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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Beds: 4 to 4

Winter Garden - 314 properties found

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  • 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


  • 15326 JOHNS LAKE POINTE BLVD, WINTER GARDEN, FL 34787

    $1,385,00026 Days on yellowkey   MLS ID: S5150851

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

    For Sale S5150851 - 15326 JOHNS LAKE POINTE BLVD, WINTER GARDEN, FL 34787 99 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3495
       Built: 2014
    Monthly Fee: $128
       Tax: $7,670 (2025)
    Community: Johns Lake Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,356 (change assumption)
    Mortgage ($7,589) + Fees ($128) + Taxes in 2025 ($639)


    Taxes:$7,670

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787

    $815,00061 Days on yellowkey   MLS ID: O6402075

    For Sale O6402075 - 925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3580
       Built: 2008
    Monthly Fee: $72
       Tax: $4,880 (2025)
    Community: Covington Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,944 (change assumption)
    Mortgage ($4,466) + Fees ($72) + Taxes in 2025 ($407)


    Taxes:$4,880

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $599,990218 Days on yellowkey   MLS ID: O6361583

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99063 Days on yellowkey   MLS ID: O6401373

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $774,54921 Days on yellowkey   MLS ID: G5113307

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113307 - 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,419 (change assumption)
    Mortgage ($4,244) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787

    $552,27521 Days on yellowkey   MLS ID: G5113297

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113297 - 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,176 (change assumption)
    Mortgage ($3,026) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787

    $844,99090 Days on yellowkey   MLS ID: O6393961

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $25,000 (2.9%) on 06/01/2026

    For Sale O6393961 - 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3338
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,726 (change assumption)
    Mortgage ($4,630) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 13023 INKWELL ALY, WINTER GARDEN, FL 34787

    $515,00035 Days on yellowkey   MLS ID: O6409443

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale O6409443 - 13023 INKWELL ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $268
       Tax: $5,162 (2025)
    Community: Storey Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,822) + Fees ($268) + Taxes in 2025 ($430)


    Taxes:$5,162

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,149,950111 Days on yellowkey   MLS ID: O6384801

    REDUCED by $50,050 (4.2%) on 06/03/2026

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3170
       Built: 2018
    Monthly Fee: $188
       Tax: $7,979 (2024)
    Community: Stanton Estates
    Single Family


    Estimated Monthly Payment: $7,154 (change assumption)
    Mortgage ($6,301) + Fees ($188) + Taxes in 2024 ($665)


    Taxes:$7,979

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview 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.