14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 114411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 214411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 314411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 414411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 514411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 614411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 714411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 814411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 914411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1014411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1114411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1214411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1314411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1414411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1514411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1614411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1714411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1814411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 1914411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2014411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2114411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2214411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2314411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2414411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2514411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2614411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2714411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2814411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 2914411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3014411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3114411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3214411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3314411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3414411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3514411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3614411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3714411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3814411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 3914411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 4014411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 4114411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 4214411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 4314411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 4414411 HAMPSHIRE BAY CIRCLE WINTER GARDEN, FL - Image 45

$870,000

4 Beds 3 / 2 Full / Half Baths 4,010 SQFT 0.30 Acres
Type: Single Family

14411 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL 34787

MLS#: O6413972
Dawn Lund
Dawn Lund
The Real Estate Advantage
Agent
Phone: 612.483.4822
Office: 952.253.5600
Presented by: STOCKWORTH REALTY GROUP with 407-909-5900. - 407-909-5900

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.


 

Interior Features

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths2
Total Baths5

Other Interior Features

LivingAreaSource0 sqft
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringCarpet, Laminate, Tile
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCeiling Fan(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)
Laundry FeaturesInside, Laundry Room
Total Stories2
Window FeaturesBlinds

General

Additional Parcels Y/NNo
Additional RoomsBreakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Loft, Media Room
AppliancesBuilt-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Assoc Fee Paid PerQuarterly
Association AmenitiesGated, Park, Playground
Association Fee IncludesPrivate Road, Recreational Facilities
Association NameBay Isle at Black Lake Homeowners Assn: c/o HMI
Attached Garage Yes
Body of WaterBLACK LAKE
Builder NameToll Orlando LP
Building Area Units0 sqft
Carport Y/NNo
CityWINTER GARDEN
Community FeaturesDock, Water Access, Association Recreation - Owned, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountyOrange
Directions429 to exit for 535/Stoneybrook Parkway head north and first Left onto Winter Garden/Vineland Road, through roundabout to first left at Bay Isle. Through gate turn left and home around curve on left.
DockY/NNo
Elementary SchoolSunRidge Elementary
Facing DirectionNorth
Flood Zone CodeX
Flood Zone Code XY
Full Baths3
Garage Spaces3
Garage Y/NYes
HOA Fee$546.25
HeatingCentral, Electric, Heat Pump
High SchoolWest Orange High
In Law Suite YNNo
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionBAY ISLE 48/16 LOT 5
LevelsTwo
Listing TermsCash, Conventional, VA Loan
Living Area Units0 sqft
Lot Size Square Feet13000
Lot Size UnitsSquare Feet
MLS Area34787 - Winter Garden/Oakland
Middle/Junior High SchoolSunRidge Middle
Minimum Lease1-2 Years
Monthly HOA Amount$182
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesCovered, Patio, Rear Porch, Screened
Pets AllowedYes
Pool FeaturesGunite, In Ground, Salt Water, Screen Enclosure, Tile
PossessionClose Of Escrow
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
Security FeaturesSmoke Detector(s)
Senior Community Y/NNo
SewerPublic Sewer
Spa FeaturesIn Ground
Standard StatusActive
StatusActive
Subdivision NameBAY ISLE 48 17
Tax Annual Amount$11,924
Tax Lot5
Tax Year2025
Total Rooms15
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Street Lights, Underground Utilities, Water Connected
Virtual TourClick here
Water Access TypeLake
Water Access Y/NYes
Water View Y/NNo
Year Built2005
ZoningR-1

Exterior

Building Area Total5,049 sqft
Covered Spaces3
Exterior AmenitiesFrench Doors, Irrigation System, Outdoor Shower, Sidewalk
Foundation DetailsSlab
Lot Dimensions100 x 130
Lot FeaturesCity Lot, Level, Sidewalk
Lot Size Acres0.3
Lot Size Area13,000 sqft
Parking FeaturesDriveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Split Garage
Private PoolYes
Road Frontage TypeStreet Paved, Private Road
Road ResponsibilityPrivate Maintained Road
Road Surface TypePaved, Asphalt
SpaYes
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

  

Similar Properties

$870,000

4 Beds 3 / 2 Full / Half Baths 4,010 SQFT 0.30 Acres
Type: Single Family

14411 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL 34787

MLS#: O6413972
Dawn Lund
Dawn Lund
The Real Estate Advantage
Agent
Phone: 612.483.4822
Office: 952.253.5600