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 - 255 homes

Winter Park Single Family Homes for Sale are located in Seminole 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:
  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $200,00019 Days on yellowkey   MLS ID: S5147029

    0 Days Off yellowkey (back on 4/23/2026)

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $1,460 (change assumption)
    Mortgage ($1,096) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1760 ALABAMA DR, WINTER PARK, FL 32789

    $2,198,00052 Days on yellowkey   MLS ID: O6386409

    REDUCED by $100,000 (4.4%) on 04/23/2026

    For Sale O6386409 - 1760 ALABAMA DR, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2841
       Built: 1971   Tax: $16,368 (2025)
    Community: J Kronenberger Sub
    Single Family


    Estimated Monthly Payment: $13,408 (change assumption)
    Mortgage ($12,044) + Taxes in 2025 ($1,364)


    Taxes:$16,368

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 318 VITORIA AVE, WINTER PARK, FL 32789

    $2,200,00029 Days on yellowkey   MLS ID: O6388489

    For Sale O6388489 - 318 VITORIA AVE, WINTER PARK, FL 32789 69 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2433
       Built: 1922   Tax: $2,960 (2024)
    Community: College Quarter
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,301 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $369,900100 Days on yellowkey   MLS ID: O6373026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,313 (change assumption)
    Mortgage ($2,027) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,00085 Days on yellowkey   MLS ID: O6362285

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,0008 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


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $4,270,000247 Days on yellowkey   MLS ID: O6330736

    REDUCED by $25,000 (0.6%) on 04/21/2026

    For Sale O6330736 - 1161 VALENCIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4181
       Built: 2021   Tax: $30,421 (2024)
    Community: Valencia Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,932 (change assumption)
    Mortgage ($23,397) + Taxes in 2024 ($2,535)


    Taxes:$30,421

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,490,000172 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.8%) on 04/23/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,197 (change assumption)
    Mortgage ($19,123) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $699,0008 Days on yellowkey   MLS ID: TB8498515

    For Sale TB8498515 - 927 FAIRWAY DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 1973   Tax: $4,784 (2025)
    Community: Golfside Sec 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,229 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($399)


    Taxes:$4,784

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $609,9009 Days on yellowkey   MLS ID: O6399014

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $4,087 (change assumption)
    Mortgage ($3,342) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 665 LYMAN AVE, WINTER PARK, FL 32789

    $450,0008 Days on yellowkey   MLS ID: O6400200

    0 Days Off yellowkey (back on 4/23/2026)

    For Sale O6400200 - 665 LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1119
       Built: 1994   Tax: $5,851 (2025)
    Community: Town Of Winter Park
    Single Family


    Estimated Monthly Payment: $2,953 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($488)


    Taxes:$5,851

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2550 VENETIAN WAY, WINTER PARK, FL 32789

    $2,399,00050 Days on yellowkey   MLS ID: O6388219

    REDUCED by $51,000 (2.1%) on 04/23/2026

    For Sale O6388219 - 2550 VENETIAN WAY, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 5051
       Built: 2008   Tax: $16,724 (2024)
    Community: Maitland Shores First Add
    Single Family


    Estimated Monthly Payment: $14,539 (change assumption)
    Mortgage ($13,145) + Taxes in 2024 ($1,394)


    Taxes:$16,724

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00079 Days on yellowkey   MLS ID: O6380333

    1 Days Off yellowkey (back on 4/5/2026)

    For Sale O6380333 - 4872 ORANGE AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1881
       Built: 1960   Tax: $4,494 (2024)
    Community: Suburban Homes First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($374)


    Taxes:$4,494

    Elementary School: Lakemont Elem

    High School: None

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1174 WILDMEADOW RUN, WINTER PARK, FL 32792

    $649,90025 Days on yellowkey   MLS ID: O6394974

    REDUCED by $20,000 (3.0%) on 04/23/2026

    For Sale O6394974 - 1174 WILDMEADOW RUN, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $150
       Tax: $6,672 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,267 (change assumption)
    Mortgage ($3,561) + Fees ($150) + Taxes in 2025 ($556)


    Taxes:$6,672

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 989 EASTBROOK BLVD, WINTER PARK, FL 32792

    $349,00085 Days on yellowkey   MLS ID: O6376456

    0 Days Off yellowkey (back on 4/23/2026)

    REDUCED by $10,000 (2.8%) on 04/15/2026

    For Sale O6376456 - 989 EASTBROOK BLVD, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 1.5   Gar: 1
    Liv Area Sq Ft: 1140
       Built: 1959   Tax: $4,334 (2025)
    Community: Eastbrook
    Single Family


    Estimated Monthly Payment: $2,273 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($361)


    Taxes:$4,334

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,00085 Days on yellowkey   MLS ID: O6377988

    For Sale O6377988 - 5275 PINE LILY CIR, WINTER PARK, FL 32792 34 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3152
       Built: 2014
    Monthly Fee: $182
       Tax: $7,425 (2024)
    Community: Sanctuary At Aloma
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,444 (change assumption)
    Mortgage ($3,644) + Fees ($182) + Taxes in 2024 ($619)


    Taxes:$7,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,425,00086 Days on yellowkey   MLS ID: O6377936

    REDUCED by $50,000 (3.4%) on 04/23/2026

    For Sale O6377936 - 1751 GOODRICH AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2016   Tax: $9,263 (2024)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $8,580 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($772)


    Taxes:$9,263

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,645,00074 Days on yellowkey   MLS ID: O6379927

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,152 (change assumption)
    Mortgage ($9,013) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 473 FLETCHER PL, WINTER PARK, FL 32789

    $3,250,000171 Days on yellowkey   MLS ID: O6357810

    2 Days Off yellowkey (back on 3/4/2026)

    For Sale O6357810 - 473 FLETCHER PL, WINTER PARK, FL 32789 50 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4296
       Built: 2017   Tax: $23,551 (2024)
    Community: Sorensen Heights
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,770 (change assumption)
    Mortgage ($17,808) + Taxes in 2024 ($1,963)


    Taxes:$23,551

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792

    $1,825,00025 Days on yellowkey   MLS ID: O6393049

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6393049 - 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792 23 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3655
       Built: 2026   Tax: $7,014 (2025)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $10,584 (change assumption)
    Mortgage ($10,000) + Taxes in 2025 ($585)


    Taxes:$7,014

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




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.