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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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  • 633 BALMORAL RD, WINTER PARK, FL 32789

    $1,795,000187 Days on yellowkey   MLS ID: O6353491

    3 Days Off yellowkey (back on 3/24/2026)

    For Sale O6353491 - 633 BALMORAL RD, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 1968   Tax: $10,321 (2024)
    Community: Kenilworth Shores Sec 06
    Single Family


    Estimated Monthly Payment: $10,695 (change assumption)
    Mortgage ($9,835) + Taxes in 2024 ($860)


    Taxes:$10,321

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000135 Days on yellowkey   MLS ID: S5139410

    For Sale S5139410 - 2612 ROXBURY RD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 0.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000173 Days on yellowkey   MLS ID: S5137596

    For Sale S5137596 - 2612 ROXBURY RD, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 207 E KINGS WAY, WINTER PARK, FL 32789

    $3,650,000214 Days on yellowkey   MLS ID: O6337304

    For Sale O6337304 - 207 E KINGS WAY, WINTER PARK, FL 32789 6 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3719
       Built: 2026   Tax: $2,975 (2024)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $20,247 (change assumption)
    Mortgage ($20,000) + Taxes in 2024 ($248)


    Taxes:$2,975

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1280 GLADIOLAS DR, WINTER PARK, FL 32792

    $489,000114 Days on yellowkey   MLS ID: O6370371

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6370371 - 1280 GLADIOLAS DR, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $5,162 (2024)
    Community: Garden Lake Estates Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,110 (change assumption)
    Mortgage ($2,679) + Taxes in 2024 ($430)


    Taxes:$5,162

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1589 VIBURNUM LN, WINTER PARK, FL 32792

    $365,00012 Days on yellowkey   MLS ID: O6398603

    For Sale O6398603 - 1589 VIBURNUM LN, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1961   Tax: $1,153 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,096 (change assumption)
    Mortgage ($2,000) + Taxes in 2024 ($96)


    Taxes:$1,153

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,00012 Days on yellowkey   MLS ID: O6398533

    For Sale O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1979   Tax: $7,265 (2025)
    Community: Golfside Sec 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,614 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($605)


    Taxes:$7,265

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,00086 Days on yellowkey   MLS ID: O6373287

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1367 TIERRA CIR, WINTER PARK, FL 32792

    $424,90095 Days on yellowkey   MLS ID: O6375221

    For Sale O6375221 - 1367 TIERRA CIR, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 1969   Tax: $4,948 (2024)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,328) + Taxes in 2024 ($412)


    Taxes:$4,948

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1822 GREENWICH AVE, WINTER PARK, FL 32789

    $995,000183 Days on yellowkey   MLS ID: A4669605

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale A4669605 - 1822 GREENWICH AVE, WINTER PARK, FL 32789 6 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1953   Tax: $2,519 (2024)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $5,662 (change assumption)
    Mortgage ($5,452) + Taxes in 2024 ($210)


    Taxes:$2,519

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1636 ELIZABETHS WALK, WINTER PARK, FL 32789

    $2,195,00022 Days on yellowkey   MLS ID: O6395638

    For Sale O6395638 - 1636 ELIZABETHS WALK, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2016
    Monthly Fee: $268
       Tax: $25,133 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,389 (change assumption)
    Mortgage ($12,027) + Fees ($268) + Taxes in 2025 ($2,094)


    Taxes:$25,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3711 VINSETTA CT, WINTER PARK, FL 32792

    $1,350,00092 Days on yellowkey   MLS ID: O6376139

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale O6376139 - 3711 VINSETTA CT, WINTER PARK, FL 32792 66 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4214
       Built: 2015
    Monthly Fee: $178
       Tax: $7,488 (2025)
    Community: Lakeside Estates
    Single Family


    Estimated Monthly Payment: $8,199 (change assumption)
    Mortgage ($7,397) + Fees ($178) + Taxes in 2025 ($624)


    Taxes:$7,488

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 543 E LAKE SUE AVE, WINTER PARK, FL 32789

    $1,875,00016 Days on yellowkey   MLS ID: O6397480

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6397480 - 543 E LAKE SUE AVE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3657
       Built: 1986   Tax: $14,126 (2025)
    Community: Lake Virginia Pt Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,451 (change assumption)
    Mortgage ($10,274) + Taxes in 2025 ($1,177)


    Taxes:$14,126

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00037 Days on yellowkey   MLS ID: O6391025

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6391025 - 2919 BOWER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2325
       Built: 1971   Tax: $9,857 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,090 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 850 JUANITA RAEL, WINTER PARK, FL 32789

    $1,425,000108 Days on yellowkey   MLS ID: O6370568

    1 Days Off yellowkey (back on 1/12/2026)

    For Sale O6370568 - 850 JUANITA RAEL, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 1966   Tax: $6,218 (2024)
    Community: Green Oaks Rep 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,326 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($518)


    Taxes:$6,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1453 VIA SANGRO PL, WINTER PARK, FL 32792

    $995,00016 Days on yellowkey   MLS ID: O6397250

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6397250 - 1453 VIA SANGRO PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3057
       Built: 2015
    Monthly Fee: $188
       Tax: $5,858 (2024)
    Community: Lakeside Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,128 (change assumption)
    Mortgage ($5,452) + Fees ($188) + Taxes in 2024 ($488)


    Taxes:$5,858

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 676 DUNBLANE DR, WINTER PARK, FL 32792

    $750,000141 Days on yellowkey   MLS ID: O6365557

    For Sale O6365557 - 676 DUNBLANE DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1962   Tax: $5,584 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,575 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($465)


    Taxes:$5,584

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00036 Days on yellowkey   MLS ID: O6383092

    For Sale O6383092 - 906 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3618
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,745 (change assumption)
    Mortgage ($10,548) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1521 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,799,90050 Days on yellowkey   MLS ID: A4685113

    REDUCED by $50,000 (2.7%) on 04/12/2026

    For Sale A4685113 - 1521 CHESTNUT AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2842
       Built: 2022   Tax: $20,570 (2024)
    Community: Lake Knowles Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,576 (change assumption)
    Mortgage ($9,862) + Taxes in 2024 ($1,714)


    Taxes:$20,570

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 520 FITZWALTER DR, WINTER PARK, FL 32792

    $1,000,00052 Days on yellowkey   MLS ID: O6380171

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

    For Sale O6380171 - 520 FITZWALTER DR, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2111
       Built: 2022   Tax: $10,205 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $6,330 (change assumption)
    Mortgage ($5,479) + Taxes in 2024 ($850)


    Taxes:$10,205

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    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.