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Winter Park Homes For Sale & Real Estate - 443 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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  • 2041 JEWELL AVE, WINTER PARK, FL 32789

    $470,00018 Days on yellowkey   MLS ID: O6420660

    For Sale O6420660 - 2041 JEWELL AVE, WINTER PARK, FL 32789 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1508
       Built: 1947   Tax: $999 (2025)
    Community: Pines
    Single Family


    Estimated Monthly Payment: $2,658 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($83)


    Taxes:$999

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00036 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


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,235,000239 Days on yellowkey   MLS ID: O6362124

    3 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $15,000 (0.7%) on 05/30/2026

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3818
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,375 (change assumption)
    Mortgage ($12,246) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,275,00029 Days on yellowkey   MLS ID: O6418198

    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: $7,590 (change assumption)
    Mortgage ($6,986) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2914 REEF KNOT PL, WINTER PARK, FL 32792

    $1,725,00029 Days on yellowkey   MLS ID: O6418185

    For Sale O6418185 - 2914 REEF KNOT PL, WINTER PARK, FL 32792 63 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4173
       Built: 2019
    Monthly Fee: $186
       Tax: $17,688 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,112 (change assumption)
    Mortgage ($9,452) + Fees ($186) + Taxes in 2025 ($1,474)


    Taxes:$17,688

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1750 WALNUT AVE, WINTER PARK, FL 32789

    $2,195,0007 Days on yellowkey   MLS ID: O6422700

    For Sale O6422700 - 1750 WALNUT AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 2019   Tax: $17,303 (2025)
    Community: Conwill Estates
    Single Family


    Estimated Monthly Payment: $13,469 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($1,442)


    Taxes:$17,303

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2500 LEE RD #104, WINTER PARK, FL 32789

    $254,90037 Days on yellowkey   MLS ID: TB8517242

    REDUCED by $5,099 (2.0%) on 07/07/2026

    For Sale TB8517242 - 2500 LEE RD #104, WINTER PARK, FL 32789 23 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $431
       Tax: $2,327 (2025)
    Community: Lakeside Manor Apts Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $2,022 (change assumption)
    Mortgage ($1,397) + Fees ($431) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792

    $445,00014 Days on yellowkey   MLS ID: O6422142

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

    For Sale O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1984   Tax: $2,369 (2025)
    Community: Springview
    Single Family


    Estimated Monthly Payment: $2,636 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($197)


    Taxes:$2,369

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,200,000113 Days on yellowkey   MLS ID: O6392394

    REDUCED by $295,000 (11.8%) on 06/29/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $12,866 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,90095 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 7450 WYNNEWOOD SQ #189, WINTER PARK, FL 32792

    $185,0001 Day on yellowkey   MLS ID: O6425486

    For Sale O6425486 - 7450 WYNNEWOOD SQ #189, WINTER PARK, FL 32792 41 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $450
       Tax: $567 (2025)
    Community: Hidden Oaks Condo Ph 10
    Condo


    Estimated Monthly Payment: $1,511 (change assumption)
    Mortgage ($1,014) + Fees ($450) + Taxes in 2025 ($47)


    Taxes:$567

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1500 GAY RD #4D, WINTER PARK, FL 32789

    $175,0002 Days on yellowkey   MLS ID: O6425078

    For Sale O6425078 - 1500 GAY RD #4D, WINTER PARK, FL 32789 15 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 732
       Built: 1972   Tax: $2,310 (2025)
    Community: Chateaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,151 (change assumption)
    Mortgage ($959) + Taxes in 2025 ($193)


    Taxes:$2,310

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2487 HARBOUR WAY, WINTER PARK, FL 32792

    $300,0002 Days on yellowkey   MLS ID: O6422155

    For Sale O6422155 - 2487 HARBOUR WAY, WINTER PARK, FL 32792 13 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1803
       Built: 1978
    Monthly Fee: $95
       Tax: $5,059 (2025)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $2,160 (change assumption)
    Mortgage ($1,644) + Fees ($95) + Taxes in 2025 ($422)


    Taxes:$5,059

    Elementary School: Eastbrook Elementary

    High School: Hagerty High

    Tax Year: 2025

    Middle School: Chiles Middle


  • 1420 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,695,00072 Days on yellowkey   MLS ID: O6404564

    REDUCED by $55,000 (3.1%) on 07/14/2026

    For Sale O6404564 - 1420 MAGNOLIA AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2015   Tax: $21,173 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,052 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,764)


    Taxes:$21,173

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $440,00034 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


  • 1622 ARBOR PARK DR, WINTER PARK, FL 32789

    $695,00016 Days on yellowkey   MLS ID: O6420928

    0 Days Off yellowkey (back on 7/15/2026)

    For Sale O6420928 - 1622 ARBOR PARK DR, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1351
       Built: 1957   Tax: $6,562 (2025)
    Community: Conwill Estates
    Single Family


    Estimated Monthly Payment: $4,355 (change assumption)
    Mortgage ($3,808) + Taxes in 2025 ($547)


    Taxes:$6,562

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1778 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,339,0004 Days on yellowkey   MLS ID: O6422941

    For Sale O6422941 - 1778 MONDRIAN CIR, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 2023
    Monthly Fee: $395
       Tax: $12,451 (2025)
    Community: Mondrian/Winter Park Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $8,769 (change assumption)
    Mortgage ($7,337) + Fees ($395) + Taxes in 2025 ($1,038)


    Taxes:$12,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1500 GAY RD #3C, WINTER PARK, FL 32789

    $248,00029 Days on yellowkey   MLS ID: O6417533

    REDUCED by $2,000 (0.8%) on 07/09/2026

    For Sale O6417533 - 1500 GAY RD #3C, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972
    Monthly Fee: $425
       Tax: $3,244 (2025)
    Community: Chateaux Du Lac
    Condo


    Estimated Monthly Payment: $2,054 (change assumption)
    Mortgage ($1,359) + Fees ($425) + Taxes in 2025 ($270)


    Taxes:$3,244

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5225 ALBERT DR, WINTER PARK, FL 32792

    $435,0004 Days on yellowkey   MLS ID: O6424623

    0 Days Off yellowkey (back on 7/15/2026)

    For Sale O6424623 - 5225 ALBERT DR, WINTER PARK, FL 32792 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1716
       Built: 1979   Tax: $4,476 (2025)
    Community: Wrenwood Unit 3 3Rd Add
    Single Family


    Estimated Monthly Payment: $2,757 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($373)


    Taxes:$4,476

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3641 HAWTHORNE LN, WINTER PARK, FL 32792

    $475,00023 Days on yellowkey   MLS ID: TB8519391

    For Sale TB8519391 - 3641 HAWTHORNE LN, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 1979   Tax: $4,051 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,940 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($338)


    Taxes:$4,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.