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Winter Park Single Family Homes For Sale - 303 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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  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $499,00040 Days on yellowkey   MLS ID: O6412851

    REDUCED by $51,000 (9.3%) on 06/15/2026

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,832 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1401 ASTER CT, WINTER PARK, FL 32792

    $429,9001 Day on yellowkey   MLS ID: O6425103

    For Sale O6425103 - 1401 ASTER CT, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1653
       Built: 1983   Tax: $3,895 (2025)
    Community: Garden Lake Estates Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,680 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($325)


    Taxes:$3,895

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1310 FAIRVIEW AVE, WINTER PARK, FL 32789

    $925,0002 Days on yellowkey   MLS ID: O6424108

    For Sale O6424108 - 1310 FAIRVIEW AVE, WINTER PARK, FL 32789 14 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2552
       Built: 1947   Tax: $8,558 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $5,782 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($713)


    Taxes:$8,558

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 250 KILLARNEY, WINTER PARK, FL 32789

    $1,600,0002 Days on yellowkey   MLS ID: O6419382

    For Sale O6419382 - 250 KILLARNEY, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2568
       Built: 1997   Tax: $16,554 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $10,146 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($1,380)


    Taxes:$16,554

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 885 CARNATION DR, WINTER PARK, FL 32792

    $375,0004 Days on yellowkey   MLS ID: S5153456

    For Sale S5153456 - 885 CARNATION DR, WINTER PARK, FL 32792 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1240
       Built: 1959   Tax: $5,196 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,488 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($433)


    Taxes:$5,196

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 450 LAKEWOOD DR, WINTER PARK, FL 32789

    $2,500,00076 Days on yellowkey   MLS ID: O6403490

    For Sale O6403490 - 450 LAKEWOOD DR, WINTER PARK, FL 32789 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4572
       Built: 2000   Tax: $11,393 (2025)
    Community: Osceola Shores Sec 03
    Single Family


    Estimated Monthly Payment: $14,648 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($949)


    Taxes:$11,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $1,199,00020 Days on yellowkey   MLS ID: O6419056

    REDUCED by $50,000 (4.0%) on 07/14/2026

    For Sale O6419056 - 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2075
       Built: 1953   Tax: $4,188 (2025)
    Community: Northwood Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,919 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($349)


    Taxes:$4,188

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 739 ROUGHBEARD RD, WINTER PARK, FL 32792

    $780,00073 Days on yellowkey   MLS ID: O6404545

    REDUCED by $20,000 (2.5%) on 07/14/2026

    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: $4,789 (change assumption)
    Mortgage ($4,274) + Taxes in 2025 ($515)


    Taxes:$6,179

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $614,99021 Days on yellowkey   MLS ID: TB8517548

    For Sale TB8517548 - 4353 STEED TER, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2275
       Built: 1989
    Monthly Fee: $29
       Tax: $7,031 (2024)
    Community: Kings Cove
    Single Family


    Estimated Monthly Payment: $3,985 (change assumption)
    Mortgage ($3,370) + Fees ($29) + Taxes in 2024 ($586)


    Taxes:$7,031

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1908 CYRIL CT, WINTER PARK, FL 32792

    $639,0007 Days on yellowkey   MLS ID: O6422937

    For Sale O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 1990
    Monthly Fee: $41
       Tax: $7,674 (2025)
    Community: Kawilla Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,182 (change assumption)
    Mortgage ($3,501) + Fees ($41) + Taxes in 2025 ($640)


    Taxes:$7,674

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2228 AZALEA PL, WINTER PARK, FL 32789

    $5,600,00019 Days on yellowkey   MLS ID: O6416342

    For Sale O6416342 - 2228 AZALEA PL, WINTER PARK, FL 32789 72 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5152
       Built: 2008   Tax: $26,904 (2025)
    Community: Maitland Shores First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $32,926 (change assumption)
    Mortgage ($30,684) + Taxes in 2025 ($2,242)


    Taxes:$26,904

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,00023 Days on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 341 E READING WAY, WINTER PARK, FL 32789

    $1,695,00016 Days on yellowkey   MLS ID: O6420387

    For Sale O6420387 - 341 E READING WAY, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3723
       Built: 2007   Tax: $20,249 (2026)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,975 (change assumption)
    Mortgage ($9,287) + Taxes in 2026 ($1,687)


    Taxes:$20,249

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Audubon Park K-8


  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $399,00029 Days on yellowkey   MLS ID: O6417098

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,487 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 462 W LYMAN AVE, WINTER PARK, FL 32789

    $1,595,0003 Days on yellowkey   MLS ID: O6423842

    For Sale O6423842 - 462 W LYMAN AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1944
       Built: 2022   Tax: $9,244 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,510 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($770)


    Taxes:$9,244

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $419,90045 Days on yellowkey   MLS ID: O6412364

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $10,090 (2.3%) on 07/09/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,373 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 230 E ROCKWOOD WAY, WINTER PARK, FL 32789

    $2,189,00042 Days on yellowkey   MLS ID: O6412857

    0 Days Off yellowkey (back on 6/9/2026)

    For Sale O6412857 - 230 E ROCKWOOD WAY, WINTER PARK, FL 32789 59 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3374
       Built: 2017   Tax: $19,191 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $13,593 (change assumption)
    Mortgage ($11,994) + Taxes in 2025 ($1,599)


    Taxes:$19,191

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $389,50095 Days on yellowkey   MLS ID: O6398450

    1 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $20,500 (5.0%) on 06/30/2026

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 44 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: $2,669 (change assumption)
    Mortgage ($2,134) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $469,90041 Days on yellowkey   MLS ID: O6413717

    REDUCED by $5,100 (1.1%) on 07/14/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,783 (change assumption)
    Mortgage ($2,575) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99962 Days on yellowkey   MLS ID: O6408461

    For Sale O6408461 - 1914 BONANZA CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1727
       Built: 1968   Tax: $4,497 (2025)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($375)


    Taxes:$4,497

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle




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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.