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Land with Home for Sale in Winter Garden, Florida

14255 Hampshire Bay Cir, Winter Garden, FL 34787

$1,300,000
6.44 acres
Active sale
ago
Est $7,407/mo

One or more photo(s) has been virtually staged. NEW ROOF (2025) ~ TWO NEW A/C UNITS (2024) ~ and a NEW WATER HEATER (2024) headline this exceptional LAKEFRONT ESTATE on Black Lake, where recent RENOVATIONS and thoughtful design have transformed the home into a must see retreat designed to impress! Ideally situated behind the gates of Bay Isle in Winter Garden, this remarkable home is the cherry on top of 6.44 ACRES surrounded by lush mature trees and sweeping LAKE VIEWS, creating a peaceful personal oasis just minutes from everything. A paver driveway and COURTYARD ENTRANCE invite you into the residence, complemented by a split 3-car garage and beautiful architectural details that set the tone for what awaits inside. Spanning OVER 4,000 SQ FT of curated living space, the home blends timeless craftsmanship with a fresh, modern edge. Sleek PORCELAIN TILE and rich WOOD FLOORS flow throughout, while intricate DESIGN WORK and CUSTOM BUILT-INS add character and sophistication from floor to ceiling. Designed with both everyday living and entertaining in mind, the layout offers MULTIPLE LIVING AREAS & FLEX SPACES, and formal living and dining rooms, all positioned to maximize NATURAL LIGHT and capture the home’s breathtaking water views. Walls of windows pull the outdoors in, creating a light-filled atmosphere that highlights the beauty of the surrounding landscape! At the heart of the home, the GOURMET KITCHEN delivers everything a home chef could want and more. Outfitted with a gas range, gas oven, waterfall island, dual pantries for abundant storage, and a rare Doyon Etuve Proofer, the space is as functional as it is impressive, easily supporting everything from quiet dinners to large gatherings. Your MAIN FLOOR OWNER’S SUITE is a true retreat with tranquil views of Black Lake, a sitting area, a dedicated dressing space, and a beautifully designed modern en-suite bath that feels straight out of a home magazine. Throughout the rest of the home, additional bedrooms and flexible spaces offer endless possibilities for guests, offices, hobbies, or creative pursuits. Step outside and the lake lifestyle truly comes to life. MULTIPLE OUTDOOR LIVING SPACES invite you to relax, entertain, or simply take in the scenery, while the PRIVATE DOCK on Black Lake makes it easy to bring your boat and enjoy everything lakefront living has to offer. Despite the sense of seclusion, this home remains incredibly convenient to daily life. Shopping, dining, and major roadways including SR-429 are just minutes away, placing you close to Winter Garden’s vibrant charm, area attractions, and world-famous theme parks. Elegance personified, this extraordinary home delivers the privacy, style, and space you have been searching for. Bring your boat, embrace the lake life, and discover the lifestyle waiting for you in Bay Isle!

4,625
Sq feet
5
Beds
4
Full baths
1
1/2 bath
2003
Built

Location

Street address
14255 Hampshire Bay Cir
Community
Bay Isle 48 17
Elevation
98 feet
Coordinates
28.5269, -81.5994

Directions

From Winter Garden Vineland Rd, turn right onto Bristol Isle Ln, turn left onto Hampshire Bay Cir, turn right to stay on Hampshire Bay Cir. Home will be on the left.

Property details

Acreage
6.44 acres
Zoning
R-1
MLS #
MFRMLS O6395612
Posted

Property taxes

2025
$12,364

Expenses

Home Owner Assessments Fee
$141 monthly

Parcels

  • 34-22-27-0162-00-190

Legal description

Open houses

DateBeginsEndsAppt neededRemarks
Apr 11, 20261:00 PM3:00 PMNo

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

Waterfront
Lake Front, Waterfront
Features
Dock

Exterior

Parking
Attached Garage, Driveway, Garage
Fencing
Gate
Features
Balcony, Courtyard, Lighting, Outdoor Grill, Paved, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors

Structure

Heating
Central, Electric, Fireplace(s), Propane
Cooling
Central Air
Materials
Block, Stucco
Roof
Shingle

Interior

Room Count
14
Rooms
Bathroom x 5, Bedroom x 5, Bonus Room, Dining Room, Family Room, Kitchen, Laundry, Living Room, Loft
Flooring
Tile, Wood
Fireplaces
Yes
Appliances
Cooktop, Dishwasher, Dryer, Garbage Disposer, Range, Refrigerator, Washer
Security
Gated Community, Smoke Detector(s)
Features
Built-In Features, Ceiling Fans(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eat-In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments

Property utilities

CategoryTypeStatus
GasPropaneConnected

Nearby schools

NameType
SunRidge ElementaryElementary
SunRidge MiddleMiddle
West Orange HighHigh

Listing history

DateEventPriceChangeSource
Apr 4, 2026New listing$1,300,000MFRMLS
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This 6.44-acre property is located at 14255 Hampshire Bay Cir in Winter Garden, FL 34787. The property is available for sale for $1,300,000. It has a 4,625 sq ft 5 bedroom, 4 bath house built in 2003.

Checked 1 hour ago — Updated

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