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Winter Park Homes For Sale & Real Estate - 420 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792

    $159,000132 Days on yellowkey   MLS ID: O6388668

    REDUCED by $6,000 (3.6%) on 06/01/2026

    For Sale O6388668 - 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792 34 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1108
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Spa: No

    Condo


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($871) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792

    $159,000132 Days on yellowkey   MLS ID: O6390662

    REDUCED by $6,000 (3.6%) on 06/01/2026

    For Sale O6390662 - 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792 35 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($871) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7522 ALOMA PINES CT, WINTER PARK, FL 32792

    $375,00065 Days on yellowkey   MLS ID: S5150544

    For Sale S5150544 - 7522 ALOMA PINES CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1872
       Built: 2017
    Monthly Fee: $407
       Tax: $4,304 (2025)
    Community: Aloma Trails
    Townhouse


    Estimated Monthly Payment: $2,820 (change assumption)
    Mortgage ($2,055) + Fees ($407) + Taxes in 2025 ($359)


    Taxes:$4,304

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $325,000114 Days on yellowkey   MLS ID: S5147029

    INCREASED by $125,000 (62.5%) on 06/01/2026

    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: $2,145 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792

    $164,99961 Days on yellowkey   MLS ID: O6411608

    For Sale O6411608 - 200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970   Tax: $2,396 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,104 (change assumption)
    Mortgage ($904) + Taxes in 2025 ($200)


    Taxes:$2,396

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1092 EASTBROOK BLVD, WINTER PARK, FL 32792

    $399,00074 Days on yellowkey   MLS ID: O6407251

    REDUCED by $11,000 (2.7%) on 05/27/2026

    For Sale O6407251 - 1092 EASTBROOK BLVD, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1122
       Built: 1959   Tax: $4,373 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($364)


    Taxes:$4,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,000120 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • WINTER PARK, FL 32792

    $430,000139 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $925,000302 Days on yellowkey   MLS ID: O6344540

    REDUCED by $24,000 (2.5%) on 05/24/2026

    For Sale O6344540 - 560 OLOLU DR, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1953   Tax: $8,617 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $5,786 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 650 DIXIE PKWY, WINTER PARK, FL 32789

    $4,250,00072 Days on yellowkey   MLS ID: O6408708

    5 Days Off yellowkey (back on 5/26/2026)

    For Sale O6408708 - 650 DIXIE PKWY, WINTER PARK, FL 32789 85 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 6007
       Built: 2018   Tax: $41,255 (2025)
    Community: Winflor Court Pt Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,725 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,438)


    Taxes:$41,255

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1725 CAROLLEE LN, WINTER PARK, FL 32789

    $1,005,00093 Days on yellowkey   MLS ID: O6402656

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $10,000 (1.0%) on 05/12/2026

    For Sale O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2335
       Built: 1960   Tax: $8,445 (2025)
    Community: Green Terrace
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($5,507) + Taxes in 2025 ($704)


    Taxes:$8,445

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00069 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1347 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,395,00075 Days on yellowkey   MLS ID: O6408189

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6408189 - 1347 CHAPMAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2922
       Built: 2013
    Monthly Fee: $268
       Tax: $16,875 (2025)
    Community: Windsong Elizabeths Walk
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,318 (change assumption)
    Mortgage ($7,644) + Fees ($268) + Taxes in 2025 ($1,406)


    Taxes:$16,875

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 207 E KINGS WAY, WINTER PARK, FL 32789

    $3,650,000309 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


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00081 Days on yellowkey   MLS ID: O6406526

    2 Days Off yellowkey (back on 5/15/2026)

    For Sale O6406526 - 266 W LYMAN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2014
    Monthly Fee: $568
       Tax: $11,410 (2024)
    Community: Lyman Ave Villas 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $9,053 (change assumption)
    Mortgage ($7,534) + Fees ($568) + Taxes in 2024 ($951)


    Taxes:$11,410

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • WINTER PARK, FL 32789

    $1,249,90078 Days on yellowkey   MLS ID: O6406381

    For Sale O6406381 - WINTER PARK, FL 32789 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2936
       Built: 2026   Tax: $3,539 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $7,144 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($295)


    Taxes:$3,539

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000189 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000189 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 408 HOLT AVE, WINTER PARK, FL 32789

    $745,00082 Days on yellowkey   MLS ID: O6405857

    For Sale O6405857 - 408 HOLT AVE, WINTER PARK, FL 32789 34 photos

    Bed: 2   Bath: 0.0
    Liv Area Sq Ft: 1440
       Built: 1942   Tax: $5,765 (2025)
    Community: Trotters Rep
    Spa: No

    Apartment


    Estimated Monthly Payment: $4,562 (change assumption)
    Mortgage ($4,082) + Taxes in 2025 ($480)


    Taxes:$5,765

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2500 LEE RD #202, WINTER PARK, FL 32789

    $224,999538 Days on yellowkey   MLS ID: O6277579

    REDUCED by $10,000 (4.3%) on 04/28/2026

    For Sale O6277579 - 2500 LEE RD #202, WINTER PARK, FL 32789 52 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $2,327 (2025)
    Community: Lakeside Manor Condominium Association, Inc.
    Condo


    Estimated Monthly Payment: $1,859 (change assumption)
    Mortgage ($1,233) + Fees ($432) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 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.