WINTER GARDEN, FL 34787 14255 HAMPSHIRE BAY CIRCLE

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Presented By: WEMERT GROUP REALTY LLC with 407-743-8356. - 407-214-3967
  • MLS# O6395612
  • 03/28/2026
  • Request Tour
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Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 5
  • Full/Half Baths • 4 / 1
  • SQFT • 4,625
  • Garage • 3

Home Details

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!
Presented By: WEMERT GROUP REALTY LLC with 407-743-8356. - 407-214-3967

Interior Features for 14255 HAMPSHIRE BAY CIRCLE

Bedrooms

Total Bedrooms5

Bathrooms

Half Baths1
Total Baths5

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace FeaturesFamily Room, Gas
Fireplace Y/NYes
FlooringPorcelain Tile, Hardwood
Furnished Y/NPartially
Heating Y/NYes
Interior AmenitiesBuilt-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 FeaturesLaundry Room
Total Stories2

General for 14255 HAMPSHIRE BAY CIRCLE

Additional Parcels Y/NNo
Additional RoomsAttic, 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
AppliancesCooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
Assoc Fee Paid PerMonthly
Association Fee IncludesPrivate Road
Association NameHMI Management
Attached Garage Yes
Body of WaterBLACK LAKE
Building Area UnitsSquare Feet
Carport Y/NNo
CityWINTER GARDEN
Community FeaturesLake, Water Access, Waterfront, Gated Community - No Guard, Park, Playground, Sidewalks
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountyOrange
DirectionsFrom 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.
DockY/NYes
Elementary SchoolSunRidge Elementary
Facing DirectionEast
Flood Zone CodeX & AE
Flood Zone Code XY
Full Baths4
Garage Spaces3
Garage Y/NYes
HOA Fee$141
HeatingCentral, Electric, Propane
High SchoolWest Orange High
ILS Total SQFT75.8
ILS Under Air SQFT75.8
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionBAY ISLE 48/16 LOT 19
LevelsTwo
Listing TermsCash, Conventional, Other, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet280513
Lot Size UnitsAcres
MLS Area34787 - Winter Garden/Oakland
Middle/Junior High SchoolSunRidge Middle
Minimum Lease1-2 Years
Monthly HOA Amount141
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Patio/Porch FeaturesCovered, Enclosed, Front Porch, Patio, Rear Porch
Pets AllowedYes
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteDescrip1 Bathroom, Attached, Private Entrance, Studio
STELLAR_InLawSuiteYNYes
Security FeaturesGated Community, Smoke Detector(s)
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameBAY ISLE 48 17
Tax Annual Amount12363.83
Tax Lot19
Tax Year2025
Total Rooms14
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected
ViewTrees/Woods, Water
Virtual TourClick here
Virtual TourClick here
Water Access TypeLake
Water Access Y/NYes
Water ViewLake
Water View Y/NYes
Waterfront FeaturesLake, Waterfront, Lake Front
Year Built2003
ZoningR-1

Exterior for 14255 HAMPSHIRE BAY CIRCLE

Building Area Total5364
Covered Spaces3
Exterior AmenitiesBalcony, Courtyard, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
Foundation DetailsBlock
Lot FeaturesLandscaped, Oversized Lot, Sidewalk
Lot Size Acres6.44
Lot Size Area6.4397
Parking FeaturesDriveway, Garage Faces Side, Split Garage
Private PoolNo
Road Frontage TypeStreet Paved
Road Surface TypePaved
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NYes

Additional Details

Price History

Steven Pugh

Broker Associate | Team Leader
Price $1,300,000
MLS#O6395612
List Date 03/28/2026
Property Type Single Family
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