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Winter Park Homes for Sale in Winter Park - 70 homes

Winter Park homes for sale are located in Orange County, Florida. Find Winter Park 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 homes.

Location: Winter Park, Winter Park

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  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00024 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


  • 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792

    $199,90048 Days on yellowkey   MLS ID: O6402025

    For Sale O6402025 - 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 1981   Tax: $3,077 (2025)
    Community: Winter Park Villas
    Condo


    Estimated Monthly Payment: $1,352 (change assumption)
    Mortgage ($1,095) + Taxes in 2025 ($256)


    Taxes:$3,077

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $114,00066 Days on yellowkey   MLS ID: O6396190

    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: $796 (change assumption)
    Mortgage ($625) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,00015 Days on yellowkey   MLS ID: O6411325

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

    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


  • 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792

    $150,000176 Days on yellowkey   MLS ID: S5140472

    For Sale S5140472 - 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1085
       Built: 1974
    Monthly Fee: $950
       Tax: $1,660 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,910 (change assumption)
    Mortgage ($822) + Fees ($950) + Taxes in 2024 ($138)


    Taxes:$1,660

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2758 BANCHORY RD, WINTER PARK, FL 32792

    $598,000320 Days on yellowkey   MLS ID: O6329628

    For Sale O6329628 - 2758 BANCHORY RD, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1539
       Built: 1965   Tax: $7,325 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,887 (change assumption)
    Mortgage ($3,277) + Taxes in 2024 ($610)


    Taxes:$7,325

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 262 LEWFIELD CIR #262, WINTER PARK, FL 32792

    $154,90037 Days on yellowkey   MLS ID: C7525448

    REDUCED by $4,100 (2.6%) on 06/01/2026

    For Sale C7525448 - 262 LEWFIELD CIR #262, WINTER PARK, FL 32792 36 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,278 (2024)
    Community: Stratford A Winter Park Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $955 (change assumption)
    Mortgage ($849) + Taxes in 2024 ($106)


    Taxes:$1,278

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 700 MELROSE AVE #H4, WINTER PARK, FL 32789

    $290,00022 Days on yellowkey   MLS ID: O6409318

    1 Days Off yellowkey (back on 6/1/2026)

    For Sale O6409318 - 700 MELROSE AVE #H4, WINTER PARK, FL 32789 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964
    Monthly Fee: $699
       Tax: $851 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,589) + Fees ($699) + Taxes in 2025 ($71)


    Taxes:$851

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00017 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


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,00074 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

    $430,00093 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


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,394,500122 Days on yellowkey   MLS ID: O6381552

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

    REDUCED by $500 (0.0%) on 04/20/2026

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,518 (change assumption)
    Mortgage ($13,120) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 700 MELROSE AVE #J24, WINTER PARK, FL 32789

    $390,00022 Days on yellowkey   MLS ID: R4911307

    For Sale R4911307 - 700 MELROSE AVE #J24, WINTER PARK, FL 32789 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 987
       Built: 1964   Tax: $3,874 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($323)


    Taxes:$3,874

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 758 WARRENTON RD, WINTER PARK, FL 32792

    $318,98573 Days on yellowkey   MLS ID: O6395298

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

    For Sale O6395298 - 758 WARRENTON RD, WINTER PARK, FL 32792 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1988
    Monthly Fee: $86
       Tax: $3,689 (2025)
    Community: Winter Park Pines Patio Homes
    Half Duplex


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,748) + Fees ($86) + Taxes in 2025 ($307)


    Taxes:$3,689

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $619,900101 Days on yellowkey   MLS ID: O6387685

    REDUCED by $4,600 (0.7%) on 05/21/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,981 (change assumption)
    Mortgage ($3,397) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 144 LEWFIELD CIR #144, WINTER PARK, FL 32792

    $137,00093 Days on yellowkey   MLS ID: O6390043

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

    REDUCED by $7,000 (4.9%) on 04/21/2026

    For Sale O6390043 - 144 LEWFIELD CIR #144, WINTER PARK, FL 32792 18 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $351
       Tax: $720 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,162 (change assumption)
    Mortgage ($751) + Fees ($351) + Taxes in 2024 ($60)


    Taxes:$720

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 346 S RANGER BLVD, WINTER PARK, FL 32792

    $475,000272 Days on yellowkey   MLS ID: S5134662

    For Sale S5134662 - 346 S RANGER BLVD, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1965   Tax: $5,339 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,048 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($445)


    Taxes:$5,339

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 739 ROUGHBEARD RD, WINTER PARK, FL 32792

    $800,00040 Days on yellowkey   MLS ID: O6404545

    For Sale O6404545 - 739 ROUGHBEARD RD, WINTER PARK, FL 32792 42 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2194
       Built: 1968   Tax: $6,179 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,898 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($515)


    Taxes:$6,179

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 205 LEWFIELD CIR #205, WINTER PARK, FL 32792

    $220,000152 Days on yellowkey   MLS ID: S5141588

    For Sale S5141588 - 205 LEWFIELD CIR #205, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973   Tax: $796 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,272 (change assumption)
    Mortgage ($1,205) + Taxes in 2024 ($66)


    Taxes:$796

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00058 Days on yellowkey   MLS ID: O6399773

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




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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.