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Winter Park Homes For Sale & Real Estate - 447 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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  • 1541 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,030,000131 Days on yellowkey   MLS ID: O6374409

    REDUCED by $60,000 (5.5%) on 05/07/2026

    For Sale O6374409 - 1541 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2578
       Built: 1935   Tax: $5,932 (2024)
    Community: Orwin Manor Westminster Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,138 (change assumption)
    Mortgage ($5,644) + Taxes in 2024 ($494)


    Taxes:$5,932

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 346 S RANGER BLVD, WINTER PARK, FL 32792

    $475,000259 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

    $800,00027 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


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $300,00087 Days on yellowkey   MLS ID: O6384755

    1 Days Off yellowkey (back on 5/16/2026)

    REDUCED by $15,000 (4.8%) on 04/28/2026

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,644) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000207 Days on yellowkey   MLS ID: O6357934

    0 Days Off yellowkey (back on 5/14/2026)

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1761 LEGION DR, WINTER PARK, FL 32789

    $3,270,000353 Days on yellowkey   MLS ID: O6302616

    REDUCED by $25,000 (0.8%) on 04/15/2026

    For Sale O6302616 - 1761 LEGION DR, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4955
       Built: 2017   Tax: $22,139 (2024)
    Community: Green Oaks Rep 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,762 (change assumption)
    Mortgage ($17,917) + Taxes in 2024 ($1,845)


    Taxes:$22,139

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 141 GLENRIDGE WAY, WINTER PARK, FL 32789

    $3,250,00065 Days on yellowkey   MLS ID: O6393616

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6393616 - 141 GLENRIDGE WAY, WINTER PARK, FL 32789 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5243
       Built: 2008   Tax: $40,155 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $21,154 (change assumption)
    Mortgage ($17,808) + Taxes in 2025 ($3,346)


    Taxes:$40,155

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7001 JACKMAN BLVD, WINTER PARK, FL 32792

    $450,00016 Days on yellowkey   MLS ID: O6408371

    For Sale O6408371 - 7001 JACKMAN BLVD, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1482
       Built: 1977   Tax: $4,421 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($368)


    Taxes:$4,421

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00022 Days on yellowkey   MLS ID: O6406526

    2 Days Off yellowkey (back on 5/15/2026)

    For Sale O6406526 - 266 W LYMAN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2014
    Monthly Fee: $568
       Tax: $11,410 (2024)
    Community: Lyman Ave Villas 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $9,053 (change assumption)
    Mortgage ($7,534) + Fees ($568) + Taxes in 2024 ($951)


    Taxes:$11,410

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $410,00049 Days on yellowkey   MLS ID: O6398450

    REDUCED by $17,500 (4.1%) on 05/15/2026

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,782 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2500 LEE RD #232, WINTER PARK, FL 32789

    $164,90025 Days on yellowkey   MLS ID: O6404916

    For Sale O6404916 - 2500 LEE RD #232, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $292
       Tax: $2,216 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,380 (change assumption)
    Mortgage ($904) + Fees ($292) + Taxes in 2025 ($185)


    Taxes:$2,216

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3627 SEAGRAPE DR, WINTER PARK, FL 32792

    $339,00029 Days on yellowkey   MLS ID: O6403218

    0 Days Off yellowkey (back on 5/15/2026)

    For Sale O6403218 - 3627 SEAGRAPE DR, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1233
       Built: 1965   Tax: $3,401 (2024)
    Community: Eastbrook Sub Unit 03
    Single Family


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,857) + Taxes in 2024 ($283)


    Taxes:$3,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $220,000139 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


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $849,90034 Days on yellowkey   MLS ID: O6402566

    REDUCED by $91,100 (9.7%) on 05/15/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,890 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $850,00037 Days on yellowkey   MLS ID: O6400331

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,581 (change assumption)
    Mortgage ($4,657) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 220 W READING WAY, WINTER PARK, FL 32789

    $1,195,00023 Days on yellowkey   MLS ID: O6405775

    2 Days Off yellowkey (back on 5/14/2026)

    For Sale O6405775 - 220 W READING WAY, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2723
       Built: 1947   Tax: $14,025 (2025)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,716 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($1,169)


    Taxes:$14,025

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


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

    $150,000163 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


  • 423 OLOLU DR, WINTER PARK, FL 32789

    $549,000143 Days on yellowkey   MLS ID: O6369976

    REDUCED by $40,000 (6.8%) on 05/14/2026

    For Sale O6369976 - 423 OLOLU DR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1920
       Built: 1981   Tax: $4,030 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($336)


    Taxes:$4,030

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2500 LEE RD #208, WINTER PARK, FL 32789

    $175,000415 Days on yellowkey   MLS ID: O6297570

    REDUCED by $5,000 (2.8%) on 05/14/2026

    For Sale O6297570 - 2500 LEE RD #208, WINTER PARK, FL 32789 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $1,519 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($959) + Fees ($432) + Taxes in 2025 ($127)


    Taxes:$1,519

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • WINTER PARK, FL 32789

    $1,249,90019 Days on yellowkey   MLS ID: O6406381

    For Sale O6406381 - WINTER PARK, FL 32789 25 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




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.