14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL $ 895,000
14411 HAMPSHIRE BAY CIRCLE
$ 895,000
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14411 HAMPSHIRE BAY CIRCLE

Winter Garden, FL, 34787
$ 895,000
Bedrooms4 Baths3.2 Sq 4,010

Monthly Estimate*

$ 5,511

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Single Family Home for sale in Winter Garden, FL

for $895,000 with 4 bedrooms and 3 full baths, 2 half baths. This 4,010 square foot home was built in 2005 on a lot size of 0.3.

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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Single Family Active

Price

$ 895,000

Bedrooms

4

Full Bath

3

Half Bath

2

Property Type

Single Family

Taxes

$ 11,923

Style

Single Family Residence

Lot Size

0.3

Year Built

2005

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6413972

Features
General
Sewer Public Sewer
Heating Central Electric Heat Pump
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Sewer Connected Street Lights Underground Utilities Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Built-In Oven Cooktop Dishwasher Disposal Electric Water Heater Microwave Range Hood Refrigerator
Zoning R-1
HOA Fee 546.25
Garage Spaces 3
Association Fee Includes Private Road Recreational Facilities
Patio/Porch Features Covered Patio Rear Porch Screened
Pool Features Gunite In Ground Salt Water Screen Enclosure Tile
Security Features Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 2005
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Dock Water Access Association Recreation - Owned Deed Restrictions Irrigation-Reclaimed Water Park Playground Sidewalks
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Gated Park Playground
Attached Garage true
Subdivision Name BAY ISLE 48 17
Facing Direction North
Garage Y/N true
Total Rooms 15
Full Baths 3
Status Active
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.
High School West Orange High
City WINTER GARDEN
Body of Water BLACK LAKE
Association Name Bay Isle at Black Lake Homeowners Assn: c/o HMI
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 13000
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features In Ground
Elementary School SunRidge Elementary
Land Lease Y/N false
Tax Annual Amount 11923.59
Middle/Junior High School SunRidge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6413972
Building Area Units Square Feet
Living Area Units Square Feet
Builder Name Toll Orlando LP
Standard Status Active
Occupancy Type Owner
Tax Lot 5
Legal Description BAY ISLE 48/16 LOT 5
Water Access Type Lake
Minimum Lease 1-2 Years
Water Access Y/N true
Monthly HOA Amount 182.08
Additional Rooms Breakfast Room Separate Den/Library/Office Family Room Formal Dining Room Separate Formal Living Room Separate Inside Utility Loft Media Room
Water View Y/N false
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities 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)
Flooring Carpet Laminate Tile
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds
Fireplace Y/N false
Half Baths 2
Laundry Features Inside Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities French Doors Irrigation System Outdoor Shower Sidewalk
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Driveway Electric Vehicle Charging Station(s) Garage Door Opener Garage Faces Side Split Garage
Lot Features City Lot Level Sidewalk
Water Source Public
Lot Size Area 13000
Foundation Details Slab
Spa true
Building Area Total 5049
Lot Dimensions 100 x 130
Lot Size Acres 0.3
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Paved Private Road
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Stockworth Realty Group

Broker

jbettosini@stockworth.com

Email

Affordability Calculator

$6,504
Per Month
85%
15%
0%
Monthly Principal & Interest
$5,511
Monthly Property Taxes
$994
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
6/6/2026$895,000 Listed Price

Map


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14411 HAMPSHIRE BAY CIRCLE, Winter Garden, FL, 34787 is a Single Family Home for sale at $895,000 with 4,010 sqft and a lot size of 0.3. 14411 HAMPSHIRE BAY CIRCLE has 4 bedrooms, 3.2 baths, and was built in 2005. The property's zip code is 34787 which is in Winter Garden, FL