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Winter Park Single Family Homes For Sale - 303 homes

Winter Park Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

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  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,099,00097 Days on yellowkey   MLS ID: O6397997

    REDUCED by $40,750 (3.6%) on 07/08/2026

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,461 (change assumption)
    Mortgage ($6,022) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 722 S RANGER BLVD, WINTER PARK, FL 32792

    $825,00014 Days on yellowkey   MLS ID: O6421873

    For Sale O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 67 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1967   Tax: $455 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,558 (change assumption)
    Mortgage ($4,520) + Taxes in 2025 ($38)


    Taxes:$455

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 525 S LAKEMONT AVE, WINTER PARK, FL 32792

    $2,099,99038 Days on yellowkey   MLS ID: O6414770

    REDUCED by $99,010 (4.5%) on 07/14/2026

    For Sale O6414770 - 525 S LAKEMONT AVE, WINTER PARK, FL 32792 76 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3330
       Built: 2026   Tax: $7,133 (2024)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,101 (change assumption)
    Mortgage ($11,507) + Taxes in 2024 ($594)


    Taxes:$7,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999157 Days on yellowkey   MLS ID: O6375415

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $50,001 (2.7%) on 05/22/2026

    For Sale O6375415 - 4469 OLD BEAR RUN, WINTER PARK, FL 32792 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4288
       Built: 1978   Tax: $10,710 (2024)
    Community: Pervis Survey For R E
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,755 (change assumption)
    Mortgage ($9,863) + Taxes in 2024 ($893)


    Taxes:$10,710

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789

    $465,50020 Days on yellowkey   MLS ID: O6419225

    For Sale O6419225 - 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1953   Tax: $5,488 (2025)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,008 (change assumption)
    Mortgage ($2,551) + Taxes in 2025 ($457)


    Taxes:$5,488

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1600 LEGION DR, WINTER PARK, FL 32789

    $3,795,00033 Days on yellowkey   MLS ID: O6415591

    REDUCED by $200,000 (5.0%) on 07/13/2026

    For Sale O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4483
       Built: 2008   Tax: $20,740 (2025)
    Community: Green Oaks Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,522 (change assumption)
    Mortgage ($20,794) + Taxes in 2025 ($1,728)


    Taxes:$20,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,569,00080 Days on yellowkey   MLS ID: O6395277

    1 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $81,000 (4.9%) on 05/30/2026

    For Sale O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 2026   Tax: $6,297 (2025)
    Community: Lake Knowles Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,122 (change assumption)
    Mortgage ($8,597) + Taxes in 2025 ($525)


    Taxes:$6,297

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00048 Days on yellowkey   MLS ID: O6412139

    REDUCED by $5,000 (1.0%) on 06/15/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2223 CONIFER AVE, WINTER PARK, FL 32792

    $435,0003 Days on yellowkey   MLS ID: O6424677

    For Sale O6424677 - 2223 CONIFER AVE, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 1970   Tax: $2,253 (2025)
    Community: Eastbrook Sub Unit 16
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($188)


    Taxes:$2,253

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 730 W SWOOPE AVE, WINTER PARK, FL 32789

    $839,00010 Days on yellowkey   MLS ID: S5152493

    INCREASED by $69,000 (9.0%) on 07/13/2026

    For Sale S5152493 - 730 W SWOOPE AVE, WINTER PARK, FL 32789 35 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2132
       Built: 1950   Tax: $6,026 (2025)
    Community: Carver Town First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,099 (change assumption)
    Mortgage ($4,597) + Taxes in 2025 ($502)


    Taxes:$6,026

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 229 ALEXANDER PL, WINTER PARK, FL 32789

    $4,250,00041 Days on yellowkey   MLS ID: O6412911

    For Sale O6412911 - 229 ALEXANDER PL, WINTER PARK, FL 32789 53 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4431
       Built: 2011   Tax: $36,713 (2025)
    Community: Alexander Place
    Spa: No

    Single Family


    Estimated Monthly Payment: $26,347 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,059)


    Taxes:$36,713

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792

    $495,00017 Days on yellowkey   MLS ID: O6420961

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6420961 - 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1955
       Built: 1964   Tax: $5,197 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $3,145 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($433)


    Taxes:$5,197

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $625,00035 Days on yellowkey   MLS ID: O6415387

    For Sale O6415387 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $244
       Tax: $4,970 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,083 (change assumption)
    Mortgage ($3,425) + Fees ($244) + Taxes in 2025 ($414)


    Taxes:$4,970

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $444,900113 Days on yellowkey   MLS ID: O6393594

    REDUCED by $5,000 (1.1%) on 07/13/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00076 Days on yellowkey   MLS ID: O6402961

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2905 PARKLAND DR, WINTER PARK, FL 32789

    $3,395,0008 Days on yellowkey   MLS ID: O6422550

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 4850
       Built: 2026   Tax: $5,748 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $19,081 (change assumption)
    Mortgage ($18,602) + Taxes in 2025 ($479)


    Taxes:$5,748

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $668,99850 Days on yellowkey   MLS ID: O6409323

    REDUCED by $2,113 (0.3%) on 07/13/2026

    For Sale O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2048
       Built: 1950   Tax: $7,927 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,326 (change assumption)
    Mortgage ($3,666) + Taxes in 2025 ($661)


    Taxes:$7,927

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000365 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $994,000122 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $1,000 (0.1%) on 07/13/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,424 (change assumption)
    Mortgage ($5,446) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $514,90075 Days on yellowkey   MLS ID: O6403855

    REDUCED by $5,000 (1.0%) on 06/24/2026

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1627
       Built: 1968   Tax: $1,630 (2024)
    Community: Casa Aloma
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,957 (change assumption)
    Mortgage ($2,821) + Taxes in 2024 ($136)


    Taxes:$1,630

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park single family home listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.