating the perfect Florida indoor-outdoor living experience for year-round enjoyment. Upstairs, you'll find three oversized bedrooms, each with its own full bathroom for ultimate privacy and convenience. The second-floor interior laundry adds everyday ease between the bedroom suites. This home presents wonderful potential for personalization and updating to match your vision. The location simply can't be beat—moments from the shops and dining of Park Avenue, beautiful Rollins College, and the tree-lined streets of the historic College Quarter neighborhood. HOA fees of $691/month include lawn maintenance for carefree living. Easy to show—schedule your private showing today and envision the possibilities!Retry
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
639 FRIAR RD, WINTER PARK, FL 32792
$795,0004 Days on yellowkey MLS ID: O6395715
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1967 Tax: $3,415 (2025)Community: Winter Park PinesSingle Family
Taxes:$3,415
Elementary School: Aloma Elem
Middle School: Glenridge Middle
Remarks: Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dianne Moore (407-494-7575)
731 BONGART RD, WINTER PARK, FL 32792
$499,99994 Days on yellowkey MLS ID: S5140952
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1826 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,910
Remarks: Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)
700 MELROSE AVE #J1, WINTER PARK, FL 32789
$350,00010 Days on yellowkey MLS ID: O6394372
0 Days Off yellowkey (back on 4/4/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1074 Built: 1964 Tax: $4,205 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$4,205
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to one of Winter Park's most sought-after addresses — a beautifully updated 2-bedroom, 2-bath condo that perfectly blends timeless Florida charm with modern finishes. Just a stroll from Park Avenue's boutiques and restaurants, the iconic Rollins College campus, the location is truly unmatched. Inside, the open-concept kitchen flows effortlessly into the living area — ideal for entertaining or relaxed everyday living. Rich wood-look ceramic tile floors run throughout, offering the warmth of hardwood with the durability of tile. Both bathrooms have been tastefully updated with fresh, contemporary finishes. The crown jewel of this home is the stunning sunroom, where floor-to-ceiling windows frame sweeping views of the community's lush 8+ acres of private gardens and a sparkling pool. Whether you're sipping your morning coffee or winding down at sunset, this serene retreat offers a daily connection to nature that feels worlds away from the city — while keeping you right in the heart of it. This is a 55+ community with room for younger owners. Call agent for details
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Olivia Maxwell (407-222-4440)
330 ELKHORN CT, WINTER PARK, FL 32792
$569,90071 Days on yellowkey MLS ID: O6376757
REDUCED by $5,099 (0.9%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1965 Tax: $2,086 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,086
Remarks: 330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Neil Chetram (407-752-1597)
151 LEWFIELD CIR #4, WINTER PARK, FL 32792
$139,000119 Days on yellowkey MLS ID: O6365536
1 Days Off yellowkey (back on 4/3/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $1,278 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$1,278
Tax Year: 2024
Remarks: Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new sliding glass door, new bathroom vanity. Updated wiring and electrical panel. Enjoy all your community amenities including a two pools, tennis courts, clubhouse and 24/7 fitness center. The HOA covers water, trash removal, Internet, common area pest control, grounds maintenance, and exterior maintenance while the pool is maintained for your enjoyment. A convenient on-site laundry room features two washers and two dryers free of charge, and the clubhouse is available for rental for gatherings or events. Situated in a prime Winter Park location, this condo is close to grocery stores, shopping centers, and major routes like the 408, Semoran Blvd and St. Rd. 50 for quick access across the area. This condo is just 20 minutes from UCF, 10 minutes from Full Sail, Rollins College, and the vibrant Park Avenue in Winter Park. Quick access to major highways (417 and I-4), everything you need is within reach. Welcome Home!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Susan Tamlin (407-808-3104)
2708 LION HEART RD, WINTER PARK, FL 32792
$629,50033 Days on yellowkey MLS ID: O6387685
REDUCED by $5,000 (0.8%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSingle Family
Taxes:$7,007
Elementary School: Brookshire Elem
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
758 WARRENTON RD, WINTER PARK, FL 32792
$318,9855 Days on yellowkey MLS ID: O6395298
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1196 Built: 1988Monthly Fee: $86 Tax: $3,689 (2025)Community: Winter Park Pines Patio HomesHalf Duplex
Taxes:$3,689
Remarks: Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The brand-new kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including new vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
837 APPALACHEE AVE, WINTER PARK, FL 32792
$439,00010 Days on yellowkey MLS ID: O6393151
1 Days Off yellowkey (back on 4/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1771 Built: 1968 Tax: $6,834 (2025)Community: Winter Park ForestSingle Family
Taxes:$6,834
Remarks: Under contract-accepting backup offers. MAY I TEMPT YOU WITH A POOL? Summer’s delight is yours daily with your own pool! Discover a new dimension of living with this terrific classic ranch style home in desirable Winter Park. Great layout home with tons of potential, wonderful split plan with 4 beds/2 baths and almost 1800sf. Entry leads to living and dining combined space to left and straight ahead to large family room and kitchen. Off kitchen, a convenient breakfast nook area and more views of the pool. Generous primary right off breakfast nook with sliders to the pool and a spacious bath that has a walk in shower with bench and large walk-in closet. Additional 3 nice-sized bedrooms on other side of home, right off the roomy family room that also leads to pool. The 2nd large bath for these bedrooms has tub/shower and double sink vanity. Home has an oversized garage with laundry facilities. Then the POOL…a tranquil spot with huge, covered patio area, pass through from kitchen, overflowing fountain and spa available. The pool and patio areas are all screened in, so great for parties and another Florida style living area. Pocket doors throughout. Home is last on a dead-end street with brick wall on one side for lots of privacy. Large side yard would be great for planting your own garden or dog run. Community has natural gas available. HVAC (2025); Roof (2018); Water Heater-gas (2008). Great Winter Park location, close to shopping, dining, major highways and hospital. Don’t’ wait on this one, it’s a winner! And why pay more for a pool-less home when you can have more fun here!
