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Winter Park Homes For Sale & Real Estate - 187 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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  • 1729 MICHIGAN AVENUE, WINTER PARK, FL 32789

    $499,00011 Days on yellowkey   MLS ID: O5971960

    For Sale O5971960 - 1729 MICHIGAN AVENUE, WINTER PARK, FL 32789 0 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1546
       Built: 1983   Tax: $3,847 (2020)
    Community: Lawndale
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,055 (change assumption)
    Mortgage ($2,734) + Taxes in 2020 ($321)

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    Taxes:$3,847

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 465 GENIUS DRIVE, WINTER PARK, FL 32789

    $3,290,00022 Days on yellowkey   MLS ID: O5969423

    REDUCED by $60,000 (1.8%) on 09/09/2021

    For Sale O5969423 - 465 GENIUS DRIVE, WINTER PARK, FL 32789 67 photos

    Bed: 5   Bath: 6.0
    Liv Area Sq Ft: 6215
       Built: 2006
    Monthly Fee: $235
       Tax: $24,061 (2020)
    Community: Windsong North Shore 4374
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $20,267 (change assumption)
    Mortgage ($18,027) + Fees ($235) + Taxes in 2020 ($2,005)

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    Taxes:$24,061

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 1584 LITTLE WREN LANE, WINTER PARK, FL 32792

    $419,00093 Days on yellowkey   MLS ID: O5952595

    REDUCED by $3,000 (0.7%) on 09/09/2021

    For Sale O5952595 - 1584 LITTLE WREN LANE, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2378
       Built: 2020
    Monthly Fee: $235
       Tax: $918 (2020)
    Community: Enclave At Hawks Crest
    Pool: No

    Townhouse


    Estimated Monthly Payment: $2,607 (change assumption)
    Mortgage ($2,296) + Fees ($235) + Taxes in 2020 ($77)

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    Taxes:$918

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 450 OLOLU DRIVE, WINTER PARK, FL 32789

    $2,199,50012 Days on yellowkey   MLS ID: O5971616

    For Sale O5971616 - 450 OLOLU DRIVE, WINTER PARK, FL 32789 0 photos

    Bed: 5   Bath: 5.5
    Liv Area Sq Ft: 4988
       Built: 2009   Tax: $18,523 (2020)
    Community: Killarney Circle
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $13,595 (change assumption)
    Mortgage ($12,052) + Taxes in 2020 ($1,544)

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    Taxes:$18,523

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1821 BRYAN AVENUE, WINTER PARK, FL 32789

    $699,90031 Days on yellowkey   MLS ID: O5967014

    REDUCED by $10,100 (1.4%) on 09/07/2021

    For Sale O5967014 - 1821 BRYAN AVENUE, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2145
       Built: 1992   Tax: $6,433 (2020)
    Community: Lakeview Terrace
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,371 (change assumption)
    Mortgage ($3,835) + Taxes in 2020 ($536)

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    Taxes:$6,433

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 2224 VENETIAN WAY, WINTER PARK, FL 32789

    $1,650,00012 Days on yellowkey   MLS ID: O5971316

    For Sale O5971316 - 2224 VENETIAN WAY, WINTER PARK, FL 32789 0 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3673
       Built: 2008
    Monthly Fee: $10
       Tax: $15,142 (2020)
    Community: Maitland Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $10,313 (change assumption)
    Mortgage ($9,041) + Fees ($10) + Taxes in 2020 ($1,262)

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    Taxes:$15,142

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1843 BARKER Drive, WINTER PARK, FL 32789

    $575,00027 Days on yellowkey   MLS ID: O5968426

    REDUCED by $24,000 (4.0%) on 09/07/2021

    For Sale O5968426 - 1843 BARKER Drive, WINTER PARK, FL 32789 0 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1697
       Built: 1957   Tax: $5,480 (2021)
    Community: South Lakemont Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,607 (change assumption)
    Mortgage ($3,151) + Taxes in 2021 ($457)

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    Taxes:$5,480

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2021

    Middle School: Glenridge Middle


  • 1003 S KENTUCKY AVENUE, WINTER PARK, FL 32789

    $486,000152 Days on yellowkey   MLS ID: O5938669

    REDUCED by $113,000 (18.9%) on 09/07/2021

    For Sale O5938669 - 1003 S KENTUCKY AVENUE, WINTER PARK, FL 32789 21 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1803
       Built: 2002   Tax: $5,730 (2020)
    Community: Fairbanks Park
    Pool: No

    Townhouse


    Estimated Monthly Payment: $3,140 (change assumption)
    Mortgage ($2,663) + Taxes in 2020 ($478)

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    Taxes:$5,730

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 2101 OAKHURST AVENUE, WINTER PARK, FL 32792

    $369,90034 Days on yellowkey   MLS ID: O5965884

    11 Days Off yellowkey (back on 8/30/2021)

    REDUCED by $10,000 (2.6%) on 09/07/2021

    For Sale O5965884 - 2101 OAKHURST AVENUE, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1812
       Built: 1959   Tax: $1,310 (2020)
    Community: Park Manor First Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,136 (change assumption)
    Mortgage ($2,027) + Taxes in 2020 ($109)

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    Taxes:$1,310

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 814 HAMILTON PLACE COURT, WINTER PARK, FL 32789

    $849,90013 Days on yellowkey   MLS ID: O5967551

    For Sale O5967551 - 814 HAMILTON PLACE COURT, WINTER PARK, FL 32789 0 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2907
       Built: 2007
    Monthly Fee: $122
       Tax: $7,700 (2020)
    Community: Hamilton Place
    Pool: No

