REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Park Single Family Homes For Sale in Winter Park - 41 homes

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

Location: Winter Park, Winter Park

Sort:
  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00071 Days on yellowkey   MLS ID: O6383092

    For Sale O6383092 - 906 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3618
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,745 (change assumption)
    Mortgage ($10,548) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,200,000Listed 05/29/2026 10:05PM   MLS ID: O6412140

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,927 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,000Listed 05/29/2026 2:51PM   MLS ID: O6411325

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2803 BANCHORY RD, WINTER PARK, FL 32792

    $495,0001 Day on yellowkey   MLS ID: O6404011

    For Sale O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1596
       Built: 1965
    Monthly Fee: $5
       Tax: $2,458 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,922 (change assumption)
    Mortgage ($2,712) + Fees ($5) + Taxes in 2025 ($205)


    Taxes:$2,458

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $765,00062 Days on yellowkey   MLS ID: O6394524

    REDUCED by $10,000 (1.3%) on 05/28/2026

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,369 (change assumption)
    Mortgage ($4,192) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,00029 Days on yellowkey   MLS ID: O6404107

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,0008 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $719,00065 Days on yellowkey   MLS ID: O6385950

    REDUCED by $10,000 (1.4%) on 05/19/2026

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,697 (change assumption)
    Mortgage ($3,940) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00010 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3858
       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


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,0001 Day on yellowkey   MLS ID: O6410963

    For Sale O6410963 - 950 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3797
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,593 (change assumption)
    Mortgage ($11,644) + 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


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,0001 Day on yellowkey   MLS ID: O6411633

    For Sale O6411633 - 946 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3989
       Built: 2026
    Monthly Fee: $375
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,118 (change assumption)
    Mortgage ($11,918) + Fees ($375) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,0001 Day on yellowkey   MLS ID: O6411550

    For Sale O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4231
       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


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $595,00039 Days on yellowkey   MLS ID: O6400395

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,729 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $554,900125 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 05/01/2026

    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: $3,214 (change assumption)
    Mortgage ($3,040) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,0003 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00016 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 505 CORNWALL RD, WINTER PARK, FL 32792

    $675,00010 Days on yellowkey   MLS ID: O6408759

    For Sale O6408759 - 505 CORNWALL RD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1813
       Built: 1965   Tax: $7,194 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,298 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($600)


    Taxes:$7,194

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,00060 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


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00071 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00010 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 3 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


123


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.