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Winter Park Homes For Sale & Real Estate - 410 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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  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,250,000133 Days on yellowkey   MLS ID: O6392216

    1 Days Off yellowkey (back on 7/30/2026)

    REDUCED by $99,900 (7.4%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,841 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1695 LEE RD #B108, WINTER PARK, FL 32789

    $89,99924 Days on yellowkey   MLS ID: O6422568

    For Sale O6422568 - 1695 LEE RD #B108, WINTER PARK, FL 32789 15 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966
    Monthly Fee: $347
       Tax: $1,781 (2025)
    Community: Waterfall Cove Of Winter Park
    Condo


    Estimated Monthly Payment: $989 (change assumption)
    Mortgage ($493) + Fees ($347) + Taxes in 2025 ($148)


    Taxes:$1,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $109,000114 Days on yellowkey   MLS ID: O6396190

    REDUCED by $5,000 (4.4%) on 07/06/2026

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $768 (change assumption)
    Mortgage ($597) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2228 AZALEA PL, WINTER PARK, FL 32789

    $5,600,00034 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


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $495,90092 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


  • 722 S RANGER BLVD, WINTER PARK, FL 32792

    $799,90029 Days on yellowkey   MLS ID: O6421873

    REDUCED by $25,100 (3.0%) on 07/27/2026

    For Sale O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1967   Tax: $455 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($38)


    Taxes:$455

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $458,50056 Days on yellowkey   MLS ID: O6413717

    REDUCED by $500 (0.1%) on 07/30/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,721 (change assumption)
    Mortgage ($2,512) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $994,000137 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $1,000 (0.1%) on 07/13/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,424 (change assumption)
    Mortgage ($5,446) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,262,50043 Days on yellowkey   MLS ID: O6418198

    REDUCED by $12,500 (1.0%) on 07/23/2026

    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: $7,521 (change assumption)
    Mortgage ($6,918) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4437 GLENMOOR CT, WINTER PARK, FL 32792

    $525,00018 Days on yellowkey   MLS ID: O6424511

    1 Days Off yellowkey (back on 7/30/2026)

    REDUCED by $14,000 (2.6%) on 07/23/2026

    For Sale O6424511 - 4437 GLENMOOR CT, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2633
       Built: 1986   Tax: $8,163 (2025)
    Community: Glenmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,557 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($680)


    Taxes:$8,163

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $759,00051 Days on yellowkey   MLS ID: O6415904

    0 Days Off yellowkey (back on 7/30/2026)

    REDUCED by $16,000 (2.1%) on 07/22/2026

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,727 (change assumption)
    Mortgage ($4,159) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792

    $267,000105 Days on yellowkey   MLS ID: O6398500

    INCREASED by $4,000 (1.5%) on 07/30/2026

    For Sale O6398500 - 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1987   Tax: $1,107 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,555 (change assumption)
    Mortgage ($1,463) + Taxes in 2025 ($92)


    Taxes:$1,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3220 NETHERWOOD DR, WINTER PARK, FL 32792

    $269,000196 Days on yellowkey   MLS ID: O6374172

    REDUCED by $10,990 (3.9%) on 04/20/2026

    For Sale O6374172 - 3220 NETHERWOOD DR, WINTER PARK, FL 32792 18 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1982   Tax: $1,222 (2025)
    Community: Coronation Add
    Half Duplex


    Estimated Monthly Payment: $1,576 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($102)


    Taxes:$1,222

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792

    $285,000302 Days on yellowkey   MLS ID: O6342993

    For Sale O6342993 - 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1669
       Built: 1986
    Monthly Fee: $511
       Tax: $3,477 (2024)
    Community: Cedarwood Village
    Spa: No

    Condo


    Estimated Monthly Payment: $2,362 (change assumption)
    Mortgage ($1,562) + Fees ($511) + Taxes in 2024 ($290)


    Taxes:$3,477

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $245,000102 Days on yellowkey   MLS ID: O6400674

    REDUCED by $5,000 (2.0%) on 07/11/2026

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,055 (change assumption)
    Mortgage ($1,342) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1113 VIA DEL MAR, WINTER PARK, FL 32789

    $1,595,000177 Days on yellowkey   MLS ID: O6379697

    For Sale O6379697 - 1113 VIA DEL MAR, WINTER PARK, FL 32789 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2012
       Built: 1957   Tax: $13,924 (2024)
    Community: Tuscany Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,740) + Taxes in 2024 ($1,160)


    Taxes:$13,924

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $609,90036 Days on yellowkey   MLS ID: TB8517548

    REDUCED by $5,090 (0.8%) on 07/29/2026

    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: $3,957 (change assumption)
    Mortgage ($3,342) + 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


  • 5444 PEACO PL, WINTER PARK, FL 32792

    $250,0003 Days on yellowkey   MLS ID: O6428383

    0 Days Off yellowkey (back on 7/29/2026)

    For Sale O6428383 - 5444 PEACO PL, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 924
       Built: 1984   Tax: $2,640 (2025)
    Community: Grand Pines
    Half Duplex


    Estimated Monthly Payment: $1,590 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($220)


    Taxes:$2,640

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7026 HAMMOCK WAY, WINTER PARK, FL 32792

    $362,0009 Days on yellowkey   MLS ID: O6427437

    1 Days Off yellowkey (back on 7/29/2026)

    For Sale O6427437 - 7026 HAMMOCK WAY, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1257
       Built: 1978   Tax: $2,472 (2025)
    Community: Wrenwood Unit 3 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,984) + Taxes in 2025 ($206)


    Taxes:$2,472

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $544,900187 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/26/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,160 (change assumption)
    Mortgage ($2,986) + Taxes in 2025 ($174)


    Taxes:$2,086

    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.