14255 Hampshire Bay CircleWinter Garden, FL 34787Price: $1,200,000

  • Price: $1,200,000
  • Est. Mortgage of $/month
  • 87 Days on Market
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Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
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14255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 3478714255 Hampshire Bay Circle Winter Garden FL 34787
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  • 4Bedrooms
  • 6.44Acreage
  • 5Bathrooms
  • 2003Year Built
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 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 Courtesy of WEMERT GROUP REALTY LLC

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More Info

Location Information

  • Road Frontage DescriptionPaved

School Information

  • Elementary SchoolSunRidge Elementary
  • High SchoolWest Orange High
  • Junior HighSunRidge Middle

Parking

  • Parking Features Driveway, Garage Faces Side, Garage

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential
  • Virtual TourView Tour
  • Virtual Tour URL Branded www.wemertgrouprealty.com

Property

  • ZoningR-1

Interior

  • Flooring Tile, Wood
  • Furnished Partially

Utilities

  • Cooling Central Air
  • Heating Central, Electric, Propane
  • Laundry Features Laundry Room
  • Sewer Public Sewer
  • Utilities
    • BB/HS Internet Available
    • Cable Available
    • Electricity Connected
    • Propane
    • Public
    • Sewer Connected
    • Water Connected
  • Water Source Public

Water Body

  • MFR Additional Water Information Lake Access, Private Boat Ramp, Skiing Allowed, Motorized Boats Allowed.
  • MFR Water Access YN Yes
  • MFR Water Frontage Feet Lake 100
  • MFR Waterfront Feet Total 100
  • Water AccessLake
  • Water Body Name BLACK LAKE
  • Water FeaturesLake Front
  • Water ViewYes
  • WaterfrontYes

Basic Information

  • List Price$1,200,000
  • ListingContractDate2026-03-28
  • MLS NumberO6395612
  • Mls Status Pending
  • OriginalListPrice1300000
  • PostalCodePlus45900
  • PublicSurveyRange27
  • StatusPEN

Rooms

  • Bedrooms4
  • Full Bath4
  • Half Baths1
  • MFR 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

Building

  • Bathroom5
  • Construction Materials Block, Stucco
  • FireplaceFamily Room, Gas
  • Fireplace YN Yes
  • Foundation Details Block
  • GarageYes
  • Garage Spaces3
  • Levels Two
  • Patio And Porch Features Covered, Enclosed, Front Porch, Patio, Rear Porch
  • RoofShingle
  • Rooms14
  • Stories2
  • Year Built2003

Amenities

  • Appliances IncludedCooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
  • Association Fee Includes Private Road
  • Association YN Yes
  • Community Features Gated Community - No Guard, Park, Playground, Sidewalks
  • MFR Amenities Additional Fees Buyer to verify any and all fees with HOA (i.e. additional amenities, transfer, capital contribution, gate access, etc…)
  • MFR Pet Restrictions Buyer to verify pet restrictions with HOA and/or city/county
  • Other Amenities
    • Dock
    • Fireplace
    • Garden
    • Lakefront
    • Water View
    • Waterfront
  • Other Equipment Irrigation Equipment
  • PetsYes
  • Security Features Gated Community, Smoke Detector(s)

Tax Information

  • Association Fee $141
  • Association Fee Frequency Monthly
  • Fees$1,692
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $141
  • Tax Year 2025
  • Taxes$12,363
  • Total Monthly Fees $141

Location

  • Address14255 Hampshire Bay Circle
  • AreaWinter Garden/Oakland
  • CountyOrange
  • Exterior Features
    • Balcony
    • Courtyard
    • Lighting
    • Outdoor Grill
    • Private Mailbox
    • Rain Gutters
    • Sidewalk
    • Sliding Doors
  • MFR Water View Lake
  • StateFL
  • SubdivisionBay Isle 48 17
  • TownWinter Garden
  • Township 22
  • Zip34787

Property Information

  • Acreage6.44
  • Attached Garage YN Yes
  • Building Area Total 5,364
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionLandscaped, Oversized Lot, Sidewalk, Paved
  • Lot Size Square Feet 280,513
  • MFR Living Area Meters 429
  • MFR Lot Size Square Meters 26060
  • MFR Total Acreage 5 to less than 10
  • MFR Water Extras Boat Ramp - Private, Skiing Allowed
  • Square Feet4,625

Other

  • Building Area Source Public Records
  • Date Listed04/03/2026
  • MFR Additional Lease Restrictions Buyer to verify leasing restrictions with HOA and/or city/county
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X & AE
  • MFR Flood Zone Date 2021-09-24
  • MFR Minimum Lease 1-2 Years
  • Status Change Timestamp2026-06-15T22:51:17
  • Usm Previous StatusActive
  • Vegetation Mature Landscaping, Trees/Landscaped
  • View Trees/Woods, Water
  • View Count2
Fusilier Realty Group
Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 28, 2026 11:32 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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