14255 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL 34787 MLS #O6395612

14255 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL, 34787
$1,300,000
4 Beds
4.5 Baths
4,625 SqFt
6.44 Acres
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MLS #O6395612 image #0
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!

Property Details

Price:
$1,300,000
MLS #:
O6395612
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ISLE 48 17
Neighborhood:
34787wintergardenoakland
Listed Date:
Apr 3, 2026
Finished Sq Ft:
4,625
Total Sq Ft:
5,364
Lot Size:
280,513 sqft / 6.44 acres (approx)
Year Built:
2003
WaterfrontLakefrontPrimary Bedroom Main FloorCommunity Gated34787 – Winter Garden/oakland34787wintergardenoaklandBay Isle 48 17Sunridge ElementarySunridge MiddleWest Orange HighBlack LakeBuyer To Verify Leasing Restrictions With Hoa And/or City/county1-2 YearsPets Allowed

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Schools

Elementary School:
SunRidge Elementary
Middle School:
SunRidge Middle
High School:
West Orange High

Interior

Appliances
Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Porcelain Tile, Hardwood
Heating
Central, Electric, Propane
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
Laundry Features
Laundry Room
Levels
Two

Exterior

Attached Garage YN
1
Community Features
Lake, Water Access, Waterfront, Gated Community – No Guard, Park, Playground, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
East
Exterior Features
Balcony, Courtyard, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
Garage Spaces
3
Lot Features
Landscaped, Oversized Lot, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Faces Side, Split Garage
Patio And Porch Features
Covered, Enclosed, Front Porch, Patio, Rear Porch
Roof
Shingle
Security Features
Gated Community, Smoke Detector(s)
View
Trees/Woods, Water
Waterfront Features
Lake, Waterfront, Lake Front

Financial

HOA Fee
$141
HOA Fee Frequency
Monthly
HOA Includes
Private Road
HOA Name
HMI Management
HOA Phone
407-392-1533
Tax Year
2025
Taxes
$12,364

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 24, 2026
780
Single Family Listed
109
Avg DOM
282
Avg $ / SqFt
$749,764
Avg List Price

Property Summary

    Located in the BAY ISLE 48 17 subdivision, 14255 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,300,000 and features 4 beds, 5 baths, and has approximately 4,625 square feet of living space, and was originally constructed in 2003. The current price per square foot is $281. The average price per square foot for Single Family listings in WINTER GARDEN is $282. The average listing price for Single Family in WINTER GARDEN is $749,764. To schedule a showing of MLS#o6395612 at 14255 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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