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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Garden - 130 properties found

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  • 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $594,00085 Days on yellowkey   MLS ID: S5143009

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

    For Sale S5143009 - 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2695
       Built: 2016
    Monthly Fee: $241
       Tax: $8,470 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,202 (change assumption)
    Mortgage ($3,255) + Fees ($241) + Taxes in 2024 ($706)


    Taxes:$8,470

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 5211 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $819,000112 Days on yellowkey   MLS ID: O6373067

    For Sale O6373067 - 5211 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2023
    Monthly Fee: $165
       Tax: $9,990 (2024)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $5,485 (change assumption)
    Mortgage ($4,488) + Fees ($165) + Taxes in 2024 ($833)


    Taxes:$9,990

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $635,5006 Days on yellowkey   MLS ID: O6403063

    For Sale O6403063 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215
       Tax: $8,922 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $4,441 (change assumption)
    Mortgage ($3,482) + Fees ($215) + Taxes in 2025 ($744)


    Taxes:$8,922

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787

    $650,00011 Days on yellowkey   MLS ID: O6401040

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

    For Sale O6401040 - 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2018
    Monthly Fee: $64
       Tax: $5,661 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,097 (change assumption)
    Mortgage ($3,562) + Fees ($64) + Taxes in 2025 ($472)


    Taxes:$5,661

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 650 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,152,1904 Days on yellowkey   MLS ID: O6403543

    For Sale O6403543 - 650 MEDORA WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,551 (change assumption)
    Mortgage ($6,313) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 264 BLUE STONE CIR, WINTER GARDEN, FL 34787

    $725,0006 Days on yellowkey   MLS ID: O6402597

    For Sale O6402597 - 264 BLUE STONE CIR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2538
       Built: 1996
    Monthly Fee: $68
       Tax: $5,063 (2025)
    Community: Westfield Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,462 (change assumption)
    Mortgage ($3,973) + Fees ($68) + Taxes in 2025 ($422)


    Taxes:$5,063

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13259 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $778,53116 Days on yellowkey   MLS ID: G5111211

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale G5111211 - 13259 SERENE GLADE RD, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2689
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,426 (change assumption)
    Mortgage ($4,266) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 17416 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $784,49048 Days on yellowkey   MLS ID: G5109744

    0 Days Off yellowkey (back on 3/17/2026)

    For Sale G5109744 - 17416 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,448 (change assumption)
    Mortgage ($4,298) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787

    $685,000199 Days on yellowkey   MLS ID: O6353593

    1 Days Off yellowkey (back on 2/4/2026)

    SHORT SALE O6353593 - 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2021
    Monthly Fee: $80
       Tax: $513 (2024)
    Community: Hamilton Gardens Ph 2A & 2B
    Single Family


    Estimated Monthly Payment: $3,876 (change assumption)
    Mortgage ($3,753) + Fees ($80) + Taxes in 2024 ($43)


    Taxes:$513

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $748,000396 Days on yellowkey   MLS ID: O6280496

    For Sale O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,163 (change assumption)
    Mortgage ($4,099) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787

    $819,99035 Days on yellowkey   MLS ID: O6394850

    0 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $30,000 (3.5%) on 04/30/2026

    For Sale O6394850 - 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,589 (change assumption)
    Mortgage ($4,493) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 15508 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $695,0009 Days on yellowkey   MLS ID: O6402010

    0 Days Off yellowkey (back on 4/30/2026)

    For Sale O6402010 - 15508 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2763
       Built: 2001
    Monthly Fee: $243
       Tax: $6,075 (2025)
    Community: Stoneybrook West 44/134
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,557 (change assumption)
    Mortgage ($3,808) + Fees ($243) + Taxes in 2025 ($506)


    Taxes:$6,075

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787

    $875,00061 Days on yellowkey   MLS ID: O6387674

    REDUCED by $13,800 (1.6%) on 04/30/2026

    For Sale O6387674 - 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2937
       Built: 2020
    Monthly Fee: $165
       Tax: $7,225 (2025)
    Community: Sanctuary / Twin Waters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,561 (change assumption)
    Mortgage ($4,794) + Fees ($165) + Taxes in 2025 ($602)


    Taxes:$7,225

    Elementary School: None

    High School: West Orange High

    Tax Year: 2025

    Middle School: None


  • 204 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $693,27016 Days on yellowkey   MLS ID: O6400441

    INCREASED by $3,000 (0.4%) on 04/30/2026

    For Sale O6400441 - 204 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2686
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $4,069 (change assumption)
    Mortgage ($3,799) + 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


  • 3467 BUOY CIR, WINTER GARDEN, FL 34787

    $629,000120 Days on yellowkey   MLS ID: G5106141

    For Sale G5106141 - 3467 BUOY CIR, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2610
       Built: 2020
    Monthly Fee: $152
       Tax: $5,995 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,098 (change assumption)
    Mortgage ($3,446) + Fees ($152) + Taxes in 2025 ($500)


    Taxes:$5,995

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $869,9965 Days on yellowkey   MLS ID: O6403252

    For Sale O6403252 - 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,132 (change assumption)
    Mortgage ($4,767) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787

    $999,990266 Days on yellowkey   MLS ID: S5132434

    For Sale S5132434 - 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2921
       Built: 2018
    Monthly Fee: $250
       Tax: $6,381 (2024)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,261 (change assumption)
    Mortgage ($5,479) + Fees ($250) + Taxes in 2024 ($532)


    Taxes:$6,381

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14843 ELLINGSWORTH LN, WINTER GARDEN, FL 34787

    $799,90072 Days on yellowkey   MLS ID: O6384593

    3 Days Off yellowkey (back on 3/9/2026)

    For Sale O6384593 - 14843 ELLINGSWORTH LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2583
       Built: 2018
    Monthly Fee: $210
       Tax: $5,772 (2024)
    Community: Oxford Chase
    Single Family


    Estimated Monthly Payment: $5,074 (change assumption)
    Mortgage ($4,383) + Fees ($210) + Taxes in 2024 ($481)


    Taxes:$5,772

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $1,100,0008 Days on yellowkey   MLS ID: O6402434

    For Sale O6402434 - 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2758
       Built: 2020
    Monthly Fee: $250
       Tax: $7,946 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $6,939 (change assumption)
    Mortgage ($6,027) + Fees ($250) + Taxes in 2025 ($662)


    Taxes:$7,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14354 WABASSO LOOP, WINTER GARDEN, FL 34787

    $939,00038 Days on yellowkey   MLS ID: O6392378

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale O6392378 - 14354 WABASSO LOOP, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2881
       Built: 2022
    Monthly Fee: $200
       Tax: $11,249 (2025)
    Community: Tilden Place/Winter Garden
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,282 (change assumption)
    Mortgage ($5,145) + Fees ($200) + Taxes in 2025 ($937)


    Taxes:$11,249

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater 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.