$1,300,000
14255 Hampshire Bay Circle
Winter Garden, FL 34787
Listing updated: May 23, 2026 at 7:57 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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!
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history50 days on market
- Status: ActiveApr 3, 2026
- Listed$1,300,000Apr 3, 2026
- Price increased$1,300,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 50
- Subdivision
- Bay Isle 48 17
- County
- Orange
- Year built
- 2003
- Living area
- 4,625 sq ft
- Price/sq ft
- $281
- Building area
- 5,364 sq ft (Public Records)
- Lot size
- 280,513 sq ft
- Lot category
- 5 to less than 10
- Flood zone
- X & AE (12095C0215H)
- Garage
- 3 spaces
- Annual taxes
- $12,364 (2025)
- Parcel #
- 34-22-27-0162-00-190
- Zoning
- R-1
- MLS #
- O6395612
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Tile, Wood
- Appliances
- Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
- Interior features
- 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
- Laundry
- Laundry Room
- Stories / Levels
- Two
- Direction faces
- East
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central, Electric, Propane
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Driveway, Garage Faces Side, Garage
HOA & Financial
- HOA fee
- $141 / Monthly
- Monthly HOA
- $141/mo
- Total monthly fees
- $141/mo
- Total annual fees
- $1,692
- HOA name
- HMI Management
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional, Other, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to verify leasing restrictions with HOA and/or city/county
- Approval process
- Buyer to verify approval restrictions with HOA and/or city/county
Exterior & Construction
- Exterior features
- Balcony, Courtyard, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Block
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 26x16 |
| Dining Room | First | 15x12 |
| Living Room | First | 14x14 |
| Family Room | First | 17x14 |
| Primary Bedroom | First | 40x14 |
| Primary Bathroom | First | 17x14 |
| Bedroom 2 | Second | 13x12 |
| Bedroom 3 | Second | 13x11 |
| Bedroom 4 | Second | 21x13 |
| Loft | Second | 20x12 |
| Florida Room | Second | 19x12 |
| Bonus Room | First | 24x20 |
| Florida Room | First | 25x13 |
| Laundry | First | 8x6 |
Listing Details
- Listing date
- 2026-03-28
- On market date
- 2026-04-03
- Original list price
- $1,300,000
- Occupant type
- Vacant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-04-03
- Tax legal description
- BAY ISLE 48/16 LOT 19
Flood risk
See FEMA for this zone’s designation and insurance requirements.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of May 23, 2026 at 7:57 AM ET. 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.
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