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Winter Garden Single Family Homes For Sale - 729 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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  • 14816 PORTER RD, WINTER GARDEN, FL 34787

    $545,00015 Days on yellowkey   MLS ID: O6423001

    REDUCED by $25,000 (4.4%) on 07/14/2026

    For Sale O6423001 - 14816 PORTER RD, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2790
       Built: 2014
    Monthly Fee: $188
       Tax: $8,946 (2025)
    Community: Summerlake
    Single Family


    Estimated Monthly Payment: $3,920 (change assumption)
    Mortgage ($2,986) + Fees ($188) + Taxes in 2025 ($746)


    Taxes:$8,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14549 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787

    $515,00012 Days on yellowkey   MLS ID: O6424107

    0 Days Off yellowkey (back on 7/14/2026)

    For Sale O6424107 - 14549 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2082
       Built: 2017
    Monthly Fee: $159
       Tax: $4,818 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,382 (change assumption)
    Mortgage ($2,822) + Fees ($159) + Taxes in 2025 ($402)


    Taxes:$4,818

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5963 GLORY BOWER DR, WINTER GARDEN, FL 34787

    $522,500398 Days on yellowkey   MLS ID: O6318887

    REDUCED by $500 (0.1%) on 07/14/2026

    For Sale O6318887 - 5963 GLORY BOWER DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2020
    Monthly Fee: $91
       Tax: $5,092 (2024)
    Community: Hamilton Gardens Ph 2A & 2B
    Single Family


    Estimated Monthly Payment: $3,378 (change assumption)
    Mortgage ($2,863) + Fees ($91) + Taxes in 2024 ($424)


    Taxes:$5,092

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 4958 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $540,00039 Days on yellowkey   MLS ID: S5151791

    For Sale S5151791 - 4958 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $166
       Tax: $7,028 (2025)
    Community: Silverleaf Reserve
    Single Family


    Estimated Monthly Payment: $3,710 (change assumption)
    Mortgage ($2,959) + Fees ($166) + Taxes in 2025 ($586)


    Taxes:$7,028

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 921 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $544,90075 Days on yellowkey   MLS ID: O6405328

    REDUCED by $5,000 (0.9%) on 07/14/2026

    For Sale O6405328 - 921 BENDING OAK TRL, WINTER GARDEN, FL 34787 66 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2517
       Built: 2012
    Monthly Fee: $125
       Tax: $3,791 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($2,986) + Fees ($125) + Taxes in 2025 ($316)


    Taxes:$3,791

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9942 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787

    $879,00083 Days on yellowkey   MLS ID: O6402319

    REDUCED by $20,000 (2.2%) on 07/14/2026

    For Sale O6402319 - 9942 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787 94 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2935
       Built: 2019
    Monthly Fee: $164
       Tax: $11,696 (2025)
    Community: Watermark
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,955 (change assumption)
    Mortgage ($4,816) + Fees ($164) + Taxes in 2025 ($975)


    Taxes:$11,696

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1645 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $439,00038 Days on yellowkey   MLS ID: O6416732

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $11,000 (2.4%) on 07/03/2026

    For Sale O6416732 - 1645 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1219
       Built: 1997
    Monthly Fee: $25
       Tax: $3,719 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,405) + Fees ($25) + Taxes in 2025 ($310)


    Taxes:$3,719

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8180 SAYINGS DR, WINTER GARDEN, FL 34787

    $599,99013 Days on yellowkey   MLS ID: O6423210

    2 Days Off yellowkey (back on 7/14/2026)

    For Sale O6423210 - 8180 SAYINGS DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2718
       Built: 2023
    Monthly Fee: $221
       Tax: $9,031 (2025)
    Community: Storey Grove Ph 4
    Single Family


    Estimated Monthly Payment: $4,261 (change assumption)
    Mortgage ($3,288) + Fees ($221) + Taxes in 2025 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,00044 Days on yellowkey   MLS ID: O6414639

    0 Days Off yellowkey (back on 6/29/2026)

    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


  • 6460 MAKRUT LIME DR, WINTER GARDEN, FL 34787

    $850,00044 Days on yellowkey   MLS ID: O6414802

    REDUCED by $19,000 (2.2%) on 07/14/2026

    For Sale O6414802 - 6460 MAKRUT LIME DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3103
       Built: 2018
    Monthly Fee: $142
       Tax: $10,250 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $5,654 (change assumption)
    Mortgage ($4,657) + Fees ($142) + Taxes in 2025 ($854)


