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Winter Park Homes For Sale & Real Estate - 416 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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  • 525 OLOLU DR, WINTER PARK, FL 32789

    $495,90090 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


  • 846 DRIVER AVE, WINTER PARK, FL 32789

    $310,00012 Days on yellowkey   MLS ID: O6426024

    For Sale O6426024 - 846 DRIVER AVE, WINTER PARK, FL 32789 25 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 824
       Built: 1953   Tax: $4,689 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $2,089 (change assumption)
    Mortgage ($1,699) + Taxes in 2025 ($391)


    Taxes:$4,689

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789

    $2,100,000179 Days on yellowkey   MLS ID: L4959060

    INCREASED by $30,000 (1.4%) on 07/26/2026

    For Sale L4959060 - 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3272
       Built: 1990   Tax: $18,439 (2024)
    Community: 147 Interlachen Place
    Condo


    Estimated Monthly Payment: $13,043 (change assumption)
    Mortgage ($11,507) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5427 PEACO PL, WINTER PARK, FL 32792

    $650,9004 Days on yellowkey   MLS ID: A4701047

    For Sale A4701047 - 5427 PEACO PL, WINTER PARK, FL 32792 16 photos

    Bed: 5   Bath: 0.0   Gar: 3
    Liv Area Sq Ft: 1974
       Built: 1982   Tax: $5,919 (2025)
    Community: Grand Pines
    Spa: No

    Apartment


    Estimated Monthly Payment: $4,060 (change assumption)
    Mortgage ($3,566) + Taxes in 2025 ($493)


    Taxes:$5,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1908 CYRIL CT, WINTER PARK, FL 32792

    $639,00020 Days on yellowkey   MLS ID: O6422937

    0 Days Off yellowkey (back on 7/25/2026)

    For Sale O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 1990
    Monthly Fee: $41
       Tax: $7,674 (2025)
    Community: Kawilla Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,182 (change assumption)
    Mortgage ($3,501) + Fees ($41) + Taxes in 2025 ($640)


    Taxes:$7,674

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5781 SHALE CT, WINTER PARK, FL 32792

    $320,00023 Days on yellowkey   MLS ID: O6422583

    For Sale O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792 46 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1086
       Built: 1985
    Monthly Fee: $69
       Tax: $2,096 (2025)
    Community: Aloma Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,753) + Fees ($69) + Taxes in 2025 ($175)


    Taxes:$2,096

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,00045 Days on yellowkey   MLS ID: O6416828

    For Sale O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2022
    Monthly Fee: $243
       Tax: $6,788 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,781 (change assumption)
    Mortgage ($3,973) + Fees ($243) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $440,00046 Days on yellowkey   MLS ID: O6416635

    REDUCED by $5,000 (1.1%) on 07/15/2026

    For Sale O6416635 - 8433 COMMANDER CV, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1903
       Built: 1986
    Monthly Fee: $76
       Tax: $3,556 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,783 (change assumption)
    Mortgage ($2,411) + Fees ($76) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $614,99034 Days on yellowkey   MLS ID: TB8517548

    For Sale TB8517548 - 4353 STEED TER, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2275
       Built: 1989
    Monthly Fee: $29
       Tax: $7,031 (2024)
    Community: Kings Cove
    Single Family


    Estimated Monthly Payment: $3,985 (change assumption)
    Mortgage ($3,370) + Fees ($29) + Taxes in 2024 ($586)


    Taxes:$7,031

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $659,99863 Days on yellowkey   MLS ID: O6409323

    REDUCED by $9,000 (1.3%) on 07/25/2026

    For Sale O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2048
       Built: 1950   Tax: $7,927 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,616) + Taxes in 2025 ($661)


    Taxes:$7,927

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 525 S LAKEMONT AVE, WINTER PARK, FL 32792

    $2,099,99051 Days on yellowkey   MLS ID: O6414770

    REDUCED by $99,010 (4.5%) on 07/14/2026

    For Sale O6414770 - 525 S LAKEMONT AVE, WINTER PARK, FL 32792 76 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3330
       Built: 2026   Tax: $7,133 (2024)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,101 (change assumption)
    Mortgage ($11,507) + Taxes in 2024 ($594)


    Taxes:$7,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000173 Days on yellowkey   MLS ID: O6380457

    4 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $51,000 (4.9%) on 05/06/2026

    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: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $1,189,00033 Days on yellowkey   MLS ID: O6419056

    REDUCED by $10,000 (0.8%) on 07/23/2026

    For Sale O6419056 - 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2075
       Built: 1953   Tax: $4,188 (2025)
    Community: Northwood Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,864 (change assumption)
    Mortgage ($6,515) + Taxes in 2025 ($349)


    Taxes:$4,188

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1886 CLEMATIS LN, WINTER PARK, FL 32792

    $425,0005 Days on yellowkey   MLS ID: O6428045

    For Sale O6428045 - 1886 CLEMATIS LN, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1238
       Built: 1960   Tax: $4,330 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,690 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($361)


    Taxes:$4,330

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1000 S SEMORAN BLVD #305, WINTER PARK, FL 32792

    $129,0005 Days on yellowkey   MLS ID: O6428044

    For Sale O6428044 - 1000 S SEMORAN BLVD #305, WINTER PARK, FL 32792 22 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 735
       Built: 1969
    Monthly Fee: $355
       Tax: $1,377 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $1,177 (change assumption)
    Mortgage ($707) + Fees ($355) + Taxes in 2025 ($115)


    Taxes:$1,377

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1546 MILLER AVE, WINTER PARK, FL 32789

    $1,419,9005 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


  • 5409 ALBERT DR, WINTER PARK, FL 32792

    $430,0005 Days on yellowkey   MLS ID: C7528794

    For Sale C7528794 - 5409 ALBERT DR, WINTER PARK, FL 32792 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1483
       Built: 1977   Tax: $5,337 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,801 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($445)


    Taxes:$5,337

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3562 BOUGAINVILLEA DR, WINTER PARK, FL 32792

    $339,0005 Days on yellowkey   MLS ID: O6427582

    For Sale O6427582 - 3562 BOUGAINVILLEA DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1960   Tax: $2,805 (2025)
    Community: Eastbrook Subd Unit No 05
    Single Family


    Estimated Monthly Payment: $2,091 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($234)


    Taxes:$2,805

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2323 DEVON CT, WINTER PARK, FL 32789

    $429,00040 Days on yellowkey   MLS ID: O6418530

    For Sale O6418530 - 2323 DEVON CT, WINTER PARK, FL 32789 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2403
       Built: 1951   Tax: $1,872 (2025)
    Community: Glencoe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,507 (change assumption)
    Mortgage ($2,351) + Taxes in 2025 ($156)


    Taxes:$1,872

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 777 HALIFAX AVE, WINTER PARK, FL 32792

    $1,500,00019 Days on yellowkey   MLS ID: O6422901

    For Sale O6422901 - 777 HALIFAX AVE, WINTER PARK, FL 32792 48 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3109
       Built: 2021   Tax: $16,519 (2025)
    Community: Park Manor First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,596 (change assumption)
    Mortgage ($8,219) + Taxes in 2025 ($1,377)


    Taxes:$16,519

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland 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.