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Winter Park Homes For Sale & Real Estate - 440 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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  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,000100 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 23 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4018
       Built: 2026   Tax: $8,522 (2024)
    Community: Kenilworth Shores Sec 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,211 (change assumption)
    Mortgage ($15,501) + Taxes in 2024 ($710)


    Taxes:$8,522

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1840 BRYAN AVE, WINTER PARK, FL 32789

    $1,725,00096 Days on yellowkey   MLS ID: O6391922

    REDUCED by $74,000 (4.1%) on 06/16/2026

    For Sale O6391922 - 1840 BRYAN AVE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3727
       Built: 2014   Tax: $19,607 (2025)
    Community: Lakeview Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,086 (change assumption)
    Mortgage ($9,452) + Taxes in 2025 ($1,634)


    Taxes:$19,607

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $465,00011 Days on yellowkey   MLS ID: O6416635

    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: $2,920 (change assumption)
    Mortgage ($2,548) + 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


  • 550 PALMER AVE, WINTER PARK, FL 32789

    $6,495,000245 Days on yellowkey   MLS ID: O6349188

    REDUCED by $400,000 (5.8%) on 05/07/2026

    For Sale O6349188 - 550 PALMER AVE, WINTER PARK, FL 32789 76 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5939
       Built: 2025   Tax: $10,292 (2025)
    Community: Osceola Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,446 (change assumption)
    Mortgage ($35,588) + Taxes in 2025 ($858)


    Taxes:$10,292

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792

    $194,90059 Days on yellowkey   MLS ID: O6402025

    REDUCED by $5,000 (2.5%) on 06/16/2026

    For Sale O6402025 - 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 1981   Tax: $3,077 (2025)
    Community: Winter Park Villas
    Condo


    Estimated Monthly Payment: $1,324 (change assumption)
    Mortgage ($1,068) + Taxes in 2025 ($256)


    Taxes:$3,077

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00082 Days on yellowkey   MLS ID: O6395137

    1 Days Off yellowkey (back on 6/16/2026)

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2142 BLOSSOM LN, WINTER PARK, FL 32789

    $399,90034 Days on yellowkey   MLS ID: O6409144

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409144 - 2142 BLOSSOM LN, WINTER PARK, FL 32789 14 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1957   Tax: $2,217 (2025)
    Community: Acreage
    Single Family


    Estimated Monthly Payment: $2,376 (change assumption)
    Mortgage ($2,191) + Taxes in 2025 ($185)


    Taxes:$2,217

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 525 S LAKEMONT AVE, WINTER PARK, FL 32792

    $2,199,90016 Days on yellowkey   MLS ID: O6414770

    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: $12,648 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($594)


    Taxes:$7,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4798 TANGERINE AVE #4798, WINTER PARK, FL 32792

    $180,00020 Days on yellowkey   MLS ID: S5150136

    REDUCED by $5,000 (2.7%) on 06/15/2026

    For Sale S5150136 - 4798 TANGERINE AVE #4798, WINTER PARK, FL 32792 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $368 (2025)
    Community: Wrenwood Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,017 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($31)


    Taxes:$368

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00026 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


  • 3641 OAK VISTA LN, WINTER PARK, FL 32792

    $475,00016 Days on yellowkey   MLS ID: O6412855

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1981   Tax: $1,562 (2025)
    Community: Garden Lake Estates Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1724 PINE AVE, WINTER PARK, FL 32789

    $3,095,00019 Days on yellowkey   MLS ID: O6414263

    4 Days Off yellowkey (back on 6/15/2026)

    For Sale O6414263 - 1724 PINE AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4425
       Built: 2012   Tax: $32,133 (2025)
    Community: Conwill Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,636 (change assumption)
    Mortgage ($16,958) + Taxes in 2025 ($2,678)


    Taxes:$32,133

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $144,500306 Days on yellowkey   MLS ID: O6337083

    REDUCED by $4,000 (2.7%) on 06/15/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,263 (change assumption)
    Mortgage ($792) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 700 MELROSE AVE #H4, WINTER PARK, FL 32789

    $290,00033 Days on yellowkey   MLS ID: O6409318

    For Sale O6409318 - 700 MELROSE AVE #H4, WINTER PARK, FL 32789 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964
    Monthly Fee: $699
       Tax: $851 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,589) + Fees ($699) + Taxes in 2025 ($71)


    Taxes:$851

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 GOODRICH AVE, WINTER PARK, FL 32789

    $709,00065 Days on yellowkey   MLS ID: O6400278

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $30,000 (4.1%) on 06/05/2026

    For Sale O6400278 - 1701 GOODRICH AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $5,023 (2025)
    Community: Sylvan Hgts
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($3,885) + Taxes in 2025 ($419)


    Taxes:$5,023

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2222 MARSH SEDGE LN, WINTER PARK, FL 32792

    $739,000322 Days on yellowkey   MLS ID: O6333145

    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


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $402,50021 Days on yellowkey   MLS ID: S5151098

    REDUCED by $2,500 (0.6%) on 06/15/2026

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,549 (change assumption)
    Mortgage ($2,205) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $617,500112 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,400 (0.4%) on 06/15/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,383) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1250 FORMOSA AVE, WINTER PARK, FL 32789

    $560,00021 Days on yellowkey   MLS ID: O6412954

    For Sale O6412954 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1937
       Built: 2022
    Monthly Fee: $252
       Tax: $8,328 (2025)
    Community: Urban Green 12
    Townhouse


    Estimated Monthly Payment: $4,014 (change assumption)
    Mortgage ($3,068) + Fees ($252) + Taxes in 2025 ($694)


    Taxes:$8,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000246 Days on yellowkey   MLS ID: O6352857

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    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.