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Winter Park Single Family Homes For Sale - 303 homes

Winter Park Single Family Homes for Sale are located in Seminole County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

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  • 1521 HERON WOOD PL, WINTER PARK, FL 32792

    $860,000158 Days on yellowkey   MLS ID: O6379884

    REDUCED by $65,000 (7.0%) on 06/05/2026

    For Sale O6379884 - 1521 HERON WOOD PL, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 3950
       Built: 1983   Tax: $6,494 (2024)
    Community: None
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,253 (change assumption)
    Mortgage ($4,712) + Taxes in 2024 ($541)


    Taxes:$6,494

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,324,00088 Days on yellowkey   MLS ID: O6398373

    REDUCED by $25,000 (1.9%) on 06/04/2026

    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: $8,172 (change assumption)
    Mortgage ($7,255) + 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


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,900123 Days on yellowkey   MLS ID: O6390670

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00074 Days on yellowkey   MLS ID: O6404105

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3114 HEARTLEAF PL, WINTER PARK, FL 32792

    $685,000115 Days on yellowkey   MLS ID: S5146048

    REDUCED by $14,900 (2.1%) on 06/02/2026

    For Sale S5146048 - 3114 HEARTLEAF PL, WINTER PARK, FL 32792 71 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2702
       Built: 1999
    Monthly Fee: $18
       Tax: $6,737 (2024)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,333 (change assumption)
    Mortgage ($3,753) + Fees ($18) + Taxes in 2024 ($561)


    Taxes:$6,737

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1627 MIZELL AVE, WINTER PARK, FL 32789

    $3,300,00058 Days on yellowkey   MLS ID: O6406300

    For Sale O6406300 - 1627 MIZELL AVE, WINTER PARK, FL 32789 24 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3421
       Built: 2026   Tax: $11,211 (2025)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $19,016 (change assumption)
    Mortgage ($18,082) + Taxes in 2025 ($934)


    Taxes:$11,211

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $325,00099 Days on yellowkey   MLS ID: S5147029

    INCREASED by $125,000 (62.5%) on 06/01/2026

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,000165 Days on yellowkey   MLS ID: O6362285

    0 Days Off yellowkey (back on 5/31/2026)

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1092 EASTBROOK BLVD, WINTER PARK, FL 32792

    $399,00059 Days on yellowkey   MLS ID: O6407251

    REDUCED by $11,000 (2.7%) on 05/27/2026

    For Sale O6407251 - 1092 EASTBROOK BLVD, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1122
       Built: 1959   Tax: $4,373 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($364)


    Taxes:$4,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,000105 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • WINTER PARK, FL 32792

    $430,000124 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $925,000287 Days on yellowkey   MLS ID: O6344540

    REDUCED by $24,000 (2.5%) on 05/24/2026

    For Sale O6344540 - 560 OLOLU DR, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1953   Tax: $8,617 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $5,786 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 650 DIXIE PKWY, WINTER PARK, FL 32789

    $4,250,00057 Days on yellowkey   MLS ID: O6408708

    5 Days Off yellowkey (back on 5/26/2026)

    For Sale O6408708 - 650 DIXIE PKWY, WINTER PARK, FL 32789 85 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 6007
       Built: 2018   Tax: $41,255 (2025)
    Community: Winflor Court Pt Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,725 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,438)


    Taxes:$41,255

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1780 BRYAN AVE, WINTER PARK, FL 32789

    $849,000216 Days on yellowkey   MLS ID: O6365369

    For Sale O6365369 - 1780 BRYAN AVE, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 1952   Tax: $7,345 (2024)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $5,264 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($612)


    Taxes:$7,345

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1725 CAROLLEE LN, WINTER PARK, FL 32789

    $1,005,00078 Days on yellowkey   MLS ID: O6402656

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $10,000 (1.0%) on 05/12/2026

    For Sale O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2335
       Built: 1960   Tax: $8,445 (2025)
    Community: Green Terrace
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($5,507) + Taxes in 2025 ($704)


    Taxes:$8,445

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00054 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1347 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,395,00060 Days on yellowkey   MLS ID: O6408189

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6408189 - 1347 CHAPMAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2922
       Built: 2013
    Monthly Fee: $268
       Tax: $16,875 (2025)
    Community: Windsong Elizabeths Walk
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,318 (change assumption)
    Mortgage ($7,644) + Fees ($268) + Taxes in 2025 ($1,406)


    Taxes:$16,875

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 207 E KINGS WAY, WINTER PARK, FL 32789

    $3,650,000294 Days on yellowkey   MLS ID: O6337304

    For Sale O6337304 - 207 E KINGS WAY, WINTER PARK, FL 32789 6 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3719
       Built: 2026   Tax: $2,975 (2024)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $20,247 (change assumption)
    Mortgage ($20,000) + Taxes in 2024 ($248)


    Taxes:$2,975

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 363 N PHELPS AVE, WINTER PARK, FL 32789

    $1,249,00082 Days on yellowkey   MLS ID: O6401811

    For Sale O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2871
       Built: 1950   Tax: $8,856 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $7,582 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($738)


    Taxes:$8,856

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7532 AZUREBROOK CT, WINTER PARK, FL 32792

    $410,00067 Days on yellowkey   MLS ID: O6406380

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale O6406380 - 7532 AZUREBROOK CT, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1402
       Built: 1979   Tax: $4,889 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,654 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($407)


    Taxes:$4,889

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.