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Winter Park Single Family Homes For Sale - 255 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

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  • 629 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,695,00056 Days on yellowkey   MLS ID: O6386610

    For Sale O6386610 - 629 COUNTRY CLUB DR, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3031
       Built: 2026   Tax: $2,028 (2025)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,456 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($169)


    Taxes:$2,028

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 151 OAKWOOD WAY, WINTER PARK, FL 32789

    $2,950,00079 Days on yellowkey   MLS ID: O6380037

    REDUCED by $105,000 (3.4%) on 04/01/2026

    For Sale O6380037 - 151 OAKWOOD WAY, WINTER PARK, FL 32789 68 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4129
       Built: 2023   Tax: $34,218 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,015 (change assumption)
    Mortgage ($16,164) + Taxes in 2025 ($2,852)


    Taxes:$34,218

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2503 VERSAILLES AVE, WINTER PARK, FL 32789

    $2,184,000136 Days on yellowkey   MLS ID: O6365961

    REDUCED by $166,000 (7.1%) on 04/04/2026

    For Sale O6365961 - 2503 VERSAILLES AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4026
       Built: 2015   Tax: $15,760 (2024)
    Community: Fontainebleau
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,280 (change assumption)
    Mortgage ($11,967) + Taxes in 2024 ($1,313)


    Taxes:$15,760

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000170 Days on yellowkey   MLS ID: O6357615

    For Sale O6357615 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,138 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,200,000172 Days on yellowkey   MLS ID: O6355858

    For Sale O6355858 - 2299 VIA TUSCANY, WINTER PARK, FL 32789 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3986
       Built: 1953   Tax: $26,035 (2025)
    Community: Maitland Shores
    Single Family


    Estimated Monthly Payment: $14,224 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($2,170)


    Taxes:$26,035

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000429 Days on yellowkey   MLS ID: O6282425

    For Sale O6282425 - 1660 PALMER AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6406
       Built: 2024   Tax: $6,144 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,635 (change assumption)
    Mortgage ($27,123) + Taxes in 2024 ($512)


    Taxes:$6,144

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1036 ARAGON AVE, WINTER PARK, FL 32789

    $510,00071 Days on yellowkey   MLS ID: O6382491

    REDUCED by $15,000 (2.9%) on 04/11/2026

    For Sale O6382491 - 1036 ARAGON AVE, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1073
       Built: 1957   Tax: $5,764 (2024)
    Community: Seville Park
    Single Family


    Estimated Monthly Payment: $3,275 (change assumption)
    Mortgage ($2,794) + Taxes in 2024 ($480)


    Taxes:$5,764

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,8009 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


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,0009 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 82 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


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,449,00022 Days on yellowkey   MLS ID: O6384358

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 49 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,854 (change assumption)
    Mortgage ($7,940) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00029 Days on yellowkey   MLS ID: O6394012

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,989,00031 Days on yellowkey   MLS ID: O6393117

    REDUCED by $60,000 (2.9%) on 04/23/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,663 (change assumption)
    Mortgage ($10,898) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $489,99043 Days on yellowkey   MLS ID: S5145746

    REDUCED by $10,000 (2.0%) on 04/15/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 17 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,554 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,690,00052 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 63 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


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,50013 Days on yellowkey   MLS ID: O6398450

    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: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $480,0005 Days on yellowkey   MLS ID: O6399199

    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: $3,199 (change assumption)
    Mortgage ($2,630) + 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


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00060 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $3,174,000103 Days on yellowkey   MLS ID: O6372165

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

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,037 (change assumption)
    Mortgage ($17,391) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1150 VIA SALERNO, WINTER PARK, FL 32789

    $4,195,000301 Days on yellowkey   MLS ID: O6321143

    REDUCED by $555,000 (11.7%) on 04/25/2026

    For Sale O6321143 - 1150 VIA SALERNO, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3850
       Built: 2025   Tax: $10,158 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,832 (change assumption)
    Mortgage ($22,986) + Taxes in 2024 ($847)


    Taxes:$10,158

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $850,0001 Day on yellowkey   MLS ID: O6400331

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

    Bed: 5   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




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.