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Winter Park Homes For Sale & Real Estate - 377 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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  • 423 OLOLU DR, WINTER PARK, FL 32789

    $589,000104 Days on yellowkey   MLS ID: O6369976

    For Sale O6369976 - 423 OLOLU DR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1920
       Built: 1981   Tax: $4,030 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,563 (change assumption)
    Mortgage ($3,227) + Taxes in 2024 ($336)


    Taxes:$4,030

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00033 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00033 Days on yellowkey   MLS ID: O6383679

    For Sale O6383679 - 905 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


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

    $115,000133 Days on yellowkey   MLS ID: O6366205

    REDUCED by $9,900 (7.9%) on 04/03/2026

    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: $1,272 (change assumption)
    Mortgage ($630) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4190 BEAR GULLY RD, WINTER PARK, FL 32792

    $524,900106 Days on yellowkey   MLS ID: O6371014

    For Sale O6371014 - 4190 BEAR GULLY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2003
    Monthly Fee: $52
       Tax: $5,630 (2024)
    Community: Bear Gully Forest
    Single Family


    Estimated Monthly Payment: $3,397 (change assumption)
    Mortgage ($2,876) + Fees ($52) + Taxes in 2024 ($469)


    Taxes:$5,630

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5180 LAZY OAKS DR #5180, WINTER PARK, FL 32792

    $290,00021 Days on yellowkey   MLS ID: O6395367

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6395367 - 5180 LAZY OAKS DR #5180, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1984
    Monthly Fee: $277
       Tax: $1,746 (2024)
    Community: Lazy Oaks Condo
    Condo


    Estimated Monthly Payment: $2,012 (change assumption)
    Mortgage ($1,589) + Fees ($277) + Taxes in 2024 ($146)


    Taxes:$1,746

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792

    $185,00057 Days on yellowkey   MLS ID: S5144503

    REDUCED by $9,900 (5.1%) on 04/08/2026

    For Sale S5144503 - 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 753
       Built: 1973
    Monthly Fee: $280
       Tax: $1,479 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,417 (change assumption)
    Mortgage ($1,014) + Fees ($280) + Taxes in 2024 ($123)


    Taxes:$1,479

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 550 PALMER AVE, WINTER PARK, FL 32789

    $6,895,000182 Days on yellowkey   MLS ID: O6349188

    For Sale O6349188 - 550 PALMER AVE, WINTER PARK, FL 32789 76 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5939
       Built: 2025   Tax: $10,292 (2025)
    Community: Osceola Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $38,638 (change assumption)
    Mortgage ($37,780) + Taxes in 2025 ($858)


    Taxes:$10,292

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00033 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


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,645,00071 Days on yellowkey   MLS ID: O6379927

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,152 (change assumption)
    Mortgage ($9,013) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,890,00033 Days on yellowkey   MLS ID: O6391179

    REDUCED by $105,000 (5.3%) on 04/08/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,411 (change assumption)
    Mortgage ($10,356) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 675 OVERSPIN DR, WINTER PARK, FL 32789

    $775,00072 Days on yellowkey   MLS ID: O6378975

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6378975 - 675 OVERSPIN DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3062
       Built: 2010   Tax: $11,578 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $5,211 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($965)


    Taxes:$11,578

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 4923 N MAGNOLIA AVE, WINTER PARK, FL 32792

    $390,00015 Days on yellowkey   MLS ID: O6396378

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale O6396378 - 4923 N MAGNOLIA AVE, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1559
       Built: 1953   Tax: $2,479 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $2,344 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1127 WILDMEADOW RUN, WINTER PARK, FL 32792

    $675,000140 Days on yellowkey   MLS ID: O6364368

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

    For Sale O6364368 - 1127 WILDMEADOW RUN, WINTER PARK, FL 32792 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2020
    Monthly Fee: $243
       Tax: $6,882 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,515 (change assumption)
    Mortgage ($3,699) + Fees ($243) + Taxes in 2024 ($574)


    Taxes:$6,882

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 4790 TANGERINE AVE #4790, WINTER PARK, FL 32792

    $194,99565 Days on yellowkey   MLS ID: O6380539

    REDUCED by $20,000 (9.3%) on 04/07/2026

    For Sale O6380539 - 4790 TANGERINE AVE #4790, WINTER PARK, FL 32792 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,253 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,256 (change assumption)
    Mortgage ($1,068) + Taxes in 2024 ($188)


    Taxes:$2,253

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,00082 Days on yellowkey   MLS ID: O6377988

    For Sale O6377988 - 5275 PINE LILY CIR, WINTER PARK, FL 32792 34 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3152
       Built: 2014
    Monthly Fee: $182
       Tax: $7,425 (2024)
    Community: Sanctuary At Aloma
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,444 (change assumption)
    Mortgage ($3,644) + Fees ($182) + Taxes in 2024 ($619)


    Taxes:$7,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1500 HARRIS CIR, WINTER PARK, FL 32789

    $1,295,00070 Days on yellowkey   MLS ID: O6379012

    For Sale O6379012 - 1500 HARRIS CIR, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 3.0
    Liv Area Sq Ft: 2096
       Built: 1994   Tax: $11,846 (2024)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $8,083 (change assumption)
    Mortgage ($7,096) + Taxes in 2024 ($987)


    Taxes:$11,846

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 823 GRANVILLE DR, WINTER PARK, FL 32789

    $1,400,00023 Days on yellowkey   MLS ID: O6394306

    1 Days Off yellowkey (back on 4/7/2026)

    For Sale O6394306 - 823 GRANVILLE DR, WINTER PARK, FL 32789 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2544
       Built: 1963   Tax: $7,623 (2025)
    Community: Park Grove
    Single Family


    Estimated Monthly Payment: $8,306 (change assumption)
    Mortgage ($7,671) + Taxes in 2025 ($635)


    Taxes:$7,623

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,00065 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2530 LEEWARD WAY, WINTER PARK, FL 32792

    $265,00070 Days on yellowkey   MLS ID: O6380907

    For Sale O6380907 - 2530 LEEWARD WAY, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1199
       Built: 1976
    Monthly Fee: $99
       Tax: $795 (2024)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,617 (change assumption)
    Mortgage ($1,452) + Fees ($99) + Taxes in 2024 ($66)


    Taxes:$795

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    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.