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Winter Garden Homes For Sale & Real Estate - 661 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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  • 15039 GROVESIDE RD, WINTER GARDEN, FL 34787

    $490,3803 Days on yellowkey   MLS ID: O6398354

    For Sale O6398354 - 15039 GROVESIDE RD, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2026
    Monthly Fee: $247
       Tax: $1,375 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,049 (change assumption)
    Mortgage ($2,687) + Fees ($247) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12780 SUNSET WALK DR, WINTER GARDEN, FL 34787

    $465,0003 Days on yellowkey   MLS ID: O6398355

    For Sale O6398355 - 12780 SUNSET WALK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1760
       Built: 2026
    Monthly Fee: $150
       Tax: $400 (2025)
    Community: Westhaven At Ovation
    Townhouse


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,548) + Fees ($150) + Taxes in 2025 ($33)


    Taxes:$400

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 196 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $580,0003 Days on yellowkey   MLS ID: O6398349

    For Sale O6398349 - 196 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 3 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2026
    Monthly Fee: $80
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,452 (change assumption)
    Mortgage ($3,178) + Fees ($80) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15027 GROVESIDE RD, WINTER GARDEN, FL 34787

    $492,6303 Days on yellowkey   MLS ID: O6398345

    For Sale O6398345 - 15027 GROVESIDE RD, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2026
    Monthly Fee: $247
       Tax: $1,375 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,061 (change assumption)
    Mortgage ($2,699) + Fees ($247) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 195 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $641,0003 Days on yellowkey   MLS ID: O6398339

    For Sale O6398339 - 195 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 3 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2460
       Built: 2026
    Monthly Fee: $80
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,786 (change assumption)
    Mortgage ($3,512) + Fees ($80) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $499,99047 Days on yellowkey   MLS ID: S5144591

    REDUCED by $25,010 (4.8%) on 04/06/2026

    For Sale S5144591 - 648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2018
    Monthly Fee: $338
       Tax: $4,171 (2024)
    Community: Heritage/Plant Street
    Townhouse


    Estimated Monthly Payment: $3,425 (change assumption)
    Mortgage ($2,740) + Fees ($338) + Taxes in 2024 ($348)


    Taxes:$4,171

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $525,00034 Days on yellowkey   MLS ID: O6389653

    0 Days Off yellowkey (back on 4/11/2026)

    REDUCED by $4,900 (0.9%) on 04/04/2026

    For Sale O6389653 - 628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787 68 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2018
    Monthly Fee: $336
       Tax: $3,620 (2025)
    Community: Heritage At Plant Street Community Assoc
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,514 (change assumption)
    Mortgage ($2,877) + Fees ($336) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $745,000113 Days on yellowkey   MLS ID: S5140531

    For Sale S5140531 - 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2023
    Monthly Fee: $300
       Tax: $1,706 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,082) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1261 WINTER GREEN WAY, WINTER GARDEN, FL 34787

    $255,00080 Days on yellowkey   MLS ID: O6372438

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6372438 - 1261 WINTER GREEN WAY, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1400
       Built: 1984
    Monthly Fee: $63
       Tax: $2,520 (2024)
    Community: Village Grove Phase 2
    Townhouse


    Estimated Monthly Payment: $1,670 (change assumption)
    Mortgage ($1,397) + Fees ($63) + Taxes in 2024 ($210)


    Taxes:$2,520

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787

    $570,00046 Days on yellowkey   MLS ID: O6386373

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6386373 - 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2508
       Built: 2008
    Monthly Fee: $243
       Tax: $3,490 (2025)
    Community: Stoneybrook West D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($3,123) + Fees ($243) + Taxes in 2025 ($291)


    Taxes:$3,490

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5526 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787

    $649,000127 Days on yellowkey   MLS ID: O6365476

    REDUCED by $31,000 (4.6%) on 04/11/2026

    For Sale O6365476 - 5526 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2013
    Monthly Fee: $184
       Tax: $8,004 (2025)
    Community: Signature Lakes
    Single Family


