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Winter Park Single Family Homes For Sale - 311 homes

Winter Park Single Family Homes for Sale are located in Orange 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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  • 1300 MAYFIELD AVE, WINTER PARK, FL 32789

    $2,490,00088 Days on yellowkey   MLS ID: O6393777

    REDUCED by $205,000 (7.6%) on 06/19/2026

    For Sale O6393777 - 1300 MAYFIELD AVE, WINTER PARK, FL 32789 50 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4389
       Built: 1958   Tax: $26,658 (2025)
    Community: Temple Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,865 (change assumption)
    Mortgage ($13,643) + Taxes in 2025 ($2,221)


    Taxes:$26,658

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 332 FLEET RD, WINTER PARK, FL 32792

    $595,0005 Days on yellowkey   MLS ID: O6414829

    2 Days Off yellowkey (back on 6/23/2026)

    For Sale O6414829 - 332 FLEET RD, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 1966   Tax: $4,919 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,670 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($410)


    Taxes:$4,919

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,000Listed 06/23/2026 1:02PM   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 437 N CAPEN AVE, WINTER PARK, FL 32789

    $849,0008 Days on yellowkey   MLS ID: O6414283

    For Sale O6414283 - 437 N CAPEN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $400
       Tax: $11,943 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,047 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($995)


    Taxes:$11,943

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $2,899,900162 Days on yellowkey   MLS ID: O6372165

    REDUCED by $274,100 (8.6%) on 06/13/2026

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,536 (change assumption)
    Mortgage ($15,889) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,00070 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00012 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1023 WORTHING CT, WINTER PARK, FL 32792

    $450,00011 Days on yellowkey   MLS ID: O6416552

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $10,000 (2.2%) on 06/15/2026

    For Sale O6416552 - 1023 WORTHING CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1184
       Built: 1983   Tax: $1,092 (2025)
    Community: Howell Estates 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($91)


    Taxes:$1,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $474,900102 Days on yellowkey   MLS ID: S5145746

    REDUCED by $5,000 (1.0%) on 06/23/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,472 (change assumption)
    Mortgage ($2,602) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,599,000133 Days on yellowkey   MLS ID: O6379927

    2 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $46,000 (2.8%) on 04/29/2026

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $535,00013 Days on yellowkey   MLS ID: O6414677

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1521 CAVENDISH RD, WINTER PARK, FL 32789

    $470,00012 Days on yellowkey   MLS ID: O6415985

    For Sale O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1036
       Built: 1946   Tax: $2,793 (2025)
    Community: Orwin Manor Westminster
    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($233)


    Taxes:$2,793

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,820,00095 Days on yellowkey   MLS ID: O6391179

    REDUCED by $70,000 (3.7%) on 05/26/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,027 (change assumption)
    Mortgage ($9,972) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $680,00067 Days on yellowkey   MLS ID: TB8498515

    0 Days Off yellowkey (back on 5/27/2026)

    REDUCED by $19,000 (2.7%) on 04/30/2026

    For Sale TB8498515 - 927 FAIRWAY DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 1973   Tax: $4,784 (2025)
    Community: Golfside Sec 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,125 (change assumption)
    Mortgage ($3,726) + Taxes in 2025 ($399)


    Taxes:$4,784

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $365,00063 Days on yellowkey   MLS ID: L4961275

    REDUCED by $10,000 (2.7%) on 06/23/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,422 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00026 Days on yellowkey   MLS ID: O6411550

    For Sale O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3831
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,224 (change assumption)
    Mortgage ($12,027) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00034 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00034 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00040 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,095,00032 Days on yellowkey   MLS ID: O6410059

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,973 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire 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.