Location: Winter Park , 32792
Do Not Show Listings
1082 WILDMEADOW RUN, WINTER PARK, FL 32792
$650,00037 Days on yellowkey MLS ID: O6408825
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2021Monthly Fee: $170 Tax: $5,154 (2025)Community: Meadows At Hawks CrestSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,154
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Tucked within the sought-after gated community of Hawk’s Crest, this beautifully appointed residence blends timeless design with effortless everyday living. Showcasing a light and airy open concept floor plan, the home features elegant flooring, crown molding, designer lighting, plantation shutters and custom window treatments, and expansive living spaces filled with natural light. The chef’s kitchen serves as the heart of the home with oversized white-quartz countertops, 42-inch cabinetry, stainless steel appliances, a spacious walk-in pantry, and a large center island ideal for gathering and entertaining. The private owner’s retreat offers peaceful backyard views, a spacious custom-designed walk-in closet and a spa-inspired bath complete with dual vanities, quartz countertops and a glass enclosed shower. The home also features a versatile flex space offering endless possibilities such as a home office, private study, additional bedroom or inviting lounge area. Designed to embrace Florida living, the screened-in covered lanai creates the ideal setting to relax and unwind while overlooking the freshly landscaped backyard and tranquil greenery beyond. Additional enhancements include epoxy garage flooring, custom garage shelving and gutters, adding functionality and convenience. Residents of Hawk’s Crest enjoy access to an impressive collection of resort-style amenities including a clubhouse, fitness center, resort pool, splash pad, playgrounds, dog park, food trucks, a virtual guard-gate and private access to Lake Howell. Ideally near Park Maitland Preschool, Kelly’s Ice Cream, Foxtail Coffee and major roadways, this exceptional home offers a balance of luxury, comfort and convenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Harif Hazera Llc (407-953-9098)
1926 NATALEN RD, WINTER PARK, FL 32792
$638,900113 Days on yellowkey MLS ID: O6388308
3 Days Off yellowkey (back on 6/8/2026)
REDUCED by $1,000 (0.2%) on 05/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1469 Built: 1957 Tax: $7,308 (2024)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,308
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.
Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)
Listing Agent: Joseph Cosgrove (407-470-0892)
418 GILBERT RD, WINTER PARK, FL 32792
$710,00093 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)
1923 LINDEN RD, WINTER PARK, FL 32792
$450,00089 Days on yellowkey MLS ID: O6393643
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $25,000 (5.3%) on 05/19/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2117 Built: 1955 Tax: $340 (2024)Community: Tanglewood Sec 4Single Family
Taxes:$340
Elementary School: None
High School: None
Middle School: None
Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Milton James (407-572-4458)
2808 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,00028 Days on yellowkey MLS ID: O6410294
0 Days Off yellowkey (back on 6/7/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $6,126 (2025)Community: Grayson SquareTownhouse
Taxes:$6,126
Remarks: Under contract-accepting backup offers. Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Sean Flatley (609-208-8204)
4772 TANGERINE AVE #4772, WINTER PARK, FL 32792
$199,00050 Days on yellowkey MLS ID: O6405042
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,825 (2025)Community: Wrenwood CondoCondo
Taxes:$2,825
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Great opportunity to own this RENOvated and Move-IN ready 2 bedroom 2 bathroom one-story condo in sought after Winter Park location. This Condo has Special Streamlined Approval for Conventional Financing and is eligible for a discounted interest rate!! Whether you’re looking to establish roots, downsize to something simpler or an investment property, this size unit, floor plan and location fits the bill. Enjoy the recently updated kitchen and two bathrooms along with tile flooring. AND all major mechanical updates already taken care of with a New Roof, Updated Electrical, Newer A/C, Replaced Water Heater and so much more... plus the community amenities include a pool, sidewalks, pet stations, and a short distance to restaurants, grocery stores, shopping and biking distance to Full Sail.
