To schedule a showing of 14255 Hampshire Bay Circle, Winter Garden, Florida, Call David Shippey at 863-521-4517 TODAY!

$1,200,000 Reduced -$100,000
14255 Hampshire Bay Circle
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

Schools

Elem:  Sunridge Elementary

Middle:  Sunridge Middle

High:  West Orange High

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 

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Price & Status History (on davidshippey.com since Fri, Apr 3rd 2026)
  • Original Price: $1,300,000
  • Current Price: $1,200,000
  • Price Reduced: $100,000
Date ChangedFromTo
06/15/2026ActivePending
06/11/2026$1,300,000 $1,200,000 Reduced by $100,000

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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.