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 - 444 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:
  • 2142 BLOSSOM LN, WINTER PARK, FL 32789

    $399,90011 Days on yellowkey   MLS ID: O6409144

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409144 - 2142 BLOSSOM LN, WINTER PARK, FL 32789 14 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1957   Tax: $2,217 (2025)
    Community: Acreage
    Single Family


    Estimated Monthly Payment: $2,376 (change assumption)
    Mortgage ($2,191) + Taxes in 2025 ($185)


    Taxes:$2,217

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $675,0005 Days on yellowkey   MLS ID: O6411329

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,410 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,0005 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789

    $1,650,0005 Days on yellowkey   MLS ID: O6407841

    For Sale O6407841 - 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2467
       Built: 1964   Tax: $4,844 (2025)
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,445 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($404)


    Taxes:$4,844

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,800,00080 Days on yellowkey   MLS ID: O6390592

    0 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $70,000 (3.7%) on 05/13/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,213 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 450 LAKEWOOD DR, WINTER PARK, FL 32789

    $2,500,00031 Days on yellowkey   MLS ID: O6403490

    For Sale O6403490 - 450 LAKEWOOD DR, WINTER PARK, FL 32789 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4572
       Built: 2000   Tax: $11,393 (2025)
    Community: Osceola Shores Sec 03
    Single Family


    Estimated Monthly Payment: $14,648 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($949)


    Taxes:$11,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $237,00045 Days on yellowkey   MLS ID: O6397587

    REDUCED by $1,500 (0.6%) on 05/27/2026

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,813 (change assumption)
    Mortgage ($1,299) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1871 BRYAN AVE, WINTER PARK, FL 32789

    $499,0006 Days on yellowkey   MLS ID: O6410779

    0 Days Off yellowkey (back on 5/27/2026)

    For Sale O6410779 - 1871 BRYAN AVE, WINTER PARK, FL 32789 3 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1232
       Built: 1985   Tax: $3,328 (2025)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($277)


    Taxes:$3,328

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1581 FOREST AVE, WINTER PARK, FL 32789

    $3,393,00081 Days on yellowkey   MLS ID: O6382377

    REDUCED by $102,000 (2.9%) on 05/21/2026

    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: $20,261 (change assumption)
    Mortgage ($18,591) + 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


  • 927 FAIRWAY DR, WINTER PARK, FL 32792

    $680,00045 Days on yellowkey   MLS ID: TB8498515

    0 Days Off yellowkey (back on 5/27/2026)

    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


  • 1200 VIA SALERNO, WINTER PARK, FL 32789

    $5,995,000108 Days on yellowkey   MLS ID: O6381761

    REDUCED by $205,000 (3.3%) on 05/07/2026

    For Sale O6381761 - 1200 VIA SALERNO, WINTER PARK, FL 32789 47 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5476
       Built: 2001   Tax: $40,087 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $36,189 (change assumption)
    Mortgage ($32,848) + Taxes in 2024 ($3,341)


    Taxes:$40,087

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 100 S INTERLACHEN AVE #503, WINTER PARK, FL 32789

    $879,000264 Days on yellowkey   MLS ID: O6343006

    2 Days Off yellowkey (back on 5/27/2026)

    For Sale O6343006 - 100 S INTERLACHEN AVE #503, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1143
       Built: 1971   Tax: $7,844 (2024)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $5,470 (change assumption)
    Mortgage ($4,816) + Taxes in 2024 ($654)


    Taxes:$7,844

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1092 EASTBROOK BLVD, WINTER PARK, FL 32792

    $399,00016 Days on yellowkey   MLS ID: O6407251

    REDUCED by $11,000 (2.7%) on 05/27/2026

    For Sale O6407251 - 1092 EASTBROOK BLVD, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1122
       Built: 1959   Tax: $4,373 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($364)


    Taxes:$4,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1593 LAWNDALE CIR, WINTER PARK, FL 32792

    $480,00017 Days on yellowkey   MLS ID: O6402014

    REDUCED by $10,000 (2.0%) on 05/27/2026

    For Sale O6402014 - 1593 LAWNDALE CIR, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1984
    Monthly Fee: $49
       Tax: $5,010 (2025)
    Community: Country Lane
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,097 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2025 ($418)


    Taxes:$5,010

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $380,00025 Days on yellowkey   MLS ID: O6403694

    1 Days Off yellowkey (back on 5/27/2026)

    For Sale O6403694 - 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 988
       Built: 1950   Tax: $4,386 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($366)


    Taxes:$4,386

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,00062 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1407 MILLER AVE, WINTER PARK, FL 32789

    $899,00018 Days on yellowkey   MLS ID: O6406408

    For Sale O6406408 - 1407 MILLER AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $200
       Tax: $6,818 (2025)
    Community: H Vanwies Sub
    Single Family


    Estimated Monthly Payment: $5,694 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($568)


    Taxes:$6,818

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00073 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00012 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00018 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland 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.