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: Lori Hutchinson (321-377-7026)
3312 HEARTWOOD AVE, WINTER PARK, FL 32792
$465,000252 Days on yellowkey MLS ID: O6352582
2 Days Off yellowkey (back on 6/8/2026)
REDUCED by $19,000 (3.9%) on 04/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 1983 Tax: $2,183 (2025)Community: Bel-Aire PinesSpa: NoSingle Family
Taxes:$2,183
Elementary School: Aloma Elem
Remarks: One or more photo(s) has been virtually staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.
Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)
Listing Agent: Stacy Morano (561-843-9537)
1052 MANCHESTER CIR, WINTER PARK, FL 32792
$460,000154 Days on yellowkey MLS ID: O6376260
REDUCED by $10,000 (2.1%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1703 Built: 1983 Tax: $5,216 (2025)Community: Howell Estates 1St AddSingle Family
Taxes:$5,216
Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!
Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)
Listing Agent: Yuleisy Marquez (407-937-8450)
4768 TANGERINE AVE #4768, WINTER PARK, FL 32792
$179,000123 Days on yellowkey MLS ID: S5144503
REDUCED by $6,000 (3.2%) on 05/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1973Monthly Fee: $280 Tax: $1,479 (2024)Community: Wrenwood CondoCondo
Taxes:$1,479
Remarks: Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Christopher Franqui (347-703-7008)
193 LEWFIELD CIR, WINTER PARK, FL 32792
$248,90032 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)
121 STEFANIK RD, WINTER PARK, FL 32792
$317,500248 Days on yellowkey MLS ID: A4669103
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1949 Tax: $3,581 (2024)Community: Slovak VillageSingle Family
Taxes:$3,581
Remarks: A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. Third bedroom has its own separate entrance as well. Large foyer and living room. Kitchen has beautiful 40 inch cabinets and granite counter tops. Septic system was just replaced in September. Close to everything.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
2756 SHERIFF WAY, WINTER PARK, FL 32792
$595,00060 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
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)
7444 WOODBURN CT #29, WINTER PARK, FL 32792
$165,000321 Days on yellowkey MLS ID: S5131940
0 Days Off yellowkey (back on 4/10/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1983 Tax: $2,549 (2024)Community: Hidden Oaks Condo Ph 02Townhouse
Taxes:$2,549
Remarks: Under contract-accepting backup offers. Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to Valencia College, 25 minutes to UCF, 30 minutes to Disney World. Top schools such as Aloma Elementary, Glenridge Middle School, and Winter Park High School. Whether you're looking for a place to call home or a smart investment, this gem combines timeless design, modern updates, and unbeatable location. Don’t miss this opportunity!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Abranette Lopez (773-858-1141)
2829 ALOMA, WINTER PARK, FL 32792
$579,00057 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 Agent: Roberto Silva (407-493-3683)
508 DUNRAVEN DR, WINTER PARK, FL 32792
$595,00025 Days on yellowkey MLS ID: O6412363
0 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1958 Tax: $2,281 (2025)Community: Kenilworth Shores Sec 03Single Family
Taxes:$2,281
Remarks: Welcome to this stylishly renovated ranch-style pool home in Kenilworth Shores, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and you'll immediately feel the warmth of the home. The renovated kitchen is truly the heart of the space, beautifully designed with stylish tile backsplash, stainless steel appliances, mission style cabinetry, bar seating, and an additional coffee or wine bar area that makes the space feel both functional and elevated. Open to the living room, the kitchen creates an easy flow for everyday living and entertaining. The home has been thoughtfully updated throughout with new flooring, plantation shutters, renovated bathrooms, and designer touches that give the home a fresh, modern feel while still keeping all the charm of a classic Winter Park ranch. A dining room along the back of the home offers views of the yard and access to the covered lanai and custom pergola overlooking the pool. This is truly a backyard retreat! The sparkling pool is surrounded by pavers, lush landscaping, bamboo for privacy, and a fully fenced yard. The