14411 Hampshire Bay Circle, FL
Stellar MLS

$895,000

14411 Hampshire Bay Circle

Winter Garden, FL 34787

Active
4
Beds
5
Baths
4,010
Sq Ft
0.3
Acres
2005
Built
Water accessPrivate pool3-car garage$223/sqft360° tour
Single Family Residence

Property type

2005

Year built

13,000 sqft

Lot size

$223

Price / sq ft

$182/mo

HOA dues

1

Day on market

3

Garage spaces

X

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$4,526
Property taxes$994
Home insurance (est.)$410
HOA dues$182

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history1 days on market

  1. Status: Active
    Jun 6, 2026
  2. Listed$895,000
    Jun 5, 2026
  3. Price increased$895,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
1
Subdivision
Bay Isle 48 17
County
Orange
Year built
2005
Living area
4,010 sq ft
Price/sq ft
$223
Building area
5,049 sq ft (Public Records)
Lot size
13,000 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X
Garage
3 spaces
Pool
Private pool
Annual taxes
$11,924 (2025)
Parcel #
34-22-27-0162-00-050
Zoning
R-1
MLS #
O6413972

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Interior Details

Bedrooms
4
Full bathrooms
3
Half bathrooms
2
Flooring
Carpet, Laminate, Tile
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Interior 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)
Laundry
Inside, Laundry Room
Stories / Levels
Two
Direction faces
North

Heating & Cooling

Heating
Central, Electric, Heat Pump
Cooling
Central Air

Parking

Garage spaces
3
Attached garage
Yes
Parking features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Garage

HOA & Financial

HOA fee
$546 / Quarterly
Monthly HOA
$182/mo
Total monthly fees
$182/mo
Total annual fees
$2,185
HOA name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Listing terms
Cash, Conventional, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
No short term rentals allowed. Buyer to confirm any lease restrictions through HOA and City

Exterior & Construction

Exterior features
French Doors, Outdoor Shower, Sidewalk
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Water access
Yes
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected

Community

Pets allowed
Yes

Schools

ElementaryBSunRidge ElementaryGreatSchools ↗
MiddleASunRidge MiddleGreatSchools ↗
High SchoolAWest Orange HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Living RoomFirst16x11
OfficeFirst13x12
Primary BedroomFirst17x16
Dining RoomFirst12x12
KitchenFirst19x14
DinetteFirst10x9
Family RoomFirst18x16
Bedroom 2Second13x13
Bedroom 3Second14x12
Bedroom 4Second13x13
LoftSecond21x12
Media RoomSecond21x13
LaundryFirst8x7
Balcony/Porch/LanaiFirst13x10
Balcony/Porch/LanaiFirst19x18

Listing Details

Listing date
2026-06-05
On market date
2026-06-05
Original list price
$895,000
Occupant type
Owner
MLS area
34787 - Winter Garden/Oakland
Listing AOR
Orlando Regional
Status changed
2026-06-06
Tax legal description
BAY ISLE 48/16 LOT 5

Flood risk

Minimal riskFEMA Zone X

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 6, 2026 at 8:04 AM ET. All data is obtained from various sources and may not have been verified by 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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