Location: Winter Park
Do Not Show Listings
2779 SANBINA ST, WINTER PARK, FL 32789
$460,00035 Days on yellowkey MLS ID: O6388746
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1960 Tax: $5,629 (2024)Community: Howell HeightsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,629
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Caroline Fiore (407-538-2381)
1782 PINE AVE, WINTER PARK, FL 32789
$4,197,00036 Days on yellowkey MLS ID: O6389039
Bed: 5 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 4782 Built: 2026 Tax: $4,880 (2025)Community: Conwill EstatesSpa: YesSingle Family
Taxes:$4,880
Elementary School: Lakemont Elem
Tax Year: 2025
Remarks: Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This seamless indoor-outdoor flow creates the ultimate setting for enjoying the Florida lifestyle in style and comfort. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Prentice Williams (321-438-8955)
1821 ENGLEWOOD RD, WINTER PARK, FL 32789
$3,135,000210 Days on yellowkey MLS ID: O6345085
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3863 Built: 2025 Tax: $11,127 (2024)Community: Forest HillsSpa: NoSingle Family
Taxes:$11,127
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,850,00067 Days on yellowkey MLS ID: O6375415
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4288 Built: 1978 Tax: $10,710 (2024)Community: Pervis Survey For R ESpa: NoSingle Family
Taxes:$10,710
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Keigan Lewis (305-393-8683)
218 ORANGE TERRACE DR, WINTER PARK, FL 32789
$600,00038 Days on yellowkey MLS ID: O6388723
0 Days Off yellowkey (back on 4/9/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1618 Built: 1955 Tax: $4,694 (2025)Community: Orange TerraceSingle Family
Taxes:$4,694
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)
Listing Agent: Arden Magee (407-276-1698)
1651 WESTCHESTER AVE, WINTER PARK, FL 32789
$1,449,00014 Days on yellowkey MLS ID: O6384358
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2426 Built: 1938 Tax: $10,973 (2025)Community: Orwin Manor Westminster SecSingle Family
Taxes:$10,973
Remarks: One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or dedicated laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include a re-roof 2020, HVAC System, Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Shawn Layton (321-514-8055)
1336 COLLEGE PT, WINTER PARK, FL 32789
$4,595,000122 Days on yellowkey MLS ID: O6367878
3 Days Off yellowkey (back on 4/9/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3181 Built: 1926 Tax: $36,033 (2025)Community: Virginia HeightsSpa: NoSingle Family
Taxes:$36,033
Remarks: Under contract-accepting backup offers. Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.
119 OAK GROVE RD, WINTER PARK, FL 32789
$285,0008 Days on yellowkey MLS ID: O6397460
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1134 Built: 1994 Tax: $608 (2025)Community: Winter Park OaksSingle Family
Taxes:$608
Elementary School: None
High School: None
Middle School: None
Remarks: Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park. Bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or enteraining. Conveniently located near shopping and dinning.
Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)
Listing Agent: Lorena Ortega (407-256-3631)
423 OLOLU DR, WINTER PARK, FL 32789
$589,00099 Days on yellowkey MLS ID: O6369976
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1920 Built: 1981 Tax: $4,030 (2024)Community: Killarney CircleSingle Family
Taxes:$4,030
Remarks: Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior & interior repaint completed in 2025. Inside, you will find bright, open living spaces and a modern kitchen designed for both everyday living and entertaining. Upstairs, a spacious family room opens to a covered balcony with serene lake views, creating an ideal space to relax or entertain. The flexible layout also allows for two separate living areas, making it well suited for multi-generational living or rental income. Step outside to enjoy the expansive gated yard with plenty of room for gatherings along with ample parking. Conveniently located just minutes from shopping, dining, Downtown Orlando, Downtown Winter Park, Full Sail University, and Rollins College, this home offers an exceptional location. The seller is offering 1% closing cost Buyer credit with a full price offer. Do not miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location. Contact us today to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
1177 KENWOOD AVE, WINTER PARK, FL 32789
$1,870,00035 Days on yellowkey MLS ID: O6390592
REDUCED by $100,000 (5.1%) on 04/01/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4363 Built: 2007 Tax: $16,206 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$16,206
Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
629 COUNTRY CLUB DR, WINTER PARK, FL 32789
$1,695,00048 Days on yellowkey MLS ID: O6386610
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3031 Built: 2026 Tax: $2,028 (2025)Community: Lords SubSpa: NoSingle Family
Taxes:$2,028
Remarks: Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views from the second level. Designer LED ambient lighting is integrated throughout — including illuminated floating stair treads and custom feature shelving — creating a dramatic yet inviting atmosphere. The kitchen is both refined and functional, featuring an oversized island, premium appliances, expansive prep space, and a generous walk-in pantry. The open layout flows seamlessly into the living and dining areas, anchored by a striking fireplace feature wall and wide-plank wood flooring. The primary suite offers a spa-level retreat with a dedicated wet area and freestanding soaking tub, delivering a luxurious, architectural bathroom experience. Designed for entertaining, the outdoor living space includes a private pool and a fully equipped summer kitchen — ideal for Florida living year-round. Additional features include: • Spray foam insulation for superior efficiency • Deeded access to a private boat ramp on Lake Killarney • No HOA dues Located in one of Central Florida’s most desirable neighborhoods, this home is just a short walk or drive to Park Avenue dining, shopping, and entertainment. A rare opportunity to own new construction with architectural character in Winter Park.