    Taxes:$10,250

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787

    $1,740,00073 Days on yellowkey   MLS ID: O6406639

    REDUCED by $5,900 (0.3%) on 07/14/2026

    For Sale O6406639 - 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787 81 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: $9,620 (change assumption)
    Mortgage ($9,534) + 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


  • 7007 OLD GREENFIELD LN, WINTER GARDEN, FL 34787

    $440,00012 Days on yellowkey   MLS ID: O6422713

    0 Days Off yellowkey (back on 7/14/2026)

    For Sale O6422713 - 7007 OLD GREENFIELD LN, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1605
       Built: 2010
    Monthly Fee: $197
       Tax: $3,764 (2025)
    Community: Signature Lakes Prcl 01C
    Single Family


    Estimated Monthly Payment: $2,922 (change assumption)
    Mortgage ($2,411) + Fees ($197) + Taxes in 2025 ($314)


    Taxes:$3,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14321 WABASSO LOOP, WINTER GARDEN, FL 34787

    $799,000133 Days on yellowkey   MLS ID: S5145413

    For Sale S5145413 - 14321 WABASSO LOOP, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3074
       Built: 2022
    Monthly Fee: $192
       Tax: $11,501 (2025)
    Community: Tilden Place
    Single Family


    Estimated Monthly Payment: $5,528 (change assumption)
    Mortgage ($4,378) + Fees ($192) + Taxes in 2025 ($958)


    Taxes:$11,501

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17134 LAKE INGRAM RD, WINTER GARDEN, FL 34787

    $725,000167 Days on yellowkey   MLS ID: G5107793

    REDUCED by $50,000 (6.5%) on 07/14/2026

    For Sale G5107793 - 17134 LAKE INGRAM RD, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1924
       Built: 1959   Tax: $400 (2025)
    Community: Mt Park Orange Grove
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($33)


    Taxes:$400

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 243 FLORIDA AVE, WINTER GARDEN, FL 34787

    $335,00068 Days on yellowkey   MLS ID: S5149991

    2 Days Off yellowkey (back on 5/28/2026)

    For Sale S5149991 - 243 FLORIDA AVE, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1100
       Built: 1939   Tax: $2,090 (2025)
    Community: Shadow Lawn L/125 Lot 9 Blk F
    Single Family


    Estimated Monthly Payment: $2,010 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($174)


    Taxes:$2,090

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 440 TIERRA VERDE LN, WINTER GARDEN, FL 34787

    $980,00051 Days on yellowkey   MLS ID: O6412260

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $220,000 (18.3%) on 06/26/2026

    For Sale O6412260 - 440 TIERRA VERDE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 3512
       Built: 2004
    Monthly Fee: $94
       Tax: $5,135 (2025)
    Community: Lake Cove Pointe
    Single Family


    Estimated Monthly Payment: $5,892 (change assumption)
    Mortgage ($5,370) + Fees ($94) + Taxes in 2025 ($428)


    Taxes:$5,135

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16736 GULLFLOSS TER, WINTER GARDEN, FL 34787

    $799,00012 Days on yellowkey   MLS ID: O6423968

    For Sale O6423968 - 16736 GULLFLOSS TER, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2806
       Built: 2018
    Monthly Fee: $184
       Tax: $5,991 (2025)
    Community: Twinwaters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,061 (change assumption)
    Mortgage ($4,378) + Fees ($184) + Taxes in 2025 ($499)


    Taxes:$5,991

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $575,00057 Days on yellowkey   MLS ID: O6410574

    REDUCED by $14,900 (2.5%) on 07/14/2026

    For Sale O6410574 - 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 2008
    Monthly Fee: $184
       Tax: $5,498 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,151) + Fees ($184) + Taxes in 2025 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $849,00077 Days on yellowkey   MLS ID: O6403387

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $16,000 (1.8%) on 07/08/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $5,509 (change assumption)
    Mortgage ($4,652) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $669,50048 Days on yellowkey   MLS ID: O6413773

    For Sale O6413773 - 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2018
    Monthly Fee: $250
       Tax: $614 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,970 (change assumption)
    Mortgage ($3,668) + Fees ($250) + Taxes in 2025 ($51)


    Taxes:$614

    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 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.