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Winter Park Homes For Sale & Real Estate - 411 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 241 W LAKE SUE AVE, WINTER PARK, FL 32789

    $995,00064 Days on yellowkey   MLS ID: O6411621

    1 Days Off yellowkey (back on 7/31/2026)

    REDUCED by $4,000 (0.4%) on 07/21/2026

    For Sale O6411621 - 241 W LAKE SUE AVE, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1950   Tax: $14,823 (2025)
    Community: Virginia Heights
    Single Family


    Estimated Monthly Payment: $6,687 (change assumption)
    Mortgage ($5,452) + Taxes in 2025 ($1,235)


    Taxes:$14,823

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2361 ROXBURY RD, WINTER PARK, FL 32789

    $599,00031 Days on yellowkey   MLS ID: O6418164

    0 Days Off yellowkey (back on 7/30/2026)

    For Sale O6418164 - 2361 ROXBURY RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1723
       Built: 1951   Tax: $2,184 (2025)
    Community: Glencoe Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,464 (change assumption)
    Mortgage ($3,282) + Taxes in 2025 ($182)


    Taxes:$2,184

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,195,000261 Days on yellowkey   MLS ID: O6359471

    REDUCED by $30,000 (1.3%) on 07/23/2026

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 59 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,533 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7771 COUNTRY PL #7, WINTER PARK, FL 32792

    $219,900241 Days on yellowkey   MLS ID: O6364384

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

    For Sale O6364384 - 7771 COUNTRY PL #7, WINTER PARK, FL 32792 15 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1230
       Built: 1987
    Monthly Fee: $340
       Tax: $2,950 (2024)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,791 (change assumption)
    Mortgage ($1,205) + Fees ($340) + Taxes in 2024 ($246)


    Taxes:$2,950

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,00051 Days on yellowkey   MLS ID: O6415098

    For Sale O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2351
       Built: 2025   Tax: $5,773 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,311 (change assumption)
    Mortgage ($7,830) + Taxes in 2025 ($481)


    Taxes:$5,773

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $139,500343 Days on yellowkey   MLS ID: O6337083

    REDUCED by $3,000 (2.1%) on 07/30/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,235 (change assumption)
    Mortgage ($764) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,000112 Days on yellowkey   MLS ID: O6397890

    For Sale O6397890 - 2600 EUSTON RD, WINTER PARK, FL 32789 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 3145
       Built: 1951   Tax: $7,446 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,072 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($620)


    Taxes:$7,446

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00050 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #E204, WINTER PARK, FL 32789

    $109,000233 Days on yellowkey   MLS ID: O6366205

    REDUCED by $5,000 (4.4%) on 07/06/2026

    For Sale O6366205 - 1695 LEE RD #E204, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $1,917 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,239 (change assumption)
    Mortgage ($597) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $399,99058 Days on yellowkey   MLS ID: S5151098

    REDUCED by $2,510 (0.6%) on 07/30/2026

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,535 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1546 MILLER AVE, WINTER PARK, FL 32789

    $1,419,9007 Days on yellowkey   MLS ID: O6428019

    For Sale O6428019 - 1546 MILLER AVE, WINTER PARK, FL 32789 36 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,078 (change assumption)
    Mortgage ($7,780) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00071 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2552 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $530,0001 Day on yellowkey   MLS ID: O6428975

    For Sale O6428975 - 2552 BROOKSHIRE AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 1.5   Gar: 1
    Liv Area Sq Ft: 1314
       Built: 1959   Tax: $1,501 (2025)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,904) + Taxes in 2025 ($125)


    Taxes:$1,501

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,250,000133 Days on yellowkey   MLS ID: O6392216

    1 Days Off yellowkey (back on 7/30/2026)

    REDUCED by $99,900 (7.4%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,841 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000269 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.9%) on 06/06/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,649 (change assumption)
    Mortgage ($18,575) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1695 LEE RD #B108, WINTER PARK, FL 32789

    $89,99924 Days on yellowkey   MLS ID: O6422568

    For Sale O6422568 - 1695 LEE RD #B108, WINTER PARK, FL 32789 15 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966
    Monthly Fee: $347
       Tax: $1,781 (2025)
    Community: Waterfall Cove Of Winter Park
    Condo


    Estimated Monthly Payment: $989 (change assumption)
    Mortgage ($493) + Fees ($347) + Taxes in 2025 ($148)


    Taxes:$1,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $109,000114 Days on yellowkey   MLS ID: O6396190

    REDUCED by $5,000 (4.4%) on 07/06/2026

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $768 (change assumption)
    Mortgage ($597) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2228 AZALEA PL, WINTER PARK, FL 32789

    $5,600,00034 Days on yellowkey   MLS ID: O6416342

    For Sale O6416342 - 2228 AZALEA PL, WINTER PARK, FL 32789 72 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5152
       Built: 2008   Tax: $26,904 (2025)
    Community: Maitland Shores First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $32,926 (change assumption)
    Mortgage ($30,684) + Taxes in 2025 ($2,242)


    Taxes:$26,904

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $495,90092 Days on yellowkey   MLS ID: S5148431

    REDUCED by $19,100 (3.7%) on 07/02/2026

    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: $2,905 (change assumption)
    Mortgage ($2,717) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 722 S RANGER BLVD, WINTER PARK, FL 32792

    $799,90029 Days on yellowkey   MLS ID: O6421873

    REDUCED by $25,100 (3.0%) on 07/27/2026

    For Sale O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1967   Tax: $455 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($38)


    Taxes:$455

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park listings.



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.