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14255 Hampshire Bay Circle, Winter Garden, FL 34787

$1,300,000

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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!

14255 Hampshire Bay Circle | MLS# O6395612

This single family home located at 14255 Hampshire Bay Circle, Winter Garden, FL 34787 is currently listed for sale with an asking price of $1,300,000. This property was built in 2003 and has 5 bedrooms and 4 full and 1 partial baths with 4625 sq. ft. Hampshire Bay Circle is located in the BAY ISLE 48 17 subdivision. Search BAY ISLE 48 17 real estate on patsybradley.watsonrealtycorp.com today.

Upcoming Open Houses

Open House Saturday April 11th, 11:30am - 1:30pm

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 3 car attached
Heating: Central, Electric, Propane
Lot Size: 6.44 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $12,363
Year Built: 2003
Square Feet: 4,625

Amenities

Built-in Features
Ceiling Fans(s)
Chair Rail
Coffered Ceiling(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Split Bedroom
Thermostat
Walk-In Closet(s)
Window Treatments
Balcony
Courtyard
Lighting
Outdoor Grill
Private Mailbox
Rain Gutters
Sidewalk
Sliding Doors

Feature Descriptions

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
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
Body of Water: BLACK LAKE
Community Features: Gated Community - No Guard, Park, Playground, Sidewalks
Days on Site: 3
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.
Exterior: Block, Stucco
Fireplace: Family Room, Gas
Fireplace Y/N: Yes
Flood Zone Code: X & AE
Flooring: Tile, Wood
Foundation: Block
Frontage Lake: 100
HOA Fee: 141/ Monthly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, Other, VA Loan
Lot: Landscaped, Oversized Lot, Sidewalk, Paved
Lot Dimensions: 6.44
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Driveway, Garage Faces Side, Garage
Parking Notes: Driveway, Garage Faces Side, Garage
Patio/Porch: Covered, Enclosed, Front Porch, Patio, Rear Porch
Pets Allowed: Yes
Pets Restrictions: Buyer to verify pet restrictions with HOA and/or city/county
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Gated Community, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Call Listing Agent 2,Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Special View Info: Water
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access: Lake
Water Access Y/N: Yes
Waterfront Features: Lake Front, Boat Ramp - Private, Skiing Allowed
Water View: Lake
Zoning: R-1

Room Sizes

Kitchen: 26x16
Dining Room: 15x12
Living Room: 14x14
Family Room: 17x14
Primary Bedroom: 40x14
Primary Bathroom: 17x14
Bedroom 2: 13x12
Bedroom 3: 13x11
Bedroom 4: 21x13
Loft: 20x12
Florida Room: 19x12
Bonus Room: 24x20
Florida Room: 25x13
Laundry: 8x6

Local Schools

High School: West Orange High
Middle School: SunRidge Middle
Elementary School: SunRidge Elementary

Listed By / Shown By

Listed By

Agency Name: WEMERT GROUP REALTY LLC
Agency Contact: 407-214-3967

Shown By

Agent Name: Patsy Bradley
Agent Phone: (386) 689-4849
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 7,982.92 per month $6,573.51 Principal & Interest $1,030.25 Property Tax $379.17 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/07/2026. The listing information on this page last changed on 04/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 04/07/2026 3:31:05 AM EST) or GAMLS (last updated Mon 04/06/2026 11:14:57 PM EST) or Stellar MLS (last updated Tue 04/07/2026 1:58:51 AM EST) or SPC MLS (last updated Mon 04/06/2026 11:20:24 PM EST) or Martin MLS (last updated Mon 04/06/2026 11:38:10 PM EST) or Indian River MLS (last updated Mon 04/06/2026 11:30:19 PM EST) or Daytona MLS (last updated Mon 04/06/2026 11:36:49 PM EST) or Northeast Florida MLS (last updated Tue 04/07/2026 12:18:41 AM EST) or Beaches MLS (last updated Tue 04/07/2026 2:36:03 AM EST) or BORMLS (last updated Mon 04/06/2026 11:14:45 PM EST) or Golden Isles MLS (last updated Mon 04/06/2026 11:26:35 PM EST) or Amelia/Nassau MLS (last updated Mon 04/06/2026 11:25:12 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 04/06/2026 11:42:16 PM EST) or NFLMLS (last updated Mon 04/06/2026 9:04:15 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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