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 - 441 homes

Winter Park homes for sale are located in Seminole 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:
  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $429,90098 Days on yellowkey   MLS ID: O6390301

    REDUCED by $20,000 (4.4%) on 06/01/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 36 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: $2,743 (change assumption)
    Mortgage ($2,356) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3243 FOREST OAKS COURT #117, WINTER PARK, FL 32792

    $172,00045 Days on yellowkey   MLS ID: O6406448

    REDUCED by $3,000 (1.7%) on 06/19/2026

    For Sale O6406448 - 3243 FOREST OAKS COURT #117, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1983   Tax: $2,723 (2025)
    Community: Hidden Oaks Condo Ph 7
    Spa: No

    Condo


    Estimated Monthly Payment: $1,169 (change assumption)
    Mortgage ($942) + Taxes in 2025 ($227)


    Taxes:$2,723

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90018 Days on yellowkey   MLS ID: O6414180

    REDUCED by $5,000 (1.3%) on 06/19/2026

    For Sale O6414180 - 1662 TREMONT LN, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1986
    Monthly Fee: $49
       Tax: $4,339 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,109) + Fees ($49) + Taxes in 2025 ($362)


    Taxes:$4,339

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1434 VIA SANGRO PL, WINTER PARK, FL 32792

    $1,300,00010 Days on yellowkey   MLS ID: O6416325

    0 Days Off yellowkey (back on 6/13/2026)

    For Sale O6416325 - 1434 VIA SANGRO PL, WINTER PARK, FL 32792 1 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3063
       Built: 2016
    Monthly Fee: $182
       Tax: $9,764 (2025)
    Community: Lakeside Estates
    Single Family


    Estimated Monthly Payment: $8,119 (change assumption)
    Mortgage ($7,123) + Fees ($182) + Taxes in 2025 ($814)


    Taxes:$9,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1871 BRYAN AVE, WINTER PARK, FL 32789

    $499,00028 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


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,800,000102 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


  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,890,000429 Days on yellowkey   MLS ID: O6301489

    REDUCED by $34,450 (1.8%) on 06/18/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,415 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $475,00064 Days on yellowkey   MLS ID: O6399199

    0 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $5,000 (1.0%) on 05/06/2026

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,172 (change assumption)
    Mortgage ($2,603) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,00021 Days on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 5 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #B204, WINTER PARK, FL 32789

    $130,000150 Days on yellowkey   MLS ID: O6375348

    INCREASED by $10,000 (8.3%) on 06/18/2026

    For Sale O6375348 - 1695 LEE RD #B204, WINTER PARK, FL 32789 21 photos

    Bed: 2   Bath: 1.0
    Built: 1966
       Tax: $2,084 (2025)
    Community: Waterfall Cove At Winter Park Condo
    Condo


    Estimated Monthly Payment: $886 (change assumption)
    Mortgage ($712) + Taxes in 2025 ($174)


    Taxes:$2,084

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000230 Days on yellowkey   MLS ID: O6357934

    0 Days Off yellowkey (back on 5/14/2026)

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $299,000136 Days on yellowkey   MLS ID: O6380753

    REDUCED by $13,000 (4.2%) on 06/18/2026

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,638) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1500 GAY RD #20D, WINTER PARK, FL 32789

    $258,000118 Days on yellowkey   MLS ID: O6385626

    REDUCED by $4,000 (1.5%) on 06/07/2026

    For Sale O6385626 - 1500 GAY RD #20D, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $3,283 (2024)
    Community: Chat6eaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,687 (change assumption)
    Mortgage ($1,414) + Taxes in 2024 ($274)


    Taxes:$3,283

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000266 Days on yellowkey   MLS ID: O6347690

    For Sale O6347690 - 2700 CADY WAY, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 1965   Tax: $8,335 (2024)
    Community: Winter Park Pines Unit 4
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($695)


    Taxes:$8,335

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 140 E MORSE BLVD #J, WINTER PARK, FL 32789

    $2,350,0006 Days on yellowkey   MLS ID: O6414891

    For Sale O6414891 - 140 E MORSE BLVD #J, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2008   Tax: $18,655 (2025)
    Community: Landmark Winter Park Condo
    Condo


    Estimated Monthly Payment: $14,431 (change assumption)
    Mortgage ($12,876) + Taxes in 2025 ($1,555)


    Taxes:$18,655

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4756 TANGERINE AVE #4756, WINTER PARK, FL 32792

    $195,0006 Days on yellowkey   MLS ID: R4911483

    For Sale R4911483 - 4756 TANGERINE AVE #4756, WINTER PARK, FL 32792 5 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,244 (2025)
    Community: Wrenwood Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,255 (change assumption)
    Mortgage ($1,068) + Taxes in 2025 ($187)


    Taxes:$2,244

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $399,0006 Days on yellowkey   MLS ID: O6417098

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,487 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0006 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1695 LEE RD #E215, WINTER PARK, FL 32789

    $135,000126 Days on yellowkey   MLS ID: O6383089

    REDUCED by $14,990 (10.0%) on 06/17/2026

    For Sale O6383089 - 1695 LEE RD #E215, WINTER PARK, FL 32789 82 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,472 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,570 (change assumption)
    Mortgage ($740) + Fees ($624) + Taxes in 2024 ($206)


    Taxes:$2,472

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $515,0008 Days on yellowkey   MLS ID: O6414369

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.