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Winter Park Single Family Homes For Sale - 127 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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  • 1891 OGLESBY AVENUE, WINTER PARK, FL 32789

    $389,9007 Days on yellowkey   MLS ID: O5917234

    3 Days Off yellowkey (back on 1/22/2021)

    For Sale O5917234 - 1891 OGLESBY AVENUE, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1195
       Built: 2021   Tax: $727 (2020)
    Community: Olympia Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,197 (change assumption)
    Mortgage ($2,136) + Taxes in 2020 ($61)

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    Taxes:$727

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2020

    Middle School: College Park Middle


  • 1877 WINTER PARK ROAD, WINTER PARK, FL 32789

    $569,0001 Day on yellowkey   MLS ID: O5918541

    For Sale O5918541 - 1877 WINTER PARK ROAD, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1900
       Built: 1950   Tax: $6,004 (2020)
    Community: Charmont
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,618 (change assumption)
    Mortgage ($3,118) + Taxes in 2020 ($500)

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    Taxes:$6,004

    Elementary School: Audubon Park K-8

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Audubon Park K-8


  • 1671 CHESTNUT AVENUE, WINTER PARK, FL 32789

    $1,019,0002 Days on yellowkey   MLS ID: O5918394

    For Sale O5918394 - 1671 CHESTNUT AVENUE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 3178
       Built: 2007   Tax: $9,461 (2020)
    Community: Lake Knowles Terrace
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $6,372 (change assumption)
    Mortgage ($5,583) + Taxes in 2020 ($788)

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    Taxes:$9,461

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 2602 AMSDEN ROAD, WINTER PARK, FL 32792

    $358,90020 Days on yellowkey   MLS ID: O5913696

    REDUCED by $1,000 (0.3%) on 01/22/2021

    For Sale O5913696 - 2602 AMSDEN ROAD, WINTER PARK, FL 32792 79 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2488
       Built: 1959   Tax: $1,513 (2020)
    Community: Winter Park Estates
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,093 (change assumption)
    Mortgage ($1,967) + Taxes in 2020 ($126)

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    Taxes:$1,513

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 7343 COOK LANE, WINTER PARK, FL 32792

    $279,0003 Days on yellowkey   MLS ID: O5918150

    For Sale O5918150 - 7343 COOK LANE, WINTER PARK, FL 32792 23 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1381
       Built: 1981   Tax: $2,419 (2020)
    Community: Oakcrest-516
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,730 (change assumption)
    Mortgage ($1,529) + Taxes in 2020 ($202)

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    Taxes:$2,419

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 3600 HAWTHORNE LANE, WINTER PARK, FL 32792

    $315,0003 Days on yellowkey   MLS ID: O5918432

    For Sale O5918432 - 3600 HAWTHORNE LANE, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1587
       Built: 1978   Tax: $1,514 (2020)
    Community: Garden Lake Estates Unit 1
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,852 (change assumption)
    Mortgage ($1,726) + Taxes in 2020 ($126)

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    Taxes:$1,514

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 2425 WHITEHALL CIRCLE, WINTER PARK, FL 32792

    $745,0003 Days on yellowkey   MLS ID: O5918055

    For Sale O5918055 - 2425 WHITEHALL CIRCLE, WINTER PARK, FL 32792 58 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3164
       Built: 2013   Tax: $5,974 (2020)
    Community: Brookshire Heights 3Rd Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,580 (change assumption)
    Mortgage ($4,082) + Taxes in 2020 ($498)

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    Taxes:$5,974

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 2844 WILL O TH GREEN, WINTER PARK, FL 32792

    $439,9003 Days on yellowkey   MLS ID: O5918409

    For Sale O5918409 - 2844 WILL O TH GREEN, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1955
       Built: 1964   Tax: $5,408 (2020)
    Community: Winter Park Pines
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,861 (change assumption)
    Mortgage ($2,410) + Taxes in 2020 ($451)

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    Taxes:$5,408

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 2843 EASTERN PARKWAY, WINTER PARK, FL 32789

    $420,0003 Days on yellowkey   MLS ID: O5918577

    For Sale O5918577 - 2843 EASTERN PARKWAY, WINTER PARK, FL 32789 22 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1692
       Built: 1952   Tax: $1,741 (2020)
    Community: Orangewood Park
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,446 (change assumption)
    Mortgage ($2,301) + Taxes in 2020 ($145)

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    Taxes:$1,741

    Elementary School: Audubon Park K-8

    High School: Winter Park High

    Tax Year: 2020

    Middle School: None


  • 1807 BARKER DRIVE, WINTER PARK, FL 32789

    $1,540,00026 Days on yellowkey   MLS ID: O5913456

    REDUCED by $85,000 (5.2%) on 01/22/2021

    For Sale O5913456 - 1807 BARKER DRIVE, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 3804
       Built: 2004   Tax: $6,439 (2020)
    Community: South Lakemont Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $8,975 (change assumption)
    Mortgage ($8,438) + Taxes in 2020 ($537)

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    Taxes:$6,439

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 567 OSCEOLA AVENUE, WINTER PARK, FL 32789

    $932,0004 Days on yellowkey   MLS ID: O5918475

    For Sale O5918475 - 567 OSCEOLA AVENUE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3019
       Built: 1916   Tax: $9,874 (2020)
    Community: Osceola Court
    Pool: No

