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Displaying: For Rent

Location: Winter Park

Property Type(s): Single Family

Price: $3,500 to $4,999

Winter Park - 8 properties found

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  • 1815 BARKER DR, WINTER PARK, FL 32789

    $4,00066 Days on yellowkey   MLS ID: O6386321

    For RENT O6386321 - 1815 BARKER DR, WINTER PARK, FL 32789 89 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1548
       Built: 1959
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year:

    Middle School: Glenridge Middle


  • 1091 WILDMEADOW RUN, WINTER PARK, FL 32792

    $4,00053 Days on yellowkey   MLS ID: O6389834

    For RENT O6389834 - 1091 WILDMEADOW RUN, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2021
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year:

    Middle School: Tuskawilla Middle


  • 1409 LONE FEATHER TRL, WINTER PARK, FL 32792

    $3,89510 Days on yellowkey   MLS ID: O6401907

    For RENT O6401907 - 1409 LONE FEATHER TRL, WINTER PARK, FL 32792 40 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2553
       Built: 2022
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $21 (change assumption)
    Mortgage ($21)


    Taxes:

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year:

    Middle School: Tuskawilla Middle


  • 1711 CHESTNUT AVE, WINTER PARK, FL 32789

    $4,15031 Days on yellowkey   MLS ID: O6396000

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

    For RENT O6396000 - 1711 CHESTNUT AVE, WINTER PARK, FL 32789 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2288
       Built: 1963
    Community: Conwill Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $23 (change assumption)
    Mortgage ($23)


    Taxes:

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year:

    Middle School: Maitland Middle


  • 1026 S LAKEMONT AVE, WINTER PARK, FL 32792

    $4,30013 Days on yellowkey   MLS ID: O6400730

    For RENT O6400730 - 1026 S LAKEMONT AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1470
       Built: 1953
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $24 (change assumption)
    Mortgage ($24)


    Taxes:

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year:

    Middle School: Glenridge Middle


  • 2115 SYCAMORE DR, WINTER PARK, FL 32789

    $3,50020 Days on yellowkey   MLS ID: O6398548

    For RENT O6398548 - 2115 SYCAMORE DR, WINTER PARK, FL 32789 23 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2099
       Built: 1953

    Single Family


    Estimated Monthly Payment: $19 (change assumption)
    Mortgage ($19)


    Taxes:

    Elementary School: None

    High School: Winter Park High

    Tax Year:

    Middle School: Audubon Park K-8


  • 668 OVERSPIN DR, WINTER PARK, FL 32789

    $4,20042 Days on yellowkey   MLS ID: O6392773

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

    For RENT O6392773 - 668 OVERSPIN DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2509
       Built: 2018
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $23 (change assumption)
    Mortgage ($23)


    Taxes:

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year:

    Middle School: College Park Middle


  • 1317 MEDINAH CT, WINTER PARK, FL 32792

    $3,65038 Days on yellowkey   MLS ID: O6393971

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

    For RENT O6393971 - 1317 MEDINAH CT, WINTER PARK, FL 32792 40 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1979
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $20 (change assumption)
    Mortgage ($20)


    Taxes:

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year:

    Middle School: Glenridge Middle






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.