Displaying: For Sale
Location: Winter Park
Property Type(s): Single Family
Price: $700,000 to $799,000
Do Not Show Listings
Winter Park - 18 properties found
1701 GOODRICH AVE, WINTER PARK, FL 32789
$739,00014 Days on yellowkey MLS ID: O6400278
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1528 Built: 1950 Tax: $5,023 (2025)Community: Sylvan HgtsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,023
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system updates have been completed, including a 2024 metal roof and 2025 HVAC system, providing peace of mind for the next owner. Additional exterior improvements include new soffits and gutters, fresh exterior paint in 2025, a whole-home surge protector, and updated breezeway or office door and windows installed in 2024. Inside, you will find a well-equipped kitchen with Samsung appliances, including a range, microwave, dishwasher and a 2023 refrigerator, along with a 2020 Samsung washer and dryer. Comfort and efficiency have also been enhanced with replaced air ducts in 2016, an Ecobee smart thermostat and updated ceiling fans. Smart home features include a Logitech Circle View wired doorbell, smart blinds and updated smoke detectors, providing modern convenience throughout the home. The property sits toward the rear of the lot, creating a private, fenced yard space ideal for pets, outdoor enjoyment or entertaining. An irrigation system is also in place to help maintain the landscaping. In the desirable Winter Park area and zoned for highly regarded Winter Park schools, this home offers a combination of location, updates and flexibility. With major systems addressed, this home presents a move-in-ready opportunity and being sold as is.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Audra Wilks (407-252-8582)
1550 NORFOLK AVE, WINTER PARK, FL 32789
$725,0004 Days on yellowkey MLS ID: O6402927
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1762 Built: 1949 Tax: $3,951 (2025)Community: Orwin Manor Stratford SecSingle Family
Taxes:$3,951
Elementary School: Princeton Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Welcome to this exceptional residence at 1550 Norfolk Ave, perfectly positioned in the highly sought-after Orwin Manor neighborhood of Winter Park. Set on a spacious corner lot, this beautifully maintained home offers 3 bedrooms and a rare 3-car garage, combining comfort, functionality, and timeless appeal. Inside, you’ll find rich hardwood floors, plantation shutters, and an extra-large family room ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry with convenient pull-out drawers, balancing style and efficiency. This home also embraces modern sustainability solar panels power the entire property, providing clean energy year-round and the capability to continue powering the home for approximately 24 hours in the event of a power outage. Peace of mind comes from thoughtful updates, including new windows (2022), new garage doors (2023), a roof replaced in (2014), and new insulation installed in (2025) to enhance energy efficiency. Step outside to your private retreat a fully fenced backyard with a sparkling pool and spa, where the spa is heated using natural gas, offering comfort and relaxation at any time of year. An outstanding opportunity to own a well-appointed, energy-efficient home in one of Winter Park’s most desirable neighborhoods.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kevin Mcclanahan (407-491-8509)
688 BRECHIN DR, WINTER PARK, FL 32792
$724,9004 Days on yellowkey MLS ID: O6403080
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 1961 Tax: $6,760 (2025)Community: Kenilworth Shores Sec 04Spa: NoSingle Family
Taxes:$6,760
Remarks: Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this four-bedroom, two-bath Florida ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready-to-move-in home. A gorgeous brick fireplace anchors an open kitchen, family and dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated main bath. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs such as home office, guest room, playroom or secondary family space. Go into the backyard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable and effortlessly low maintenance), complete with a putting green that will make this yard the destination for every playdate, summer barbecue or birthday party. Completed upgrades include new roof (2021), resurfaced pool (2021), new irrigation and well (2022), new wood fence (2023), new dishwasher and built-in microwave (2023), HVAC (late 2023), new washer and dryer (2024), and new pool pump motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle and WP High, some of the best Orange County Schools. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. This location checks all the boxes. Schedule your private showing today.
Listing Agent: Alison Mosley (407-304-6458)
418 GILBERT RD, WINTER PARK, FL 32792
$729,00039 Days on yellowkey MLS ID: O6385950
REDUCED by $11,000 (1.5%) on 05/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1964 Tax: $9,094 (2025)Community: Winter Park Pines Ut 5Single Family
Taxes:$9,094
Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
1437 MILLER AVE, WINTER PARK, FL 32789
$750,0004 Days on yellowkey MLS ID: O6403858
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2150 Built: 1932 Tax: $6,987 (2025)Community: LawndaleSingle Family
Taxes:$6,987
Elementary School: None
High School: None
Middle School: None
Remarks: A rare infill opportunity in one of Central Florida's most desirable communities. This 0.32 acre double lot is zoned R-2 and subdivides into two buildable parcels, each ready for a custom single-family residence or duplex, offering up to four doors in a market where new construction consistently performs. Winter Park is a proven, high-demand submarket with limited land supply, top-rated schools, and strong price-per-square-foot on finished product. The location offers easy access to 17/92, Park Avenue, Rollins College, and the established neighborhood character that defines the best of Winter Park living. Opportunities like this are increasingly scarce as the city continues to fill in. Contact us today to discuss lot dimensions, zoning details, and next steps.
