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 Single Family Homes For Sale - 313 homes

Winter Park Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

Sort:
  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00023 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


  • 1398 GROVE TER, WINTER PARK, FL 32789

    $2,195,00059 Days on yellowkey   MLS ID: O6399698

    For Sale O6399698 - 1398 GROVE TER, WINTER PARK, FL 32789 58 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3450
       Built: 2004   Tax: $24,548 (2025)
    Community: Sylvan Lake Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,073 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($2,046)


    Taxes:$24,548

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 241 W LAKE SUE AVE, WINTER PARK, FL 32789

    $1,100,00017 Days on yellowkey   MLS ID: O6411621

    REDUCED by $100,000 (8.3%) on 06/08/2026

    For Sale O6411621 - 241 W LAKE SUE AVE, WINTER PARK, FL 32789 60 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1950   Tax: $14,823 (2025)
    Community: Virginia Heights
    Single Family


    Estimated Monthly Payment: $7,262 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($1,235)


    Taxes:$14,823

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 800 JUANITA RAEL, WINTER PARK, FL 32789

    $2,300,00067 Days on yellowkey   MLS ID: O6396611

    5 Days Off yellowkey (back on 6/8/2026)

    For Sale O6396611 - 800 JUANITA RAEL, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4021
       Built: 1961   Tax: $9,773 (2025)
    Community: Green Oaks Rep 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,417 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($814)


    Taxes:$9,773

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,235,000206 Days on yellowkey   MLS ID: O6362124

    REDUCED by $15,000 (0.7%) on 05/30/2026

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3818
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,375 (change assumption)
    Mortgage ($12,246) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000239 Days on yellowkey   MLS ID: O6352582

    2 Days Off yellowkey (back on 6/8/2026)

    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


  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,499,999158 Days on yellowkey   MLS ID: O6371649

    REDUCED by $50,001 (3.2%) on 05/14/2026

    For Sale O6371649 - 1523 MILLER AVE, WINTER PARK, FL 32789 65 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3164
       Built: 2026   Tax: $3,620 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $8,521 (change assumption)
    Mortgage ($8,219) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $589,00054 Days on yellowkey   MLS ID: O6400395

    REDUCED by $6,000 (1.0%) on 06/08/2026

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,696 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,0007 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


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $460,000141 Days on yellowkey   MLS ID: O6376260

    REDUCED by $10,000 (2.1%) on 05/28/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,955 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $480,00010 Days on yellowkey   MLS ID: O6409433

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,022 (change assumption)
    Mortgage ($2,630) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $2,000,00017 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $12,282 (change assumption)
    Mortgage ($10,959) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00024 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,00064 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    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: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,139,75065 Days on yellowkey   MLS ID: O6397997

    REDUCED by $35,250 (3.0%) on 05/18/2026

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,684 (change assumption)
    Mortgage ($6,245) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,395,00017 Days on yellowkey   MLS ID: O6411722

    For Sale O6411722 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3046
       Built: 2025   Tax: $1,383 (2025)
    Community: Na
    Single Family


    Estimated Monthly Payment: $7,759 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($115)


    Taxes:$1,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,200,00016 Days on yellowkey   MLS ID: O6412140

    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: $7,927 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,000110 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500235 Days on yellowkey   MLS ID: A4669103

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2756 SHERIFF WAY, WINTER PARK, FL 32792

    $595,00047 Days on yellowkey   MLS ID: O6402570

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

    REDUCED by $30,000 (4.8%) on 06/05/2026

    For Sale O6402570 - 2756 SHERIFF WAY, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1965   Tax: $5,547 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,722 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($462)


    Taxes:$5,547

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.