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Winter Park Homes For Sale & Real Estate - 439 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

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  • 1618 INDIANA AVE, WINTER PARK, FL 32789

    $675,00077 Days on yellowkey   MLS ID: O6398673

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

    REDUCED by $10,000 (1.5%) on 05/08/2026

    For Sale O6398673 - 1618 INDIANA AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1604
       Built: 1963   Tax: $5,477 (2025)
    Community: Lawndale
    Apartment


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($456)


    Taxes:$5,477

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3114 HEARTLEAF PL, WINTER PARK, FL 32792

    $685,000100 Days on yellowkey   MLS ID: S5146048

    REDUCED by $14,900 (2.1%) on 06/02/2026

    For Sale S5146048 - 3114 HEARTLEAF PL, WINTER PARK, FL 32792 71 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2702
       Built: 1999
    Monthly Fee: $18
       Tax: $6,737 (2024)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,333 (change assumption)
    Mortgage ($3,753) + Fees ($18) + Taxes in 2024 ($561)


    Taxes:$6,737

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,00031 Days on yellowkey   MLS ID: O6411325

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

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1516 MILLER AVE, WINTER PARK, FL 32789

    $1,549,90028 Days on yellowkey   MLS ID: O6412745

    0 Days Off yellowkey (back on 6/1/2026)

    For Sale O6412745 - 1516 MILLER AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3144
       Built: 2026   Tax: $4,868 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,898 (change assumption)
    Mortgage ($8,492) + Taxes in 2025 ($406)


    Taxes:$4,868

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1627 MIZELL AVE, WINTER PARK, FL 32789

    $3,300,00043 Days on yellowkey   MLS ID: O6406300

    For Sale O6406300 - 1627 MIZELL AVE, WINTER PARK, FL 32789 24 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3421
       Built: 2026   Tax: $11,211 (2025)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $19,016 (change assumption)
    Mortgage ($18,082) + Taxes in 2025 ($934)


    Taxes:$11,211

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792

    $159,000102 Days on yellowkey   MLS ID: O6388668

    REDUCED by $6,000 (3.6%) on 06/01/2026

    For Sale O6388668 - 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792 34 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1108
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Spa: No

    Condo


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($871) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792

    $159,000102 Days on yellowkey   MLS ID: O6390662

    REDUCED by $6,000 (3.6%) on 06/01/2026

    For Sale O6390662 - 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792 35 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($871) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7522 ALOMA PINES CT, WINTER PARK, FL 32792

    $375,00035 Days on yellowkey   MLS ID: S5150544

    For Sale S5150544 - 7522 ALOMA PINES CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1872
       Built: 2017
    Monthly Fee: $407
       Tax: $4,304 (2025)
    Community: Aloma Trails
    Townhouse


    Estimated Monthly Payment: $2,820 (change assumption)
    Mortgage ($2,055) + Fees ($407) + Taxes in 2025 ($359)


    Taxes:$4,304

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $325,00084 Days on yellowkey   MLS ID: S5147029

    INCREASED by $125,000 (62.5%) on 06/01/2026

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 262 LEWFIELD CIR #262, WINTER PARK, FL 32792

    $154,90053 Days on yellowkey   MLS ID: C7525448

    REDUCED by $4,100 (2.6%) on 06/01/2026

    For Sale C7525448 - 262 LEWFIELD CIR #262, WINTER PARK, FL 32792 36 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,278 (2024)
    Community: Stratford A Winter Park Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $955 (change assumption)
    Mortgage ($849) + Taxes in 2024 ($106)


    Taxes:$1,278

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,000150 Days on yellowkey   MLS ID: O6362285

    0 Days Off yellowkey (back on 5/31/2026)

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $689,00030 Days on yellowkey   MLS ID: O6412258

    REDUCED by $70,000 (9.2%) on 05/31/2026

    For Sale O6412258 - 2157 LAKE DR, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2124
       Built: 1962   Tax: $1,605 (2025)
    Community: Killarney Point
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,775) + Taxes in 2025 ($134)


    Taxes:$1,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,649,000117 Days on yellowkey   MLS ID: O6384756

    REDUCED by $41,000 (2.4%) on 05/14/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $9,947 (change assumption)
    Mortgage ($9,035) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792

    $164,99931 Days on yellowkey   MLS ID: O6411608

    For Sale O6411608 - 200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792 27 photos

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


    Estimated Monthly Payment: $1,104 (change assumption)
    Mortgage ($904) + Taxes in 2025 ($200)


    Taxes:$2,396

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3220 NETHERWOOD DR, WINTER PARK, FL 32792

    $269,000164 Days on yellowkey   MLS ID: O6374172

    5 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $10,990 (3.9%) on 04/20/2026

    For Sale O6374172 - 3220 NETHERWOOD DR, WINTER PARK, FL 32792 18 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1982   Tax: $1,222 (2025)
    Community: Coronation Add
    Half Duplex


    Estimated Monthly Payment: $1,576 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($102)


    Taxes:$1,222

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792

    $185,000352 Days on yellowkey   MLS ID: O6326460

    REDUCED by $4,000 (2.1%) on 05/11/2026

    For Sale O6326460 - 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $420
       Tax: $2,549 (2024)
    Community: Hidden Oaks Condo Ph 09
    Condo


    Estimated Monthly Payment: $1,646 (change assumption)
    Mortgage ($1,014) + Fees ($420) + Taxes in 2024 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00033 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


  • 1200 VIA SALERNO, WINTER PARK, FL 32789

    $5,995,000136 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


  • 1092 EASTBROOK BLVD, WINTER PARK, FL 32792

    $399,00044 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


  • 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $380,00053 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




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.