14255 Hampshire Bay Circle, WINTER GARDEN, FL

$1,300,000

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4

Beds

5

Baths

4,625

Square feet

6.44

Acres

About 14255 Hampshire Bay Circle

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!

Features of 14255 Hampshire Bay Circle

MLS® # O6395612
Price $1,300,000
Bedrooms 4
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 4,625
Acres 6.44
Year Built 2003
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 14255 Hampshire Bay Circle
Area Winter Garden/Oakland
Subdivision BAY ISLE 48 17
City WINTER GARDEN
County Orange
State FL
Zip Code 34787-5900

Amenities

Parking Driveway, Garage Faces Side, Split Garage
# of Garages 3
View Trees/Woods, Water
Is Waterfront Yes
Waterfront Lake, Waterfront, Lake Front
Has Pool No

Interior

Interior Features Built-in Features, Ceiling Fan(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments
Appliances Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
Heating Central, Electric, Propane
Cooling Central Air
Fireplace Yes
Fireplaces Family Room, Gas
# of Stories 2

Exterior

Exterior Features Balcony, Courtyard, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
Lot Description Landscaped, Oversized Lot, Sidewalk
Roof Shingle
Foundation Block

School Information

Elementary SunRidge Elementary
Middle SunRidge Middle
High West Orange High

Additional Information

Date Listed April 3rd, 2026
Days on Market 11
Zoning R-1
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeWEMERT GROUP REALTY LLC

Listing Map

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