Listing is courtesy of: CLASSIC HOMES (407-493-8553)
Listing Agent: Randy Lazarus (407-247-9337)
4190 BEAR GULLY RD, WINTER PARK, FL 32792
$524,900101 Days on yellowkey MLS ID: O6371014
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2058 Built: 2003Monthly Fee: $52 Tax: $5,630 (2024)Community: Bear Gully ForestSingle Family
Taxes:$5,630
Elementary School: Eastbrook Elementary
Remarks: Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.
Listing is courtesy of: ADVANCE REALTY & MANAGEMENT LLC (407-901-3636)
Listing Agent: Craig Swetnam (407-802-0405)
550 PALMER AVE, WINTER PARK, FL 32789
$6,895,000177 Days on yellowkey MLS ID: O6349188
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5939 Built: 2025 Tax: $10,292 (2025)Community: Osceola PlaceSpa: YesSingle Family
Taxes:$10,292
Remarks: Exquisite new construction 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
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: John Mcdade (407-721-7275)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00028 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Gar: 2 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.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
234 DETMAR DR, WINTER PARK, FL 32789
$1,645,00066 Days on yellowkey MLS ID: O6379927
Bed: 5 Bath: 5.5 Gar: 1 Liv Area Sq Ft: 3609 Built: 1935 Tax: $13,664 (2025)Community: Osceola Shores Sec 1Spa: NoSingle Family
Taxes:$13,664
Remarks: Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.
Listing Agent: Nicole Seybold (407-808-9374)
1750 CAROLLEE LANE, WINTER PARK, FL 32789
$1,890,00028 Days on yellowkey MLS ID: O6391179
REDUCED by $105,000 (5.3%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3249 Built: 2012 Tax: $24,658 (2025)Community: Green Terrace V/140 Lot 3 Blk BSingle Family
Taxes:$24,658
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully designed living space, enhanced by a comprehensive series of recent upgrades. The fully renovated 2025 kitchen serves as centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink, refinished cabinetry and designer hardware, all anchored by an expansive island ideal for gathering and entertaining. The first-floor primary suite provides a private retreat, complemented by a completely renovated spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and an upgraded walk-in shower. Additional 2025 renovations include the powder bath and laundry room, along with new lighting, fresh interior paint, plantation shutters and custom built-ins throughout. Designed for comfort and versatility, the home also features a dedicated office and a spacious upstairs loft with a custom built-in dry bar and beverage refrigerator. Outdoor living is equally inviting, with a private backyard oasis featuring a saltwater pool and spa with sun shelf, travertine decking, and a fully equipped outdoor kitchen with quartzite countertops and custom cabinetry. Electronic roll-down screens and updated landscaping, including a Clusia hedge, provide enhanced privacy and year-round enjoyment. Additional improvements include a new downstairs HVAC system, updated irrigation and sod, exterior paint and a whole-home security system. Move-in ready and ideally located, this home offers a seamless blend of modern upgrades and timeless design.
Listing Agent: Michelle Hochfelder (407-221-5073)
675 OVERSPIN DR, WINTER PARK, FL 32789
$775,00067 Days on yellowkey MLS ID: O6378975
0 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3062 Built: 2010 Tax: $11,578 (2025)Community: Dubsdread HeightsSingle Family
Taxes:$11,578
Elementary School: Princeton Elem
Remarks: Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV lights (2025), FRESH INTERIOR PAINT, NEWER WATER HEATER (2021), double-pane windows, and the aerobic septic system was recently serviced (2022). All that is left is to move in and enjoy the lifestyle! This home’s flexible floor plan delivers TWO PRIMARY SUITES – one on the first floor and another upstairs – making it ideal for multi-generational living, in-laws, long-term guests, or simply room to grow. The downstairs suite features a spa-like en-suite bath with dual sinks, a SOAKING TUB, large glass shower, and a WALK-IN/THROUGH CLOSET that connects directly to the main floor laundry. Upstairs, the second suite offers a private bath and direct access to a balcony. The SECOND LAUNDRY ROOM upstairs and huge 30x11 BONUS/UTILITY ROOM provide even more convenience and space. At the heart of the home you will find a GOURMET KITCHEN, crafted with the home chef in mind offering an LG STUDIO REFRIGERATOR, INDUCTION COOKTOP, DOUBLE WALL OVEN, sleek stone counters and a complementary backsplash, upgraded cabinetry, and a large ISLAND with bar seating and chic pendant lighting. The kitchen flows seamlessly into the OPEN LIVING AND DINING AREAS, making everyday living or hosting family and friends a breeze. The LOFT at the top of the stairs delivers additional flexible living space and includes a wet bar with fridge, perfect for a casual hangout space, movie room, office space or anything else you or your family might need. TILE AND WOOD FLOORS, crown molding, and an abundance of natural light give the interior a modern yet timeless feel. Outside you will enjoy stylish curb appeal with a paver driveway – plus a COVERED LANAI overlooking a FENCED BACKYARD, and the spacious lot offers plenty of room for outdoor living. From golf, fine and casual dining to shopping, top-rated schools like Princeton Elementary, and easy access to I-4, 426, and 436, everything you love about Winter Park is right at your fingertips! This home offers the upgrades, the space, and the location you have been waiting for. Call today to schedule a tour and fall in love with your new HOME SWEET HOME!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
4923 N MAGNOLIA AVE, WINTER PARK, FL 32792
$390,00010 Days on yellowkey MLS ID: O6396378
0 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1559 Built: 1953 Tax: $2,479 (2025)Community: Suburban HomesSingle Family
Taxes:$2,479
Remarks: Charming MOVE-IN Ready Solid Block 3 bedroom, 2 bath Winter Park home. This home features updated kitchen and baths, newer flooring, newer Roof- 2021, Water heater-2023, AC-2016. The home has been re-plumbed and offers newer windows-2018. Beautiful Tongue-N-Grove Woodwork covers the ceiling & walls Bonus room/Den. The home offers a split floor plan and is constructed with plaster walls, its solid and energy efficient. The home is zoned for Top-Rated, sought after Winter Park High School, Maitland Middle and Lakemont Elementary. The very best location. This one won't last long..............
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Darlene Chance (407-247-2307)
1127 WILDMEADOW RUN, WINTER PARK, FL 32792
$675,000135 Days on yellowkey MLS ID: O6364368
0 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2196 Built: 2020Monthly Fee: $243 Tax: $6,882 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$6,882
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This is not just a listing—it is the rare, fully-curated luxury opportunity you’ve been waiting for inside Winter Park’s security-gated Hawks Crest community. This 4-Bedroom, 2.5-Bathroom Taylor Morrison home, built just 5 years ago, professionally cleaned and has been elevated by a recent $20,000+ DESIGNER transformation, making it superior to any comparable new construction. We've handled every high-end detail; you simply move in. The curb appeal is instant, featuring freshly trimmed landscaping, a paver driveway and tile roof for longevity. The interior is pure sophistication. The open-concept living area boasts architectural drama, highlighted by stunning, custom-made 18-FOOT CURTAIN DRAPES (a $5,000 investment) that accentuate the room's height. The kitchen is a chef’s dream, centered around the cutting-edge Samsung BESPOKE refrigerator, complemented by refined cabinetry hardware and brand-new, premium plumbing fixtures. Your HOA DUES COVER FITNESS CENTER, POOL, DOCK, CLUBHOUSE, AND FULL LAWN MAINTENANCE, ensuring a low-maintenance, turn-key experience from day one. Every space radiates quality: the new Designer LIGHTING PACKAGE creates the perfect ambiance throughout, while all baths are appointed with sleek contemporary mirrors and modern accents, including a premium Kohler toilet in the Master Suite. Functionality is also premium, featuring a newly installed, $7,000 value of top-quality exterior GUTTERS for superior drainage and protection. Step outside to your private, beautifully constructed enclosed outdoor sanctuary, offering comfortable, year-round enjoyment. The location is unparalleled: less than a short distance from Park Maitland Preschool, Kelly’s Ice Cream, and Foxtail Coffee right at the community entrance. You are moments from everything: 15 minutes to Park Avenue and rapid access to Orlando's best. It is also perfectly positioned for easy access to world-class entertainment, being just 40 minutes from Walt Disney World and Universal's Epic Studios. This is the chance to secure a truly turn-key, designer-finished home in Winter Park, positioned to sell immediately. With a level of finish this immaculate and demand this high. If you want this home, tell your agent to secure your time slot immediately.
Listing Agent: Christopher Beverly (407-394-7424)
5275 PINE LILY CIR, WINTER PARK, FL 32792
$665,00077 Days on yellowkey MLS ID: O6377988
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3152 Built: 2014Monthly Fee: $182 Tax: $7,425 (2024)Community: Sanctuary At AlomaSpa: YesSingle Family
Taxes:$7,425
Remarks: Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. SELLER WILL PAY OFF SOLAR PANELS AT CLOSING! Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kathy Williams (407-230-7305)
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