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Winter Park Homes For Sale & Real Estate - 414 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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  • 722 S RANGER BLVD, WINTER PARK, FL 32792

    $799,90028 Days on yellowkey   MLS ID: O6421873

    REDUCED by $25,100 (3.0%) on 07/27/2026

    For Sale O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1967   Tax: $455 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($38)


    Taxes:$455

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,995,00016 Days on yellowkey   MLS ID: O6424685

    For Sale O6424685 - 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3440
       Built: 2001   Tax: $10,684 (2025)
    Community: Tantum Add
    Single Family


    Estimated Monthly Payment: $11,822 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($890)


    Taxes:$10,684

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $458,50055 Days on yellowkey   MLS ID: O6413717

    REDUCED by $500 (0.1%) on 07/30/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,721 (change assumption)
    Mortgage ($2,512) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $994,000136 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $1,000 (0.1%) on 07/13/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,424 (change assumption)
    Mortgage ($5,446) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,262,50042 Days on yellowkey   MLS ID: O6418198

    REDUCED by $12,500 (1.0%) on 07/23/2026

    For Sale O6418198 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $7,521 (change assumption)
    Mortgage ($6,918) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 125 S INTERLACHEN AVE #1, WINTER PARK, FL 32789

    $3,895,000Listed 07/30/2026 7:47AM   MLS ID: O6428952

    For Sale O6428952 - 125 S INTERLACHEN AVE #1, WINTER PARK, FL 32789 70 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3878
       Built: 2019
    Monthly Fee: $1,771
       Tax: $35,806 (2025)
    Community: South Interlachen Place
    Townhouse


    Estimated Monthly Payment: $26,097 (change assumption)
    Mortgage ($21,342) + Fees ($1,771) + Taxes in 2025 ($2,984)


    Taxes:$35,806

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4437 GLENMOOR CT, WINTER PARK, FL 32792

    $525,00017 Days on yellowkey   MLS ID: O6424511

    REDUCED by $14,000 (2.6%) on 07/23/2026

    For Sale O6424511 - 4437 GLENMOOR CT, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2633
       Built: 1986   Tax: $8,163 (2025)
    Community: Glenmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,557 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($680)


    Taxes:$8,163

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $759,00050 Days on yellowkey   MLS ID: O6415904

    0 Days Off yellowkey (back on 7/30/2026)

    REDUCED by $16,000 (2.1%) on 07/22/2026

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,727 (change assumption)
    Mortgage ($4,159) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2552 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $530,0001 Day on yellowkey   MLS ID: O6428975

    For Sale O6428975 - 2552 BROOKSHIRE AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 1.5   Gar: 1
    Liv Area Sq Ft: 1314
       Built: 1959   Tax: $1,501 (2025)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,904) + Taxes in 2025 ($125)


    Taxes:$1,501

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2138 TALMAN CT, WINTER PARK, FL 32792

    $1,450,0001 Day on yellowkey   MLS ID: O6428377

    For Sale O6428377 - 2138 TALMAN CT, WINTER PARK, FL 32792 93 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4249
       Built: 2009
    Monthly Fee: $157
       Tax: $15,260 (2025)
    Community: Talman Mews Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,374 (change assumption)
    Mortgage ($7,945) + Fees ($157) + Taxes in 2025 ($1,272)


    Taxes:$15,260

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792

    $267,000104 Days on yellowkey   MLS ID: O6398500

    INCREASED by $4,000 (1.5%) on 07/30/2026

    For Sale O6398500 - 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1987   Tax: $1,107 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,555 (change assumption)
    Mortgage ($1,463) + Taxes in 2025 ($92)


    Taxes:$1,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7733 COUNTRY PL #G2, WINTER PARK, FL 32792

    $229,50038 Days on yellowkey   MLS ID: O6418682

    REDUCED by $5,000 (2.1%) on 07/17/2026

    For Sale O6418682 - 7733 COUNTRY PL #G2, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1982   Tax: $371 (2025)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,288 (change assumption)
    Mortgage ($1,258) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3220 NETHERWOOD DR, WINTER PARK, FL 32792

    $269,000195 Days on yellowkey   MLS ID: O6374172

    REDUCED by $10,990 (3.9%) on 04/20/2026

    For Sale O6374172 - 3220 NETHERWOOD DR, WINTER PARK, FL 32792 18 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1982   Tax: $1,222 (2025)
    Community: Coronation Add
    Half Duplex


    Estimated Monthly Payment: $1,576 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($102)


    Taxes:$1,222

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792

    $285,000301 Days on yellowkey   MLS ID: O6342993

    For Sale O6342993 - 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1669
       Built: 1986
    Monthly Fee: $511
       Tax: $3,477 (2024)
    Community: Cedarwood Village
    Spa: No

    Condo


    Estimated Monthly Payment: $2,362 (change assumption)
    Mortgage ($1,562) + Fees ($511) + Taxes in 2024 ($290)


    Taxes:$3,477

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 632 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,050,000642 Days on yellowkey   MLS ID: O6250417

    0 Days Off yellowkey (back on 9/29/2025)

    For Sale O6250417 - 632 COUNTRY CLUB DR, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2342
       Built: 1952   Tax: $4,638 (2023)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,140 (change assumption)
    Mortgage ($5,753) + Taxes in 2023 ($387)


    Taxes:$4,638

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2023

    Middle School: College Park Middle


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $245,000101 Days on yellowkey   MLS ID: O6400674

    REDUCED by $5,000 (2.0%) on 07/11/2026

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,055 (change assumption)
    Mortgage ($1,342) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1113 VIA DEL MAR, WINTER PARK, FL 32789

    $1,595,000176 Days on yellowkey   MLS ID: O6379697

    For Sale O6379697 - 1113 VIA DEL MAR, WINTER PARK, FL 32789 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2012
       Built: 1957   Tax: $13,924 (2024)
    Community: Tuscany Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,740) + Taxes in 2024 ($1,160)


    Taxes:$13,924

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $609,90035 Days on yellowkey   MLS ID: TB8517548

    REDUCED by $5,090 (0.8%) on 07/29/2026

    For Sale TB8517548 - 4353 STEED TER, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2275
       Built: 1989
    Monthly Fee: $29
       Tax: $7,031 (2024)
    Community: Kings Cove
    Single Family


    Estimated Monthly Payment: $3,957 (change assumption)
    Mortgage ($3,342) + Fees ($29) + Taxes in 2024 ($586)


    Taxes:$7,031

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5444 PEACO PL, WINTER PARK, FL 32792

    $250,0002 Days on yellowkey   MLS ID: O6428383

    0 Days Off yellowkey (back on 7/29/2026)

    For Sale O6428383 - 5444 PEACO PL, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 924
       Built: 1984   Tax: $2,640 (2025)
    Community: Grand Pines
    Half Duplex


    Estimated Monthly Payment: $1,590 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($220)


    Taxes:$2,640

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7026 HAMMOCK WAY, WINTER PARK, FL 32792

    $362,0008 Days on yellowkey   MLS ID: O6427437

    1 Days Off yellowkey (back on 7/29/2026)

    For Sale O6427437 - 7026 HAMMOCK WAY, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1257
       Built: 1978   Tax: $2,472 (2025)
    Community: Wrenwood Unit 3 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,984) + Taxes in 2025 ($206)


    Taxes:$2,472

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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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.