To schedule a showing of 14411 Hampshire Bay Circle, Winter Garden, Florida, Call David Shippey at 863-521-4517 TODAY!
$895,000 | 4 beds | 3 full baths | 2 half baths | 4,010 sqft
Winter Garden, FL 34787
- 4Beds
- 5.00Total Baths
- 3 Full, 2 HalfBaths
- 4,010SqFt
- 2005Year Built
- 0.30Acres
- MLS# O6413972
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market11 days
- Area34787 - Winter Garden/oakland
- CountyOrange
- Subdivision Bay Isle 48 17
Overview
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.
Agriculture / Farm
Association Fees / Info
Community Features: Dock, Playground, Park, RecreationArea, WaterAccess, StreetLights, Sidewalks
Pets Allowed: Yes
Hoa Frequency Rate: 546.25
Association: Yes
Association Amenities: Gated, Playground, Park
Hoa Fees Frequency: Quarterly
Association Fee Includes: RecreationFacilities, RoadMaintenance
Bathroom Info
Total Baths: 5.00
Fullbaths: 3
Building Info
Window Features: Blinds
Roof: Shingle
Builder: Toll Orlando LP
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Pool Features: Gunite, InGround, ScreenEnclosure, SaltWater, Tile
Patio: RearPorch, Covered, Patio, Screened
Pool Private: Yes
Exterior Features: FrenchPatioDoors, SprinklerIrrigation, OutdoorShower
Fees / Restrictions
Financial
Original Price: $895,000
Disclosures: CovenantsRestrictionsDisclosure
Garage / Parking
Parking Features: Driveway, ElectricVehicleChargingStations, Garage, GarageDoorOpener, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Green Water Conservation: WaterRecycling
Interior Features
Floors: Carpet, Laminate, Tile
Levels: Two
Spa: Yes
Laundry Features: Inside, LaundryRoom
Interior Features: BuiltInFeatures, CeilingFans, CrownMolding, HighCeilings, KitchenFamilyRoomCombo, MainLevelPrimary, OpenFloorplan, StoneCounters, SplitBedrooms, WalkInClosets, WoodCabinets, SeparateFormalDiningRoom, SeparateFormalLivingRoom, Loft
Appliances: BuiltInOven, Cooktop, Dishwasher, ElectricWaterHeater, Disposal, Microwave, Refrigerator, RangeHood
Spa Features: InGround
Lot Info
Direction Remarks: 429 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.
Lot Size Units: Acres
Lot Size Acres: 0.3
Lot Sqft: 13,000
Est Lotsize: 100x130
Vegetation: PartiallyWooded
Lot Desc: CityLot, Flat, Level, PrivateRoad, Landscaped
Misc
Other
Special Conditions: None
Security Features: SmokeDetectors
Other Rooms Info
Property Info
Section: 34
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 2
Total Stories: 2
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 15
Sqft Info
Sqft: 4,010
Bulding Area Sqft: 5,049
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 5
Tax Legal Description: BAY ISLE 48/16 LOT 5
Tax Block: 00
Tax Annual Amount: 11923.59
Tax Book Number: 48/16
Unit Info
Utilities / Hvac
Heating: Central, Electric, HeatPump
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityConnected, HighSpeedInternetAvailable, SewerConnected, UndergroundUtilities, WaterConnected
Waterfront / Water
Waterfront Features: LakePrivileges
Water Body Name: BLACK LAKE
Directions
429 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.This listing courtesy of Stockworth Realty Group
MLS# O6414519 
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MLS IDX data last updated on 06-17-2026 2:00 AM EST.
If you have any questions on 14411 Hampshire Bay Circle, Winter Garden, Florida, please call David Shippey at 863-521-4517.
MLS# O6413972 located at 14411 Hampshire Bay Circle, Winter Garden, Florida is brought to you by David Shippey REALTOR®
14411 Hampshire Bay Circle, Winter Garden, Florida has 4 Beds, 3 Full Bath, and 2 Half Bath.
The MLS Number for 14411 Hampshire Bay Circle, Winter Garden, Florida is O6413972.
The price for 14411 Hampshire Bay Circle, Winter Garden, Florida is $895,000.
The status of 14411 Hampshire Bay Circle, Winter Garden, Florida is Active.
The subdivision of 14411 Hampshire Bay Circle, Winter Garden, Florida is Bay Isle 48 17.
The home located at 14411 Hampshire Bay Circle, Winter Garden, Florida was built in 2026.