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 - 342 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:
  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00026 Days on yellowkey   MLS ID: O6391025

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6391025 - 2919 BOWER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2325
       Built: 1971   Tax: $9,857 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,090 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 647 RANDY LN, WINTER PARK, FL 32789

    $1,795,00036 Days on yellowkey   MLS ID: O6387217

    For Sale O6387217 - 647 RANDY LN, WINTER PARK, FL 32789 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 1957   Tax: $5,627 (2025)
    Community: Timberlane
    Single Family


    Estimated Monthly Payment: $10,304 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 850 JUANITA RAEL, WINTER PARK, FL 32789

    $1,425,00097 Days on yellowkey   MLS ID: O6370568

    1 Days Off yellowkey (back on 1/12/2026)

    For Sale O6370568 - 850 JUANITA RAEL, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 1966   Tax: $6,218 (2024)
    Community: Green Oaks Rep 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,326 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($518)


    Taxes:$6,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000178 Days on yellowkey   MLS ID: O6352582

    1 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3021 AARON BURR AVE #3, WINTER PARK, FL 32792

    $140,0001 Day on yellowkey   MLS ID: S5147382

    For Sale S5147382 - 3021 AARON BURR AVE #3, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $479
       Tax: $1,992 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($767) + Fees ($479) + Taxes in 2025 ($166)


    Taxes:$1,992

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1453 VIA SANGRO PL, WINTER PARK, FL 32792

    $995,0005 Days on yellowkey   MLS ID: O6397250

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6397250 - 1453 VIA SANGRO PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3057
       Built: 2015
    Monthly Fee: $188
       Tax: $5,858 (2024)
    Community: Lakeside Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,128 (change assumption)
    Mortgage ($5,452) + Fees ($188) + Taxes in 2024 ($488)


    Taxes:$5,858

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 851 MILES AVE #13, WINTER PARK, FL 32789

    $209,999117 Days on yellowkey   MLS ID: O6368234

    For Sale O6368234 - 851 MILES AVE #13, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 808
       Built: 1984   Tax: $2,694 (2025)
    Community: Aragon Condo
    Condo


    Estimated Monthly Payment: $1,375 (change assumption)
    Mortgage ($1,151) + Taxes in 2025 ($224)


    Taxes:$2,694

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $975,00012 Days on yellowkey   MLS ID: O6395355

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $5,574 (change assumption)
    Mortgage ($5,342) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $550,00040 Days on yellowkey   MLS ID: G5108643

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,441 (change assumption)
    Mortgage ($3,014) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 661 SELKIRK DR, WINTER PARK, FL 32792

    $675,000174 Days on yellowkey   MLS ID: O6354700

    REDUCED by $25,000 (3.6%) on 04/12/2026

    For Sale O6354700 - 661 SELKIRK DR, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 1962   Tax: $2,353 (2024)
    Community: Kenilworth Shores Sec 05
    Single Family


    Estimated Monthly Payment: $3,895 (change assumption)
    Mortgage ($3,699) + Taxes in 2024 ($196)


    Taxes:$2,353

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7336 FOREST HILL CT #240, WINTER PARK, FL 32792

    $169,90046 Days on yellowkey   MLS ID: O6386461

    REDUCED by $10,000 (5.6%) on 04/08/2026

    For Sale O6386461 - 7336 FOREST HILL CT #240, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984
    Monthly Fee: $450
       Tax: $2,899 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,622 (change assumption)
    Mortgage ($931) + Fees ($450) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 676 DUNBLANE DR, WINTER PARK, FL 32792

    $750,000130 Days on yellowkey   MLS ID: O6365557

    For Sale O6365557 - 676 DUNBLANE DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1962   Tax: $5,584 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,575 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($465)


    Taxes:$5,584

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


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

    $184,90093 Days on yellowkey   MLS ID: O6367842

    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


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $470,0003 Days on yellowkey   MLS ID: O6398273

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,869 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 318 VITORIA AVE, WINTER PARK, FL 32789

    $2,200,00018 Days on yellowkey   MLS ID: O6388489

    For Sale O6388489 - 318 VITORIA AVE, WINTER PARK, FL 32789 69 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2433
       Built: 1922   Tax: $2,960 (2024)
    Community: College Quarter
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,301 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00025 Days on yellowkey   MLS ID: O6383092

    For Sale O6383092 - 906 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3618
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,745 (change assumption)
    Mortgage ($10,548) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00026 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,425,00032 Days on yellowkey   MLS ID: O6390504

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $8,140 (change assumption)
    Mortgage ($7,808) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,395,00062 Days on yellowkey   MLS ID: O6381552

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,521 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $3,199,00092 Days on yellowkey   MLS ID: O6372165

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,174 (change assumption)
    Mortgage ($17,528) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    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.