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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Living Area Square Feet: 1000 to 1499

Winter Park - 35 properties found

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  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,00040 Days on yellowkey   MLS ID: O6393594

    REDUCED by $999 (0.2%) on 04/25/2026

    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: $2,628 (change assumption)
    Mortgage ($2,515) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,80018 Days on yellowkey   MLS ID: O6400055

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $4,054 (change assumption)
    Mortgage ($3,725) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1926 NATALEN RD, WINTER PARK, FL 32792

    $639,90059 Days on yellowkey   MLS ID: O6388308

    REDUCED by $10,000 (1.5%) on 04/24/2026

    For Sale O6388308 - 1926 NATALEN RD, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1469
       Built: 1957   Tax: $7,308 (2024)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,115 (change assumption)
    Mortgage ($3,506) + Taxes in 2024 ($609)


    Taxes:$7,308

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3627 SEAGRAPE DR, WINTER PARK, FL 32792

    $339,0002 Days on yellowkey   MLS ID: O6403218

    For Sale O6403218 - 3627 SEAGRAPE DR, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1233
       Built: 1965   Tax: $3,401 (2024)
    Community: Eastbrook Sub Unit 03
    Single Family


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,857) + Taxes in 2024 ($283)


    Taxes:$3,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,0003 Days on yellowkey   MLS ID: O6404115

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

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER PARK, FL 32792

    $430,00053 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,90060 Days on yellowkey   MLS ID: O6387500

    For Sale O6387500 - 1354 INDIANA AVE, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1269
       Built: 1947   Tax: $5,352 (2024)
    Community: Metzingers Add
    Single Family


    Estimated Monthly Payment: $3,678 (change assumption)
    Mortgage ($3,232) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7761 FOX KNOLL PL, WINTER PARK, FL 32792

    $425,00011 Days on yellowkey   MLS ID: O6401159

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

    For Sale O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1485
       Built: 1989
    Monthly Fee: $20
       Tax: $4,308 (2024)
    Community: Bridgewater
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,329) + Fees ($20) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $449,00052 Days on yellowkey   MLS ID: O6388746

    REDUCED by $11,000 (2.4%) on 04/29/2026

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,929 (change assumption)
    Mortgage ($2,460) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 3374 HAMLET LOOP, WINTER PARK, FL 32792

    $370,0004 Days on yellowkey   MLS ID: O6403488

    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: $2,534 (change assumption)
    Mortgage ($2,027) + 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


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,00095 Days on yellowkey   MLS ID: O6373287

    0 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500109 Days on yellowkey   MLS ID: O6373026

    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


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $525,00060 Days on yellowkey   MLS ID: G5108643

    1 Days Off yellowkey (back on 4/29/2026)

    REDUCED by $25,000 (4.5%) on 04/16/2026

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($2,877) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1307 FORMOSA AVE, WINTER PARK, FL 32789

    $375,00013 Days on yellowkey   MLS ID: O6400711

    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: $2,555 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($501)


    Taxes:$6,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $405,00035 Days on yellowkey   MLS ID: S5146768

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale S5146768 - 5503 ALBERT DR, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,241 (2024)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($353)


    Taxes:$4,241

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $399,50013 Days on yellowkey   MLS ID: L4961275

    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: $2,611 (change assumption)
    Mortgage ($2,189) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500194 Days on yellowkey   MLS ID: A4669103

    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


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000292 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


  • 1036 ARAGON AVE, WINTER PARK, FL 32789

    $510,00080 Days on yellowkey   MLS ID: O6382491

    REDUCED by $15,000 (2.9%) on 04/11/2026

    For Sale O6382491 - 1036 ARAGON AVE, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1073
       Built: 1957   Tax: $5,764 (2024)
    Community: Seville Park
    Single Family


    Estimated Monthly Payment: $3,275 (change assumption)
    Mortgage ($2,794) + Taxes in 2024 ($480)


    Taxes:$5,764

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $489,99052 Days on yellowkey   MLS ID: S5145746

    REDUCED by $10,000 (2.0%) on 04/15/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 17 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,554 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


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