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Winter Garden Homes For Sale & Real Estate - 585 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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  • 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,000Listed 04/05/2026 4:46PM   MLS ID: O6394975

    For Sale O6394975 - 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2015
    Monthly Fee: $332
       Tax: $8,849 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,110 (change assumption)
    Mortgage ($3,041) + Fees ($332) + Taxes in 2025 ($737)


    Taxes:$8,849

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $649,000121 Days on yellowkey   MLS ID: A4674195

    For Sale A4674195 - 1005 CHASE DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,086 (2024)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $4,215 (change assumption)
    Mortgage ($3,556) + Fees ($68) + Taxes in 2024 ($591)


    Taxes:$7,086

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15831 GEM VIEW ST, WINTER GARDEN, FL 34787

    $399,590144 Days on yellowkey   MLS ID: O6360251

    For Sale O6360251 - 15831 GEM VIEW ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 2026
    Monthly Fee: $596
       Tax: $1,614 (2025)
    Community: Del Webb Oasis
    Villa


    Estimated Monthly Payment: $2,920 (change assumption)
    Mortgage ($2,189) + Fees ($596) + Taxes in 2025 ($134)


    Taxes:$1,614

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787

    $825,0009 Days on yellowkey   MLS ID: O6393190

    REDUCED by $25,000 (2.9%) on 04/05/2026

    For Sale O6393190 - 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787 89 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3902
       Built: 2005
    Monthly Fee: $243
       Tax: $7,653 (2025)
    Community: Stoneybrook West
    Single Family


    Estimated Monthly Payment: $5,401 (change assumption)
    Mortgage ($4,520) + Fees ($243) + Taxes in 2025 ($638)


    Taxes:$7,653

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900219 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


  • 838 BETHUNE AVE, WINTER GARDEN, FL 34787

    $275,00029 Days on yellowkey   MLS ID: O6388596

    REDUCED by $2,000 (0.7%) on 04/02/2026

    For Sale O6388596 - 838 BETHUNE AVE, WINTER GARDEN, FL 34787 8 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 985
       Built: 1961   Tax: $1,340 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $1,618 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($112)


    Taxes:$1,340

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15663 KINNOW MANDARIN LN, WINTER GARDEN, FL 34787

    $405,000127 Days on yellowkey   MLS ID: O6363767

    REDUCED by $11,000 (2.6%) on 04/02/2026

    For Sale O6363767 - 15663 KINNOW MANDARIN LN, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2017
    Monthly Fee: $347
       Tax: $6,304 (2025)
    Community: Highlands/Summerlake Grvs #1
    Townhouse


    Estimated Monthly Payment: $3,091 (change assumption)
    Mortgage ($2,219) + Fees ($347) + Taxes in 2025 ($525)


    Taxes:$6,304

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13332 SUBURBAN TER, WINTER GARDEN, FL 34787

    $749,900170 Days on yellowkey   MLS ID: O6352569

    For Sale O6352569 - 13332 SUBURBAN TER, WINTER GARDEN, FL 34787 80 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2706
       Built: 1994   Tax: $2,841 (2024)
    Community: Citrus Cove Unit 01
    Single Family


    Estimated Monthly Payment: $4,346 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($237)


    Taxes:$2,841

    Elementary School: Grassy Lake Elementary

    High School: East Ridge High

    Tax Year: 2024

    Middle School: Windy Hill Middle


  • 17723 JAPONICA BLOOM DR, WINTER GARDEN, FL 34787

    $449,50045 Days on yellowkey   MLS ID: O6383994

    For Sale O6383994 - 17723 JAPONICA BLOOM DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2024
    Monthly Fee: $266
       Tax: $6,064 (2025)
    Community: Northlake At Ovation
    Townhouse


    Estimated Monthly Payment: $3,234 (change assumption)
    Mortgage ($2,463) + Fees ($266) + Taxes in 2025 ($505)


    Taxes:$6,064

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 107 TRADITIONS DR, WINTER GARDEN, FL 34787