Listing is courtesy of: ORLANDO REAL ESTATE LLC (321-217-8572)
Listing Agent: Rodger Marty (321-217-8572)
1108 FAIRWAY DR, WINTER PARK, FL 32792
$725,00066 Days on yellowkey MLS ID: O6386266
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1978 Tax: $6,713 (2024)Community: Golfside Sec 03Single Family
Taxes:$6,713
Tax Year: 2024
Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rene Droz, Iii (407-484-8786)
350 CORNWALL RD, WINTER PARK, FL 32792
$775,00036 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: One or more photo(s) has been virtually staged. 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-Dumpster to be removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/09.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Butterfield (407-463-1289)
2681 FITZHUGH RD, WINTER PARK, FL 32792
$750,00074 Days on yellowkey MLS ID: O6383699
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1966 Tax: $5,903 (2024)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$5,903
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Rebecca Bininger Junod (407-230-3650)
639 FRIAR RD, WINTER PARK, FL 32792
$795,00032 Days on yellowkey MLS ID: O6395715
1 Days Off yellowkey (back on 4/20/2026)
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
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)
1340 BLUE STEM LN, WINTER PARK, FL 32792
$724,900125 Days on yellowkey MLS ID: O6365415
0 Days Off yellowkey (back on 4/17/2026)
REDUCED by $5,000 (0.7%) on 04/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2587 Built: 2022Monthly Fee: $235 Tax: $6,594 (2025)Community: Landings At Hawks CrestSingle Family
Taxes:$6,594
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Located within the gated community of Hawk’s Crest, one of Winter Park’s most desirable neighborhoods, this beautifully maintained two-story home is set on an oversized lot with tranquil pond views and a layout designed to live effortlessly. Light-filled, open, and thoughtfully upgraded, the home offers a balance of comfort, style, and everyday functionality. A pavered driveway and walkway create an inviting arrival, leading into a bright interior with soaring ceilings and abundant natural light. The main living space flows seamlessly, anchored by a chef’s kitchen featuring quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous island with breakfast bar—perfect for casual meals, entertaining, or gathering at the end of the day. The kitchen opens naturally to the dining and family rooms, creating a connected space that feels both open and welcoming. Sliding doors lead to a covered lanai overlooking the pond, extending the living space outdoors and providing a peaceful backdrop for morning coffee or evening relaxation. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and a polished finish throughout the main living areas. The first-floor primary suite offers a private retreat with serene water views, a spacious walk-in closet, and a spa-inspired bath with dual vanities and a walk-in shower. A dedicated office on the main level adds flexibility and can easily function as a fifth bedroom if needed. Upstairs, a generous loft provides additional living space—ideal for a media room, play area, or secondary lounge—while three well-sized bedrooms offer comfort and versatility for guests, hobbies, or working from home. Energy-efficient features, ample storage, and thoughtful design make the home as practical as it is inviting. Residents of Hawk’s Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playgrounds, and scenic walking paths, along with HOA-included lawn care for low-maintenance living. Ideally situated near shopping, dining, outdoor recreation, and major roadways, this home offers both convenience and a sense of retreat within Winter Park. Come experience the lifestyle and setting that make this home truly special—schedule your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Beth Hobart (407-227-8192)
2919 BOWER RD, WINTER PARK, FL 32792
$779,00046 Days on yellowkey MLS ID: O6391025
3 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 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 Agent: Nick Mckee (407-913-0171)
676 DUNBLANE DR, WINTER PARK, FL 32792
$750,000150 Days on yellowkey MLS ID: O6365557
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 1962 Tax: $5,584 (2024)Community: Kenilworth Shores Sec 04Single Family
Taxes:$5,584
Remarks: This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as a home office, creative studio, workout space or playroom — all with tranquil views of the pool and backyard. The property features a beautifully landscaped, fully fenced yard and a private pool area, perfect for entertaining, relaxing, or enjoying the Florida lifestyle. Originally updated in 2012, the home benefits from a well-balanced and comfortable floorplan, complemented by key mechanical upgrades including a newer HVAC system and roof, and a brand-new water heater installed in 2024. With these major updates already completed, the property is truly move-in ready — offering peace of mind and lasting value. Don’t miss your opportunity to own a beautifully maintained home in a location that continues to deliver on both lifestyle and convenience. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, the location also offers close proximity to top institutions and amenities, including Rollins College (2.3 miles), Full Sail University (2.4 miles), AdventHealth Winter Park (0.9 miles), and the VA Medical Center (1.3 miles). Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, all within a short drive, offering walking paths, open green space, and recreational opportunities. ASSUMABLE VA LOAN at 2.25% Interest Incredible opportunity to assume the seller’s VA mortgage at just 2.25% interest. Just minutes from the vibrant centers of Baldwin Park and Park Avenue, this property provides convenient access to an array of restaurants, boutique shops, cafés, and year-round events. 676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY!
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Emma Kaplan (407-942-7542)
675 OVERSPIN DR, WINTER PARK, FL 32789
$775,00084 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
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)
781 NORTHWOOD CIR, WINTER PARK, FL 32789
$775,00033 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
Middle School: Maitland Middle
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)
1418 LONE FEATHER TRL, WINTER PARK, FL 32792
$759,99993 Days on yellowkey MLS ID: O6378636
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2197 Built: 2022Monthly Fee: $235 Tax: $5,856 (2024)Community: Landings At Hawks CrestSingle Family
Taxes:$5,856
Remarks: *** Seller will contribute $5k towards Buyer's closing costs with an acceptable offer.*** Welcome to the stunning 4 bedroom, 2.5 bath home known as 1418 Lone Feather Trail. This open concept home is nestled in the desirable, gated community of Landings at Hawks Crest. This well appointed two-story home boasts a lot of upgrades including; gourmet kitchen, upgraded cabinets, quartz countertops, stainless steel appliances, spacious rooms, and luxurious tile throughout the first floor with carpet upstairs, just to name a few! Wake up and enjoy a nice cup of tea relaxing under your covered lanai or unwind in the evening under the stars. Conveniently located near shopping, dining, and major roadways which provide quick and seamless connections to Downtown Winter Park, Oviedo, and Orlando! The community amenities include a substantial clubhouse featuring a pool, fitness area, playground and scenic walking trails.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
770 W WEBSTER AVE, WINTER PARK, FL 32789
$725,000305 Days on yellowkey MLS ID: O6323574
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1967 Tax: $4,856 (2024)Community: Capens AddSingle Family
Taxes:$4,856
Remarks: Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.
Listing Agent: Lisa Gould (407-721-7612)
2222 MARSH SEDGE LN, WINTER PARK, FL 32792
$764,900271 Days on yellowkey MLS ID: O6333145
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2192 Built: 2019Community: Preserve At Hawks CrestSingle Family
Taxes:
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Remarks: Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent space for family gatherings. Other features include a walk-in pantry and fantastic lighting. The luxurious kitchen integrates with the dining and living areas. The dining area is enhanced by a screened-in deck overlooking a pond. The backyard features a new, large, extended patio for entertaining. The master bedroom has an ensuite bathroom with a double vanity, a small closet, and a large walk-in closet that can be customized for a future owner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with a clubhouse, a splash pad, a fitness center, barbecue grills, playgrounds, a dog park, and a community fishing pier with views and access to beautiful Lake Howell. Nearby, you'll find shops, restaurants, and specialty physicians such as Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry, and the Park Maitland Preschool Campus, along with excellent schools in the area. Enjoy a short drive to Downtown Winter Park, with its extensive dining and shopping options. Hawk's Crest is also very close to Rollins College and UCF. Schedule your private tour today!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carmen Molina (321-331-5679)
2625 SUMMERFIELD RD, WINTER PARK, FL 32792
$724,900 MLS ID: O6384757
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2199 Built: 1968Community: Golfside Golf Course Sec 01Single Family
Remarks: Under contract-accepting backup offers. Welcome to 2625 Summerfield Rd in Winter Park, FL. A beautifully maintained pool home on one of Winter Park’s most picturesque tree-lined streets. What makes this home so rare? It has 5 bedrooms, 3 full bathrooms, a split floor plan, and a private pool with full screen enclosure in a highly sought-after Winter Park location. That combination is incredibly hard to find in Winter Park, Florida. The split-bedroom floor plan provides privacy and functionality. The spacious primary suite opens directly to the pool and features generous closet space. A convenient Jack and Jill bathroom connects two secondary bedrooms, while a dedicated pool bath adds flexibility for guests and entertaining. New tile flooring throughout most of the home creates a clean, cohesive look. Formal living and dining rooms provide elegant gathering spaces, centered around a charming fireplace focal point. The kitchen offers Corian countertops, warm cabinetry, and a functional breakfast bar overlooking the family room. Sliding glass doors lead to the private pool with full screen enclosure, waterfall feature, and variable speed pump, all surrounded by a fenced yard with mature privacy hedges. Major system updates include a 2022 roof, 2021 water heater, automated hurricane shutters, backup generator, upgraded alarm system, and refreshed attic insulation. Ideally located near Winter Pines Golf Club, Park Avenue dining and shopping, AdventHealth Winter Park, and the Crosby Wellness Center. Enjoy easy access to the Cady Way walking and biking trail, nearby parks, pickleball courts, Rollins College, UCF, Full Sail University, Baldwin Park, and Orlando International Airport. This address reflects the walkable charm, tree-lined beauty, and established character that make Winter Park one of Central Florida’s most admired communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
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