14255 HAMPSHIRE BAY CIRCLE, Winter Garden, FL 34787

• 5 beds |
• 5 baths |
• 4,625 sqft

Property Description

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!

Listing Status:

Active

Date Added:

April 3, 2026

Data Last Updated:

April 5, 2026 at 7:23AM

Listing Office:

WEMERT GROUP REALTY LLC : 407-743-8356

Listing Agent:

Jenny Wemert : 407-809-1193

MLS ID:

O6395612

Interior

• General: Built-in FeaturesCeiling Fans(s)Chair RailCoffered Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorSplit BedroomThermostatWalk-In Closet(s)Window Treatments
• Rooms: AtticBonus RoomDen/Library/OfficeFamily RoomFlorida RoomFormal Dining Room SeparateFormal Living Room SeparateInterior In-Law Suite w/Private EntryLoft
• Appliances: CooktopDishwasherDisposalDryerRangeRange HoodRefrigeratorWasher
• Laundry: Laundry Room
• Flooring: TileWood
• A/C: Central Air
• Heating: CentralElectricPropane
• Fireplace: Family RoomGasFireplace

Exterior

• General: BalconyCourtyardLightingOutdoor GrillPrivate MailboxRain GuttersSidewalkSliding Doors
• Other Structures: EnclosedFront PorchRear PorchPatioCovered
• Parking: DrivewayGarage Faces SideGarage

Construction

• Roofing: Shingle
• General: BlockStuccoTwoBlock

Location

• Road/Access: Paved
• HOA Amenities: Private Road141.0Monthly
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1BAY ISLE 48/16 LOT 1934-22-27-0162-00-190
• View: Trees/WoodsWater

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedPropanePublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple