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 Single Family Homes For Sale - 243 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

Sort:
  • 1840 BRYAN AVE, WINTER PARK, FL 32789

    $1,849,00032 Days on yellowkey   MLS ID: O6391922

    REDUCED by $50,500 (2.7%) on 04/20/2026

    For Sale O6391922 - 1840 BRYAN AVE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3727
       Built: 2014   Tax: $19,607 (2025)
    Community: Lakeview Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,765 (change assumption)
    Mortgage ($10,131) + Taxes in 2025 ($1,634)


    Taxes:$19,607

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1841 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,895,000113 Days on yellowkey   MLS ID: O6369653

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6369653 - 1841 HARLAND PARK DR, WINTER PARK, FL 32789 78 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3470
       Built: 2014
    Monthly Fee: $262
       Tax: $21,031 (2024)
    Community: Windsong-Knowles Place
    Single Family


    Estimated Monthly Payment: $12,398 (change assumption)
    Mortgage ($10,383) + Fees ($262) + Taxes in 2024 ($1,753)


    Taxes:$21,031

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000279 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


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,00087 Days on yellowkey   MLS ID: O6376260

    REDUCED by $5,000 (1.1%) on 04/13/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,399,00039 Days on yellowkey   MLS ID: O6390504

    REDUCED by $26,000 (1.8%) on 04/19/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,997 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2020 VIA TUSCANY, WINTER PARK, FL 32789

    $4,195,0005 Days on yellowkey   MLS ID: O6400063

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6400063 - 2020 VIA TUSCANY, WINTER PARK, FL 32789 94 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4665
       Built: 2026   Tax: $12,585 (2025)
    Community: Tuscania
    Single Family


    Estimated Monthly Payment: $24,034 (change assumption)
    Mortgage ($22,986) + Taxes in 2025 ($1,049)


    Taxes:$12,585

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,690,00048 Days on yellowkey   MLS ID: O6384756

    REDUCED by $105,000 (5.8%) on 04/08/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 60 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $10,172 (change assumption)
    Mortgage ($9,260) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900196 Days on yellowkey   MLS ID: O6350503

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,256 (change assumption)
    Mortgage ($8,958) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 731 BONGART RD, WINTER PARK, FL 32792

    $499,999109 Days on yellowkey   MLS ID: S5140952

    For Sale S5140952 - 731 BONGART RD, WINTER PARK, FL 32792 25 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1826
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2681 FITZHUGH RD, WINTER PARK, FL 32792

    $750,00061 Days on yellowkey   MLS ID: O6383699

    For Sale O6383699 - 2681 FITZHUGH RD, WINTER PARK, FL 32792 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2375
       Built: 1966   Tax: $5,903 (2024)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,601 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($492)


    Taxes:$5,903

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 639 FRIAR RD, WINTER PARK, FL 32792

    $795,00019 Days on yellowkey   MLS ID: O6395715

    1 Days Off yellowkey (back on 4/20/2026)

    For Sale O6395715 - 639 FRIAR RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1967   Tax: $3,415 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,641 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($285)


    Taxes:$3,415

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $925,00019 Days on yellowkey   MLS ID: O6395355

    REDUCED by $50,000 (5.1%) on 04/20/2026

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 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: $5,300 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $659,000217 Days on yellowkey   MLS ID: O6344482

    REDUCED by $5,000 (0.8%) on 04/20/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,237 (change assumption)
    Mortgage ($3,611) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,0005 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 87 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,659 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,0004 Days on yellowkey   MLS ID: O6398373

    For Sale O6398373 - 802 HAMILTON PLACE CT, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2843
       Built: 2018
    Monthly Fee: $142
       Tax: $9,300 (2025)
    Community: Hamilton Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,392) + Fees ($142) + Taxes in 2025 ($775)


    Taxes:$9,300

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $460,00039 Days on yellowkey   MLS ID: O6388746

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,990 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $525,00047 Days on yellowkey   MLS ID: G5108643

    REDUCED by $25,000 (4.5%) on 04/16/2026

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($2,877) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $450,00077 Days on yellowkey   MLS ID: O6379323

    REDUCED by $6,000 (1.3%) on 04/15/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,8005 Days on yellowkey   MLS ID: O6400055

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $4,054 (change assumption)
    Mortgage ($3,725) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 661 SELKIRK DR, WINTER PARK, FL 32792

    $650,000181 Days on yellowkey   MLS ID: O6354700

    REDUCED by $25,000 (3.7%) on 04/16/2026

    For Sale O6354700 - 661 SELKIRK DR, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 1962   Tax: $2,353 (2024)
    Community: Kenilworth Shores Sec 05
    Single Family


    Estimated Monthly Payment: $3,758 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($196)


    Taxes:$2,353

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.