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Property for sale at 14411 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL, 34787
Property for sale at 14411 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL, 34787
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14411 Hampshire Bay CircleWinter Garden, FL, 34787

4beds
5baths
4,010sqft
Single Family Residence
Built in 2005
$546 Quarterly HOA Fee
$870,000
For sale
$895,000−$25,000 (3%)
Price per sqft
$217
Days on market
124
Listed Jun 6, 2026
Last reduction
−$15,000
Aug 21, 2026
MLS #O6413972Updated Sep 26, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
14411 Hampshire Bay Circle
City
Winter Garden
State
FL
ZIP code
34787
Year built
2005
New construction
No
Faces
North
Rooms
15
Building stories
2
Living area
4,010 sqft
Total building area
5,049 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

Asking price reduced by $25,000 (2.8%) since first listed.

EventPrice
Price reducedMLS #O6413972$870,000Change: −2.8%−$25,000
Listed for saleMLS #O6413972$895,000
SoldMLS #O6042992$850,000
Listed for saleMLS #O6042992$869,000
History may be incomplete.
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Property for sale at 14411 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL, 34787
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