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Winter Garden Homes For Sale & Real Estate - 973 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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  • 10509 SPRING ARBOR LN, WINTER GARDEN, FL 34787

    $439,0005 Days on yellowkey   MLS ID: O6426898

    For Sale O6426898 - 10509 SPRING ARBOR LN, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2020
    Monthly Fee: $338
       Tax: $6,555 (2025)
    Community: Winding Bay Preserve
    Townhouse


    Estimated Monthly Payment: $3,290 (change assumption)
    Mortgage ($2,405) + Fees ($338) + Taxes in 2025 ($546)


    Taxes:$6,555

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9240 BRADLEIGH DR, WINTER GARDEN, FL 34787

    $1,050,00021 Days on yellowkey   MLS ID: O6421967

    For Sale O6421967 - 9240 BRADLEIGH DR, WINTER GARDEN, FL 34787 66 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4124
       Built: 2018
    Monthly Fee: $116
       Tax: $13,272 (2025)
    Community: Latham Park South
    Single Family


    Estimated Monthly Payment: $6,975 (change assumption)
    Mortgage ($5,753) + Fees ($116) + Taxes in 2025 ($1,106)


    Taxes:$13,272

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $739,90024 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


  • 14252 CREEKBED CIR, WINTER GARDEN, FL 34787

    $779,90047 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


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $875,00056 Days on yellowkey   MLS ID: O6412033

    REDUCED by $75,000 (7.9%) on 07/20/2026

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $5,963 (change assumption)
    Mortgage ($4,794) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $996,975107 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 71 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


  • 420 E CYPRESS ST, WINTER GARDEN, FL 34787

    $410,00056 Days on yellowkey   MLS ID: O6412414

    REDUCED by $10,000 (2.4%) on 07/17/2026

    For Sale O6412414 - 420 E CYPRESS ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1616
       Built: 1950   Tax: $5,517 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $2,706 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($460)


    Taxes:$5,517

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 93 WINDTREE LN #102, WINTER GARDEN, FL 34787

    $199,9993 Days on yellowkey   MLS ID: O6426740

    For Sale O6426740 - 93 WINDTREE LN #102, WINTER GARDEN, FL 34787 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $203 (2025)
    Community: Windtree Gardens
    Condo


    Estimated Monthly Payment: $1,413 (change assumption)
    Mortgage ($1,096) + Fees ($300) + Taxes in 2025 ($17)


    Taxes:$203

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6208 ARALIA IVY LN, WINTER GARDEN, FL 34787

    $400,0004 Days on yellowkey   MLS ID: O6427212

    For Sale O6427212 - 6208 ARALIA IVY LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2020
    Monthly Fee: $289
       Tax: $6,543 (2025)
    Community: Hamilton Gardens
    Townhouse


    Estimated Monthly Payment: $3,026 (change assumption)
    Mortgage ($2,192) + Fees ($289) + Taxes in 2025 ($545)


    Taxes:$6,543

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787

    $600,00025 Days on yellowkey   MLS ID: O6421867

    For Sale O6421867 - 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2021
    Monthly Fee: $225
       Tax: $7,057 (2025)
    Community: Encore/Ovation Ph 2
    Single Family


    Estimated Monthly Payment: $4,101 (change assumption)
    Mortgage ($3,288) + Fees ($225) + Taxes in 2025 ($588)


    Taxes:$7,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15415 SHONAN GOLD DR, WINTER GARDEN, FL 34787

    $549,99011 Days on yellowkey   MLS ID: O6424833

    For Sale O6424833 - 15415 SHONAN GOLD DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,414 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,857 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($701)


    Taxes:$8,414

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8060 BOWERY DR, WINTER GARDEN, FL 34787

    $640,00018 Days on yellowkey   MLS ID: O6421395

    REDUCED by $10,000 (1.5%) on 07/18/2026

    For Sale O6421395 - 8060 BOWERY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3013
       Built: 2017
    Monthly Fee: $190
       Tax: $7,459 (2026)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $4,318 (change assumption)
    Mortgage ($3,507) + Fees ($190) + Taxes in 2026 ($622)


    Taxes:$7,459

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 16596 POINT ROCK DR, WINTER GARDEN, FL 34787

    $539,90053 Days on yellowkey   MLS ID: O6412721

    REDUCED by $20,100 (3.6%) on 06/10/2026

    For Sale O6412721 - 16596 POINT ROCK DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2023
    Monthly Fee: $254
       Tax: $8,961 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,959 (change assumption)
    Mortgage ($2,958) + Fees ($254) + Taxes in 2025 ($747)


    Taxes:$8,961

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00096 Days on yellowkey   MLS ID: TB8500322

    REDUCED by $40,000 (7.4%) on 06/12/2026

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787

    $579,900103 Days on yellowkey   MLS ID: O6396640

    For Sale O6396640 - 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2626
       Built: 2013
    Monthly Fee: $128
       Tax: $6,746 (2025)
    Community: Johns Lake Pointe A & S
    Single Family


    Estimated Monthly Payment: $3,868 (change assumption)
    Mortgage ($3,177) + Fees ($128) + Taxes in 2025 ($562)


    Taxes:$6,746

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $575,000333 Days on yellowkey   MLS ID: O6337436

    REDUCED by $15,000 (2.5%) on 06/20/2026

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,148 (change assumption)
    Mortgage ($3,151) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 706 STRIHAL LOOP, WINTER GARDEN, FL 34787

    $599,00010 Days on yellowkey   MLS ID: O6426152

    For Sale O6426152 - 706 STRIHAL LOOP, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2001
    Monthly Fee: $96
       Tax: $8,436 (2025)
    Community: Johns Landing Ph 01 44/47
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,081 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2025 ($703)


    Taxes:$8,436

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787

    $1,099,0005 Days on yellowkey   MLS ID: S5154193

    INCREASED by $1,097,901 (99900.0%) on 07/23/2026

    For Sale S5154193 - 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2700
       Built: 2020   Tax: $12,866 (2026)
    Community: Downtown Winter Garden
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,094 (change assumption)
    Mortgage ($6,022) + Taxes in 2026 ($1,072)


    Taxes:$12,866

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 7720 SUMMERLAKE POINTE BLVD, WINTER GARDEN, FL 34787

    $800,000102 Days on yellowkey   MLS ID: O6399030

    4 Days Off yellowkey (back on 7/26/2026)

    For Sale O6399030 - 7720 SUMMERLAKE POINTE BLVD, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3893
       Built: 2013
    Monthly Fee: $252
       Tax: $7,628 (2025)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,271 (change assumption)
    Mortgage ($4,383) + Fees ($252) + Taxes in 2025 ($636)


    Taxes:$7,628

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17167 WRITING ALY, WINTER GARDEN, FL 34787

    $535,00076 Days on yellowkey   MLS ID: O6406920

    For Sale O6406920 - 17167 WRITING ALY, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 2020
    Monthly Fee: $110
       Tax: $7,916 (2025)
    Community: Storey Grove Ph 1B
    Single Family


    Estimated Monthly Payment: $3,701 (change assumption)
    Mortgage ($2,931) + Fees ($110) + Taxes in 2025 ($660)


    Taxes:$7,916

    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.