14411 Hampshire Bay Circle
WINTER GARDEN, FL 34787
4
Bed
5
Bath
4,010Sqft
0.30Acre(Lot)
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 finishe
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total Bedroom: 4Bathroom Information
Total Baths: 5 Full Baths: 3 Half Baths: 2Interior 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) Roof: Shingle Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator Laundry Features: Inside, Laundry RoomRoofing Information
Shingle -
Flooring Information
Flooring: Carpet, Laminate, Tile Construction Materials: Block, Stucco -
Heating & Cooling
Heating: Central, Electric, Heat Pump Cooling: Central Air WaterSource: Public
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Building Information
Year Built: 2005 -
Exterior Features
French Doors, Outdoor Shower, Sidewalk Construction Materials: Block, Stucco Foundation Details: Slab Road Responsibility: Private Maintained Road -
Pool Features
Private Pool: 1 Gunite, In Ground, Salt Water, Screen Enclosure, Tile
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Lot Information
Lot Dimensions: 100x130 Lot Description: City Limits, Level, Sidewalk, Paved, Private Lot Square Feet: 13000 Lot Acres: 0.3 Lot Size (SqMt): 1208Property Information
Property Type: Residential Sub Type: Single Family Residence
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Listing Price Information
Original List Price:$895000
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Tax Information
Tax Block: 00 Tax Book Number: 48/16 Tax Lot: 5 Tax Legal Description: BAY ISLE 48/16 LOT 5 Annual Tax: $11923.59 Tax Year: 2025 Parcel Number: 34-22-27-0162-00-050
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Virtual Tour
Parking Information
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, GarageGarage Information
Has Garage: Yes Garage Space: 3Homeowners Association Information
Included Fees: Private Road, Recreational Facilities Included Amenities: Gated, Park, Playground HOA: $546.25 Quarterly
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School Information
Elementary School: SunRidge Elementary Junior High School: SunRidge Middle Senior High School: West Orange High -
Utility Information
BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected Sewer: Public Sewer Water Source: Public -
Location Information
Subdivision: BAY ISLE 48 17 City: WINTER GARDEN Direction: 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.
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 921 Westcliffe Drive, Winter Garden, FL, 34787 | $750,000 | 4 | 3 | 2,354 | 2,354 SqFt |
| Undisclosed Address, Winter Garden, FL, 34787 | $599,000 | 3 | 2 | 1,827 | 1,827 SqFt |
| Undisclosed Address, Winter Garden, FL, 34787 | $320,000 | 2 | 2 | 1,434 | 1,434 SqFt |
| 15806 Gem View St, Winter Garden, FL, 34787 | $495,000 | 2 | 2 | -- | |
| 15115 Pigeon Plum Lane, Winter Garden, FL, 34787 | $505,000 | 3 | 2 | 1,728 | 1,728 SqFt |
| 120 Blue Stone Circle, Winter Garden, FL, 34787 | $747,900 | 4 | 3 | 2,529 | 2,529 SqFt |
| 1701 E Bay Street, Winter Garden, FL, 34787 | $295,000 | 2 | 2 | 825 | 825 SqFt |
| 12513 Scarlett Sage Court, Winter Garden, FL, 34787 | $875,000 | 5 | 3 | 3,570 | 3,570 SqFt |
| 849 Shadowmoss Drive, Winter Garden, FL, 34787 | $710,000 | 5 | 3 | 2,620 | 2,620 SqFt |
| 680 Dunbar Avenue, Winter Garden, FL, 34787 | $465,000 | 4 | 2 | 1,713 | 1,713 SqFt |
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Based on information submitted to the MLS GRID as of 06/22/2026 @ 18:20. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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ByOwner last updated this listing 06/22/2026 @ 18:20
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