    Single Family


    Estimated Monthly Payment: $5,930 (change assumption)
    Mortgage ($5,107) + Taxes in 2020 ($823)

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    Taxes:$9,874

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 720 W WEBSTER AVENUE, WINTER PARK, FL 32789

    $319,0004 Days on yellowkey   MLS ID: O5917975

    For Sale O5917975 - 720 W WEBSTER AVENUE, WINTER PARK, FL 32789 16 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1970   Tax: $2,912 (2020)
    Community: Carver Town
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,991 (change assumption)
    Mortgage ($1,748) + Taxes in 2020 ($243)

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    Taxes:$2,912

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 2834 EUSTON ROAD, WINTER PARK, FL 32789

    $255,00022 Days on yellowkey   MLS ID: O5914158

    7 Days Off yellowkey (back on 1/22/2021)

    REDUCED by $9,000 (3.4%) on 01/22/2021

    For Sale O5914158 - 2834 EUSTON ROAD, WINTER PARK, FL 32789 23 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1320
       Built: 1955   Tax: $858 (2020)
    Community: Fairbanks Shores 4Th Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,469 (change assumption)
    Mortgage ($1,397) + Taxes in 2020 ($72)

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    Taxes:$858

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2020

    Middle School: College Park Middle


  • 1004 LAKE BELL DRIVE, WINTER PARK, FL 32789

    $304,90053 Days on yellowkey   MLS ID: O5909337

    2 Days Off yellowkey (back on 1/14/2021)

    REDUCED by $5,000 (1.6%) on 01/22/2021

    For Sale O5909337 - 1004 LAKE BELL DRIVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1387
       Built: 1956   Tax: $2,881 (2019)
    Community: Albert Lee Ridge Add 02
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,911 (change assumption)
    Mortgage ($1,671) + Taxes in 2019 ($240)

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    Taxes:$2,881

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2019

    Middle School: College Park Middle


  • 2278 MARSH SEDGE LANE, WINTER PARK, FL 32792

    $881,218159 Days on yellowkey   MLS ID: O5885959

    INCREASED by $6,000 (0.7%) on 01/22/2021

    For Sale O5885959 - 2278 MARSH SEDGE LANE, WINTER PARK, FL 32792 24 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 4266
       Built: 2018
    Monthly Fee: $170
       Tax: $1,196 (2020)
    Community: Hawks Crest
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $5,098 (change assumption)
    Mortgage ($4,828) + Fees ($170) + Taxes in 2020 ($100)

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    Taxes:$1,196

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 1637 MAGNOLIA AVENUE, WINTER PARK, FL 32789

    $1,489,0005 Days on yellowkey   MLS ID: O5918165

    For Sale O5918165 - 1637 MAGNOLIA AVENUE, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 3616
       Built: 2020   Tax: $5,615 (2020)
    Community: Flora Park 2Nd Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $8,627 (change assumption)
    Mortgage ($8,159) + Taxes in 2020 ($468)

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    Taxes:$5,615

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1970 LAUREL ROAD, WINTER PARK, FL 32789

    $1,290,000128 Days on yellowkey   MLS ID: O5892520

    REDUCED by $10,000 (0.8%) on 01/19/2021

    For Sale O5892520 - 1970 LAUREL ROAD, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3440
       Built: 2015   Tax: $15,726 (2020)
    Community: Charmont
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $8,379 (change assumption)
    Mortgage ($7,068) + Taxes in 2020 ($1,311)

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    Taxes:$15,726

    Elementary School: Audubon Park K-8

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 2174 TALMAN COURT, WINTER PARK, FL 32792

    $1,195,00079 Days on yellowkey   MLS ID: O5903269

    11 Days Off yellowkey (back on 1/19/2021)

    For Sale O5903269 - 2174 TALMAN COURT, WINTER PARK, FL 32792 70 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 4998
       Built: 2009
    Monthly Fee: $157
       Tax: $8,959 (2020)
    Community: Talman Mews
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $7,451 (change assumption)
    Mortgage ($6,548) + Fees ($157) + Taxes in 2020 ($747)

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    Taxes:$8,959

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 5614 WINTERBROOK WAY, WINTER PARK, FL 32792

    $459,99948 Days on yellowkey   MLS ID: O5910243

    5 Days Off yellowkey (back on 1/19/2021)

    REDUCED by $10,001 (2.1%) on 01/12/2021

    For Sale O5910243 - 5614 WINTERBROOK WAY, WINTER PARK, FL 32792 21 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2144
       Built: 2020
    Monthly Fee: $155
       Tax: $1,098 (2020)
    Community: Winterbrook
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,767 (change assumption)
    Mortgage ($2,520) + Fees ($155) + Taxes in 2020 ($91)

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    Taxes:$1,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 1061 CHEROKEE AVENUE, WINTER PARK, FL 32789

    $299,9006 Days on yellowkey   MLS ID: O5917652

    For Sale O5917652 - 1061 CHEROKEE AVENUE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 936
       Built: 1959   Tax: $2,613 (2020)
    Community: Not In Subdivision
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,861 (change assumption)
    Mortgage ($1,643) + Taxes in 2020 ($218)

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    Taxes:$2,613

    Elementary School: Hungerford Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland 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®, 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.