Home in 14411 Hampshire Bay Cir Winter Garden for sale with MLS# O6413972
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.
14411 Hampshire Bay Cir, Winter Garden, FL 34787
- Price:
- $885,000.00
- Previous Asking Price:
- $895,000.00
- Original List Price:
- $895,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $220.7
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6413972
- Bedrooms:
- 4
- Bathrooms Total:
- 5
- Full Bath:
- 3
- Half Bath:
- 2
- Additional Rooms:
- Den/library/office, Inside Utility, Loft, Media Room, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Breakfast Room Separate
- Living Area:
- 4,010 Sqft
- Built-Up Area:
- 5,049 Sqft
- Lot Area:
- 13,000 Sqft
- Lot Size Dimensions and Info:
- 100x130
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- Paved, Level, City Limits, Sidewalk, Private
- Lot Size Acres:
- 0.3
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Gunite, In Ground, Salt Water, Screen Enclosure, Tile
- Spa
- Spa Features:
- In Ground
- Security:
- Smoke Detector(s)
- Furnished:
- Unfurnished
- Appliances:
- Dishwasher, Disposal, Microwave, Refrigerator, Cooktop, Built-in Oven, Electric Water Heater, Range Hood
- Interior:
- High Ceilings, Walk-In Closet(s), Ceiling Fans(s), Kitchen/family Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Solid Wood Cabinets, Crown Molding, Primary Bedroom Main Floor
- Exterior:
- Outdoor Shower, Sidewalk, French Doors
- Patio and Porch:
- Patio, Screened, Covered, Rear Porch
- Windows:
- Blinds
- Laundry:
- Inside, Laundry Room
- Air Conditioning System:
- Central Air
- Heating System:
- Central, Electric, Heat Pump
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping
- Property Entrance Faces:
- North
- Road Responsibility:
- Private Maintained Road
- Other Equipment:
- Irrigation Equipment
- Water Access
- Water Access Features:
- Lake
- Water Extras
- Water Extra Details:
- Fishing Pier
- Year Built:
- 2005
- Roof:
- Shingle
- Builder Name:
- Toll Orlando LP
- Levels:
- Two
- Construction Materials:
- Block, Stucco
- Flooring:
- Carpet, Tile, Laminate
- Number of stories:
- 2
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $11,923.59
- Tax Year:
- 2025
- Association Fee:
- $546.25
- Association Fee Frequency:
- Quarterly
- Total Annual Fees:
- $2,185.00
- Total Monthly Fees:
- $182.08
- Garage
- Garage Spaces:
- 3
- Attached Garage
- Parking Features:
- Driveway, Garage, Garage Door Opener, Electric Vehicle Charging Station(s), Garage Faces Side
- Sewer:
- Public Sewer
- Utilities Available:
- Cable Available, Underground Utilities, Electricity Connected, Sewer Connected, Water Connected, Broadband/High Speed Internet Available
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 1-2 Years
- Pets Allowed?
- Amenities Provided by the Homeowner's Association (HOA):
- Playground, Gated, Park
- Subdivision Name:
- BAY ISLE 48 17
- Community Features:
- Sidewalks, Street Lights, Park, Playground, Association Recreation - Owned, Irrigation-reclaimed Water, Deed Restrictions
- Association Fee Includes:
- Recreational Facilities, Private Road
- Senior Community:
- No
- Association Fee Required:
- Required
- Planned Unit Development
- Association Management:
- Bay Isle at Black Lake Homeowners Assn: c/o HMI
- Association Phone:
- 407-392-1533
- Listing Terms Considered by Seller:
- Cash, Conventional, VA Loan
- Occupant Type:
- Owner
- Buyer Possession:
- Close Of Escrow
- Lease Considered:
- Yes
- Tax Legal Description:
- BAY ISLE 48/16 LOT 5
- Real Estate Folio Number (Parcel Number):
- 34-22-27-0162-00-050
- Zoning:
- R-1
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Sunset
- High School:
- West Orange High
- Middle Or Junior School:
- Sunridge Middle
- Originally published on:
- June 6, 2026 2:41 am
- Active on the market since:
- June 5, 2026
- Listing Agreement executed on:
- June 5, 2026
- Price change occurred on:
- July 24, 2026 11:53 pm
- Listing Status Last Changed On:
- June 6, 2026 2:41 am
- Photos updated on:
- June 6, 2026 2:43 am
- Last Modified:
- July 24, 2026 11:54 pm
- Courtesy of:
- STOCKWORTH REALTY GROUP
- Attribution:
- 407-909-5900
- Road Surface Type:
- Asphalt
- Street Name:
- HAMPSHIRE BAY
- Street Number:
- 14411
- City:
- WINTER GARDEN
- State:
- Florida
- Zip Code:
- 34787
- County:
- Orange
- Latitude:
- N28° 31' 32.8''
- Longitude:
- W82° 24' 27.2''

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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates