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Winter Garden Homes For Sale & Real Estate - 979 homes

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

Location: Winter Garden

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  • 15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787

    $340,00090 Days on yellowkey   MLS ID: O6401625

    REDUCED by $4,900 (1.4%) on 07/20/2026

    For Sale O6401625 - 15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 2008
    Monthly Fee: $285
       Tax: $4,779 (2025)
    Community: Tucker Oaks
    Condo


    Estimated Monthly Payment: $2,546 (change assumption)
    Mortgage ($1,863) + Fees ($285) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $749,99027 Days on yellowkey   MLS ID: O6418908

    REDUCED by $30,000 (3.8%) on 07/21/2026

    For Sale O6418908 - 12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $169
       Tax: $2,512 (2025)
    Community: Encore At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,488 (change assumption)
    Mortgage ($4,109) + Fees ($169) + Taxes in 2025 ($209)


    Taxes:$2,512

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9561 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $729,0005 Days on yellowkey   MLS ID: O6426027

    For Sale O6426027 - 9561 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3267
       Built: 2018
    Monthly Fee: $255
       Tax: $6,570 (2025)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $4,797 (change assumption)
    Mortgage ($3,994) + Fees ($255) + Taxes in 2025 ($548)


    Taxes:$6,570

    Elementary School: Atwater Bay Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $599,99955 Days on yellowkey   MLS ID: O6411451

    REDUCED by $1 (0.0%) on 07/09/2026

    For Sale O6411451 - 1005 CHASE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,087 (2025)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,946 (change assumption)
    Mortgage ($3,288) + Fees ($68) + Taxes in 2025 ($591)


    Taxes:$7,087

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1300 EASTERN PECAN PL #208, WINTER GARDEN, FL 34787

    $287,00026 Days on yellowkey   MLS ID: O6420493

    REDUCED by $8,000 (2.7%) on 07/21/2026

    For Sale O6420493 - 1300 EASTERN PECAN PL #208, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1453
       Built: 2005   Tax: $3,625 (2024)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $1,875 (change assumption)
    Mortgage ($1,573) + Taxes in 2024 ($302)


    Taxes:$3,625

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $620,00023 Days on yellowkey   MLS ID: G5114379

    REDUCED by $10,000 (1.6%) on 07/05/2026

    For Sale G5114379 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215

    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $3,612 (change assumption)
    Mortgage ($3,397) + Fees ($215) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 304 ERON WAY #2, WINTER GARDEN, FL 34787

    $175,90030 Days on yellowkey   MLS ID: O6419000

    REDUCED by $2,000 (1.1%) on 07/21/2026

    For Sale O6419000 - 304 ERON WAY #2, WINTER GARDEN, FL 34787 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1984
    Monthly Fee: $450
       Tax: $2,151 (2025)
    Community: Townhomes Winter Garden
    Condo


    Estimated Monthly Payment: $1,593 (change assumption)
    Mortgage ($964) + Fees ($450) + Taxes in 2025 ($179)


    Taxes:$2,151

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14252 CREEKBED CIR, WINTER GARDEN, FL 34787

    $779,90042 Days on yellowkey   MLS ID: O6408908

    REDUCED by $10,000 (1.3%) on 07/21/2026

    For Sale O6408908 - 14252 CREEKBED CIR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3572
       Built: 2014
    Monthly Fee: $180

    Community: Bradford Creek
    Single Family


    Estimated Monthly Payment: $4,453 (change assumption)
    Mortgage ($4,273) + Fees ($180) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,225,000114 Days on yellowkey   MLS ID: O6394059

    REDUCED by $34,000 (2.7%) on 06/17/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $298
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,501 (change assumption)
    Mortgage ($6,712) + Fees ($298) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $996,975102 Days on yellowkey   MLS ID: O6397262

    REDUCED by $25 (0.0%) on 05/28/2026

    For Sale O6397262 - 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 1984
    Monthly Fee: $71
       Tax: $10,303 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,463) + Fees ($71) + Taxes in 2025 ($859)


    Taxes:$10,303

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 721 S WOODLAND ST, WINTER GARDEN, FL 34787

    $450,00026 Days on yellowkey   MLS ID: O6419636

    For Sale O6419636 - 721 S WOODLAND ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1034
       Built: 1955   Tax: $508 (2025)
    Community: Borders & Woosley Sub
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($42)


