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Winter Park Single Family Homes For Sale - 257 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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  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,00030 Days on yellowkey   MLS ID: O6394524

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000284 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99046 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


  • 633 LANDER RD, WINTER PARK, FL 32792

    $424,90046 Days on yellowkey   MLS ID: O6390096

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

    For Sale O6390096 - 633 LANDER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1400
       Built: 1956   Tax: $1,562 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,458 (change assumption)
    Mortgage ($2,328) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,0006 Days on yellowkey   MLS ID: O6399931

    For Sale O6399931 - 2838 WRIGHT AVE, WINTER PARK, FL 32789 10 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $6,037 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,648 (change assumption)
    Mortgage ($13,145) + Taxes in 2025 ($503)


    Taxes:$6,037

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $595,0007 Days on yellowkey   MLS ID: O6400395

    1 Days Off yellowkey (back on 4/24/2026)

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,729 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500188 Days on yellowkey   MLS ID: A4669103

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 363 N PHELPS AVE, WINTER PARK, FL 32789

    $1,249,0005 Days on yellowkey   MLS ID: O6401811

    For Sale O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2871
       Built: 1950   Tax: $8,856 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $7,582 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($738)


    Taxes:$8,856

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2111 MALLARD CIR, WINTER PARK, FL 32789

    $1,350,0005 Days on yellowkey   MLS ID: O6401350

    For Sale O6401350 - 2111 MALLARD CIR, WINTER PARK, FL 32789 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 1973   Tax: $7,352 (2025)
    Community: Quail Hollow
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,010 (change assumption)
    Mortgage ($7,397) + Taxes in 2025 ($613)


    Taxes:$7,352

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3330 COLEUS CT, WINTER PARK, FL 32792

    $384,90077 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


  • 1398 GROVE TER, WINTER PARK, FL 32789

    $2,195,00012 Days on yellowkey   MLS ID: O6399698

    For Sale O6399698 - 1398 GROVE TER, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3450
       Built: 2004   Tax: $24,548 (2025)
    Community: Sylvan Lake Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,073 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($2,046)


    Taxes:$24,548

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $200,00022 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


  • 1760 ALABAMA DR, WINTER PARK, FL 32789

    $2,198,00055 Days on yellowkey   MLS ID: O6386409

    REDUCED by $100,000 (4.4%) on 04/23/2026

    For Sale O6386409 - 1760 ALABAMA DR, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2841
       Built: 1971   Tax: $16,368 (2025)
    Community: J Kronenberger Sub
    Single Family


    Estimated Monthly Payment: $13,408 (change assumption)
    Mortgage ($12,044) + Taxes in 2025 ($1,364)


    Taxes:$16,368

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $369,900103 Days on yellowkey   MLS ID: O6373026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,313 (change assumption)
    Mortgage ($2,027) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,00088 Days on yellowkey   MLS ID: O6362285

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,00011 Days on yellowkey   MLS ID: O6398373

    For Sale O6398373 - 802 HAMILTON PLACE CT, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2843
       Built: 2018
    Monthly Fee: $142
       Tax: $9,300 (2025)
    Community: Hamilton Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,392) + Fees ($142) + Taxes in 2025 ($775)


    Taxes:$9,300

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $4,270,000250 Days on yellowkey   MLS ID: O6330736

    REDUCED by $25,000 (0.6%) on 04/21/2026

    For Sale O6330736 - 1161 VALENCIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4181
       Built: 2021   Tax: $30,421 (2024)
    Community: Valencia Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,932 (change assumption)
    Mortgage ($23,397) + Taxes in 2024 ($2,535)


    Taxes:$30,421

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $699,00011 Days on yellowkey   MLS ID: TB8498515

    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: $4,229 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($399)


    Taxes:$4,784

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $609,90012 Days on yellowkey   MLS ID: O6399014

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $4,087 (change assumption)
    Mortgage ($3,342) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 665 LYMAN AVE, WINTER PARK, FL 32789

    $450,00011 Days on yellowkey   MLS ID: O6400200

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

    For Sale O6400200 - 665 LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1119
       Built: 1994   Tax: $5,851 (2025)
    Community: Town Of Winter Park
    Single Family


    Estimated Monthly Payment: $2,953 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($488)


    Taxes:$5,851

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8




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.