Property
ActiveResidential
1/60
$895,000

14411 HAMPSHIRE BAY CIRCLE

Winter Garden, FL 34787
4
Beds
5
Baths
4,010
SqFt
0.3
Acres
STELLAR
#O6413972
Updated: Jun 6, 2026, 10:38am

Property Description

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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Included Appliances
Built-In OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigerator

Property Details

Interior
Additional Rooms
Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityLoftMedia Room
Appliances
Built-In OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigerator
Bathrooms Total Decimal
4
Building Area Total
5049
Cooling
Central Air
Flooring
CarpetLaminateTile
Furnished
Unfurnished
Heating
CentralElectricHeat Pump
Interior Features
Ceiling Fan(s)Crown MoldingHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s)
Laundry Features
InsideLaundry Room
Living Area
4010
Rooms Total
15
Security Features
Smoke Detector(s)
Window Features
Blinds
Construction
Builder Name
Toll Orlando LP
Building Area Source
Public Records
Building Area Units
Square Feet
Construction Materials
BlockStucco
Direction Faces
North
Foundation Details
Slab
Levels
Two
Living Area Source
Public Records
Living Area Units
Square Feet
Roof
Shingle
Stories Total
2
Year Built
2005
Site & Exterior
Covered Spaces
3
Exterior Features
French DoorsIrrigation SystemOutdoor ShowerSidewalk
Flood Zone Code
X
Garage Spaces
3
I D X Participation
Yes
Lot Features
City LotLevelSidewalk
Lot Size Acres
0.3
Lot Size Area
13000
Lot Size Dimensions
100 x 130
Lot Size Square Feet
13000
Lot Size Units
Square Feet
Open Parking
Yes
Parking Features
DrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces SideSplit Garage
Patio And Porch Features
CoveredPatioRear PorchScreened
Pool Features
GuniteIn GroundSalt WaterScreen EnclosureTile
Public Survey Range
27
Public Survey Section
34
Road Frontage Type
Street PavedPrivate Road
Road Responsibility
Private Maintained Road
Road Surface Type
PavedAsphalt
Sewer
Public Sewer
Spa Features
In Ground
Total Acreage
1/4 to less than 1/2
Utilities
BB/HS Internet AvailableCable AvailableElectricity ConnectedSewer ConnectedStreet LightsUnderground UtilitiesWater Connected
Vegetation
Mature LandscapingTrees/Landscaped
Water Access
Yes
Water Body Name
BLACK LAKE
Water Extras
Yes
Water Source
Public
Zoning
R-1
Financials
Association Fee
546.25
Association Fee Frequency
Quarterly
Association Fee Includes
Private RoadRecreational Facilities
Calculated List Price By Calculated Sq Ft
223.19
Contract Status Change Date
2026-06-05
Current Price
895000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
1-2 Years
Monthly H O A Amount
182.08
Owner Name
WITHHELD
Ownership
Fee Simple
Parcel Number
342227016200050
Public Survey Township
22
Tax Annual Amount
11923.59
Tax Block
00
Tax Book Number
48/16
Tax Legal Description
BAY ISLE 48/16 LOT 5
Tax Lot
5
Tax Year
2025
Total Annual Fees
2185
Total Monthly Fees
182.08

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
No short term rentals allowed. Buyer to confirm any lease restrictions through HOA and City
Association Amenities
GatedParkPlayground
Association Email
Danyell Pino - danyell@hmimgmt.com
Association Fee Requirement
Required
Association Name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
Association Phone
407-392-1533
Community Features
DockWater AccessAssociation Recreation - OwnedDeed RestrictionsIrrigation-Reclaimed WaterParkPlaygroundSidewalks
Lease Restrictions
Yes
M L S Area Major
34787 - Winter Garden/Oakland
Pet Restrictions
Buyer to confirm any pet restrictions through HOA and City
Pets Allowed
Yes
Subdivision Name
BAY ISLE 48 17
Schools
Ratings
Elementary
SunRidge Elementary
Middle
SunRidge Middle
High
West Orange High
Listing provided courtesy of STELLAR via IDX. Updated: Jun 6, 2026, 10:38am.
Julie Bettosini, PA

Listing Agent

STOCKWORTH REALTY GROUP

Call Agent