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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 3500+

Winter Garden - 114 properties found

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  • 16768 SANCTUARY DR, WINTER GARDEN, FL 34787

    $1,575,000105 Days on yellowkey   MLS ID: O6374904

    REDUCED by $15,000 (0.9%) on 04/14/2026

    For Sale O6374904 - 16768 SANCTUARY DR, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 4258
       Built: 2021
    Monthly Fee: $165
       Tax: $13,171 (2024)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,893 (change assumption)
    Mortgage ($8,630) + Fees ($165) + Taxes in 2024 ($1,098)


    Taxes:$13,171

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787

    $3,330,0005 Days on yellowkey   MLS ID: O6403188

    For Sale O6403188 - 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 6   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5290
       Built: 2001
    Monthly Fee: $300
       Tax: $32,571 (2025)
    Community: Isles Lake Hancock
    Single Family


    Estimated Monthly Payment: $21,260 (change assumption)
    Mortgage ($18,246) + Fees ($300) + Taxes in 2025 ($2,714)


    Taxes:$32,571

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,084,99938 Days on yellowkey   MLS ID: O6392997

    REDUCED by $1 (0.0%) on 05/01/2026

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3617
       Built: 2023
    Monthly Fee: $225
       Tax: $12,929 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $7,247 (change assumption)
    Mortgage ($5,945) + Fees ($225) + Taxes in 2025 ($1,077)


    Taxes:$12,929

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $1,175,0005 Days on yellowkey   MLS ID: O6403044

    For Sale O6403044 - 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 75 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3698
       Built: 1988
    Monthly Fee: $71
       Tax: $6,208 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $7,027 (change assumption)
    Mortgage ($6,438) + Fees ($71) + Taxes in 2025 ($517)


    Taxes:$6,208

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2015 SANDY GARDEN LN, WINTER GARDEN, FL 34787

    $765,000122 Days on yellowkey   MLS ID: O6370025

    For Sale O6370025 - 2015 SANDY GARDEN LN, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3871
       Built: 2015
    Monthly Fee: $113
       Tax: $10,989 (2025)
    Community: Reserve At Carriage Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,220 (change assumption)
    Mortgage ($4,192) + Fees ($113) + Taxes in 2025 ($916)


    Taxes:$10,989

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15196 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787

    $1,155,0006 Days on yellowkey   MLS ID: O6397637

    For Sale O6397637 - 15196 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3505
       Built: 2017
    Monthly Fee: $235
       Tax: $7,580 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,195 (change assumption)
    Mortgage ($6,329) + Fees ($235) + Taxes in 2025 ($632)


    Taxes:$7,580

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787

    $1,325,00012 Days on yellowkey   MLS ID: O6401205

    For Sale O6401205 - 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787 70 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3904
       Built: 2016
    Monthly Fee: $235
       Tax: $8,218 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,180 (change assumption)
    Mortgage ($7,260) + Fees ($235) + Taxes in 2025 ($685)


    Taxes:$8,218

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787

    $1,450,00017 Days on yellowkey   MLS ID: V4948569

    For Sale V4948569 - 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787 78 photos

    Bed: 7   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4700
       Built: 2019
    Monthly Fee: $97
       Tax: $9,199 (2025)
    Community: Mcallister Lndg
    Single Family


    Estimated Monthly Payment: $8,809 (change assumption)
    Mortgage ($7,945) + Fees ($97) + Taxes in 2025 ($767)


    Taxes:$9,199

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5340 BOWMAN DR, WINTER GARDEN, FL 34787

    $2,195,00020 Days on yellowkey   MLS ID: O6398618

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

    For Sale O6398618 - 5340 BOWMAN DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5749
       Built: 2017
    Monthly Fee: $230
       Tax: $16,854 (2026)
    Community: The Cove At Hamlin
    Single Family


    Estimated Monthly Payment: $13,662 (change assumption)
    Mortgage ($12,027) + Fees ($230) + Taxes in 2026 ($1,405)


    Taxes:$16,854

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $1,300,00031 Days on yellowkey   MLS ID: O6395612

