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Winter Park Single Family Homes For Sale - 278 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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  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $554,90098 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 05/01/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,214 (change assumption)
    Mortgage ($3,040) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $449,00051 Days on yellowkey   MLS ID: O6388746

    REDUCED by $11,000 (2.4%) on 04/29/2026

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,929 (change assumption)
    Mortgage ($2,460) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,695,0006 Days on yellowkey   MLS ID: O6402113

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,972 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1437 MILLER AVE, WINTER PARK, FL 32789

    $750,0003 Days on yellowkey   MLS ID: O6403858

    For Sale O6403858 - 1437 MILLER AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2150
       Built: 1932   Tax: $6,987 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,692 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($582)


    Taxes:$6,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,0003 Days on yellowkey   MLS ID: S5148431

    For Sale S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1786
       Built: 1966   Tax: $2,249 (2025)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3374 HAMLET LOOP, WINTER PARK, FL 32792

    $370,0003 Days on yellowkey   MLS ID: O6403488

    For Sale O6403488 - 3374 HAMLET LOOP, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1397
       Built: 1994
    Monthly Fee: $63
       Tax: $5,326 (2024)
    Community: Villas Of Casselberry Ph 3
    Single Family


    Estimated Monthly Payment: $2,534 (change assumption)
    Mortgage ($2,027) + Fees ($63) + Taxes in 2024 ($444)


    Taxes:$5,326

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7917 PLEASANT PINE CIR, WINTER PARK, FL 32792

    $599,0005 Days on yellowkey   MLS ID: O6402666

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale O6402666 - 7917 PLEASANT PINE CIR, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2157
       Built: 2014
    Monthly Fee: $118
       Tax: $4,073 (2024)
    Community: Enclave At Aloma
    Single Family


    Estimated Monthly Payment: $3,740 (change assumption)
    Mortgage ($3,282) + Fees ($118) + Taxes in 2024 ($339)


    Taxes:$4,073

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,00094 Days on yellowkey   MLS ID: O6373287

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

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $649,90016 Days on yellowkey   MLS ID: O6399993

    REDUCED by $25,000 (3.7%) on 04/30/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $3,894 (change assumption)
    Mortgage ($3,561) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,9959 Days on yellowkey   MLS ID: O6402209

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

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,499,900194 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,100 (3.2%) on 04/15/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,646 (change assumption)
    Mortgage ($8,218) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00087 Days on yellowkey   MLS ID: O6380333

    1 Days Off yellowkey (back on 4/5/2026)

    For Sale O6380333 - 4872 ORANGE AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1881
       Built: 1960   Tax: $4,494 (2024)
    Community: Suburban Homes First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($374)


    Taxes:$4,494

    Elementary School: Lakemont Elem

    High School: None

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500108 Days on yellowkey   MLS ID: O6373026

    REDUCED by $2,400 (0.6%) on 04/30/2026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,300 (change assumption)
    Mortgage ($2,014) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $680,00016 Days on yellowkey   MLS ID: TB8498515

    REDUCED by $19,000 (2.7%) on 04/30/2026

    For Sale TB8498515 - 927 FAIRWAY DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 1973   Tax: $4,784 (2025)
    Community: Golfside Sec 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,125 (change assumption)
    Mortgage ($3,726) + Taxes in 2025 ($399)


    Taxes:$4,784

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $625,00060 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,500 (0.4%) on 04/30/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,009 (change assumption)
    Mortgage ($3,425) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1761 LEGION DR, WINTER PARK, FL 32789

    $3,270,000325 Days on yellowkey   MLS ID: O6302616

    REDUCED by $25,000 (0.8%) on 04/15/2026

    For Sale O6302616 - 1761 LEGION DR, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4955
       Built: 2017   Tax: $22,139 (2024)
    Community: Green Oaks Rep 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,762 (change assumption)
    Mortgage ($17,917) + Taxes in 2024 ($1,845)


    Taxes:$22,139

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 7120 BROOKSIDE TRL, WINTER PARK, FL 32792

    $510,00010 Days on yellowkey   MLS ID: O6398534

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

    For Sale O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1753
       Built: 1976   Tax: $3,098 (2025)
    Community: Replat Of Lts 1 2 & 3 Brookside Sub
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,794) + Taxes in 2025 ($258)


    Taxes:$3,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,795,00032 Days on yellowkey   MLS ID: O6395062

    REDUCED by $55,000 (1.9%) on 04/21/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 84 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,355 (change assumption)
    Mortgage ($15,315) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 420 OHIO ST, WINTER PARK, FL 32789

    $1,360,0005 Days on yellowkey   MLS ID: O6399541

    For Sale O6399541 - 420 OHIO ST, WINTER PARK, FL 32789 8 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3735
       Built: 2026   Tax: $1,281 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $7,559 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($107)


    Taxes:$1,281

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,000101 Days on yellowkey   MLS ID: O6375545

    2 Days Off yellowkey (back on 3/11/2026)

    For Sale O6375545 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 35 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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®, 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.