REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Park Homes For Sale & Real Estate - 416 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

Sort:
  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000281 Days on yellowkey   MLS ID: O6352857

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

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,250,000131 Days on yellowkey   MLS ID: O6392216

    REDUCED by $99,900 (7.4%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,841 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,195,000259 Days on yellowkey   MLS ID: O6359471

    REDUCED by $30,000 (1.3%) on 07/23/2026

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 62 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,533 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2525 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,749,000Listed 07/28/2026 9:45PM   MLS ID: O6428823

    For Sale O6428823 - 2525 LAFAYETTE AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2715
       Built: 2026   Tax: $4,700 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $9,975 (change assumption)
    Mortgage ($9,583) + Taxes in 2025 ($392)


    Taxes:$4,700

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99076 Days on yellowkey   MLS ID: O6407713

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale O6407713 - 5117 CYPRESS CT, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1972   Tax: $3,877 (2025)
    Community: Wrenwood Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7509 GLENMOOR LN, WINTER PARK, FL 32792

    $499,50027 Days on yellowkey   MLS ID: O6421887

    0 Days Off yellowkey (back on 7/5/2026)

    For Sale O6421887 - 7509 GLENMOOR LN, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2067
       Built: 1986   Tax: $2,931 (2025)
    Community: Glenmoor
    Single Family


    Estimated Monthly Payment: $2,981 (change assumption)
    Mortgage ($2,737) + Taxes in 2025 ($244)


    Taxes:$2,931

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,025,00033 Days on yellowkey   MLS ID: O6420090

    REDUCED by $25,000 (2.4%) on 07/22/2026

    For Sale O6420090 - 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2434
       Built: 2005
    Monthly Fee: $500
       Tax: $10,213 (2025)
    Community: Virginia Heights Rep
    Townhouse


    Estimated Monthly Payment: $6,967 (change assumption)
    Mortgage ($5,616) + Fees ($500) + Taxes in 2025 ($851)


    Taxes:$10,213

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $399,900356 Days on yellowkey   MLS ID: O6333863

    REDUCED by $8,100 (2.0%) on 07/02/2026

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,495 (change assumption)
    Mortgage ($2,191) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $360,00057 Days on yellowkey   MLS ID: O6412514

    REDUCED by $10,000 (2.7%) on 06/25/2026

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,283 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1840 LAUREL RD, WINTER PARK, FL 32789

    $2,299,000Listed 07/28/2026 9:49PM   MLS ID: O6428841

    For Sale O6428841 - 1840 LAUREL RD, WINTER PARK, FL 32789 12 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2026   Tax: $12,141 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,609 (change assumption)
    Mortgage ($12,597) + Taxes in 2025 ($1,012)


    Taxes:$12,141

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1133 BELLA LAGO CV, WINTER PARK, FL 32792

    $2,100,00014 Days on yellowkey   MLS ID: O6425181

    For Sale O6425181 - 1133 BELLA LAGO CV, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1765
       Built: 1945   Tax: $4,801 (2025)
    Community: None
    Single Family


    Estimated Monthly Payment: $11,907 (change assumption)
    Mortgage ($11,507) + Taxes in 2025 ($400)


    Taxes:$4,801

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 700 MELROSE AVE #H4, WINTER PARK, FL 32789

    $290,00068 Days on yellowkey   MLS ID: O6409318

    2 Days Off yellowkey (back on 6/27/2026)

    For Sale O6409318 - 700 MELROSE AVE #H4, WINTER PARK, FL 32789 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964
    Monthly Fee: $699
       Tax: $851 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,589) + Fees ($699) + Taxes in 2025 ($71)


    Taxes:$851

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4437 GLENMOOR CT, WINTER PARK, FL 32792

    $525,00016 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


  • 1250 FORMOSA AVE, WINTER PARK, FL 32789

    $560,00056 Days on yellowkey   MLS ID: O6412954

    For Sale O6412954 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1937
       Built: 2022
    Monthly Fee: $252
       Tax: $8,328 (2025)
    Community: Urban Green 12
    Townhouse


    Estimated Monthly Payment: $4,014 (change assumption)
    Mortgage ($3,068) + Fees ($252) + Taxes in 2025 ($694)


    Taxes:$8,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $404,900134 Days on yellowkey   MLS ID: O6390301

    0 Days Off yellowkey (back on 7/28/2026)

    REDUCED by $5,000 (1.2%) on 07/24/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,606 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 256 LEWFIELD CIR #256, WINTER PARK, FL 32792

    $184,900199 Days on yellowkey   MLS ID: O6367842

    1 Days Off yellowkey (back on 6/19/2026)

    For Sale O6367842 - 256 LEWFIELD CIR #256, WINTER PARK, FL 32792 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973
    Monthly Fee: $465
       Tax: $1,916 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,013) + Fees ($465) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7327 FOREST HILL CT #223, WINTER PARK, FL 32792

    $175,00086 Days on yellowkey   MLS ID: O6403841

    REDUCED by $5,000 (2.8%) on 07/28/2026

    For Sale O6403841 - 7327 FOREST HILL CT #223, WINTER PARK, FL 32792 24 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $450
       Tax: $2,597 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,625 (change assumption)
    Mortgage ($959) + Fees ($450) + Taxes in 2025 ($216)


    Taxes:$2,597

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $414,90058 Days on yellowkey   MLS ID: O6412364

    REDUCED by $5,000 (1.2%) on 07/28/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,345 (change assumption)
    Mortgage ($2,273) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,150,00061 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 07/01/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,653 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,000106 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    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.