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Winter Garden, FL · Single Family Residence

14411 Hampshire Bay Cir

$870,000
MLS MFRO6413972
4Bedrooms
5Bathrooms
4,010Square feet
0.3Acres

THE SETTING, AND THE DETAILS

A closer look.

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.

Private poolGarage

The details that help you decide.

Details supplied with the listing. Information that was not provided is marked below.

Home essentials
Price per square foot
$217
Full bathrooms
3
Half bathrooms
2
Heated living area
4010
Lot size (acres)
0.3
Lot size (sq ft)
13000
Year built
2005
Property type
Residential
Property style
Not provided
Interior & rooms
Interior features
Ceiling Fans(s), Crown Molding, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Flooring
Carpet, Laminate, Tile
Additional rooms
Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility,Loft,Media Room
Land, water & community
Waterfront
No
Waterfront type
Not provided
Water body / lake name
BLACK LAKE
Water view
Not provided
Dock
No
Dock features
Dock - Open
Other views
Not provided
Lot features
City Limits, Level, Sidewalk, Paved, Private
Exterior features
Outdoor Shower, Sidewalk
Community amenities
Association Recreation - Owned, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks, Street Lights
Zoning
R-1
Current use
Not provided
Horse amenities
Not provided
Fencing
Not provided
Other structures
Not provided
Pool, parking & systems
Private pool
Yes
Pool features
Gunite, In Ground, Salt Water, Screen Enclosure, Tile
Garage
Yes
Garage spaces
3
Carport
No
Carport spaces
Not provided
Parking features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Garage
Fireplace
No
Fireplace features
Not provided
Heating
Central, Electric, Heat Pump
Cooling
Central Air
Water supply
Public
Sewer
Public Sewer
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
Construction
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Stories
2
Levels
Two
Location & schools
City
WINTER GARDEN
Subdivision
BAY ISLE 48 17
County
Orange
ZIP code
34787
Elementary school
SunRidge Elementary
Middle school
SunRidge Middle
High school
West Orange High
Association, taxes & listing
HOA / association
Yes
Association fee
$546.25
Fee frequency
Quarterly
Included services
Private Road, Recreational Facilities
Association amenities
Gated, Park, Playground
Additional association fee
Not provided
Additional fee frequency
Not provided
Condo fee
Not provided
Condo fee frequency
Not provided
Annual property taxes
$11,923.59
Tax year
2025
Other annual assessments
Not provided
CDD
No
Listing status
Active
Days on market
113
Listing broker
STOCKWORTH REALTY GROUP
MLS number
MFRO6413972

Explore the area

Location supplied with the listing. Confirm boundaries and access for the property.

Listed by STOCKWORTH REALTY GROUP · MLS MFRO6413972
Source: mfrmls · Listing updated 2026-09-26 19:05:19 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.

Listing photograph

MLS MFRO6413972 · STOCKWORTH REALTY GROUP

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