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Winter Park Homes For Sale & Real Estate - 382 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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  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,0006 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


  • 1250 S DENNING DR #117, WINTER PARK, FL 32789

    $240,000Listed 04/23/2026 3:07PM   MLS ID: O6401802

    For Sale O6401802 - 1250 S DENNING DR #117, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 908
       Built: 1967   Tax: $2,763 (2025)
    Community: Mead Garden
    Condo


    Estimated Monthly Payment: $1,545 (change assumption)
    Mortgage ($1,315) + Taxes in 2025 ($230)


    Taxes:$2,763

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,750,00021 Days on yellowkey   MLS ID: O6395692

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,660 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $4,270,000245 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


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $315,00049 Days on yellowkey   MLS ID: O6384755

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,247 (change assumption)
    Mortgage ($1,726) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $241,9006 Days on yellowkey   MLS ID: O6397587

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,840 (change assumption)
    Mortgage ($1,325) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,989,00029 Days on yellowkey   MLS ID: O6393117

    REDUCED by $60,000 (2.9%) on 04/23/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,663 (change assumption)
    Mortgage ($10,898) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,490,000170 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.8%) on 04/23/2026

    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: $20,197 (change assumption)
    Mortgage ($19,123) + 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


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $699,0006 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

    $609,9007 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


  • 736 WARRENTON RD, WINTER PARK, FL 32792

    $300,00015 Days on yellowkey   MLS ID: O6397291

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6397291 - 736 WARRENTON RD, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1320
       Built: 1986
    Monthly Fee: $86
       Tax: $4,378 (2025)
    Community: Winter Park Pines Patio Homes
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,095 (change assumption)
    Mortgage ($1,644) + Fees ($86) + Taxes in 2025 ($365)


    Taxes:$4,378

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,99929 Days on yellowkey   MLS ID: O6393594

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,633 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,890,00093 Days on yellowkey   MLS ID: O6372947

    REDUCED by $35,000 (1.8%) on 04/22/2026

    For Sale O6372947 - 640 ARJAY WAY, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3953
       Built: 1958   Tax: $11,586 (2024)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $11,321 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($965)


    Taxes:$11,586

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 665 LYMAN AVE, WINTER PARK, FL 32789

    $450,0006 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


  • 7120 BROOKSIDE TRL, WINTER PARK, FL 32792

    $510,000Listed 04/23/2026 12:52PM   MLS ID: O6398534

    For Sale O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1753
       Built: 1976   Tax: $3,098 (2025)
    Community: Replat Of Lts 1 2 & 3 Brookside Sub
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,794) + Taxes in 2025 ($258)


    Taxes:$3,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,0001 Day 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


  • 629 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,695,00054 Days on yellowkey   MLS ID: O6386610

    For Sale O6386610 - 629 COUNTRY CLUB DR, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3031
       Built: 2026   Tax: $2,028 (2025)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,456 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($169)


    Taxes:$2,028

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $470,00012 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


  • 2550 VENETIAN WAY, WINTER PARK, FL 32789

    $2,399,00048 Days on yellowkey   MLS ID: O6388219

    REDUCED by $51,000 (2.1%) on 04/23/2026

    For Sale O6388219 - 2550 VENETIAN WAY, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 5051
       Built: 2008   Tax: $16,724 (2024)
    Community: Maitland Shores First Add
    Single Family


    Estimated Monthly Payment: $14,539 (change assumption)
    Mortgage ($13,145) + Taxes in 2024 ($1,394)


    Taxes:$16,724

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00077 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




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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.