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Winter Park Homes For Sale & Real Estate - 342 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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  • 770 CARVER ST, WINTER PARK, FL 32789

    $375,000194 Days on yellowkey   MLS ID: O6349509

    0 Days Off yellowkey (back on 10/15/2025)

    For Sale O6349509 - 770 CARVER ST, WINTER PARK, FL 32789 6 photos

    Bed: 4   Bath: 1.5
    Liv Area Sq Ft: 1248
       Built: 1954   Tax: $634 (2024)
    Community: Magnolia Gardens Sub
    Single Family


    Estimated Monthly Payment: $2,108 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($53)


    Taxes:$634

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,00098 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,00098 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 872 GRANVILLE DR, WINTER PARK, FL 32789

    $2,200,00020 Days on yellowkey   MLS ID: O6391464

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6391464 - 872 GRANVILLE DR, WINTER PARK, FL 32789 40 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3195
       Built: 1961   Tax: $12,465 (2025)
    Community: Park Grove W/125 Lot 10 Blk D
    Single Family


    Estimated Monthly Payment: $13,093 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($1,039)


    Taxes:$12,465

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,265,000154 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Single Family


    Estimated Monthly Payment: $12,917 (change assumption)
    Mortgage ($12,411) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2500 LEE RD. #222, WINTER PARK, FL 32789

    $189,500115 Days on yellowkey   MLS ID: O6368580

    For Sale O6368580 - 2500 LEE RD. #222, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $245
       Tax: $926 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,038) + Fees ($245) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $315,00041 Days on yellowkey   MLS ID: O6384755

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,247 (change assumption)
    Mortgage ($1,726) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,275,000146 Days on yellowkey   MLS ID: O6362124

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3828
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Single Family


    Estimated Monthly Payment: $13,594 (change assumption)
    Mortgage ($12,465) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1873 CASSELWOOD ST, WINTER PARK, FL 32792

    $295,00053 Days on yellowkey   MLS ID: O6378028

    For Sale O6378028 - 1873 CASSELWOOD ST, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1291
       Built: 1984
    Monthly Fee: $57
       Tax: $3,924 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,000 (change assumption)
    Mortgage ($1,616) + Fees ($57) + Taxes in 2024 ($327)


    Taxes:$3,924

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3127 ASH PARK LOOP, WINTER PARK, FL 32792

    $400,00040 Days on yellowkey   MLS ID: O6388568

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale O6388568 - 3127 ASH PARK LOOP, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1986
    Monthly Fee: $37
       Tax: $3,995 (2025)
    Community: Hyde Park
    Single Family


    Estimated Monthly Payment: $2,562 (change assumption)
    Mortgage ($2,192) + Fees ($37) + Taxes in 2025 ($333)


    Taxes:$3,995

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1909 EDWIN BLVD, WINTER PARK, FL 32792

    $440,000144 Days on yellowkey   MLS ID: O6362682

    1 Days Off yellowkey (back on 12/2/2025)

    For Sale O6362682 - 1909 EDWIN BLVD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1355
       Built: 1955   Tax: $4,703 (2024)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($392)


    Taxes:$4,703

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $949,000197 Days on yellowkey   MLS ID: O6344540

    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: $5,918 (change assumption)
    Mortgage ($5,200) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $234,999433 Days on yellowkey   MLS ID: O6277579

    For Sale O6277579 - 2500 LEE RD #202, WINTER PARK, FL 32789 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $398
       Tax: $2,427 (2024)
    Community: Lakeside Manor Condominium Association, Inc.
    Condo


    Estimated Monthly Payment: $1,888 (change assumption)
    Mortgage ($1,288) + Fees ($398) + Taxes in 2024 ($202)


    Taxes:$2,427

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1552 FLORENTINO LN, WINTER PARK, FL 32792

    $360,00096 Days on yellowkey   MLS ID: O6371271

    4 Days Off yellowkey (back on 3/30/2026)

    For Sale O6371271 - 1552 FLORENTINO LN, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $170
       Tax: $4,466 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,973) + Fees ($170) + Taxes in 2025 ($372)


    Taxes:$4,466

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 628 DUNBLANE DR, WINTER PARK, FL 32792

    $849,00041 Days on yellowkey   MLS ID: O6387091

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6387091 - 628 DUNBLANE DR, WINTER PARK, FL 32792 54 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2114
       Built: 1963   Tax: $3,865 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,974 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($322)


    Taxes:$3,865

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


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

    $165,00027 Days on yellowkey   MLS ID: O6388668

    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
    Condo


    Estimated Monthly Payment: $1,546 (change assumption)
    Mortgage ($904) + 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


  • 2500 LEE RD #208, WINTER PARK, FL 32789

    $180,000369 Days on yellowkey   MLS ID: O6297570

    For Sale O6297570 - 2500 LEE RD #208, WINTER PARK, FL 32789 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $1,519 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,545 (change assumption)
    Mortgage ($986) + Fees ($432) + Taxes in 2025 ($127)


    Taxes:$1,519

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $165,00027 Days on yellowkey   MLS ID: O6390662

    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: $1,546 (change assumption)
    Mortgage ($904) + 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


  • 765 BAFFIE AVE, WINTER PARK, FL 32789

    $380,00049 Days on yellowkey   MLS ID: O6384768

    1 Days Off yellowkey (back on 3/30/2026)

    For Sale O6384768 - 765 BAFFIE AVE, WINTER PARK, FL 32789 23 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 936
       Built: 1952   Tax: $2,063 (2024)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($172)


    Taxes:$2,063

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 649 BERWICK DR, WINTER PARK, FL 32792

    $610,00019 Days on yellowkey   MLS ID: O6388752

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale O6388752 - 649 BERWICK DR, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1943
       Built: 1966   Tax: $3,635 (2024)
    Community: Brookshire Heights 4Th Add
    Single Family


    Estimated Monthly Payment: $3,645 (change assumption)
    Mortgage ($3,342) + Taxes in 2024 ($303)


    Taxes:$3,635

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge 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.