$895,000
14411 Hampshire Bay Circle
Winter Garden, FL 34787
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
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
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
- Status: ActiveJun 6, 2026
- Listed$895,000Jun 5, 2026
- 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
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
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 16x11 |
| Office | First | 13x12 |
| Primary Bedroom | First | 17x16 |
| Dining Room | First | 12x12 |
| Kitchen | First | 19x14 |
| Dinette | First | 10x9 |
| Family Room | First | 18x16 |
| Bedroom 2 | Second | 13x13 |
| Bedroom 3 | Second | 14x12 |
| Bedroom 4 | Second | 13x13 |
| Loft | Second | 21x12 |
| Media Room | Second | 21x13 |
| Laundry | First | 8x7 |
| Balcony/Porch/Lanai | First | 13x10 |
| Balcony/Porch/Lanai | First | 19x18 |
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-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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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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA