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Winter Garden Homes For Sale & Real Estate - 947 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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  • 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787

    $435,00069 Days on yellowkey   MLS ID: TB8497081

    REDUCED by $10,000 (2.2%) on 06/06/2026

    For Sale TB8497081 - 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1296
       Built: 2003
    Monthly Fee: $46
       Tax: $5,808 (2025)
    Community: Stone Crk
    Single Family


    Estimated Monthly Payment: $2,913 (change assumption)
    Mortgage ($2,384) + Fees ($46) + Taxes in 2025 ($484)


    Taxes:$5,808

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00077 Days on yellowkey   MLS ID: O6397592

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

    For Sale O6397592 - 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,265,00035 Days on yellowkey   MLS ID: O6406556

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

    For Sale O6406556 - 16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2018
    Monthly Fee: $215
       Tax: $9,540 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,941 (change assumption)
    Mortgage ($6,931) + Fees ($215) + Taxes in 2025 ($795)


    Taxes:$9,540

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $895,00019 Days on yellowkey   MLS ID: O6413972

    For Sale O6413972 - 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4010
       Built: 2005
    Monthly Fee: $182
       Tax: $11,924 (2025)
    Community: Bay Isle 48 17
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,080 (change assumption)
    Mortgage ($4,904) + Fees ($182) + Taxes in 2025 ($994)


    Taxes:$11,924

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 12570 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $962,89219 Days on yellowkey   MLS ID: O6414289

    For Sale O6414289 - 12570 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3636
       Built: 2026
    Monthly Fee: $96
       Tax: $15,480 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $6,662 (change assumption)
    Mortgage ($5,276) + Fees ($96) + Taxes in 2026 ($1,290)


    Taxes:$15,480

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1651 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787

    $1,080,00019 Days on yellowkey   MLS ID: O6414027

    For Sale O6414027 - 1651 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3881
       Built: 2017
    Monthly Fee: $184
       Tax: $6,540 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,647 (change assumption)
    Mortgage ($5,918) + Fees ($184) + Taxes in 2025 ($545)


    Taxes:$6,540

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 20 E DIVISION ST, WINTER GARDEN, FL 34787

    $1,149,00019 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


  • 12003 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $445,00051 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


  • 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787

    $580,00041 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

    $747,90034 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


  • 5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787

    $969,900177 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

    $215,000405 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


  • 10089 SALT POINT DR, WINTER GARDEN, FL 34787

    $465,00086 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

    $389,00022 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


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

    $340,00036 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

    $1,049,90060 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


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $535,00048 Days on yellowkey   MLS ID: O6404652

    REDUCED by $4,000 (0.7%) on 06/05/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,919 (change assumption)
    Mortgage ($2,931) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17552 LAKE STAR RD, WINTER GARDEN, FL 34787

    $999,000270 Days on yellowkey   MLS ID: O6344668

    For Sale O6344668 - 17552 LAKE STAR RD, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2605
       Built: 2023
    Monthly Fee: $83
       Tax: $12,990 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $6,639 (change assumption)
    Mortgage ($5,474) + Fees ($83) + Taxes in 2024 ($1,083)


    Taxes:$12,990

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9468 KOMIKA LN, WINTER GARDEN, FL 34787

    $459,90028 Days on yellowkey   MLS ID: S5150415

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

    FORECLOSURE S5150415 - 9468 KOMIKA LN, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $300
       Tax: $7,605 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,454 (change assumption)
    Mortgage ($2,520) + Fees ($300) + Taxes in 2025 ($634)


    Taxes:$7,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16283 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $649,00068 Days on yellowkey   MLS ID: O6399528

    REDUCED by $21,000 (3.1%) on 06/04/2026

    For Sale O6399528 - 16283 HONEY HARVEST ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2927
       Built: 2024
    Monthly Fee: $229
       Tax: $9,705 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,594 (change assumption)
    Mortgage ($3,556) + Fees ($229) + Taxes in 2025 ($809)


    Taxes:$9,705

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    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.