covered lanai and custom pergola create the perfect setting for morning coffee, quiet evenings, or hosting friends by the pool. This is the kind of backyard that makes Florida living feel easy. A large storage area and laundry room provide extra space for bikes and yard tools just off the carport. The bedrooms are tucked together along the hall, with the primary bedroom positioned on the back of the home for privacy, with an additional bathroom featuring an updated vanity and shower and a door to the pool area. The additional bedrooms share the hall bathroom with stylish modern updates including all new tile, a frameless glass shower, vanity, and fixtures. The thoughtfully designed spaces feel modern while also remaining timeless and classic. Other notable additions over the years include a metal roof, irrigation on well, lush landscaping, and a refinished pool with tile surround. The 2-car carport provides plenty of covered parking for rainy days! Located in the City of Winter Park, this home offers incredible access to Park Avenue shopping and dining, Audubon Park with Michelin-star restaurants and local favorites, Sprouts Market, Lake Baldwin Dog Park, nearby parks, coffee shops, boutiques, and more. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. Style, location, privacy, sparkling pool! This Winter Park home checks all the boxes. Schedule your private showing today!
Listing Agent: Kathryn Stelljes (407-982-7240)
7470 CANFORD CT #23, WINTER PARK, FL 32792
$245,900225 Days on yellowkey MLS ID: O6360198
REDUCED by $3,000 (1.2%) on 06/05/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1580 Built: 1974Monthly Fee: $575 Tax: $3,119 (2024)Community: Whisperwood CondoTownhouse
Taxes:$3,119
Remarks: New updates, a new fence, and extra outdoor space on a desirable corner lot. Beautifully updated 3 bedroom, 2.5 bath corner unit townhome located in the heart of Winter Park, offering 1,580 square feet of bright and open living space. This home features a deluxe vinyl-fenced backyard with plenty of privacy and no rear neighbors. The property is currently tenant occupied,making it a great investment opportunity and the tenants are ready to move out after the sale. The spacious living area features sliding doors that open to the private fenced courtyard, perfect for relaxing or entertaining. The kitchen includes modern appliances and plenty of cabinet space and overlooks the dining and living rooms, creating an easy and open flow. The AC system was replaced in 2022, and the new roof was recently replaced by the HOA in 2024 Upstairs, you will find generously sized bedrooms with great natural light, updated bathrooms, and excellent storage space. The home also offers an assigned covered parking space, inside laundry hookups, and a low-maintenance lifestyle. The HOA includes water, sewer, trash, exterior maintenance, and access to the community pool. Conveniently located just minutes from Full Sail, UCF, Sam’s Club, Costco, Winter Park shopping and dining, and major highways including the 417 and 408. Public transportation is also available right in front of the community, making it easy to travel throughout the area.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Sam Nguyen (321-301-9709)
1521 HERON WOOD PL, WINTER PARK, FL 32792
$860,000141 Days on yellowkey MLS ID: O6379884
REDUCED by $65,000 (7.0%) on 06/05/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 3950 Built: 1983 Tax: $6,494 (2024)Community: NoneSpa: YesSingle Family
Taxes:$6,494
Remarks: Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.
Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)
Listing Agent: Ronald Trotter (321-331-1585)
1340 BLUE STEM LN, WINTER PARK, FL 32792
$724,900179 Days on yellowkey MLS ID: O6365415
0 Days Off yellowkey (back on 6/4/2026)
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
Remarks: Under contract-accepting backup offers. 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)
715 S RANGER BLVD, WINTER PARK, FL 32792
$695,00032 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)
676 DUNBLANE DR, WINTER PARK, FL 32792
$699,000204 Days on yellowkey MLS ID: O6365557
REDUCED by $51,000 (6.8%) on 05/12/2026
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: Under contract-accepting backup offers. !! PRICE IMPROVEMENT!! 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)
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