14255 HAMPSHIRE BAY CIRCLE Winter Garden, FL $ 1,300,000
14255 HAMPSHIRE BAY CIRCLE
$ 1,300,000
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14255 HAMPSHIRE BAY CIRCLE

Winter Garden, FL, 34787
$ 1,300,000
Bedrooms4 Baths4.1 Sq 4,625

Monthly Estimate*

$ 8,004

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Single Family Home for sale in Winter Garden, FL

for $1,300,000 with 4 bedrooms and 4 full baths, 1 half bath. This 4,625 square foot home was built in 2003 on a lot size of 6.44.

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!

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Single Family Active

Price

$ 1,300,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 12,363

Style

Single Family Residence

Lot Size

6.44

Year Built

2003

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6395612

Features
General
Sewer Public Sewer
Heating Central Electric Propane
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Propane Public Sewer Connected Water Connected
Roof Shingle
Appliances Cooktop Dishwasher Disposal Dryer Range Range Hood Refrigerator Washer
Zoning R-1
HOA Fee 141
Garage Spaces 3
Association Fee Includes Private Road
Patio/Porch Features Covered Enclosed Front Porch Patio Rear Porch
Security Features Gated Community Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 2003
View Trees/Woods Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Waterfront Features Lake Waterfront Lake Front
Community Features Lake Water Access Waterfront Gated Community - No Guard Park Playground Sidewalks
Assoc Fee Paid Per Monthly
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name BAY ISLE 48 17
Facing Direction East
Garage Y/N true
Total Rooms 14
Full Baths 4
Status Active
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.
High School West Orange High
City WINTER GARDEN
Body of Water BLACK LAKE
Association Name HMI Management
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Acres
Lot Size Square Feet 280513
Carport Y/N false
Listing Terms Cash Conventional Other VA Loan
Elementary School SunRidge Elementary
Land Lease Y/N false
Tax Annual Amount 12363.83
Middle/Junior High School SunRidge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/f8cf90f3-a31c-4c9b-83fd-b69fd4069849/?utm_source=captureapp www.wemertgrouprealty.com
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 19
Legal Description BAY ISLE 48/16 LOT 19
Water View Lake
Water Access Type Lake
Minimum Lease 1-2 Years
Water Access Y/N true
Monthly HOA Amount 141
Additional Rooms Attic Bonus Room Den/Library/Office Family Room Florida Room Formal Dining Room Separate Formal Living Room Separate Interior In-Law Suite w/Private Entry Loft
ILS Total SQFT 75.8
ILS Under Air SQFT 75.8
Water View Y/N true
Flood Zone Code X & AE
DockY/N true
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Interior
Interior Amenities 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
Flooring Porcelain Tile Hardwood
Furnished Y/N Partially
Fireplace Features Family Room Gas
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities Balcony Courtyard Irrigation System Lighting Outdoor Grill Private Mailbox Rain Gutters Sidewalk Sliding Doors
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Driveway Garage Faces Side Split Garage
Lot Features Landscaped Oversized Lot Sidewalk
Water Source Public
Lot Size Area 6.4397
Foundation Details Block
Building Area Total 5364
Lot Size Acres 6.44
Road Surface Type Paved
Private Pool false
Waterfront Y/N true
Covered Spaces 3
Road Frontage Type Street Paved
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* Excluded Features
List By
Wemert Group Realty Llc

Broker

listingteam@wemertgrouprealty.com

Email

Affordability Calculator

$9,035
Per Month
89%
11%
0%
Monthly Principal & Interest
$8,004
Monthly Property Taxes
$1,030
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
4/4/2026$1,300,000 Listed Price

Map


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14255 HAMPSHIRE BAY CIRCLE, Winter Garden, FL, 34787 is a Single Family Home for sale at $1,300,000 with 4,625 sqft and a lot size of 6.44. 14255 HAMPSHIRE BAY CIRCLE has 4 bedrooms, 4.1 baths, and was built in 2003. The property's zip code is 34787 which is in Winter Garden, FL