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Winter Park Single Family Homes For Sale - 283 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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  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $444,900126 Days on yellowkey   MLS ID: O6393594

    REDUCED by $5,000 (1.1%) on 07/13/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00089 Days on yellowkey   MLS ID: O6402961

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2905 PARKLAND DR, WINTER PARK, FL 32789

    $3,395,00021 Days on yellowkey   MLS ID: O6422550

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 4850
       Built: 2026   Tax: $5,748 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $19,081 (change assumption)
    Mortgage ($18,602) + Taxes in 2025 ($479)


    Taxes:$5,748

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000378 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 439 N CAPEN AVE, WINTER PARK, FL 32789

    $849,00022 Days on yellowkey   MLS ID: O6422949

    3 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422949 - 439 N CAPEN AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2017
    Monthly Fee: $400
       Tax: $11,803 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,036 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($984)


    Taxes:$11,803

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1956 JAPONICA RD, WINTER PARK, FL 32792

    $549,00028 Days on yellowkey   MLS ID: O6421731

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6421731 - 1956 JAPONICA RD, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1923
       Built: 1972
    Monthly Fee: $2
       Tax: $4,849 (2025)
    Community: Winter Woods
    Single Family


    Estimated Monthly Payment: $3,414 (change assumption)
    Mortgage ($3,008) + Fees ($2) + Taxes in 2025 ($404)


    Taxes:$4,849

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $569,900104 Days on yellowkey   MLS ID: O6399014

    REDUCED by $25,100 (4.2%) on 07/13/2026

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $3,868 (change assumption)
    Mortgage ($3,123) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1782 PINE AVE, WINTER PARK, FL 32789

    $3,697,000139 Days on yellowkey   MLS ID: O6389039

    0 Days Off yellowkey (back on 7/12/2026)

    REDUCED by $178,000 (4.6%) on 07/08/2026

    For Sale O6389039 - 1782 PINE AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 6.5   Gar: 4
    Liv Area Sq Ft: 4782
       Built: 2026   Tax: $4,880 (2025)
    Community: Conwill Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,664 (change assumption)
    Mortgage ($20,257) + Taxes in 2025 ($407)


    Taxes:$4,880

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 437 N CAPEN AVE, WINTER PARK, FL 32789

    $849,00044 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


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,625,00093 Days on yellowkey   MLS ID: O6402113

    REDUCED by $70,000 (4.1%) on 06/18/2026

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,589 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,00064 Days on yellowkey   MLS ID: O6410899

    For Sale O6410899 - 715 S RANGER BLVD, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1967
    Monthly Fee: $4
       Tax: $2,773 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,808) + Fees ($4) + Taxes in 2025 ($231)


    Taxes:$2,773

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00069 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $430,00055 Days on yellowkey   MLS ID: O6409433

    1 Days Off yellowkey (back on 7/12/2026)

    INCREASED by $5,000 (1.2%) on 07/05/2026

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,748 (change assumption)
    Mortgage ($2,356) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00062 Days on yellowkey   MLS ID: O6411633

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

    Bed: 5   Bath: 4.5   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


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00062 Days 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


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00062 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

    $2,235,00070 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 6 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

    $2,099,00070 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

    $1,899,00076 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


  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00076 Days on yellowkey   MLS ID: O6403032

    For Sale O6403032 - 930 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3813
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,182 (change assumption)
    Mortgage ($11,233) + 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




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.