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

    Bed: 4   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


  • 12934 CANOPY WOODS WAY WAY, WINTER GARDEN, FL 34787

    $1,350,00050 Days on yellowkey   MLS ID: O6390704

    REDUCED by $20,000 (1.5%) on 04/19/2026

    For Sale O6390704 - 12934 CANOPY WOODS WAY WAY, WINTER GARDEN, FL 34787 90 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3665
       Built: 2018
    Monthly Fee: $299
       Tax: $12,379 (2025)
    Community: Canopy Oaks Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,728 (change assumption)
    Mortgage ($7,397) + Fees ($299) + Taxes in 2025 ($1,032)


    Taxes:$12,379

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000529 Days on yellowkey   MLS ID: O6258009

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,00020 Days on yellowkey   MLS ID: O6398720

    For Sale O6398720 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8978 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $1,299,50039 Days on yellowkey   MLS ID: O6393744

    1 Days Off yellowkey (back on 5/2/2026)

    For Sale O6393744 - 8978 SONOMA COAST DR, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3911
       Built: 2022
    Monthly Fee: $277
       Tax: $13,033 (2025)
    Community: Waterleigh
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,483 (change assumption)
    Mortgage ($7,120) + Fees ($277) + Taxes in 2025 ($1,086)


    Taxes:$13,033

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9827 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,374,9003 Days on yellowkey   MLS ID: O6403588

    For Sale O6403588 - 9827 BEACH PORT DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2020
    Monthly Fee: $277
       Tax: $11,122 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,737 (change assumption)
    Mortgage ($7,534) + Fees ($277) + Taxes in 2025 ($927)


    Taxes:$11,122

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999196 Days on yellowkey   MLS ID: O6353975

    REDUCED by $100,001 (6.3%) on 04/13/2026

    For Sale O6353975 - 241 N DILLARD ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 3507
       Built: 1953   Tax: $2,959 (2024)
    Community: J L Dillard Sub 3
    Single Family


    Estimated Monthly Payment: $8,466 (change assumption)
    Mortgage ($8,219) + Taxes in 2024 ($247)


    Taxes:$2,959

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 7692 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787

    $875,00010 Days on yellowkey   MLS ID: O6401130

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

    For Sale O6401130 - 7692 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3855
       Built: 2016
    Monthly Fee: $252
       Tax: $7,767 (2025)
    Community: Summerlake Pd Ph 3A
    Single Family


    Estimated Monthly Payment: $5,694 (change assumption)
    Mortgage ($4,794) + Fees ($252) + Taxes in 2025 ($647)


    Taxes:$7,767

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7766 MINUTEMEN LOOP, WINTER GARDEN, FL 34787

    $1,745,000289 Days on yellowkey   MLS ID: O6328707

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

    REDUCED by $79,888 (4.4%) on 04/22/2026

    For Sale O6328707 - 7766 MINUTEMEN LOOP, WINTER GARDEN, FL 34787 39 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4716
       Built: 2014
    Monthly Fee: $201
       Tax: $14,959 (2024)
    Community: West Lake Hancock Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,009 (change assumption)
    Mortgage ($9,561) + Fees ($201) + Taxes in 2024 ($1,247)


    Taxes:$14,959

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787

    $649,000154 Days on yellowkey   MLS ID: S5139023

    4 Days Off yellowkey (back on 3/24/2026)

    For Sale S5139023 - 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3638
       Built: 2016
    Monthly Fee: $140
       Tax: $9,261 (2024)
    Community: Black Lake Preserve
    Single Family


    Estimated Monthly Payment: $4,468 (change assumption)
    Mortgage ($3,556) + Fees ($140) + Taxes in 2024 ($772)


    Taxes:$9,261

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787

    $1,800,0004 Days on yellowkey   MLS ID: O6402785

    For Sale O6402785 - 16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787 53 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5284
       Built: 2024
    Monthly Fee: $225
       Tax: $2,826 (2025)
    Community: Avalon Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,323 (change assumption)
    Mortgage ($9,863) + Fees ($225) + Taxes in 2025 ($236)


    Taxes:$2,826

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle






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.