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 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

Sort:
  • 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792

    $225,00072 Days on yellowkey   MLS ID: O6395720

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

    For Sale O6395720 - 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1266
       Built: 1970
    Monthly Fee: $451
       Tax: $2,131 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,861 (change assumption)
    Mortgage ($1,233) + Fees ($451) + Taxes in 2025 ($178)


    Taxes:$2,131

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $475,00054 Days on yellowkey   MLS ID: O6399199

    0 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $5,000 (1.0%) on 05/06/2026

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,172 (change assumption)
    Mortgage ($2,603) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5236 ALBERT DR, WINTER PARK, FL 32792

    $489,00030 Days on yellowkey   MLS ID: O6404725

    0 Days Off yellowkey (back on 5/17/2026)

    For Sale O6404725 - 5236 ALBERT DR, WINTER PARK, FL 32792 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1843
       Built: 1979   Tax: $5,820 (2024)
    Community: Wrenwood Unit 3 3Rd Add
    Single Family


    Estimated Monthly Payment: $3,164 (change assumption)
    Mortgage ($2,679) + Taxes in 2024 ($485)


    Taxes:$5,820

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 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


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $300,000100 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

    $320,000220 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


  • 141 GLENRIDGE WAY, WINTER PARK, FL 32789

    $3,250,00078 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


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00035 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

    $410,00062 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

    $164,90038 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


  • 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


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $849,90047 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


  • 423 OLOLU DR, WINTER PARK, FL 32789

    $549,000156 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

    $175,000428 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

    $1,249,90032 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


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,00064 Days on yellowkey   MLS ID: O6397890

    For Sale O6397890 - 2600 EUSTON RD, WINTER PARK, FL 32789 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 3145
       Built: 1951   Tax: $7,446 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,072 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($620)


    Taxes:$7,446

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000143 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 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


  • 721 DUNBAR ST, WINTER PARK, FL 32789

    $399,99936 Days on yellowkey   MLS ID: O6405338

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

    For Sale O6405338 - 721 DUNBAR ST, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1018
       Built: 1950   Tax: $5,267 (2025)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($439)


    Taxes:$5,267

    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.