Displaying: For Sale
Location: Winter Park
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Winter Park - 48 properties found
316 BECKETT CT, WINTER PARK, FL 32792
$450,00028 Days on yellowkey MLS ID: O6411108
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1966 Tax: $2,232 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,232
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!
Listing is courtesy of: ITS REALTY (321-437-7363)
Listing Agent: Patrick Westervelt, Llc (407-533-1000)
WINTER PARK, FL 32792
$430,000104 Days on yellowkey MLS ID: S5145631
REDUCED by $10,000 (2.3%) on 04/15/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1958 Tax: $4,968 (2025)Community: Winter Park EstatesSingle Family
Taxes:$4,968
Remarks: Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Arlenys Oviedo (786-803-4342)
7532 AZUREBROOK CT, WINTER PARK, FL 32792
$410,00047 Days on yellowkey MLS ID: O6406380
0 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1402 Built: 1979 Tax: $4,889 (2025)Community: Laurel SpgsSingle Family
Taxes:$4,889
Elementary School: Aloma Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Located on a quiet cul-de-sac with NO HOA, this adorable Winter Park home sits on an oversized lot with an incredible backyard and endless room for entertaining, relaxing, or play. With a mid-century modern feel and charming curb appeal, this 3-bedroom, 2-bath home is full of character and functionality. As you enter through the foyer, you’re welcomed by an oversized living room to the left, complete with a cute flex space perfect for a home office, reading nook, or play area. The updated kitchen sits at the center of the home and features quartz countertops, bar seating, and views overlooking the dining room, creating a seamless flow for everyday living and entertaining. Laminate flooring runs throughout all main living areas and bedrooms for a clean and modern look. Down the hallway, you’ll find all three bedrooms and two bathrooms, including the spacious primary suite with a large closet and an updated ensuite bathroom featuring a brand-new vanity and stylish paneling details. The dining room and flex area both lead out to the screened-in patio, giving you the perfect indoor-outdoor setup. Step outside to the true showstopper — a massive backyard with endless possibilities, a fire pit area, and plenty of room for activities, gatherings, pets, or even future additions. (zoned R-1A) Additional highlights include an extra-long driveway with space for up to 6 cars plus a 2-car garage. A rare find in Winter Park!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Christina Frucci (321-303-6881)
346 S RANGER BLVD, WINTER PARK, FL 32792
$475,000283 Days on yellowkey MLS ID: S5134662
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 1965 Tax: $5,339 (2024)Community: Winter Park PinesSingle Family
Taxes:$5,339
Tax Year: 2024
Remarks: PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.
Listing is courtesy of: IMPERIAL REALTY OF FLORIDA INC (407-346-4746)
Listing Agent: Tanya Vyushkina (407-346-4746)
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$410,00073 Days on yellowkey MLS ID: O6398450
REDUCED by $17,500 (4.1%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Remarks: Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And here is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one not to be on the market long at this REDUCED price.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
814 DENSMORE DR, WINTER PARK, FL 32792
$425,00069 Days on yellowkey MLS ID: O6399773
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1960 Tax: $5,402 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,402
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
5331 OAK CT, WINTER PARK, FL 32792
$460,000343 Days on yellowkey MLS ID: S5130868
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1976 Tax: $2,311 (2024)Community: Wrenwood Heights Unit 2Spa: NoSingle Family
Taxes:$2,311
Remarks: Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)
2020 COCOS CT, WINTER PARK, FL 32792
$458,990103 Days on yellowkey MLS ID: O6389901
1 Days Off yellowkey (back on 4/24/2026)
REDUCED by $1,000 (0.2%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1715 Built: 1966 Tax: $1,410 (2024)Community: Eastbrook Sub Unit 8Spa: NoSingle Family
Taxes:$1,410
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Julimar Barreiro Pastrana (407-590-8604)
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