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Winter Park Homes For Sale & Real Estate - 417 homes

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

Location: Winter Park

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  • 2525 TEMPLE DR, WINTER PARK, FL 32789

    $4,750,0001 Day on yellowkey   MLS ID: O6427787

    For Sale O6427787 - 2525 TEMPLE DR, WINTER PARK, FL 32789 51 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4542
       Built: 2019   Tax: $31,039 (2025)
    Community: Lake Maitland
    Spa: No

    Single Family


    Estimated Monthly Payment: $28,613 (change assumption)
    Mortgage ($26,027) + Taxes in 2025 ($2,587)


    Taxes:$31,039

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3621 HAWTHORNE LN, WINTER PARK, FL 32792

    $415,00023 Days on yellowkey   MLS ID: S5153086

    For Sale S5153086 - 3621 HAWTHORNE LN, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1979   Tax: $1,108 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,366 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($92)


    Taxes:$1,108

    Elementary School: Evans Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 786 MCINTYRE AVE, WINTER PARK, FL 32789

    $625,00017 Days on yellowkey   MLS ID: O6424399

    0 Days Off yellowkey (back on 7/27/2026)

    For Sale O6424399 - 786 MCINTYRE AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1934
       Built: 1988   Tax: $4,061 (2025)
    Community: Trotters Rep
    Townhouse


    Estimated Monthly Payment: $3,763 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($338)


    Taxes:$4,061

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $500,00053 Days on yellowkey   MLS ID: O6412851

    INCREASED by $1,000 (0.2%) on 07/24/2026

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $850,000118 Days on yellowkey   MLS ID: O6395355

    REDUCED by $49,000 (5.5%) on 07/03/2026

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $4,889 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2223 CONIFER AVE, WINTER PARK, FL 32792

    $435,00016 Days on yellowkey   MLS ID: O6424677

    0 Days Off yellowkey (back on 7/27/2026)

    For Sale O6424677 - 2223 CONIFER AVE, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 1970   Tax: $2,253 (2025)
    Community: Eastbrook Sub Unit 16
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($188)


    Taxes:$2,253

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,000104 Days on yellowkey   MLS ID: O6399773

    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


  • 2833 PRINCE JOHN RD, WINTER PARK, FL 32792

    $684,0007 Days on yellowkey   MLS ID: O6427246

    For Sale O6427246 - 2833 PRINCE JOHN RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1605
       Built: 1963   Tax: $6,145 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,260 (change assumption)
    Mortgage ($3,748) + Taxes in 2025 ($512)


    Taxes:$6,145

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER PARK, FL 32789

    $1,249,90078 Days on yellowkey   MLS ID: O6406381

    For Sale O6406381 - WINTER PARK, FL 32789 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2936
       Built: 2026   Tax: $3,539 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $7,144 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($295)


    Taxes:$3,539

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1850 BRYAN AVE, WINTER PARK, FL 32789

    $795,0005 Days on yellowkey   MLS ID: R4911701

    For Sale R4911701 - 1850 BRYAN AVE, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1563
       Built: 1984   Tax: $5,938 (2025)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $4,851 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($495)


    Taxes:$5,938

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 207 E KINGS WAY, WINTER PARK, FL 32789

    $3,650,000309 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


  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $389,00042 Days on yellowkey   MLS ID: O6417098

    REDUCED by $10,000 (2.5%) on 07/27/2026

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,432 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1351 ONECO AVE, WINTER PARK, FL 32789

    $1,150,00013 Days on yellowkey   MLS ID: O6425827

    For Sale O6425827 - 1351 ONECO AVE, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2474
       Built: 1951   Tax: $9,725 (2025)
    Community: Lake Knowles Terrace 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,112 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($810)


    Taxes:$9,725

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2041 JEWELL AVE, WINTER PARK, FL 32789

    $439,90030 Days on yellowkey   MLS ID: O6420660

    REDUCED by $30,100 (6.4%) on 07/27/2026

    For Sale O6420660 - 2041 JEWELL AVE, WINTER PARK, FL 32789 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1508
       Built: 1947   Tax: $999 (2025)
    Community: Pines
    Single Family


    Estimated Monthly Payment: $2,494 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($83)


    Taxes:$999

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 722 S RANGER BLVD, WINTER PARK, FL 32792

    $799,90027 Days on yellowkey   MLS ID: O6421873

    REDUCED by $25,100 (3.0%) on 07/27/2026

    For Sale O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1967   Tax: $455 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($38)


    Taxes:$455

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $998,00068 Days on yellowkey   MLS ID: O6410059

    REDUCED by $52,000 (5.0%) on 07/27/2026

    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: $6,442 (change assumption)
    Mortgage ($5,468) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 724 MONMOUTH WAY, WINTER PARK, FL 32792

    $849,94918 Days on yellowkey   MLS ID: O6424409

    For Sale O6424409 - 724 MONMOUTH WAY, WINTER PARK, FL 32792 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2832
       Built: 1969   Tax: $9,215 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,425 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($768)


    Taxes:$9,215

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7450 WYNNEWOOD SQ #189, WINTER PARK, FL 32792

    $185,00014 Days on yellowkey   MLS ID: O6425486

    For Sale O6425486 - 7450 WYNNEWOOD SQ #189, WINTER PARK, FL 32792 41 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $450
       Tax: $567 (2025)
    Community: Hidden Oaks Condo Ph 10
    Condo


    Estimated Monthly Payment: $1,511 (change assumption)
    Mortgage ($1,014) + Fees ($450) + Taxes in 2025 ($47)


    Taxes:$567

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2487 HARBOUR WAY, WINTER PARK, FL 32792

    $290,00014 Days on yellowkey   MLS ID: O6422155

    REDUCED by $10,000 (3.3%) on 07/27/2026

    For Sale O6422155 - 2487 HARBOUR WAY, WINTER PARK, FL 32792 13 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1803
       Built: 1978
    Monthly Fee: $95
       Tax: $5,059 (2025)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $2,106 (change assumption)
    Mortgage ($1,589) + Fees ($95) + Taxes in 2025 ($422)


    Taxes:$5,059

    Elementary School: Eastbrook Elementary

    High School: Hagerty High

    Tax Year: 2025

    Middle School: Chiles Middle


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,669,00058 Days on yellowkey   MLS ID: O6412554

    REDUCED by $56,000 (3.2%) on 07/24/2026

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $10,678 (change assumption)
    Mortgage ($9,145) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

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