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Winter Garden Homes For Sale & Real Estate - 934 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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  • 20 E DIVISION ST, WINTER GARDEN, FL 34787

    $1,149,0009 Days on yellowkey   MLS ID: O6413659

    For Sale O6413659 - 20 E DIVISION ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2729
       Built: 1959   Tax: $7,197 (2025)
    Community: Winter Garden Shores First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,895 (change assumption)
    Mortgage ($6,296) + Taxes in 2025 ($600)


    Taxes:$7,197

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12427 CLEAR SAPPHIRE DR #238, WINTER GARDEN, FL 34787

    $608,2239 Days on yellowkey   MLS ID: O6413423

    For Sale O6413423 - 12427 CLEAR SAPPHIRE DR #238, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2026
    Monthly Fee: $96
       Tax: $9,123 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,189 (change assumption)
    Mortgage ($3,333) + Fees ($96) + Taxes in 2026 ($760)


    Taxes:$9,123

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787

    $350,0009 Days on yellowkey   MLS ID: O6411620

    For Sale O6411620 - 1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787 71 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 2014
    Monthly Fee: $300
       Tax: $3,213 (2025)
    Community: Tucker Oaks
    Townhouse


    Estimated Monthly Payment: $2,486 (change assumption)
    Mortgage ($1,918) + Fees ($300) + Taxes in 2025 ($268)


    Taxes:$3,213

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1219 SADDLEBACK DR, WINTER GARDEN, FL 34787

    $1,050,0009 Days on yellowkey   MLS ID: O6412381

    For Sale O6412381 - 1219 SADDLEBACK DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2022
    Monthly Fee: $215
       Tax: $11,474 (2025)
    Community: Oakland Parkb-1
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,924 (change assumption)
    Mortgage ($5,753) + Fees ($215) + Taxes in 2025 ($956)


    Taxes:$11,474

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12003 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $445,00041 Days on yellowkey   MLS ID: L4961121

    For Sale L4961121 - 12003 HOLYSTONE ST, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1814
       Built: 2023
    Monthly Fee: $269
       Tax: $5,292 (2025)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $3,148 (change assumption)
    Mortgage ($2,438) + Fees ($269) + Taxes in 2025 ($441)


    Taxes:$5,292

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $696,00074 Days on yellowkey   MLS ID: S5146881

    REDUCED by $3,000 (0.4%) on 05/22/2026

    For Sale S5146881 - 15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2025
    Monthly Fee: $233
       Tax: $9,545 (2024)
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,842 (change assumption)
    Mortgage ($3,814) + Fees ($233) + Taxes in 2024 ($795)


    Taxes:$9,545

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787

    $580,00031 Days on yellowkey   MLS ID: O6408082

    For Sale O6408082 - 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 2004
    Monthly Fee: $253
       Tax: $8,397 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,131 (change assumption)
    Mortgage ($3,178) + Fees ($253) + Taxes in 2025 ($700)


    Taxes:$8,397

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 120 BLUE STONE CIR, WINTER GARDEN, FL 34787

    $747,90024 Days on yellowkey   MLS ID: O6409811

    REDUCED by $2,000 (0.3%) on 06/05/2026

    For Sale O6409811 - 120 BLUE STONE CIR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2529
       Built: 1998
    Monthly Fee: $68
       Tax: $4,291 (2025)
    Community: Westfield Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,098) + Fees ($68) + Taxes in 2025 ($358)


    Taxes:$4,291

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9586 MEADOW HUNT WAY, WINTER GARDEN, FL 34787

    $1,099,00017 Days on yellowkey   MLS ID: S5150536

    For Sale S5150536 - 9586 MEADOW HUNT WAY, WINTER GARDEN, FL 34787 70 photos

    Bed: 6   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3942
       Built: 2018
    Monthly Fee: $164
       Tax: $9,212 (2025)
    Community: Watermark Ph 2B
    Single Family


    Estimated Monthly Payment: $6,953 (change assumption)
    Mortgage ($6,022) + Fees ($164) + Taxes in 2025 ($768)


    Taxes:$9,212

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787

    $786,868107 Days on yellowkey   MLS ID: O6382140

    0 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $7,132 (0.9%) on 04/21/2026

    For Sale O6382140 - 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3324
       Built: 2022
    Monthly Fee: $70
       Tax: $7,567 (2025)
    Community: Lake Apopka Sound
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,012 (change assumption)
    Mortgage ($4,311) + Fees ($70) + Taxes in 2025 ($631)


    Taxes:$7,567

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15506 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787

    $894,000275 Days on yellowkey   MLS ID: O6343579

    REDUCED by $5,000 (0.6%) on 06/05/2026

    For Sale O6343579 - 15506 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2018
    Monthly Fee: $110
       Tax: $8,619 (2024)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $5,727 (change assumption)
    Mortgage ($4,899) + Fees ($110) + Taxes in 2024 ($718)


    Taxes:$8,619

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787

    $1,700,000104 Days on yellowkey   MLS ID: TB8481106

    REDUCED by $250,000 (12.8%) on 05/20/2026

    For Sale TB8481106 - 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4365
       Built: 2007
    Monthly Fee: $225
       Tax: $8,970 (2024)
    Community: Bronsons Lndgs F & M
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,287 (change assumption)
    Mortgage ($9,315) + Fees ($225) + Taxes in 2024 ($748)


    Taxes:$8,970

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787

    $969,900167 Days on yellowkey   MLS ID: O6369788

    REDUCED by $5,100 (0.5%) on 06/02/2026

    For Sale O6369788 - 5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 7   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4720
       Built: 2021
    Monthly Fee: $115
       Tax: $11,152 (2023)
    Community: Wincey Groves
    Single Family


    Estimated Monthly Payment: $6,359 (change assumption)
    Mortgage ($5,314) + Fees ($115) + Taxes in 2023 ($929)


    Taxes:$11,152

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Hamlin Middle


  • 14501 GROVE RESORT AVE #2438, WINTER GARDEN, FL 34787

    $215,000395 Days on yellowkey   MLS ID: O6306977

    REDUCED by $9,000 (4.0%) on 06/05/2026

    For Sale O6306977 - 14501 GROVE RESORT AVE #2438, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1396
       Built: 2018   Tax: $8,035 (2024)
    Community: Grove Residence Y Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,178) + Taxes in 2024 ($670)


    Taxes:$8,035

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 231 DOE RUN DR, WINTER GARDEN, FL 34787

    $500,00015 Days on yellowkey   MLS ID: O6412284

    For Sale O6412284 - 231 DOE RUN DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1972
       Built: 2006
    Monthly Fee: $57
       Tax: $3,202 (2025)
    Community: Deerfield Place A-G
    Single Family


    Estimated Monthly Payment: $3,063 (change assumption)
    Mortgage ($2,740) + Fees ($57) + Taxes in 2025 ($267)


    Taxes:$3,202

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10089 SALT POINT DR, WINTER GARDEN, FL 34787

    $465,00076 Days on yellowkey   MLS ID: O6392385

    REDUCED by $10,000 (2.1%) on 06/05/2026

    For Sale O6392385 - 10089 SALT POINT DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1654
       Built: 2022
    Monthly Fee: $260
       Tax: $6,886 (2025)
    Community: Waterleigh Ph 2E
    Townhouse


    Estimated Monthly Payment: $3,382 (change assumption)
    Mortgage ($2,548) + Fees ($260) + Taxes in 2025 ($574)


    Taxes:$6,886

    Elementary School: Avalon Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787

    $389,00012 Days on yellowkey   MLS ID: O6412643

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6412643 - 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2006
    Monthly Fee: $46
       Tax: $5,857 (2025)
    Community: Stone Creek Unit 4
    Single Family


    Estimated Monthly Payment: $2,666 (change assumption)
    Mortgage ($2,131) + Fees ($46) + Taxes in 2025 ($488)


    Taxes:$5,857

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15615 HONEYBELL DR, WINTER GARDEN, FL 34787

    $389,90033 Days on yellowkey   MLS ID: O6406267

    1 Days Off yellowkey (back on 6/5/2026)

    For Sale O6406267 - 15615 HONEYBELL DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $418
       Tax: $6,085 (2025)
    Community: Hamlin Reserve
    Townhouse


    Estimated Monthly Payment: $3,062 (change assumption)
    Mortgage ($2,136) + Fees ($418) + Taxes in 2025 ($507)


    Taxes:$6,085

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15625 BOGGY OAK CIR #108B, WINTER GARDEN, FL 34787

    $340,00026 Days on yellowkey   MLS ID: G5112579

    REDUCED by $4,900 (1.4%) on 06/05/2026

    For Sale G5112579 - 15625 BOGGY OAK CIR #108B, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1419
       Built: 2010   Tax: $3,605 (2025)
    Community: Tucker Oaks Ph 8
    Condo


    Estimated Monthly Payment: $2,163 (change assumption)
    Mortgage ($1,863) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,90050 Days on yellowkey   MLS ID: O6402332

    For Sale O6402332 - 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3998
       Built: 2023
    Monthly Fee: $208
       Tax: $12,135 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,972 (change assumption)
    Mortgage ($5,753) + Fees ($208) + Taxes in 2024 ($1,011)


    Taxes:$12,135

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.