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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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  • 1036 MANCHESTER CIR, WINTER PARK, FL 32792

    $400,00032 Days on yellowkey   MLS ID: O6395138

    1 Days Off yellowkey (back on 5/2/2026)

    For Sale O6395138 - 1036 MANCHESTER CIR, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1974   Tax: $4,126 (2024)
    Community: Howell Estates Rep
    Single Family


    Estimated Monthly Payment: $2,536 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($344)


    Taxes:$4,126

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 517 ROUGHBEARD RD, WINTER PARK, FL 32792

    $565,00020 Days on yellowkey   MLS ID: O6399029

    1 Days Off yellowkey (back on 5/2/2026)

    For Sale O6399029 - 517 ROUGHBEARD RD, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1971   Tax: $4,323 (2025)
    Community: Winter Park Pines Unit 17
    Single Family


    Estimated Monthly Payment: $3,456 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($360)


    Taxes:$4,323

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $525,0002 Days on yellowkey   MLS ID: O6403855

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 45 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: $3,012 (change assumption)
    Mortgage ($2,877) + Taxes in 2024 ($136)


    Taxes:$1,630

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,0003 Days on yellowkey   MLS ID: O6404107

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 GOODRICH AVE, WINTER PARK, FL 32789

    $739,00014 Days on yellowkey   MLS ID: O6400278

    For Sale O6400278 - 1701 GOODRICH AVE, WINTER PARK, FL 32789 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $5,023 (2025)
    Community: Sylvan Hgts
    Single Family


    Estimated Monthly Payment: $4,468 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($419)


    Taxes:$5,023

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1205 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $450,00033 Days on yellowkey   MLS ID: O6394946

    For Sale O6394946 - 1205 VALLEY CREEK RUN, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1815
       Built: 1997
    Monthly Fee: $22
       Tax: $2,237 (2024)
    Community: Lost Creek
    Single Family


    Estimated Monthly Payment: $2,674 (change assumption)
    Mortgage ($2,466) + Fees ($22) + Taxes in 2024 ($186)


    Taxes:$2,237

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1550 NORFOLK AVE, WINTER PARK, FL 32789

    $725,0004 Days on yellowkey   MLS ID: O6402927

    For Sale O6402927 - 1550 NORFOLK AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1762
       Built: 1949   Tax: $3,951 (2025)
    Community: Orwin Manor Stratford Sec
    Single Family


    Estimated Monthly Payment: $4,302 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($329)


    Taxes:$3,951

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2707 TIERRA CIR, WINTER PARK, FL 32792

    $495,0005 Days on yellowkey   MLS ID: O6398979

    For Sale O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1710
       Built: 1970   Tax: $3,237 (2025)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,982 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($270)


    Taxes:$3,237

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,50022 Days on yellowkey   MLS ID: O6398450

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 688 BRECHIN DR, WINTER PARK, FL 32792

    $724,9004 Days on yellowkey   MLS ID: O6403080

    For Sale O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1961   Tax: $6,760 (2025)
    Community: Kenilworth Shores Sec 04
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,972) + Taxes in 2025 ($563)


    Taxes:$6,760

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00069 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $729,00039 Days on yellowkey   MLS ID: O6385950

    REDUCED by $11,000 (1.5%) on 05/01/2026

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,752 (change assumption)
    Mortgage ($3,994) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001147 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $1,050,00087 Days on yellowkey   MLS ID: O6380457

    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: $6,752 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $420,0008 Days on yellowkey   MLS ID: O6401731

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,480 (change assumption)
    Mortgage ($2,301) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $470,00023 Days on yellowkey   MLS ID: O6398273

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,869 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $554,90099 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 05/01/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,214 (change assumption)
    Mortgage ($3,040) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,0004 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


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,99510 Days on yellowkey   MLS ID: O6402209

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

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00088 Days on yellowkey   MLS ID: O6380333

    1 Days Off yellowkey (back on 4/5/2026)

    For Sale O6380333 - 4872 ORANGE AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1881
       Built: 1960   Tax: $4,494 (2024)
    Community: Suburban Homes First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($374)


    Taxes:$4,494

    Elementary School: Lakemont Elem

    High School: None

    Tax Year: 2024

    Middle School: Maitland 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.