    Estimated Monthly Payment: $4,407 (change assumption)
    Mortgage ($3,556) + Fees ($184) + Taxes in 2025 ($667)


    Taxes:$8,004

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #1721, WINTER GARDEN, FL 34787

    $249,5003 Days on yellowkey   MLS ID: O6397131

    For Sale O6397131 - 14501 GROVE RESORT AVE #1721, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1396
       Built: 2017
    Monthly Fee: $904
       Tax: $7,146 (2025)
    Community: Grove Resort And Spa Hotel Condominium
    Condo


    Estimated Monthly Payment: $2,867 (change assumption)
    Mortgage ($1,367) + Fees ($904) + Taxes in 2025 ($595)


    Taxes:$7,146

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15285 HAMLIN PARK DR, WINTER GARDEN, FL 34787

    $489,9907 Days on yellowkey   MLS ID: TB8494889

    For Sale TB8494889 - 15285 HAMLIN PARK DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2026
    Monthly Fee: $248
       Tax: $1,375 (2025)
    Community: Parkview/Hamlin
    Townhouse


    Estimated Monthly Payment: $3,047 (change assumption)
    Mortgage ($2,685) + Fees ($248) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14267 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787

    $350,00028 Days on yellowkey   MLS ID: O6390455

    For Sale O6390455 - 14267 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787 29 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1289
       Built: 2008
    Monthly Fee: $139
       Tax: $3,450 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Townhouse


    Estimated Monthly Payment: $2,344 (change assumption)
    Mortgage ($1,918) + Fees ($139) + Taxes in 2025 ($287)


    Taxes:$3,450

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15006 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $499,9005 Days on yellowkey   MLS ID: S5147405

    1 Days Off yellowkey (back on 4/11/2026)

    For Sale S5147405 - 15006 PIGEON PLUM LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2016
    Monthly Fee: $252
       Tax: $7,351 (2025)
    Community: Summerlake
    Single Family


    Estimated Monthly Payment: $3,604 (change assumption)
    Mortgage ($2,739) + Fees ($252) + Taxes in 2025 ($613)


    Taxes:$7,351

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900228 Days on yellowkey   MLS ID: S5133690

    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: $3,415 (change assumption)
    Mortgage ($2,849) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 16413 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $490,0004 Days on yellowkey   MLS ID: O6397513

    For Sale O6397513 - 16413 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1626
       Built: 2021
    Monthly Fee: $284
       Tax: $6,711 (2025)
    Community: Hawksmoor
    Townhouse


    Estimated Monthly Payment: $3,528 (change assumption)
    Mortgage ($2,685) + Fees ($284) + Taxes in 2025 ($559)


    Taxes:$6,711

    Elementary School: Water Spring Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5943 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $746,650208 Days on yellowkey   MLS ID: G5102277

    0 Days Off yellowkey (back on 3/17/2026)

    For Sale G5102277 - 5943 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,241 (change assumption)
    Mortgage ($4,091) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $880,00052 Days on yellowkey   MLS ID: O6384565

    REDUCED by $5,000 (0.6%) on 04/11/2026

    For Sale O6384565 - 276 SUMMER PINE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3147
       Built: 2025
    Monthly Fee: $240
       Tax: $1,914 (2024)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,221 (change assumption)
    Mortgage ($4,822) + Fees ($240) + Taxes in 2024 ($160)


    Taxes:$1,914

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 744 LAKE BRIM DR, WINTER GARDEN, FL 34787

    $995,00035 Days on yellowkey   MLS ID: O6388775

    For Sale O6388775 - 744 LAKE BRIM DR, WINTER GARDEN, FL 34787 87 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 2016
    Monthly Fee: $203
       Tax: $9,275 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $6,428 (change assumption)
    Mortgage ($5,452) + Fees ($203) + Taxes in 2025 ($773)


    Taxes:$9,275

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview 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.