14255 Hampshire Bay Circle, FL
Stellar MLS

$1,300,000

14255 Hampshire Bay Circle

Winter Garden, FL 34787

Listing updated: May 23, 2026 at 7:57 AM ET

Active
4
Beds
5
Baths
4,625
Sq Ft
6.44
Acres
2003
Built
WaterfrontWater accessIn-law suiteFireplace3-car garage6.44 acres$281/sqft
Single Family Residence

Property type

2003

Year built

280,513 sqft

Lot size

$281

Price / sq ft

$141/mo

HOA dues

50

Days on market

3

Garage spaces

X & AE

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

Principal & interest$6,574
Property taxes$1,030
Home insurance (est.)$596
HOA dues$141

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

  1. Status: Active
    Apr 3, 2026
  2. Listed$1,300,000
    Apr 3, 2026
  3. 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

ElementaryBSunRidge ElementaryGreatSchools ↗
MiddleASunRidge MiddleGreatSchools ↗
High SchoolAWest Orange HighGreatSchools ↗

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

RoomLevelDimensions
KitchenFirst26x16
Dining RoomFirst15x12
Living RoomFirst14x14
Family RoomFirst17x14
Primary BedroomFirst40x14
Primary BathroomFirst17x14
Bedroom 2Second13x12
Bedroom 3Second13x11
Bedroom 4Second21x13
LoftSecond20x12
Florida RoomSecond19x12
Bonus RoomFirst24x20
Florida RoomFirst25x13
LaundryFirst8x6

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

Zone X & AEFEMA Zone X & AEPanel 12095C0215H

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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MLS GRID

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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