Location: Winter Park, Winter Park
Do Not Show Listings
938 ENCLAVE PL, WINTER PARK, FL 32792
$2,099,00024 Days on yellowkey MLS ID: O6408090
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3865 Built: 2026Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,900
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2026
Middle School: Maitland Middle
Remarks: Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG Schaub Custom Homes. Nestled beneath mature oak canopies and surrounded by lush natural beauty, this private enclave offers the perfect balance of tranquility, sophistication, and walkable convenience. Ideally located just moments from Phelps Park, the YMCA, premier dining, shopping, and the vibrant charm of downtown Winter Park, residents enjoy an elevated lifestyle in one of Central Florida’s most desirable locations. This stunning custom-designed residence showcases timeless architecture with clean modern farmhouse influences, highlighted by striking curb appeal, refined exterior detailing, and thoughtfully curated landscaping. Inside, exceptional craftsmanship and upscale finishes define every space. Features include high-performance low-E double-pane windows, 8-foot solid-core interior doors, tankless gas water heaters, and an open, livable floor plan designed for both everyday comfort and elegant entertaining. The gourmet kitchen is appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a refined palette of materials and colors. Expansive indoor-outdoor living spaces include a resort-style pool and a fully equipped summer kitchen, creating the ultimate Florida lifestyle experience. Spacious interiors, elevated detailing, and quality construction come together to create a home that is both luxurious and inviting. Buyers still have the opportunity to personalize select finishes and explore certain floor plan modifications. Additional upgrade options may include a detached cabana and/or guest house, subject to lot compatibility, community guidelines, and additional pricing. A rare opportunity to own a truly custom home in one of Winter Park’s most intimate and architecturally distinctive new communities.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Laura Earl (443-994-9441)
942 ENCLAVE PL, WINTER PARK, FL 32792
$2,195,00016 Days on yellowkey MLS ID: O6411550
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3831 Built: 2026Monthly Fee: $372 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Pre-Construction. To be built. 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. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing Agent: Matthew Burks (407-257-5347)
950 ENCLAVE PL, WINTER PARK, FL 32792
$2,125,00016 Days on yellowkey MLS ID: O6410963
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3797 Built: 2027Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Remarks: Pre-Construction. To be built. Discover refined modern living in The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 custom residences by FG Schaub Custom Homes. Tucked beneath mature oak canopies and surrounded by lush natural beauty, this intimate neighborhood offers a rare blend of privacy, walkability, and timeless architectural design. Ideally located just moments from Phelps Park, the YMCA, exceptional dining, boutique shopping, and the cultural attractions of downtown Winter Park, The Enclave delivers an elevated lifestyle in one of Central Florida’s most sought-after locations. This striking custom residence showcases contemporary architecture with clean lines, dramatic windows, and exceptional curb appeal. Thoughtfully designed for both everyday living and upscale entertaining, the home features expansive open-concept spaces, soaring ceilings, and seamless indoor-outdoor flow. Every detail reflects superior craftsmanship and designer-selected finishes curated to create a timeless yet modern aesthetic. Luxury appointments include premium Wolf and Sub-Zero appliances, high-performance low-E double-pane windows, 8-foot solid-core interior doors, and tankless gas water heaters for comfort and efficiency. Spacious living areas are complemented by a resort-style outdoor experience featuring a sparkling pool and a fully equipped summer kitchen, ideal for year-round entertaining. Beautifully landscaped grounds and quality construction create a private retreat while remaining connected to the very best of Winter Park living. Buyers still have the opportunity to personalize select finishes and explore certain floor plan modifications. Optional upgrades may include a detached cabana and/or guest house, subject to lot compatibility, community guidelines, and additional pricing. A rare opportunity to build a truly custom luxury home within one of Winter Park’s most exclusive new communities.
946 ENCLAVE PL, WINTER PARK, FL 32792
$2,175,00016 Days on yellowkey MLS ID: O6411633
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3989 Built: 2026Monthly Fee: $375 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$735,0005 Days on yellowkey MLS ID: S5151458
0 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1739 Built: 1925 Tax: $2,730 (2025)Community: Winter ParkSingle Family
Taxes:$2,730
Elementary School: Audubon Park K8
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Justin Jodha (689-250-8606)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$519,9005 Days on yellowkey MLS ID: O6415084
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1565 Built: 1963 Tax: $7,101 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$7,101
Elementary School: Brookshire Elem
Remarks: GREAT HOME & GREAT VALUE — add your TLC and DIY and you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
1695 LEE RD #E116, WINTER PARK, FL 32789
$110,00040 Days on yellowkey MLS ID: O6399346
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $15,000 (12.0%) on 06/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966Monthly Fee: $624 Tax: $2,263 (2025)Community: Waterfall Cove/Winter ParkCondo
Taxes:$2,263
Remarks: Under contract-accepting backup offers. Located in the heart of Winter Park, this 3-bedroom, 2-bathroom condo offers an excellent opportunity for both investors and buyers looking to customize a space in a highly desirable location. Whether you’re looking to renovate and create a strong rental or take advantage of the value for a primary residence, the potential here is undeniable. Inside, the spacious living and dining areas are filled with natural light, creating an open and inviting layout. The split floor plan offers three generously sized bedrooms, each with ample space and storage. A dedicated laundry room with washer and dryer adds everyday convenience. Step outside to your private courtyard with peaceful pond views, offering a quiet place to enjoy your morning coffee or unwind in the evening. The community features a pool, clubhouse, and well-maintained common areas, creating a welcoming environment for residents. This pet-friendly community also includes cable and high-speed internet through the HOA. Ideally located just minutes from shopping, dining, and major roadways including I-4, with easy access to downtown Orlando, area beaches, and theme parks. A great opportunity to own in Winter Park with flexibility, location, and value.
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Cara Edwards (407-616-3204)
119 OAK GROVE RD, WINTER PARK, FL 32789
$285,00065 Days on yellowkey MLS ID: O6397460
0 Days Off yellowkey (back on 4/11/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1134 Built: 1994 Tax: $608 (2025)Community: Winter Park OaksSingle Family
Taxes:$608
Remarks: OPEN HOUSE CANCELLED. 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 entertaining. 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)
505 CORNWALL RD, WINTER PARK, FL 32792
$675,00024 Days on yellowkey MLS ID: O6408759
1 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1813 Built: 1965 Tax: $7,194 (2025)Community: Winter Park PinesSingle Family
Taxes:$7,194
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated four-bedroom, two-bathroom pool home offering 1,813 square feet of thoughtfully designed living space in one of Winter Park’s most desirable locations. Perfectly positioned on a spacious lot backing up to the scenic Cady Way Trail, this residence seamlessly blends modern updates, timeless charm, and exceptional outdoor living. Inside, the versatile floor plan includes a dedicated den, office, or playroom, ideal for today’s flexible lifestyle needs. Engineered hardwood flooring flows throughout the home and is complemented by recessed lighting, crown molding, plantation shutters, ceiling fans, and elegant French doors that add warmth and character to every space. A spacious laundry/utility room offers additional storage and convenience, complete with a washer and dryer replaced in 2024. The beautifully remodeled kitchen, updated in 2020, serves as the heart of the home and showcases white shaker-style cabinetry, sleek black granite countertops, matte grey stainless steel appliances, a striking herringbone tile backsplash, and a charming exposed wood beam feature that adds architectural interest. A breakfast bar with seating for three creates the perfect gathering space for casual dining and entertaining, while the spacious dining room easily accommodates sit-down meals and larger gatherings. The private primary suite offers a relaxing retreat featuring a shiplap accent wall, ceiling fan, and an updated ensuite bathroom remodeled in 2020 with a single vanity and beautifully tiled shower with a glass partition. The secondary bedrooms are generously sized and share an updated hall bathroom featuring a tiled tub and shower combination along with a contemporary single vanity. Step outside into your own backyard oasis where a screened, heated, salt-generated pool installed in 2022 creates the ultimate setting for year-round enjoyment. The fully fenced backyard, updated in 2022, offers privacy and plenty of room for pets, play, and entertaining while overlooking the picturesque Cady Way Trail. A private gate provides direct access to the trail, allowing for convenient access to Brookshire Elementary and nearby community amenities. Additional exterior highlights include a spacious two-car carport, whole-house generator hookup, and two included storage sheds providing excellent functionality and additional storage space. This exceptional location places you just minutes from some of Central Florida’s most sought-after amenities including the Winter Park Pines Golf Course, the Cady Way Trail, and the popular Cady Way recreational amenities featuring a community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Conveniently located near University of Central Florida, Rollins College, and Full Sail University, this home also offers quick access to AdventHealth Winter Park and the Crosby Wellness Center, both less than five minutes away, while Orlando International Airport is approximately 25 minutes from home. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this property offers an incredible opportunity to enjoy the very best of Winter Park living. ROOF - 2014 HVAC - 2023 ELECTRICAL - 2021(new panel)
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
650 DOUGLAS AVE, WINTER PARK, FL 32789
$550,0005 Days on yellowkey MLS ID: O6414807
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1280 Built: 2003 Tax: $7,799 (2025)Community: Winter ParkSingle Family
Taxes:$7,799
Remarks: Welcome to 650 Douglas Avenue, a beautifully updated 3-bedroom, 2-bath home ideally situated in one of Winter Park’s most desirable locations. This move-in-ready residence features luxury vinyl plank flooring throughout, quartz countertops, updated bathrooms with upgraded tile, modern lighting and plumbing fixtures, fresh interior paint, and a complete appliance package including washer and dryer. Beyond the home’s tasteful updates, the location truly sets it apart. Enjoy being just minutes from the vibrant shops, restaurants, and community events of Hannibal Square and renowned Park Avenue. Spend weekends exploring Winter Park’s award-winning dining, boutique shopping, farmers markets, museums, and picturesque parks, all just moments from your doorstep. This home offers the perfect combination of modern updates, walkable convenience, and the unmatched Winter Park lifestyle. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Danielle Funaro (407-276-0326)
418 GILBERT RD, WINTER PARK, FL 32792
$710,00079 Days on yellowkey MLS ID: O6385950
REDUCED by $9,000 (1.3%) on 06/02/2026
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)
1319 BESSMOR RD, WINTER PARK, FL 32789
$589,00053 Days on yellowkey MLS ID: O6400395
REDUCED by $6,000 (1.0%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1126 Built: 1956 Tax: $5,626 (2025)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$5,626
Elementary School: Dream Lake Elem
Remarks: Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.
Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)
Listing Agent: Sidney Galloway (407-421-9990)
193 LEWFIELD CIR, WINTER PARK, FL 32792
$248,90018 Days on yellowkey MLS ID: O6409075
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1300 Built: 1973Monthly Fee: $533 Tax: $2,286 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$2,286
Remarks: Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms, recessed lighting, ceiling fans, and sliding glass doors that bring in natural light. The kitchen offers ample cabinet storage, stainless steel appliances, tile flooring, and a functional pass-through breakfast bar that opens to the main living area, creating a seamless layout for everyday living and entertaining. Upstairs, the oversized primary suite includes a walk-in closet, private en-suite bathroom, and generous floor space, while the secondary bedroom also features wood-look flooring, natural light, and easy access to the second full bathroom. Additional highlights include inside laundry, updated lighting fixtures, open parking, and plenty of storage throughout. Residents enjoy access to community amenities including a pool, fitness center, tennis courts, sidewalks, and maintained grounds, with HOA dues covering water, exterior maintenance, recreational facilities, and grounds maintenance. Conveniently located near Howell Branch Rd and SR 436, this Winter Park townhome provides quick access to shopping, dining, Downtown Winter Park, Maitland, Full Sail University, UCF, and Downtown Orlando. Located near highly rated Seminole County schools, parks, restaurants, and everyday conveniences, this property offers low maintenance living in a well-connected Central Florida location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Efrain Reyes (407-575-4226)
413 W MORSE BLVD, WINTER PARK, FL 32789
$2,695,0007 Days on yellowkey MLS ID: O6412134
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3048 Built: 2018Monthly Fee: $386 Tax: $19,919 (2026)Community: Town Of Winter ParkTownhouse
Taxes:$19,919
Remarks: LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Av Blalock (407-579-9056)
1404 BORDER DR, WINTER PARK, FL 32789
$1,200,00015 Days on yellowkey MLS ID: O6412140
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2469 Built: 2023 Tax: $16,220 (2025)Community: Winter Park VillageSingle Family
Taxes:$16,220
Elementary School: Dommerich Elem
Remarks: Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
2756 SHERIFF WAY, WINTER PARK, FL 32792
$595,00046 Days on yellowkey MLS ID: O6402570
0 Days Off yellowkey (back on 6/6/2026)
REDUCED by $30,000 (4.8%) on 06/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1812 Built: 1965 Tax: $5,547 (2025)Community: Winter Park PinesSingle Family
Taxes:$5,547
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. **$30,000 Price Improvement!! Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you’ll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE—perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you’re hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!
Listing is courtesy of: PALM CIRCLE REALTY (352-988-4975)
Listing Agent: Kasey Hilyard, Pllc (407-488-9879)
2430 CHANTILLY AVE, WINTER PARK, FL 32789
$1,665,00030 Days on yellowkey MLS ID: O6401352
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 2026 Tax: $4,730 (2025)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$4,730
Remarks: Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
2829 ALOMA, WINTER PARK, FL 32792
$579,00043 Days on yellowkey MLS ID: O6404107
2 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1821 Built: 1963 Tax: $4,277 (2025)Community: Winter Park EstatesSingle Family
Taxes:$4,277
Remarks: Under contract-accepting backup offers. Under contract but accepting back up offers – 2829 Aloma Avenue, Winter Park This is the one you’ve been waiting for. A completely remodeled home with a private pool in one of the most desirable areas of Central Florida—all for under $600,000. Enjoy the perfect blend of modern upgrades and unbeatable location, just minutes from top-rated restaurants, shopping, excellent schools, and everything that makes Winter Park so special. 4 Bedrooms + Den 2 Bathroom 1,821 Sq Ft Private Pool (Resurfaced) + New Pump Fully Renovated Homes like this don’t come around often—whether you’re looking for your primary residence or a smart investment, this property checks every box. If you want a home that delivers both lifestyle and location, this is your opportunity. ?? Message me today for more details or to schedule your private showing before it’s gone!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Roberto Silva (407-493-3683)
715 S RANGER BLVD, WINTER PARK, FL 32792
$695,00018 Days on yellowkey MLS ID: O6410899
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2312 Built: 1967Monthly Fee: $4 Tax: $2,773 (2025)Community: Winter Park PinesSingle Family
Taxes:$2,773
Remarks: Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!
Listing is courtesy of: DAHLIA REALTY GROUP (689-777-4111)
Listing Agent: Chuck Tolfa (407-782-3518)
330 ELKHORN CT, WINTER PARK, FL 32792
$549,900139 Days on yellowkey MLS ID: O6376757
REDUCED by $5,000 (0.9%) on 06/04/2026
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 home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.