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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Park - 22 properties found

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  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $365,00065 Days on yellowkey   MLS ID: L4961275

    REDUCED by $10,000 (2.7%) on 06/23/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,422 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90020 Days on yellowkey   MLS ID: O6414180

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $5,000 (1.3%) on 06/19/2026

    For Sale O6414180 - 1662 TREMONT LN, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1986
    Monthly Fee: $49
       Tax: $4,339 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,109) + Fees ($49) + Taxes in 2025 ($362)


    Taxes:$4,339

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7505 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $390,00038 Days on yellowkey   MLS ID: O6405854

    0 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $10,000 (2.5%) on 06/05/2026

    For Sale O6405854 - 7505 LAUREL SPRINGS DR, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1471
       Built: 1972   Tax: $1,205 (2025)
    Community: Laurel Springs
    Single Family


    Estimated Monthly Payment: $2,237 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($100)


    Taxes:$1,205

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $399,0008 Days on yellowkey   MLS ID: O6417098

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,487 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3374 HAMLET LOOP, WINTER PARK, FL 32792

    $365,00056 Days on yellowkey   MLS ID: O6403488

    REDUCED by $5,000 (1.4%) on 06/16/2026

    For Sale O6403488 - 3374 HAMLET LOOP, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1397
       Built: 1994
    Monthly Fee: $63
       Tax: $5,326 (2024)
    Community: Villas Of Casselberry Ph 3
    Single Family


    Estimated Monthly Payment: $2,507 (change assumption)
    Mortgage ($2,000) + Fees ($63) + Taxes in 2024 ($444)


    Taxes:$5,326

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $370,00023 Days on yellowkey   MLS ID: O6412514

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,338 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1760 PERUVIAN LN, WINTER PARK, FL 32792

    $324,000110 Days on yellowkey   MLS ID: A4685217

    REDUCED by $15,000 (4.4%) on 06/09/2026

    For Sale A4685217 - 1760 PERUVIAN LN, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1960   Tax: $3,470 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,064 (change assumption)
    Mortgage ($1,775) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,00092 Days on yellowkey   MLS ID: O6393303

    For Sale O6393303 - 1920 HEATHWOOD DR, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 1980   Tax: $4,895 (2025)
    Community: Cedar Ridge Unit 1
    Single Family


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($408)


    Taxes:$4,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2482 ROXBURY RD, WINTER PARK, FL 32789

    $375,00048 Days on yellowkey   MLS ID: O6406443

    0 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $25,000 (6.3%) on 06/02/2026

    For Sale O6406443 - 2482 ROXBURY RD, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 913
       Built: 1948   Tax: $5,020 (2025)
    Community: Glencoe
    Single Family


    Estimated Monthly Payment: $2,473 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($418)


    Taxes:$5,020

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1761 GLADIOLAS DR, WINTER PARK, FL 32792

    $375,00027 Days on yellowkey   MLS ID: O6411912

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

    For Sale O6411912 - 1761 GLADIOLAS DR, WINTER PARK, FL 32792 7 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1979   Tax: $1,453 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,176 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($121)


    Taxes:$1,453

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500246 Days on yellowkey   MLS ID: A4669103

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2006 CORNELL AVE, WINTER PARK, FL 32789

    $338,00023 Days on yellowkey   MLS ID: O6412789

    For Sale O6412789 - 2006 CORNELL AVE, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 797
       Built: 1940   Tax: $4,795 (2025)
    Community: Stansbury Estates
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,852) + Taxes in 2025 ($400)


    Taxes:$4,795

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,00027 Days on yellowkey   MLS ID: O6411325

    1 Days Off yellowkey (back on 6/2/2026)

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $325,00080 Days on yellowkey   MLS ID: S5147029

    INCREASED by $125,000 (62.5%) on 06/01/2026

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1433 ASTER CT, WINTER PARK, FL 32792

    $389,00042 Days on yellowkey   MLS ID: O6407873

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $10,000 (2.5%) on 05/21/2026

    For Sale O6407873 - 1433 ASTER CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1363
       Built: 1984   Tax: $1,057 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,220 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($88)


    Taxes:$1,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1092 EASTBROOK BLVD, WINTER PARK, FL 32792

    $399,00040 Days on yellowkey   MLS ID: O6407251

    REDUCED by $11,000 (2.7%) on 05/27/2026

    For Sale O6407251 - 1092 EASTBROOK BLVD, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1122
       Built: 1959   Tax: $4,373 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($364)


    Taxes:$4,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $380,00049 Days on yellowkey   MLS ID: O6403694

    1 Days Off yellowkey (back on 5/27/2026)

    For Sale O6403694 - 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 988
       Built: 1950   Tax: $4,386 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($366)


    Taxes:$4,386

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1307 FORMOSA AVE, WINTER PARK, FL 32789

    $373,80065 Days on yellowkey   MLS ID: O6400711

    1 Days Off yellowkey (back on 5/27/2026)

    REDUCED by $100 (0.0%) on 05/26/2026

    For Sale O6400711 - 1307 FORMOSA AVE, WINTER PARK, FL 32789 33 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1150
       Built: 1946   Tax: $6,007 (2025)
    Community: Golfview
    Single Family


    Estimated Monthly Payment: $2,549 (change assumption)
    Mortgage ($2,048) + Taxes in 2025 ($501)


    Taxes:$6,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500161 Days on yellowkey   MLS ID: O6373026

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $2,400 (0.6%) on 04/30/2026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,300 (change assumption)
    Mortgage ($2,014) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2973 SANBINA ST, WINTER PARK, FL 32789

    $377,88041 Days on yellowkey   MLS ID: O6407521

    For Sale O6407521 - 2973 SANBINA ST, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1128
       Built: 1965   Tax: $5,253 (2025)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,071) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


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