To schedule a showing of 14255 Hampshire Bay Circle, Winter Garden, Florida, Call David Shippey at 863-521-4517 TODAY!
Winter Garden, FL 34787
- 4Beds
- 5.00Total Baths
- 4 Full, 1 HalfBaths
- 4,625SqFt
- 2003Year Built
- 6.44Acres
- MLS# O6395612
- Residential
- SingleFamilyResidence
- Pending
- Approx Time on Market2 months, 15 days
- Area34787 - Winter Garden/oakland
- CountyOrange
- Subdivision Bay Isle 48 17
Overview
Under contract-accepting backup offers. 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. Bring your MOTORIZED BOATS and embrace the ultimate waterfront lifestyle from your own private slice of paradise! 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 homes 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 OWNERS 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 Gardens 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!
Agriculture / Farm
Association Fees / Info
Community Features: Lake, Playground, Park, Waterfront, WaterAccess, Gated, Sidewalks
Pets Allowed: Yes
Hoa Frequency Rate: 141
Association: Yes
Hoa Fees Frequency: Monthly
Association Fee Includes: RoadMaintenance
Bathroom Info
Total Baths: 5.00
Fullbaths: 4
Building Info
Window Features: WindowTreatments
Roof: Shingle
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Patio: RearPorch, Covered, Enclosed, FrontPorch, Patio, Balcony
Exterior Features: Balcony, Courtyard, SprinklerIrrigation, Lighting, OutdoorGrill, RainGutters
Fees / Restrictions
Financial
Original Price: $1,300,000
Garage / Parking
Parking Features: Driveway, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: FamilyRoom, Gas
Fireplace: Yes
Floors: PorcelainTile, Wood
Levels: Two
Laundry Features: LaundryRoom
Interior Features: BuiltInFeatures, ChairRail, CeilingFans, CrownMolding, CofferedCeilings, EatInKitchen, HighCeilings, KitchenFamilyRoomCombo, MainLevelPrimary, SplitBedrooms, WalkInClosets, WindowTreatments, Attic, SeparateFormalDiningRoom, SeparateFormalLivingRoom, Loft
Appliances: Cooktop, Dryer, Dishwasher, Disposal, Range, Refrigerator, RangeHood, Washer
Lot Info
Direction Remarks: 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.
Lot Size Units: Acres
Lot Size Acres: 6.44
Lot Sqft: 280,513
Vegetation: PartiallyWooded
Lot Desc: OversizedLot, Landscaped
Misc
Other
Special Conditions: None
Security Features: SmokeDetectors, GatedCommunity
Other Rooms Info
Property Info
Section: 34
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 2
Total Stories: 2
Foundation: Block
Human Modified: Yes
Room Info
Total Rooms: 14
Sqft Info
Sqft: 4,625
Bulding Area Sqft: 5,364
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 19
Tax Legal Description: BAY ISLE 48/16 LOT 19
Tax Block: 00
Tax Annual Amount: 12363.83
Tax Book Number: 48/16
Unit Info
Utilities / Hvac
Heating: Central, Electric, Propane
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityConnected, HighSpeedInternetAvailable, Propane, MunicipalUtilities, SewerConnected, WaterConnected
Waterfront / Water
Waterfront: Yes
Waterfront Features: LakeFront, LakePrivileges
View: Yes
Water Body Name: BLACK LAKE
View: Lake, TreesWoods, Water
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.This listing courtesy of Wemert Group Realty Llc
If you have any questions on 14255 Hampshire Bay Circle, Winter Garden, Florida, please call David Shippey at 863-521-4517.
MLS# O6395612 located at 14255 Hampshire Bay Circle, Winter Garden, Florida is brought to you by David Shippey REALTOR®
14255 Hampshire Bay Circle, Winter Garden, Florida has 4 Beds, 4 Full Bath, and 1 Half Bath.
The MLS Number for 14255 Hampshire Bay Circle, Winter Garden, Florida is O6395612.
The price for 14255 Hampshire Bay Circle, Winter Garden, Florida is $1,200,000.
The status of 14255 Hampshire Bay Circle, Winter Garden, Florida is Pending.
The subdivision of 14255 Hampshire Bay Circle, Winter Garden, Florida is Bay Isle 48 17.
The home located at 14255 Hampshire Bay Circle, Winter Garden, Florida was built in 2026.
MLS# O6409098
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MLS IDX data last updated on 06-18-2026 7:51 PM EST.