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 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:
  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00095 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


  • 1927 ELAND AVE, WINTER PARK, FL 32789

    $820,000132 Days on yellowkey   MLS ID: O6381009

    REDUCED by $5,000 (0.6%) on 06/15/2026

    For Sale O6381009 - 1927 ELAND AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2242
       Built: 1957   Tax: $3,190 (2024)
    Community: Lake Bell Terrace
    Single Family


    Estimated Monthly Payment: $4,759 (change assumption)
    Mortgage ($4,493) + Taxes in 2024 ($266)


    Taxes:$3,190

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 205 LEWFIELD CIR #205, WINTER PARK, FL 32792

    $182,900162 Days on yellowkey   MLS ID: S5141588

    REDUCED by $37,100 (16.9%) on 06/20/2026

    For Sale S5141588 - 205 LEWFIELD CIR #205, WINTER PARK, FL 32792 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973   Tax: $796 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,069 (change assumption)
    Mortgage ($1,002) + Taxes in 2024 ($66)


    Taxes:$796

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,0009 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


  • 151 NORTH ORLANDO AVENUE #142, WINTER PARK, FL 32789

    $199,90013 Days on yellowkey   MLS ID: O6412768

    For Sale O6412768 - 151 NORTH ORLANDO AVENUE #142, WINTER PARK, FL 32789 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 582
       Built: 1960
    Monthly Fee: $398
       Tax: $2,017 (2025)
    Community: Lake Killarney Condominium Assn Inc.
    Condo


    Estimated Monthly Payment: $1,661 (change assumption)
    Mortgage ($1,095) + Fees ($398) + Taxes in 2025 ($168)


    Taxes:$2,017

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00016 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2914 REEF KNOT PL, WINTER PARK, FL 32792

    $1,725,0005 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


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,950,0004 Days on yellowkey   MLS ID: O6413031

    For Sale O6413031 - 2625 PARK PLACE DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2002
    Monthly Fee: $146
       Tax: $9,695 (2025)
    Community: Winter Park Place 45/148
    Single Family


    Estimated Monthly Payment: $11,639 (change assumption)
    Mortgage ($10,685) + Fees ($146) + Taxes in 2025 ($808)


    Taxes:$9,695

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00060 Days on yellowkey   MLS ID: O6400331

    REDUCED by $22,000 (2.6%) on 06/19/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,444 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


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

    $184,900163 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


  • 200 SAINT ANDREWS BLVD #312, WINTER PARK, FL 32792

    $170,00097 Days on yellowkey   MLS ID: S5145794

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

    For Sale S5145794 - 200 SAINT ANDREWS BLVD #312, WINTER PARK, FL 32792 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Monthly Fee: $451
       Tax: $2,396 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,582 (change assumption)
    Mortgage ($931) + Fees ($451) + Taxes in 2025 ($200)


    Taxes:$2,396

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00032 Days on yellowkey   MLS ID: O6409911

    For Sale O6409911 - 616 BRECHIN DR, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2638
       Built: 1961   Tax: $4,251 (2025)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $6,080 (change assumption)
    Mortgage ($5,726) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1261 INDIANA AVE, WINTER PARK, FL 32789

    $534,90064 Days on yellowkey   MLS ID: O6400698

    REDUCED by $4,100 (0.8%) on 06/09/2026

    For Sale O6400698 - 1261 INDIANA AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 2005
    Monthly Fee: $360
       Tax: $2,892 (2025)
    Community: Townhomes/Harper Place
    Townhouse


    Estimated Monthly Payment: $3,532 (change assumption)
    Mortgage ($2,931) + Fees ($360) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $650,00027 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.7%) on 06/19/2026

    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: $4,273 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #E204, WINTER PARK, FL 32789

    $114,000195 Days on yellowkey   MLS ID: O6366205

    REDUCED by $1,000 (0.9%) on 06/01/2026

    For Sale O6366205 - 1695 LEE RD #E204, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $1,917 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,266 (change assumption)
    Mortgage ($625) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1571 WOODLAND AVE, WINTER PARK, FL 32789

    $6,000,00025 Days on yellowkey   MLS ID: O6411706

    For Sale O6411706 - 1571 WOODLAND AVE, WINTER PARK, FL 32789 75 photos

    Bed: 5   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7397
       Built: 2007   Tax: $31,040 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $35,463 (change assumption)
    Mortgage ($32,876) + Taxes in 2025 ($2,587)


    Taxes:$31,040

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $504,90015 Days on yellowkey   MLS ID: O6415084

    REDUCED by $15,000 (2.9%) on 06/19/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,358 (change assumption)
    Mortgage ($2,767) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,699,00082 Days on yellowkey   MLS ID: O6395692

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

    REDUCED by $51,000 (2.9%) on 05/19/2026

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,381 (change assumption)
    Mortgage ($9,309) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789

    $475,000145 Days on yellowkey   MLS ID: O6375307

    For Sale O6375307 - 630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789 55 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1428
       Built: 1986   Tax: $6,595 (2025)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $3,152 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($550)


    Taxes:$6,595

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1500 GAY RD #5, WINTER PARK, FL 32789

    $170,000138 Days on yellowkey   MLS ID: S5143213

    0 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $15,000 (8.1%) on 04/29/2026

    For Sale S5143213 - 1500 GAY RD #5, WINTER PARK, FL 32789 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 732
       Built: 1972   Tax: $2,098 (2024)
    Community: Chateaux Du Lac
    Condo


    Estimated Monthly Payment: $1,106 (change assumption)
    Mortgage ($931) + Taxes in 2024 ($175)


    Taxes:$2,098

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.