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Winter Park Homes For Sale & Real Estate - 413 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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  • 1707 HARMON AVE, WINTER PARK, FL 32789

    $639,00072 Days on yellowkey   MLS ID: O6409180

    REDUCED by $10,000 (1.5%) on 07/19/2026

    For Sale O6409180 - 1707 HARMON AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1669
       Built: 1927   Tax: $4,658 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $3,889 (change assumption)
    Mortgage ($3,501) + Taxes in 2025 ($388)


    Taxes:$4,658

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,000110 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792

    $279,90028 Days on yellowkey   MLS ID: O6421422

    For Sale O6421422 - 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499

    Community: Cedarwood Village
    Condo


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,534) + Fees ($499) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $315,00068 Days on yellowkey   MLS ID: O6408841

    REDUCED by $20,000 (6.0%) on 07/12/2026

    For Sale O6408841 - 1540 FLORENTINO LN, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $175
       Tax: $5,340 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,726) + Fees ($175) + Taxes in 2025 ($445)


    Taxes:$5,340

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789

    $1,895,00083 Days on yellowkey   MLS ID: O6406368

    REDUCED by $30,000 (1.6%) on 07/13/2026

    For Sale O6406368 - 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1960
    Monthly Fee: $2,471
       Tax: $16,493 (2025)
    Community: Whispering Waters/Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $14,229 (change assumption)
    Mortgage ($10,383) + Fees ($2,471) + Taxes in 2025 ($1,374)


    Taxes:$16,493

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2803 RIDDLE DR, WINTER PARK, FL 32789

    $569,00020 Days on yellowkey   MLS ID: O6423829

    REDUCED by $20,000 (3.4%) on 07/20/2026

    For Sale O6423829 - 2803 RIDDLE DR, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 1955   Tax: $6,477 (2025)
    Community: Fairshores Place
    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($3,118) + Taxes in 2025 ($540)


    Taxes:$6,477

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,00050 Days on yellowkey   MLS ID: O6415098

    For Sale O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2351
       Built: 2025   Tax: $5,773 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,311 (change assumption)
    Mortgage ($7,830) + Taxes in 2025 ($481)


    Taxes:$5,773

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1581 FOREST AVE, WINTER PARK, FL 32789

    $3,275,000140 Days on yellowkey   MLS ID: O6382377

    REDUCED by $118,000 (3.5%) on 07/20/2026

    For Sale O6382377 - 1581 FOREST AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4683
       Built: 1954   Tax: $20,042 (2024)
    Community: Ellno Willo
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,615 (change assumption)
    Mortgage ($17,945) + Taxes in 2024 ($1,670)


    Taxes:$20,042

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,399,500282 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,400 (3.5%) on 07/11/2026

    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: $8,096 (change assumption)
    Mortgage ($7,668) + 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


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00049 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789

    $290,000240 Days on yellowkey   MLS ID: O6362403

    REDUCED by $8,000 (2.7%) on 06/28/2026

    For Sale O6362403 - 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 710
       Built: 1960   Tax: $2,965 (2025)
    Community: Lake Killarney Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,836 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($247)


    Taxes:$2,965

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 846 DRIVER AVE, WINTER PARK, FL 32789

    $310,00013 Days on yellowkey   MLS ID: O6426024

    For Sale O6426024 - 846 DRIVER AVE, WINTER PARK, FL 32789 25 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 824
       Built: 1953   Tax: $4,689 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $2,089 (change assumption)
    Mortgage ($1,699) + Taxes in 2025 ($391)


    Taxes:$4,689

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789

    $2,100,000180 Days on yellowkey   MLS ID: L4959060

    INCREASED by $30,000 (1.4%) on 07/26/2026

    For Sale L4959060 - 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3272
       Built: 1990   Tax: $18,439 (2024)
    Community: 147 Interlachen Place
    Condo


    Estimated Monthly Payment: $13,043 (change assumption)
    Mortgage ($11,507) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5427 PEACO PL, WINTER PARK, FL 32792

    $650,9005 Days on yellowkey   MLS ID: A4701047

    For Sale A4701047 - 5427 PEACO PL, WINTER PARK, FL 32792 16 photos

    Bed: 5   Bath: 0.0   Gar: 3
    Liv Area Sq Ft: 1974
       Built: 1982   Tax: $5,919 (2025)
    Community: Grand Pines
    Spa: No

    Apartment


    Estimated Monthly Payment: $4,060 (change assumption)
    Mortgage ($3,566) + Taxes in 2025 ($493)


    Taxes:$5,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1908 CYRIL CT, WINTER PARK, FL 32792

    $639,00021 Days on yellowkey   MLS ID: O6422937

    0 Days Off yellowkey (back on 7/25/2026)

    For Sale O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 1990
    Monthly Fee: $41
       Tax: $7,674 (2025)
    Community: Kawilla Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,182 (change assumption)
    Mortgage ($3,501) + Fees ($41) + Taxes in 2025 ($640)


    Taxes:$7,674

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5781 SHALE CT, WINTER PARK, FL 32792

    $320,00024 Days on yellowkey   MLS ID: O6422583

    For Sale O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792 46 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1086
       Built: 1985
    Monthly Fee: $69
       Tax: $2,096 (2025)
    Community: Aloma Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,753) + Fees ($69) + Taxes in 2025 ($175)


    Taxes:$2,096

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,00046 Days on yellowkey   MLS ID: O6416828

    For Sale O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2022
    Monthly Fee: $243
       Tax: $6,788 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,781 (change assumption)
    Mortgage ($3,973) + Fees ($243) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $440,00047 Days on yellowkey   MLS ID: O6416635

    REDUCED by $5,000 (1.1%) on 07/15/2026

    For Sale O6416635 - 8433 COMMANDER CV, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1903
       Built: 1986
    Monthly Fee: $76
       Tax: $3,556 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,783 (change assumption)
    Mortgage ($2,411) + Fees ($76) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $659,99864 Days on yellowkey   MLS ID: O6409323

    REDUCED by $9,000 (1.3%) on 07/25/2026

    For Sale O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2048
       Built: 1950   Tax: $7,927 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,616) + Taxes in 2025 ($661)


    Taxes:$7,927

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000174 Days on yellowkey   MLS ID: O6380457

    4 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $51,000 (4.9%) on 05/06/2026

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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®, 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.