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    Based on information submitted to the MLS GRID as of 2026-09-10 09:47:35 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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    Home / Winter Garden / 14411 HAMPSHIRE BAY CIRCLE
    14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL 34787 View All Photos

    $6,000

    | Active

    14411 HAMPSHIRE BAY CIRCLE

    Winter Garden, FL 34787

    5,049
    Square Feet
    4
    Beds
    4
    Baths
    0.30
    Acres
    37
    Days on Market
    MFRO6430003
    MLS#
    Rental
    Type
    House
    Structure
    Residential
    Zone
    Contact

    Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

    Property Details
    Interior
    Ceiling Fans(s), Crown Molding, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood
    Heating
    Central, Electric, Heat Pump
    Cooling Features
    Central Air
    Bedrooms
    4
    Bathrooms
    4.0
    Full Baths
    3
    Half Baths
    2
    Lot Features
    City Limits, Level, Sidewalk, Paved, Private
    Stories
    2
    Lot Description
    City Limits, Level, Sidewalk, Paved, Private
    Pool
    1
    Pool Description
    Gunite, In Ground, Salt Water, Screen Enclosure, Tile
    Pool Features
    Gunite, In Ground, Salt Water, Screen Enclosure, Tile
    Exterior Materials
    French Doors, Outdoor Shower, Sidewalk
    Acres
    0.3
    Square Feet
    5049.0
    Parking Features
    Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
    Parking
    1
    Parking Type
    Driveway
    Parking Garage Spaces
    3.0
    Property Type
    Rental
    Year Built
    2005
    Sewer Information
    Public Sewer
    Utility Source
    Public
    Utility Features
    BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
    Appliances
    Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
    Subdivision
    BAY ISLE 48 17
    Community Features
    Association Recreation - Owned, Irrigation-Reclaimed Water, Park, Playground, Sidewalks, Street Lights
    Elementary School
    SunRidge Elementary
    Middle School
    SunRidge Middle
    High School
    West Orange High
    County
    Orange
    Region
    WINTER GARDEN
    Date Available
    August 04, 2026
    Original List Price
    $6,000
    Days on Market (Cumulative)
    37
    HOA
    1
    Pets
    1
    Pets Allowed
    1
    MLS #
    O6430003
    Location
    Legal

    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: George Fleischmann | AveNew Realty

    Provided By
    Listed by Julie Bettosini, PA (#MFR261069744)
    Listing Office: STOCKWORTH REALTY GROUP (#MFR50198)

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