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Winter Park Homes For Sale & Real Estate - 438 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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  • 2652 ABBEY RD, WINTER PARK, FL 32792

    $625,0007 Days on yellowkey   MLS ID: O6419026

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6419026 - 2652 ABBEY RD, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 1967   Tax: $7,337 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,036 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($611)


    Taxes:$7,337

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $535,00011 Days on yellowkey   MLS ID: O6417190

    For Sale O6417190 - 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1994
    Monthly Fee: $22
       Tax: $2,283 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,144 (change assumption)
    Mortgage ($2,931) + Fees ($22) + Taxes in 2025 ($190)


    Taxes:$2,283

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $675,000332 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.9%) on 06/29/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,145 (change assumption)
    Mortgage ($3,699) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,200,00095 Days on yellowkey   MLS ID: O6392394

    REDUCED by $295,000 (11.8%) on 06/29/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $12,866 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792

    $154,50060 Days on yellowkey   MLS ID: O6403912

    REDUCED by $15,000 (8.8%) on 05/28/2026

    For Sale O6403912 - 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792 27 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984   Tax: $2,899 (2025)
    Community: Hidden Oaks Condominium Association, Inc
    Condo


    Estimated Monthly Payment: $1,088 (change assumption)
    Mortgage ($847) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,225,000229 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 56 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: $12,698 (change assumption)
    Mortgage ($12,191) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2222 MARSH SEDGE LN, WINTER PARK, FL 32792

    $739,000327 Days on yellowkey   MLS ID: O6333145

    4 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $25,900 (3.4%) on 06/13/2026

    For Sale O6333145 - 2222 MARSH SEDGE LN, WINTER PARK, FL 32792 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2192
       Built: 2019
    Monthly Fee: $243
       Tax: $7,847 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($4,049) + Fees ($243) + Taxes in 2024 ($654)


    Taxes:$7,847

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 700 MELROSE AVE #J24, WINTER PARK, FL 32789

    $390,00038 Days on yellowkey   MLS ID: R4911307

    For Sale R4911307 - 700 MELROSE AVE #J24, WINTER PARK, FL 32789 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 987
       Built: 1964   Tax: $3,874 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($323)


    Taxes:$3,874

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,795,00028 Days on yellowkey   MLS ID: O6412554

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $11,368 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2228 AZALEA PL, WINTER PARK, FL 32789

    $5,600,0002 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


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900251 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792

    $275,00076 Days on yellowkey   MLS ID: O6398856

    REDUCED by $5,000 (1.8%) on 06/29/2026

    For Sale O6398856 - 5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792 38 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1984   Tax: $668 (2024)
    Community: Lazy Oaks Condo
    Condo


    Estimated Monthly Payment: $1,563 (change assumption)
    Mortgage ($1,507) + Taxes in 2024 ($56)


    Taxes:$668

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 644 N KNOWLES AVE #3, WINTER PARK, FL 32789

    $475,0001 Day on yellowkey   MLS ID: O6420484

    For Sale O6420484 - 644 N KNOWLES AVE #3, WINTER PARK, FL 32789 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 767
       Built: 1974   Tax: $4,218 (2025)
    Community: Knowles Manor North Condo
    Condo


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($352)


    Taxes:$4,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $299,000142 Days on yellowkey   MLS ID: O6380753

    1 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $13,000 (4.2%) on 06/18/2026

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,638) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792

    $109,500247 Days on yellowkey   MLS ID: O6355536

    REDUCED by $400 (0.4%) on 06/29/2026

    For Sale O6355536 - 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792 8 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 785
       Built: 1974
    Monthly Fee: $2,097
       Tax: $1,271 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($600) + Fees ($2,097) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000146 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 06/17/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,275,00011 Days on yellowkey   MLS ID: O6418198

    For Sale O6418198 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $7,590 (change assumption)
    Mortgage ($6,986) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00031 Days on yellowkey   MLS ID: O6412139

    REDUCED by $5,000 (1.0%) on 06/15/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2774 BANCHORY RD, WINTER PARK, FL 32792

    $645,0004 Days on yellowkey   MLS ID: O6418821

    For Sale O6418821 - 2774 BANCHORY RD, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1965   Tax: $7,220 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,136 (change assumption)
    Mortgage ($3,534) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7733 COUNTRY PL #G2, WINTER PARK, FL 32792

    $239,5007 Days on yellowkey   MLS ID: O6418682

    REDUCED by $4,500 (1.8%) on 06/28/2026

    For Sale O6418682 - 7733 COUNTRY PL #G2, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1982   Tax: $371 (2025)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,343 (change assumption)
    Mortgage ($1,312) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.