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Winter Park Single Family Homes For Sale - 279 homes

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

Location: Winter Park

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  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,000121 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • WINTER PARK, FL 32792

    $430,000140 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


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $925,000303 Days on yellowkey   MLS ID: O6344540

    REDUCED by $24,000 (2.5%) on 05/24/2026

    For Sale O6344540 - 560 OLOLU DR, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1953   Tax: $8,617 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $5,786 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1725 CAROLLEE LN, WINTER PARK, FL 32789

    $1,005,00094 Days on yellowkey   MLS ID: O6402656

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $10,000 (1.0%) on 05/12/2026

    For Sale O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2335
       Built: 1960   Tax: $8,445 (2025)
    Community: Green Terrace
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($5,507) + Taxes in 2025 ($704)


    Taxes:$8,445

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00070 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000190 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,000125 Days on yellowkey   MLS ID: O6394012

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

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 811 OVERSPIN DR, WINTER PARK, FL 32789

    $349,000105 Days on yellowkey   MLS ID: O6400009

    For Sale O6400009 - 811 OVERSPIN DR, WINTER PARK, FL 32789 9 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 749
       Built: 1950   Tax: $3,998 (2025)
    Community: Dubsdread Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($333)


    Taxes:$3,998

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000231 Days on yellowkey   MLS ID: S5139410

    For Sale S5139410 - 2612 ROXBURY RD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 0.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000269 Days on yellowkey   MLS ID: S5137596

    For Sale S5137596 - 2612 ROXBURY RD, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1870 STAUNTON AVE, WINTER PARK, FL 32789

    $1,250,000118 Days on yellowkey   MLS ID: O6391469

    For Sale O6391469 - 1870 STAUNTON AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2525
       Built: 1935   Tax: $1,302 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $6,958 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($109)


    Taxes:$1,302

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1630 ELM AVE, WINTER PARK, FL 32789

    $2,385,000136 Days on yellowkey   MLS ID: O6388606

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

    For Sale O6388606 - 1630 ELM AVE, WINTER PARK, FL 32789 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2026   Tax: $1,673 (2024)
    Community: Temple Estates
    Single Family


    Estimated Monthly Payment: $13,208 (change assumption)
    Mortgage ($13,068) + Taxes in 2024 ($139)


    Taxes:$1,673

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 512 N LAKEMONT AVE, WINTER PARK, FL 32792

    $500,000132 Days on yellowkey   MLS ID: O6392353

    For Sale O6392353 - 512 N LAKEMONT AVE, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1413
       Built: 1955   Tax: $2,136 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($178)


    Taxes:$2,136

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1996 INDIANA AVE, WINTER PARK, FL 32789

    $249,900203 Days on yellowkey   MLS ID: O6372229

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

    For Sale O6372229 - 1996 INDIANA AVE, WINTER PARK, FL 32789 18 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 818
       Built: 1938   Tax: $1,401 (2024)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $1,486 (change assumption)
    Mortgage ($1,369) + Taxes in 2024 ($117)


    Taxes:$1,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1120 PRESERVE POINT DR, WINTER PARK, FL 32789

    $8,950,000297 Days on yellowkey   MLS ID: O6350054

    For Sale O6350054 - 1120 PRESERVE POINT DR, WINTER PARK, FL 32789 89 photos

    Bed: 7   Bath: 10.0
    Liv Area Sq Ft: 11255
       Built: 2009
    Community: Windsong-Preserve Point
    Single Family


    Estimated Monthly Payment: $49,040 (change assumption)
    Mortgage ($49,040)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1137 OAKS BLVD, WINTER PARK, FL 32789

    $634,900175 Days on yellowkey   MLS ID: O6379388

    0 Days Off yellowkey (back on 3/21/2026)

    For Sale O6379388 - 1137 OAKS BLVD, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1149
       Built: 1958
    Community: Dixie Terrace
    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($3,479)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1823 MAYWOOD RD, WINTER PARK, FL 32792

    $249,900135 Days on yellowkey   MLS ID: O6385188

    1 Days Off yellowkey (back on 3/19/2026)

    For Sale O6385188 - 1823 MAYWOOD RD, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1232
       Built: 1956
    Community: Tanglewood Sec 3 Rep
    Single Family


    Estimated Monthly Payment: $1,369 (change assumption)
    Mortgage ($1,369)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2625 SUMMERFIELD RD, WINTER PARK, FL 32792

    $724,900   MLS ID: O6384757

    For Sale O6384757 - 2625 SUMMERFIELD RD, WINTER PARK, FL 32792 47 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2199
       Built: 1968
    Community: Golfside Golf Course Sec 01
    Single Family


    Estimated Monthly Payment: $3,972 (change assumption)
    Mortgage ($3,972)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 5233 LAKE HOWELL RD, WINTER PARK, FL 32792

    $562,0001064 Days on yellowkey   MLS ID: O6137445

    1 Days Off yellowkey (back on 10/24/2023)

    For Sale O6137445 - 5233 LAKE HOWELL RD, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1778
       Built: 1956   Tax: $4,888 (2022)
    Community: Tanglewood Sec 3 Rep
    Single Family


    Estimated Monthly Payment: $3,487 (change assumption)
    Mortgage ($3,079) + Taxes in 2022 ($407)


    Taxes:$4,888

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2022

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.