    Single Family


    Estimated Monthly Payment: $5,421 (change assumption)
    Mortgage ($4,657) + Fees ($122) + Taxes in 2020 ($642)

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    Taxes:$7,700

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1620 OAKHURST AVENUE, WINTER PARK, FL 32789

    $1,250,00029 Days on yellowkey   MLS ID: O5967683

    REDUCED by $50,000 (3.8%) on 09/06/2021

    For Sale O5967683 - 1620 OAKHURST AVENUE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2941
       Built: 2006   Tax: $13,544 (2020)
    Community: Comstock Park
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $7,978 (change assumption)
    Mortgage ($6,849) + Taxes in 2020 ($1,129)

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    Taxes:$13,544

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 532 S RANGER BOULEVARD, WINTER PARK, FL 32792

    $519,88079 Days on yellowkey   MLS ID: O5954570

    REDUCED by $10,000 (1.9%) on 09/06/2021

    For Sale O5954570 - 532 S RANGER BOULEVARD, WINTER PARK, FL 32792 28 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2120
       Built: 1966   Tax: $5,037 (2020)
    Community: Winter Park Pines
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $3,268 (change assumption)
    Mortgage ($2,849) + Taxes in 2020 ($420)

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    Taxes:$5,037

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 101 S LAKEMONT AVENUE, WINTER PARK, FL 32792

    $519,00090 Days on yellowkey   MLS ID: S5052456

    REDUCED by $10,900 (2.1%) on 09/06/2021

    For Sale S5052456 - 101 S LAKEMONT AVENUE, WINTER PARK, FL 32792 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1641
       Built: 1951   Tax: $4,327 (2020)
    Community: Tangerine Court
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,204 (change assumption)
    Mortgage ($2,844) + Taxes in 2020 ($361)

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    Taxes:$4,327

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 2051 LYNWOOD Lane, WINTER PARK, FL 32789

    $564,90016 Days on yellowkey   MLS ID: O5970248

    For Sale O5970248 - 2051 LYNWOOD Lane, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2269
       Built: 1957   Tax: $4,357 (2020)
    Community: South Lakemont Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,458 (change assumption)
    Mortgage ($3,095) + Taxes in 2020 ($363)

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    Taxes:$4,357

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 2500 LEE ROAD UNIT 233, WINTER PARK, FL 32789

    $197,90082 Days on yellowkey   MLS ID: O5954689

    REDUCED by $2,000 (1.0%) on 09/06/2021

    For Sale O5954689 - 2500 LEE ROAD UNIT 233, WINTER PARK, FL 32789 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $162
       Tax: $1,498 (2020)
    Community: Lakeside Manor Apts Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $1,371 (change assumption)
    Mortgage ($1,084) + Fees ($162) + Taxes in 2020 ($125)

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    Taxes:$1,498

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1570 ELM AVENUE, WINTER PARK, FL 32789

    $1,295,00087 Days on yellowkey   MLS ID: O5956714

    9 Days Off yellowkey (back on 8/19/2021)

    REDUCED by $29,000 (2.2%) on 09/06/2021

    For Sale O5956714 - 1570 ELM AVENUE, WINTER PARK, FL 32789 36 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 3755
       Built: 1998   Tax: $10,641 (2020)
    Community: Temple Estates
    Pool: No

    Single Family


    Estimated Monthly Payment: $7,982 (change assumption)
    Mortgage ($7,096) + Taxes in 2020 ($887)

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    Taxes:$10,641

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • WINTER PARK, FL 32792

    $419,50032 Days on yellowkey   MLS ID: O5967055

    REDUCED by $6,400 (1.5%) on 09/06/2021

    For Sale O5967055 - WINTER PARK, FL 32792 23 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1608
       Built: 1964   Tax: $5,078 (2020)

    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,722 (change assumption)
    Mortgage ($2,299) + Taxes in 2020 ($423)

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    Taxes:$5,078

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 1281 WOODMERE DRIVE, WINTER PARK, FL 32789

    $2,095,00065 Days on yellowkey   MLS ID: O5958349

    REDUCED by $300,000 (12.5%) on 09/06/2021

    For Sale O5958349 - 1281 WOODMERE DRIVE, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 5.5
    Liv Area Sq Ft: 4027
       Built: 2010   Tax: $14,739 (2020)
    Community: Woodmere Terrace Rep
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $12,707 (change assumption)
    Mortgage ($11,479) + Taxes in 2020 ($1,228)

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    Taxes:$14,739

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 807 HUNTINGTON COURT, WINTER PARK, FL 32789

    $399,00044 Days on yellowkey   MLS ID: O5960773

    REDUCED by $11,000 (2.7%) on 09/06/2021

    For Sale O5960773 - 807 HUNTINGTON COURT, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1202
       Built: 1982   Tax: $2,371 (2020)
    Community: Huntington Court
    Pool: No

    Townhouse


    Estimated Monthly Payment: $2,384 (change assumption)
    Mortgage ($2,186) + Taxes in 2020 ($198)

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    Taxes:$2,371

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Audubon Park K-8


  • 1591 CARDINAL COURT, WINTER PARK, FL 32789

    $1,015,00068 Days on yellowkey   MLS ID: O5958275

    REDUCED by $30,000 (2.9%) on 09/06/2021

    For Sale O5958275 - 1591 CARDINAL COURT, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3523
       Built: 1957   Tax: $0 (2020)
    Community: Winflor Court Pt Rep
    Pool: No

    Single Family


    Estimated Monthly Payment: $5,562 (change assumption)
    Mortgage ($5,562) + Taxes in 2020 ($0)

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    Taxes:$0

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    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®, South Broward Board of REALTORS®, MIAMI MLS, JTHS MLS, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2021 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.