Listing Agent: Teresa Jones (407-376-2130)
350 CORNWALL RD, WINTER PARK, FL 32792
$775,0008 Days on yellowkey MLS ID: O6394524
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2038 Built: 1963 Tax: $2,127 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$2,127
Remarks: Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. FYI-Cool Deck texture on front and back patio and final exterior paint W/O 03/29, New Sod on 04/06, Dumpster removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/08.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Butterfield (407-463-1289)
621 HUNTINGTON AVE, WINTER PARK, FL 32789
$1,795,0006 Days on yellowkey MLS ID: O6394464
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2399 Built: 2008 Tax: $12,854 (2025)Community: Winter Park RevSingle Family
Taxes:$12,854
Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Noelle Leblanc (407-491-2744)
2652 ABBEY RD, WINTER PARK, FL 32792
$450,0008 Days on yellowkey MLS ID: O6394577
0 Days Off yellowkey (back on 3/31/2026)
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1967 Tax: $7,337 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$7,337
Remarks: Under contract-accepting backup offers. Welcome to 2625 Abbey Rd—where opportunity meets location in the heart of Winter Park! Tucked away on a quiet cul-de-sac and sitting on a spacious corner lot in the highly sought-after Winter Park Estates subdivision, this 1,938 sq ft solid block home is what we like to call a “diamond in the rough”… emphasis on the diamond. Let’s be honest—she’s ready for a glow-up. But the good news? Most of the important stuff is already done. With a newer roof ( 2021), updated A/C, and double-pane windows and slider(2021), you can focus your budget on making it beautiful instead of worrying about some of the big-ticket items. Inside, you’ll find a generous layout with multiple living spaces, a formal dining area, and plenty of natural light just waiting to shine even brighter with your updates. Whether you're an investor, renovator, or a buyer with vision, this home is your blank canvas. A standout feature is the separate entrance leading to a full second kitchen—offering incredible flexibility. This space could be ideal for guests, multi-generational living, or even future income potential as an Airbnb or private ensuite. Outside, the oversized corner lot and mature landscaping give you plenty of space to create your own outdoor retreat—or finally start that garden you’ve been talking about. Everyday conveniences are just around the corner, including Sprouts Farmers Market, Publix, Costco, boutique shopping, cafés, and fine dining along Park Avenue and Baldwin Park. Enjoy quick access to major highways for easy connectivity throughout Central Florida, all while being surrounded by established neighborhoods and consistent buyer demand—making this not just a home, but a smart investment in location. If you’re not afraid of a little elbow grease and can see the potential, this one might just be your next masterpiece.
Listing Agent: Jennifer Draper (321-439-7204)
744 CORNWALL RD, WINTER PARK, FL 32792
$715,000248 Days on yellowkey MLS ID: O6332168
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSingle Family
Taxes:$5,359
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
905 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,00017 Days on yellowkey MLS ID: O6383679
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2756 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Taxes:$9,900
Tax Year: 2026
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00017 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3617 Built: 2026Monthly Fee: $372 Tax: $10,000 (2025)Community: The Enclave Winter ParkSingle Family
Taxes:$10,000
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.
906 ENCLAVE PL, WINTER PARK, FL 32792
$1,925,00017 Days on yellowkey MLS ID: O6383092
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3618 Built: 2026Monthly Fee: $372 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.
Listing Agent: Laura Earl (443-994-9441)
901 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,00017 Days on yellowkey MLS ID: O6383602
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2738 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Remarks: Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.
2919 BOWER RD, WINTER PARK, FL 32792
$779,00018 Days on yellowkey MLS ID: O6391025
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2325 Built: 1971 Tax: $9,857 (2025)Community: Winter Park PinesSingle Family
Taxes:$9,857
Remarks: Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of Winter Park! This move-in ready home offers a bright, open layout with multiple living spaces, perfect for both everyday living and entertaining. The upgraded kitchen features stainless steel appliances, granite countertops, breakfast bar, custom cabinetry, and a farmhouse-style undermount sink, all opening to a spacious dining area with a stunning exposed brick fireplace. A newly enclosed and fully air-conditioned back room (converted from the former porch) offers exceptional flex space—perfect for a bonus room, playroom, or additional living area. Designed to maximize Florida living, this space features an expansive sliding glass door that seamlessly blends indoor and outdoor living, while a separate dedicated HVAC system ensures optimal comfort year-round. The primary suite includes a walk-in closet, dressing area, and en suite bath with dual-sink granite vanity and step-in shower. Just off the primary bedroom is a newly added office/nursery space, perfect for working from home or a private retreat. Split floor plan with two additional generously sized bedrooms and a full bath for added privacy. Enjoy Florida living outdoors with a spacious patio, sparkling pool, and large backyard featuring brand-new sod—perfect for entertaining or relaxing. Additional upgrades include fresh paint and a high-end seamless metal roof. Prime location just minutes to Cady Way Park, shopping, dining, and zoned for top-rated schools. Don’t miss this one—schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
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