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Winter Garden Single Family Homes For Sale - 609 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 15480 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $749,90014 Days on yellowkey   MLS ID: O6399241

    For Sale O6399241 - 15480 SANDFIELD LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2574
       Built: 2013
    Monthly Fee: $114
       Tax: $7,534 (2025)
    Community: Reserve/Carriage Point Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,851 (change assumption)
    Mortgage ($4,109) + Fees ($114) + Taxes in 2025 ($628)


    Taxes:$7,534

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787

    $1,199,90069 Days on yellowkey   MLS ID: O6385964

    1 Days Off yellowkey (back on 5/9/2026)

    INCREASED by $80,900 (7.2%) on 04/02/2026

    For Sale O6385964 - 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4001
       Built: 2000
    Monthly Fee: $83
       Tax: $5,551 (2024)
    Community: Courtlea Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,120 (change assumption)
    Mortgage ($6,575) + Fees ($83) + Taxes in 2024 ($463)


    Taxes:$5,551

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787

    $689,0006 Days on yellowkey   MLS ID: O6404614

    REDUCED by $10,000 (1.4%) on 05/12/2026

    For Sale O6404614 - 5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2742
       Built: 2023
    Monthly Fee: $271
       Tax: $8,755 (2025)
    Community: Lakeside At Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,776 (change assumption)
    Mortgage ($3,775) + Fees ($271) + Taxes in 2025 ($730)


    Taxes:$8,755

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $548,0006 Days on yellowkey   MLS ID: O6404652

    REDUCED by $10,000 (1.8%) on 05/12/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 86 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: $3,991 (change assumption)
    Mortgage ($3,003) + 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


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $563,90055 Days on yellowkey   MLS ID: O6388784

    REDUCED by $11,100 (1.9%) on 05/12/2026

    For Sale O6388784 - 16736 OAKBORO ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $6,967 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,927 (change assumption)
    Mortgage ($3,090) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,150,00062 Days on yellowkey   MLS ID: O6389100

    REDUCED by $40,000 (3.4%) on 05/05/2026

    For Sale O6389100 - 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3624
       Built: 2019
    Monthly Fee: $255
       Tax: $16,181 (2025)
    Community: Canopy Oaks Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,905 (change assumption)
    Mortgage ($6,301) + Fees ($255) + Taxes in 2025 ($1,348)


    Taxes:$16,181

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 615 LAKE COVE POINTE CIR, WINTER GARDEN, FL 34787

    $849,95016 Days on yellowkey   MLS ID: O6402551

    For Sale O6402551 - 615 LAKE COVE POINTE CIR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2465
       Built: 2014
    Monthly Fee: $94
       Tax: $8,422 (2025)
    Community: Lake Cove Pointe Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,453 (change assumption)
    Mortgage ($4,657) + Fees ($94) + Taxes in 2025 ($702)


    Taxes:$8,422

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


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

    $1,155,00015 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


  • 17261 HEARTWOOD LOOP, WINTER GARDEN, FL 34787

    $1,999,000195 Days on yellowkey   MLS ID: O6354268

    15 Days Off yellowkey (back on 3/26/2026)

    For Sale O6354268 - 17261 HEARTWOOD LOOP, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 6.0   Gar: 5
    Liv Area Sq Ft: 6400
       Built: 2002   Tax: $17,256 (2024)
    Community: Avalon Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,391 (change assumption)
    Mortgage ($10,953) + Taxes in 2024 ($1,438)


    Taxes:$17,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12529 DALLINGTON TER, WINTER GARDEN, FL 34787

    $869,99023 Days on yellowkey   MLS ID: O6400678

    REDUCED by $15,000 (1.7%) on 05/12/2026

    For Sale O6400678 - 12529 DALLINGTON TER, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2006
    Monthly Fee: $130
       Tax: $6,735 (2025)
    Community: Foxcrest A-N & P
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,458 (change assumption)
    Mortgage ($4,767) + Fees ($130) + Taxes in 2025 ($561)


    Taxes:$6,735

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787

    $3,330,00014 Days on yellowkey   MLS ID: O6403188

    For Sale O6403188 - 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787 69 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


  • 838 BETHUNE AVE, WINTER GARDEN, FL 34787

    $275,00067 Days on yellowkey   MLS ID: O6388596

    2 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $2,000 (0.7%) on 04/02/2026

    For Sale O6388596 - 838 BETHUNE AVE, WINTER GARDEN, FL 34787 8 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 985
       Built: 1961   Tax: $1,340 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $1,618 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($112)


    Taxes:$1,340

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $664,90029 Days on yellowkey   MLS ID: O6399123

    REDUCED by $10,100 (1.5%) on 04/20/2026

    For Sale O6399123 - 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2018
    Monthly Fee: $142
       Tax: $6,366 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($3,643) + Fees ($142) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $599,9901 Day on yellowkey   MLS ID: O6404948

    For Sale O6404948 - 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2016
    Monthly Fee: $252
       Tax: $6,086 (2025)
    Community: Summerlake Pd Ph 2C
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,288) + Fees ($252) + Taxes in 2025 ($507)


    Taxes:$6,086

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $479,0001 Day on yellowkey   MLS ID: B4902258

    For Sale B4902258 - 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1858
       Built: 1990
    Monthly Fee: $25
       Tax: $2,403 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $2,850 (change assumption)
    Mortgage ($2,625) + Fees ($25) + Taxes in 2025 ($200)


    Taxes:$2,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5978 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $681,2402 Days on yellowkey   MLS ID: G5112233

    For Sale G5112233 - 5978 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 5 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2802
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,883 (change assumption)
    Mortgage ($3,733) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15136 TEA TREE DR, WINTER GARDEN, FL 34787

    $959,6472 Days on yellowkey   MLS ID: G5112230

    For Sale G5112230 - 15136 TEA TREE DR, WINTER GARDEN, FL 34787 4 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3543
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,433 (change assumption)
    Mortgage ($5,258) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $557,1232 Days on yellowkey   MLS ID: G5112227

    For Sale G5112227 - 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,203 (change assumption)
    Mortgage ($3,053) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15130 TEA TREE DR, WINTER GARDEN, FL 34787

    $926,5822 Days on yellowkey   MLS ID: G5112226

    For Sale G5112226 - 15130 TEA TREE DR, WINTER GARDEN, FL 34787 4 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150
       Tax: $18,489 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $6,768 (change assumption)
    Mortgage ($5,077) + Fees ($150) + Taxes in 2025 ($1,541)


    Taxes:$18,489

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787

    $460,0003 Days on yellowkey   MLS ID: O6406656

    For Sale O6406656 - 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2018
    Monthly Fee: $108
       Tax: $3,977 (2025)
    Community: Storey Grove Ph 1B-2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,960 (change assumption)
    Mortgage ($2,520) + Fees ($108) + Taxes in 2025 ($331)


    Taxes:$3,977

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.