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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Park - 71 properties found

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  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $680,00017 Days on yellowkey   MLS ID: TB8498515

    REDUCED by $19,000 (2.7%) on 04/30/2026

    For Sale TB8498515 - 927 FAIRWAY DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 1973   Tax: $4,784 (2025)
    Community: Golfside Sec 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,125 (change assumption)
    Mortgage ($3,726) + Taxes in 2025 ($399)


    Taxes:$4,784

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $625,00061 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,500 (0.4%) on 04/30/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,009 (change assumption)
    Mortgage ($3,425) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 7120 BROOKSIDE TRL, WINTER PARK, FL 32792

    $510,00011 Days on yellowkey   MLS ID: O6398534

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

    For Sale O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1753
       Built: 1976   Tax: $3,098 (2025)
    Community: Replat Of Lts 1 2 & 3 Brookside Sub
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,794) + Taxes in 2025 ($258)


    Taxes:$3,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,000102 Days on yellowkey   MLS ID: O6375545

    2 Days Off yellowkey (back on 3/11/2026)

    For Sale O6375545 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 35 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $941,0007 Days on yellowkey   MLS ID: O6402566

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $5,390 (change assumption)
    Mortgage ($5,156) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1780 BRYAN AVE, WINTER PARK, FL 32789

    $849,000145 Days on yellowkey   MLS ID: O6365369

    For Sale O6365369 - 1780 BRYAN AVE, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 1952   Tax: $7,345 (2024)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $5,264 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($612)


    Taxes:$7,345

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1822 YORKSHIRE DR, WINTER PARK, FL 32792

    $624,00010 Days on yellowkey   MLS ID: O6401364

    For Sale O6401364 - 1822 YORKSHIRE DR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1620
       Built: 1957   Tax: $5,959 (2025)
    Community: Park Manor
    Single Family


    Estimated Monthly Payment: $3,916 (change assumption)
    Mortgage ($3,419) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $449,90048 Days on yellowkey   MLS ID: O6390301

    REDUCED by $10,000 (2.2%) on 04/29/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,852 (change assumption)
    Mortgage ($2,465) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1108 FAIRWAY DR, WINTER PARK, FL 32792

    $725,00066 Days on yellowkey   MLS ID: O6386266

    For Sale O6386266 - 1108 FAIRWAY DR, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 1978   Tax: $6,713 (2024)
    Community: Golfside Sec 03
    Single Family


    Estimated Monthly Payment: $4,532 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($559)


    Taxes:$6,713

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3245 COLEUS CT, WINTER PARK, FL 32792

    $379,90036 Days on yellowkey   MLS ID: O6390829

    REDUCED by $10,000 (2.6%) on 04/28/2026

    For Sale O6390829 - 3245 COLEUS CT, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1529
       Built: 1968   Tax: $986 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($82)


    Taxes:$986

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $659,000230 Days on yellowkey   MLS ID: O6344482

    REDUCED by $5,000 (0.8%) on 04/20/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,237 (change assumption)
    Mortgage ($3,611) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,00021 Days on yellowkey   MLS ID: O6398533

    3 Days Off yellowkey (back on 4/27/2026)

    For Sale O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1979   Tax: $7,265 (2025)
    Community: Golfside Sec 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,614 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($605)


    Taxes:$7,265

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2009 SHADYHILL TER, WINTER PARK, FL 32792

    $535,0008 Days on yellowkey   MLS ID: O6402256

    For Sale O6402256 - 2009 SHADYHILL TER, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 1987
    Monthly Fee: $56
       Tax: $1,742 (2025)
    Community: Autumn Glen Ph 2
    Single Family


    Estimated Monthly Payment: $3,133 (change assumption)
    Mortgage ($2,931) + Fees ($56) + Taxes in 2025 ($145)


    Taxes:$1,742

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1174 WILDMEADOW RUN, WINTER PARK, FL 32792

    $649,90034 Days on yellowkey   MLS ID: O6394974

    REDUCED by $20,000 (3.0%) on 04/23/2026

    For Sale O6394974 - 1174 WILDMEADOW RUN, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $150
       Tax: $6,672 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,267 (change assumption)
    Mortgage ($3,561) + Fees ($150) + Taxes in 2025 ($556)


    Taxes:$6,672

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00046 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $480,00014 Days on yellowkey   MLS ID: O6399199

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,199 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99052 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

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3330 COLEUS CT, WINTER PARK, FL 32792

    $384,90083 Days on yellowkey   MLS ID: O6378218

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

    For Sale O6378218 - 3330 COLEUS CT, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1988
       Built: 1968   Tax: $5,410 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,109) + Taxes in 2024 ($451)


    Taxes:$5,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $200,00028 Days on yellowkey   MLS ID: S5147029

    0 Days Off yellowkey (back on 4/23/2026)

    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: $1,460 (change assumption)
    Mortgage ($1,096) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $678,000192 Days on yellowkey   MLS ID: G5103499

    REDUCED by $1,000 (0.1%) on 04/21/2026

    For Sale G5103499 - 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1761
       Built: 1954   Tax: $6,623 (2024)
    Community: Northwood Terrace
    Single Family


    Estimated Monthly Payment: $4,267 (change assumption)
    Mortgage ($3,715) + Taxes in 2024 ($552)


    Taxes:$6,623

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8






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