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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 3500+

Winter Garden - 166 properties found

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  • WINTER GARDEN, FL 34787

    $877,27514 Days on yellowkey   MLS ID: G5113601

    0 Days Off yellowkey (back on 6/10/2026)

    For Sale G5113601 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,932 (change assumption)
    Mortgage ($4,807) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,00016 Days on yellowkey   MLS ID: O6414639

    For Sale O6414639 - 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787 69 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4882
       Built: 2016
    Monthly Fee: $168
       Tax: $11,216 (2025)
    Community: Waterside/Johns Lake Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,294 (change assumption)
    Mortgage ($8,192) + Fees ($168) + Taxes in 2025 ($935)


    Taxes:$11,216

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787

    $679,000205 Days on yellowkey   MLS ID: S5139023

    1 Days Off yellowkey (back on 6/10/2026)

    INCREASED by $30,000 (4.6%) on 05/11/2026

    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: $4,632 (change assumption)
    Mortgage ($3,720) + Fees ($140) + Taxes in 2024 ($772)


    Taxes:$9,261

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787

    $1,790,00045 Days on yellowkey   MLS ID: O6406639

    REDUCED by $35,000 (1.9%) on 06/10/2026

    For Sale O6406639 - 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4977
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star/Ovation Ph 1B
    Single Family


    Estimated Monthly Payment: $9,894 (change assumption)
    Mortgage ($9,808) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16826 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,449,000112 Days on yellowkey   MLS ID: O6387379

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $50,000 (3.3%) on 05/29/2026

    For Sale O6387379 - 16826 BROADWATER AVE, WINTER GARDEN, FL 34787 58 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2019
    Monthly Fee: $218
       Tax: $9,892 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $8,982 (change assumption)
    Mortgage ($7,940) + Fees ($218) + Taxes in 2025 ($824)


    Taxes:$9,892

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 279 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $1,675,00041 Days on yellowkey   MLS ID: O6408014

    For Sale O6408014 - 279 ZACHARY WADE ST, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4473
       Built: 2003
    Monthly Fee: $67
       Tax: $8,609 (2025)
    Community: Lakeview Reserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,962 (change assumption)
    Mortgage ($9,178) + Fees ($67) + Taxes in 2025 ($717)


    Taxes:$8,609

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15058 SUNSTAR WAY, WINTER GARDEN, FL 34787

    $1,900,00026 Days on yellowkey   MLS ID: O6411520

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6411520 - 15058 SUNSTAR WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3607
       Built: 2021
    Monthly Fee: $110
       Tax: $645 (2025)
    Community: Highlands/Summerlake Grvs Ph 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,574 (change assumption)
    Mortgage ($10,411) + Fees ($110) + Taxes in 2025 ($54)


    Taxes:$645

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,499,00019 Days on yellowkey   MLS ID: O6413249

    For Sale O6413249 - 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2018
    Monthly Fee: $266
       Tax: $2,479 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $8,686 (change assumption)
    Mortgage ($8,213) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $1,190,00051 Days on yellowkey   MLS ID: O6403198

    For Sale O6403198 - 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 94 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3693
       Built: 2021
    Monthly Fee: $225
       Tax: $12,882 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $7,819 (change assumption)
    Mortgage ($6,520) + Fees ($225) + Taxes in 2025 ($1,074)


    Taxes:$12,882

    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


  • 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


  • 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


  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999247 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 52 photos

    Bed: 4   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


  • 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,199,99947 Days on yellowkey   MLS ID: O6404708

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

    REDUCED by $1 (0.0%) on 05/20/2026

    For Sale O6404708 - 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3513
       Built: 2019
    Monthly Fee: $240
       Tax: $13,161 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,912 (change assumption)
    Mortgage ($6,575) + Fees ($240) + Taxes in 2025 ($1,097)


    Taxes:$13,161

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $855,52020 Days on yellowkey   MLS ID: G5113317

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

    For Sale G5113317 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,688) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $909,99020 Days on yellowkey   MLS ID: G5113315

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

    For Sale G5113315 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,111 (change assumption)
    Mortgage ($4,986) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $1,032,000133 Days on yellowkey   MLS ID: O6381734

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

    INCREASED by $10,000 (1.0%) on 06/01/2026

    For Sale O6381734 - 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3894
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $5,925 (change assumption)
    Mortgage ($5,655) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.