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Winter Park Homes For Sale & Real Estate - 444 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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  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,00043 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


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,425,000121 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


  • 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792

    $236,80093 Days on yellowkey   MLS ID: O6385942

    REDUCED by $13,000 (5.2%) on 04/23/2026

    For Sale O6385942 - 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1565
       Built: 2011
    Monthly Fee: $385
       Tax: $3,776 (2024)
    Community: Village/Whisperwood
    Condo


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,298) + Fees ($385) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792

    $1,825,00060 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


  • 2713 EASTERN PKWY, WINTER PARK, FL 32789

    $670,00050 Days on yellowkey   MLS ID: O6398076

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale O6398076 - 2713 EASTERN PKWY, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1304
       Built: 1988   Tax: $2,713 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $3,897 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($226)


    Taxes:$2,713

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 225 LEWFIELD CIR #225, WINTER PARK, FL 32792

    $220,000361 Days on yellowkey   MLS ID: O6314817

    For Sale O6314817 - 225 LEWFIELD CIR #225, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 953
       Built: 1973
    Monthly Fee: $465
       Tax: $1,020 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,755 (change assumption)
    Mortgage ($1,205) + Fees ($465) + Taxes in 2024 ($85)


    Taxes:$1,020

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792

    $265,00066 Days on yellowkey   MLS ID: S5146437

    REDUCED by $20,000 (7.0%) on 04/21/2026

    For Sale S5146437 - 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1495
       Built: 1984   Tax: $3,702 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,452) + Taxes in 2024 ($308)


    Taxes:$3,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,000128 Days on yellowkey   MLS ID: O6375881

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6375881 - 1792 CHILEAN LN, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 984
       Built: 1959   Tax: $2,677 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,004 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($223)


    Taxes:$2,677

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000296 Days on yellowkey   MLS ID: O6333863

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000302 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $825,00053 Days on yellowkey   MLS ID: O6396971

    For Sale O6396971 - 1369 BLUE STEM LN, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $413
       Tax: $6,074 (2024)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,440 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1570 PALMER AVE, WINTER PARK, FL 32789

    $1,640,00067 Days on yellowkey   MLS ID: O6383529

    REDUCED by $50,000 (3.0%) on 04/13/2026

    For Sale O6383529 - 1570 PALMER AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2007   Tax: $10,527 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,863 (change assumption)
    Mortgage ($8,986) + Taxes in 2024 ($877)


    Taxes:$10,527

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1701 SUMMERLAND AVE, WINTER PARK, FL 32789

    $4,550,00043 Days on yellowkey   MLS ID: O6398762

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6398762 - 1701 SUMMERLAND AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5253
       Built: 2026   Tax: $21,630 (2025)
    Community: Green Oaks Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,733 (change assumption)
    Mortgage ($24,931) + Taxes in 2025 ($1,803)


    Taxes:$21,630

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2330 COLDSTREAM DR, WINTER PARK, FL 32792

    $650,00068 Days on yellowkey   MLS ID: O6384436

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6384436 - 2330 COLDSTREAM DR, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1750
       Built: 1958   Tax: $6,951 (2024)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $4,141 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($579)


    Taxes:$6,951

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3172 CROWN JEWEL CT, WINTER PARK, FL 32792

    $339,90045 Days on yellowkey   MLS ID: O6397498

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6397498 - 3172 CROWN JEWEL CT, WINTER PARK, FL 32792 24 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1406
       Built: 2019
    Monthly Fee: $146
       Tax: $4,977 (2025)
    Community: Coronado Twnhms
    Townhouse


    Estimated Monthly Payment: $2,423 (change assumption)
    Mortgage ($1,862) + Fees ($146) + Taxes in 2025 ($415)


    Taxes:$4,977

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2015 N PARK AVE, WINTER PARK, FL 32789

    $2,295,000117 Days on yellowkey   MLS ID: O6372603

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6372603 - 2015 N PARK AVE, WINTER PARK, FL 32789 64 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3963
       Built: 2023   Tax: $27,508 (2024)
    Community: Twin Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,867 (change assumption)
    Mortgage ($12,575) + Taxes in 2024 ($2,292)


    Taxes:$27,508

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 811 OVERSPIN DR, WINTER PARK, FL 32789

    $349,00044 Days on yellowkey   MLS ID: O6400009

    For Sale O6400009 - 811 OVERSPIN DR, WINTER PARK, FL 32789 9 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 749
       Built: 1950   Tax: $3,998 (2025)
    Community: Dubsdread Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($333)


    Taxes:$3,998

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 7336 FOREST HILL CT #240, WINTER PARK, FL 32792

    $169,90092 Days on yellowkey   MLS ID: O6386461

    REDUCED by $10,000 (5.6%) on 04/08/2026

    For Sale O6386461 - 7336 FOREST HILL CT #240, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984
    Monthly Fee: $450
       Tax: $2,899 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,622 (change assumption)
    Mortgage ($931) + Fees ($450) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,925,000221 Days on yellowkey   MLS ID: O6352857

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,838 (change assumption)
    Mortgage ($10,548) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 800 JUANITA RAEL, WINTER PARK, FL 32789

    $2,300,00052 Days on yellowkey   MLS ID: O6396611

    For Sale O6396611 - 800 JUANITA RAEL, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4021
       Built: 1961   Tax: $9,773 (2025)
    Community: Green Oaks Rep 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,417 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($814)


    Taxes:$9,773

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland 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.