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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Park - 78 properties found

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  • 2652 ABBEY RD, WINTER PARK, FL 32792

    $625,0002 Days on yellowkey   MLS ID: O6419026

    For Sale O6419026 - 2652 ABBEY RD, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 1967   Tax: $7,337 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,036 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($611)


    Taxes:$7,337

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00055 Days on yellowkey   MLS ID: S5148431

    For Sale S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1786
       Built: 1966   Tax: $2,249 (2025)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $400,000166 Days on yellowkey   MLS ID: O6372653

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

    For Sale O6372653 - 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1677
       Built: 1972   Tax: $1,289 (2024)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,299 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($107)


    Taxes:$1,289

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $514,90053 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


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90019 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


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,0001 Day on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $470,000321 Days on yellowkey   MLS ID: O6330690

    REDUCED by $9,900 (2.1%) on 06/23/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,093 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $439,90023 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,000 (2.2%) on 06/21/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 437 N CAPEN AVE, WINTER PARK, FL 32789

    $849,0009 Days on yellowkey   MLS ID: O6414283

    For Sale O6414283 - 437 N CAPEN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $400
       Tax: $11,943 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,047 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($995)


    Taxes:$11,943

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $535,00014 Days on yellowkey   MLS ID: O6414677

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $680,00068 Days on yellowkey   MLS ID: TB8498515

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

    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


  • 5350 ORANGE AVE, WINTER PARK, FL 32792

    $469,9005 Days on yellowkey   MLS ID: O6415309

    1 Days Off yellowkey (back on 6/23/2026)

    For Sale O6415309 - 5350 ORANGE AVE, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1863
       Built: 2011   Tax: $5,520 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $3,035 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($460)


    Taxes:$5,520

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1016 MANCHESTER CIR, WINTER PARK, FL 32792

    $417,50016 Days on yellowkey   MLS ID: O6414031

    0 Days Off yellowkey (back on 6/18/2026)

    For Sale O6414031 - 1016 MANCHESTER CIR, WINTER PARK, FL 32792 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1625
       Built: 1976   Tax: $4,388 (2025)
    Community: Howell Estates Rep
    Single Family


    Estimated Monthly Payment: $2,653 (change assumption)
    Mortgage ($2,288) + Taxes in 2025 ($366)


    Taxes:$4,388

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2344 WOODCREST DR, WINTER PARK, FL 32792

    $729,9003 Days on yellowkey   MLS ID: O6418782

    For Sale O6418782 - 2344 WOODCREST DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1764
       Built: 1960   Tax: $6,366 (2025)
    Community: Kenilworth Estates 1St Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,530 (change assumption)
    Mortgage ($3,999) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7134 WRENWOOD WAY, WINTER PARK, FL 32792

    $445,0005 Days on yellowkey   MLS ID: O6418289

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

    For Sale O6418289 - 7134 WRENWOOD WAY, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1712
       Built: 1975   Tax: $4,266 (2025)
    Community: Wrenwood Heights Unit 2
    Single Family


    Estimated Monthly Payment: $2,794 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($356)


    Taxes:$4,266

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $775,00014 Days on yellowkey   MLS ID: O6415904

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

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines Merrie Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000327 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $450,00020 Days on yellowkey   MLS ID: O6409433

    REDUCED by $15,000 (3.2%) on 06/22/2026

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,857 (change assumption)
    Mortgage ($2,466) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00033 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000138 Days on yellowkey   MLS ID: O6380457

    REDUCED by $51,000 (4.9%) on 05/06/2026

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle






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.