    Taxes:$508

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787

    $330,00012 Days on yellowkey   MLS ID: O6423147

    For Sale O6423147 - 455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1588
       Built: 2006
    Monthly Fee: $123
       Tax: $4,229 (2025)
    Community: Westpoint Townhomes
    Townhouse


    Estimated Monthly Payment: $2,284 (change assumption)
    Mortgage ($1,808) + Fees ($123) + Taxes in 2025 ($352)


    Taxes:$4,229

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8289 TOPSAIL PL, WINTER GARDEN, FL 34787

    $890,00049 Days on yellowkey   MLS ID: S5151179

    2 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $30,000 (3.3%) on 06/16/2026

    For Sale S5151179 - 8289 TOPSAIL PL, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2755
       Built: 2020
    Monthly Fee: $350
       Tax: $11,564 (2024)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,190 (change assumption)
    Mortgage ($4,877) + Fees ($350) + Taxes in 2024 ($964)


    Taxes:$11,564

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 13822 JOMATT LOOP, WINTER GARDEN, FL 34787

    $975,00054 Days on yellowkey   MLS ID: O6411926

    0 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $25,000 (2.5%) on 06/24/2026

    For Sale O6411926 - 13822 JOMATT LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2016
    Monthly Fee: $75
       Tax: $12,039 (2025)
    Community: Cypress Reserve Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,421 (change assumption)
    Mortgage ($5,342) + Fees ($75) + Taxes in 2025 ($1,003)


    Taxes:$12,039

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $479,900327 Days on yellowkey   MLS ID: S5133690

    REDUCED by $20,000 (4.0%) on 07/14/2026

    For Sale S5133690 - 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2001
    Monthly Fee: $33
       Tax: $6,403 (2024)
    Community: Tuscany Ph 02
    Single Family


    Estimated Monthly Payment: $3,196 (change assumption)
    Mortgage ($2,630) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 15935 GRAFTON WAY, WINTER GARDEN, FL 34787

    $510,00094 Days on yellowkey   MLS ID: O6400426

    REDUCED by $10,000 (1.9%) on 06/09/2026

    For Sale O6400426 - 15935 GRAFTON WAY, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1833
       Built: 2023
    Monthly Fee: $330
       Tax: $6,255 (2025)
    Community: Encore At Ovation
    Townhouse


    Estimated Monthly Payment: $3,646 (change assumption)
    Mortgage ($2,794) + Fees ($330) + Taxes in 2025 ($521)


    Taxes:$6,255

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 261 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $1,599,000262 Days on yellowkey   MLS ID: O6357233

    REDUCED by $46,000 (2.8%) on 07/09/2026

    For Sale O6357233 - 261 ZACHARY WADE ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3728
       Built: 2005
    Monthly Fee: $67
       Tax: $15,019 (2024)
    Community: Lakeview Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,080 (change assumption)
    Mortgage ($8,761) + Fees ($67) + Taxes in 2024 ($1,252)


    Taxes:$15,019

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $1,160,000244 Days on yellowkey   MLS ID: O6361968

    REDUCED by $10,000 (0.9%) on 07/21/2026

    For Sale O6361968 - 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 97 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2020
    Monthly Fee: $159
       Tax: $13,997 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $7,681 (change assumption)
    Mortgage ($6,356) + Fees ($159) + Taxes in 2024 ($1,166)


    Taxes:$13,997

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $739,90019 Days on yellowkey   MLS ID: O6420606

    For Sale O6420606 - 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2017
    Monthly Fee: $342
       Tax: $5,019 (2025)
    Community: Waterleigh Phase 1C
    Single Family


    Estimated Monthly Payment: $4,814 (change assumption)
    Mortgage ($4,054) + Fees ($342) + Taxes in 2025 ($418)


    Taxes:$5,019

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $549,990139 Days on yellowkey   MLS ID: O6387508

    For Sale O6387508 - 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $108
       Tax: $6,865 (2024)
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $3,694 (change assumption)
    Mortgage ($3,014) + Fees ($108) + Taxes in 2024 ($572)


    Taxes:$6,865

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

Winter Garden 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 Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden 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 Garden 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.