14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL 34787 MLS #O6413972

14411 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL, 34787
$895,000
4 Beds
4 Baths
4,010 SqFt
0.3 Acres
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MLS #O6413972 image #0
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.

Property Details

Price:
$895,000
MLS #:
O6413972
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ISLE 48 17
Neighborhood:
34787wintergardenoakland
Listed Date:
Jun 5, 2026
Finished Sq Ft:
4,010
Total Sq Ft:
5,049
Lot Size:
13,000 sqft / 0.30 acres (approx)
Year Built:
2005
PoolPrimary Bedroom Main FloorCommunity Gated34787 – Winter Garden/oakland34787wintergardenoaklandBay Isle 48 17Sunridge ElementarySunridge MiddleWest Orange HighBlack LakeNo Short Term Rentals Allowed. Buyer To Confirm Any Lease Restrictions Through Hoa And City1-2 YearsPets Allowed

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Schools

Elementary School:
SunRidge Elementary
Middle School:
SunRidge Middle
High School:
West Orange High

Interior

Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central, Electric, Heat Pump
Interior Features
Ceiling 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 Features
Inside, Laundry Room
Levels
Two

Exterior

Association Amenities
Gated, Park, Playground
Attached Garage YN
1
Community Features
Dock, Water Access, Association Recreation – Owned, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
North
Exterior Features
French Doors, Irrigation System, Outdoor Shower, Sidewalk
Garage Spaces
3
Lot Features
City Lot, Level, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Split Garage
Patio And Porch Features
Covered, Patio, Rear Porch, Screened
Roof
Shingle
Security Features
Smoke Detector(s)
Spa Features
In Ground
Window Features
Blinds

Financial

HOA Fee
$546
HOA Fee Frequency
Quarterly
HOA Includes
Private Road, Recreational Facilities
HOA Name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
HOA Phone
407-392-1533
Tax Year
2025
Taxes
$11,924

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Jun 08, 2026
831
Single Family Listed
104
Avg DOM
281
Avg $ / SqFt
$768,882
Avg List Price

Property Summary

    Located in the BAY ISLE 48 17 subdivision, 14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $895,000 and features 4 beds, 4 baths, and has approximately 4,010 square feet of living space, and was originally constructed in 2005. The current price per square foot is $223. The average price per square foot for Single Family listings in WINTER GARDEN is $281. The average listing price for Single Family in WINTER GARDEN is $768,882. To schedule a showing of MLS#o6413972 at 14411 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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14411 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL