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$1,300,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,625 Sq. Ft.
  • Updated 7 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 4/4 1:00 PM - 3:00 PM

14255 Hampshire Bay Circle,Winter Garden, FL 34787

14255 Hampshire Bay CircleWinter GardenFL34787

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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!

Full Property Details for 14255 Hampshire Bay Cir

General

  • Price: $1,300,000
  • HOA FEE: $141/month
  • Taxes: $12,363 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6395612
  • Updated: 4/3/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 14
  • Interior Features: Built-in Features, Ceiling Fan(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Family Room, Gas
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
  • Furnishings: Partially
  • Flooring: Porcelain Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Security/Safety: Gated Community, Smoke Detector(s)

Exterior

  • Exterior Features: Balcony, Courtyard, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Enclosed, Front Porch, Patio, Rear Porch
  • Porch/Patio/Deck: Covered, Enclosed, Front Porch, Patio, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Driveway, Garage Faces Side, Split Garage

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: BAY ISLE 48 17
  • Driving 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.
  • Direction Faces: East

School Information

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

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Lake, Water Access, Waterfront, Gated Community - No Guard, Park, Playground, Sidewalks
  • Association: Yes
  • Assoc. Name: HMI Management
  • Assoc. Fees Include: Private Road
  • Pet Restrictions: Buyer to verify pet restrictions with HOA and/or city/county

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric, Propane

Utilities

  • Sewer: Public Sewer
  • Water District: BLACK LAKE
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 4,625
  • Sq. Ft. Source: Public Records
  • Year Built: 2003

Lot Features

  • Property View: Trees/Woods, Water
  • Lot Size (Acres): 6.44
  • Lot Size (Sq. Ft.): 280,513
  • Lot Size: 6.4397
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: BLACK LAKE
  • Water Front Desc.: Lake, Waterfront, Lake Front

Financial Considerations

  • Association Fee: $141
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $12,363.83
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BAY ISLE 48/16 LOT 19
  • Flood Zone Info: X & AE
  • APN: 342227016200190
  • Property ID: 342227016200190

Listed by Wemert Group Realty Llc

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Listing agents

— 14255 Hampshire Bay Cir —

  • Wemert Group Realty Llc

  • Wemert Group Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14255 Hampshire Bay Cir

School District:Orange County School District
NameGradesDistance
Sunridge Elementary School
14455 Sunridge Boulevard, Winter Garden, FL 34787
PK-50.9 mi
SunRidge Middle School
14955 Sunridge Boulevard, Winter Garden, FL 34787
6-80.9 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14255 Hampshire Bay Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/03/2026
Listed
$1,300,000
71.05%
MLS
5/12/2023
Sold
$760,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14255 Hampshire Bay Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$12,365
—
$787,050
3%
2024
$12,365
-7%
$762,585
-7%
2023
$13,243
103%
$819,810
92%
2021
$6,509
-37%
$427,551
-33%
2022
$10,365
59%
$636,522
51%
2021
$6,509
2%
$421,648
2%
2019
$6,411
1%
$412,168
2%
2018
$6,361
3%
$404,483
2%
2017
$6,203
—
$396,164
2%
2016
$6,195
-2%
$388,016
1%
2015
$6,300
-1%
$385,319
1%
2014
$6,343
2%
$382,261
1%
2013
$6,206
—
$376,612
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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with our affiliated lender
NMLS#: 1598647

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Listed by Wemert Group Realty Llc

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14255 Hampshire Bay Circle, Winter Garden, FL 34787 (MLS# O6395612) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 14255 Hampshire Bay Circle is currently listed for $1,300,000 and was received on April 03, 2026. Want to learn more about 14255 Hampshire Bay Circle? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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