    $499,99519 Days on yellowkey   MLS ID: S5145650

    REDUCED by $24,980 (4.8%) on 04/01/2026

    For Sale S5145650 - 107 TRADITIONS DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1582
       Built: 1999
    Monthly Fee: $45
       Tax: $1,458 (2024)
    Community: Traditions Sub
    Single Family


    Estimated Monthly Payment: $2,906 (change assumption)
    Mortgage ($2,740) + Fees ($45) + Taxes in 2024 ($121)


    Taxes:$1,458

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 1710 E BAY ST, WINTER GARDEN, FL 34787

    $254,99533 Days on yellowkey   MLS ID: O6376343

    REDUCED by $19,400 (7.1%) on 04/05/2026

    For Sale O6376343 - 1710 E BAY ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 972
       Built: 1957   Tax: $958 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,477 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($80)


    Taxes:$958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787

    $570,00037 Days on yellowkey   MLS ID: O6386373

    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
    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


  • 10768 RHETT BUTLER ALY, WINTER GARDEN, FL 34787

    $424,000Listed 04/04/2026 8:12PM   MLS ID: O6396023

    For Sale O6396023 - 10768 RHETT BUTLER ALY, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1636
       Built: 2023
    Monthly Fee: $268
       Tax: $5,866 (2025)
    Community: Storey Grove
    Townhouse


    Estimated Monthly Payment: $3,080 (change assumption)
    Mortgage ($2,323) + Fees ($268) + Taxes in 2025 ($489)


    Taxes:$5,866

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10540 TRIBUTE DR, WINTER GARDEN, FL 34787

    $415,000197 Days on yellowkey   MLS ID: O6346155

    For Sale O6346155 - 10540 TRIBUTE DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1636
       Built: 2023
    Monthly Fee: $225
       Tax: $6,096 (2024)
    Community: Storey Grove Ph 4
    Townhouse


    Estimated Monthly Payment: $3,007 (change assumption)
    Mortgage ($2,274) + Fees ($225) + Taxes in 2024 ($508)


    Taxes:$6,096

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 10534 TRIBUTE DR, WINTER GARDEN, FL 34787

    $425,000197 Days on yellowkey   MLS ID: O6345956

    For Sale O6345956 - 10534 TRIBUTE DR, WINTER GARDEN, FL 34787 6 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1636
       Built: 2023
    Monthly Fee: $225
       Tax: $6,094 (2024)
    Community: Storey Grove Ph 4
    Townhouse


    Estimated Monthly Payment: $3,062 (change assumption)
    Mortgage ($2,329) + Fees ($225) + Taxes in 2024 ($508)


    Taxes:$6,094

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $829,965199 Days on yellowkey   MLS ID: G5102265

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102265 - 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 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: $4,698 (change assumption)
    Mortgage ($4,548) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $1,300,0001 Day on yellowkey   MLS ID: O6395612

    For Sale O6395612 - 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 73 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4625
       Built: 2003
    Monthly Fee: $141
       Tax: $12,364 (2025)
    Community: Bay Isle 48 17
    Single Family


    Estimated Monthly Payment: $8,294 (change assumption)
    Mortgage ($7,123) + Fees ($141) + Taxes in 2025 ($1,030)


    Taxes:$12,364

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 730 RIVER GRASS LN, WINTER GARDEN, FL 34787

    $649,90070 Days on yellowkey   MLS ID: G5107248

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

    For Sale G5107248 - 730 RIVER GRASS LN, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2647
       Built: 2014
    Monthly Fee: $72
       Tax: $3,572 (2024)
    Community: Covington Chase Ph 2C
    Single Family


    Estimated Monthly Payment: $3,931 (change assumption)
    Mortgage ($3,561) + Fees ($72) + Taxes in 2024 ($298)


    Taxes:$3,572

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $573,00069 Days on yellowkey   MLS ID: NS1087076

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,140) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $525,00025 Days on yellowkey   MLS ID: O6389653

    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
    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




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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.