CONTACT
FAVORITE
SHARE
CLAIM

14255 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL 34787

$1,300,000
USD CAD EUR GBP BTC
14255 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL 34787 - MLS#MFRO6395612 14255 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL 34787 - MLS#MFRO6395612 14255 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL 34787 - MLS#MFRO6395612 14255 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL 34787 - MLS#MFRO6395612

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Request Info, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

Overview of 14255 Hampshire Bay Cir

4 Bedrooms
4/1 Bathrooms
3 Car Garage
5,364 Square Feet
4,625SF Living Area
Pool:
No
Water
Year Built 2003
Listed For 4 Days

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!

This luxury single family home was built in 2003 and features 4 bedrooms, and 4 full bathrooms plus 1 half bath. This home for sale is 5,364 square feet, with 4,625 sq ft being air conditioned living space. The home has a 3 car garage and does not have a private swimming pool.

Directions to this property are as follows: 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.

Please contact your ZFC agent for more information about MLS# MFRO6395612 or any other homes for sale in Winter Garden or elsewhere in the Orange County area.

Features & Amenities

Appliances

Cooktop, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer

Other Equipment

Irrigation Equipment

Cooling

Central Air

Heating

Central, Electric, Propane

Flooring

Tile, Wood

Parking

Driveway, Garage Faces Side, Garage

Lot Size

280513

View

Trees/Woods, Water view

Construction Materials

Block, Stucco

Security Features

Gated Community, Smoke Detector(s)

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

Furnished

Partially

Exterior Features

Balcony, Courtyard, Lighting, Outdoor Grill, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors

Lot Features

Landscaped, Oversized Lot, Sidewalk, Paved

Patio And Porch Features

Covered, Enclosed, Front Porch, Patio, Rear Porch

Roof

Shingle

Utilities

B B/H S Internet Available, Cable Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected

Waterfront Features

Lake Front

Water Body Name

B L A C K L A K E

Laundry

Laundry Room

Fireplace

Family Room, Gas

Zoning

R-1

Year Built

2003

Pets Allowed

Yes

Annual Real Estate Taxes

$12,364 (2025)

Legal Description

Bay Isle 48/16 Lot 19

Property Type

Single Family Home

HOA Fees

$141 /Monthly

Association Fee Includes

Private Road

Community Features

Gated Community -No Guard, Park, Playground, Sidewalks

Direction Faces

East

MLS Number

MFRO6395612

Universal Property Id

U S-12095-N-342227016200190-R-N

Days On Market

4

Community Name

Bay Isle 48 17

14255 Hampshire Bay Circle Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 14255 Hampshire Bay Cir should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $12,364 but will likely change when this home sells. These estimations are calculated from a list price of $1,300,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 14255 Hampshire Bay Circle

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRO6395612 Listing History

03/28/2026 Listed for sale by WEMERT GROUP REALTY LLC with MLS# MFRO6395612 with a list price of $1,300,000.

Orange County Schools

Elementary School

Middle School

Open House Schedule for 14255 HAMPSHIRE BAY CIR

Apr 11
11:30 am - 1:30 pm
This listing of 14255 Hampshire Bay Circle Winter Garden FL 34787 was last updated on 2026-04-07 15:12:09. Listing courtesy of WEMERT GROUP REALTY LLC.
MLS

Map of 14255 Hampshire Bay Circle Winter Garden FL 34787

Similar Homes For Sale

14039 Hampshire Bay Cir, WINTER GARDEN
Reduced
$819,900
$920,000

Bay Isle

14039 Hampshire Bay Cir
Winter Garden, FL 34787

4

5

2

4,590 SqFt

0.4 Acres

17144 Phil C Peters Rd, WINTER GARDEN
Reduced
$2,599,000
$2,700,000

MLS#MFRO6260561

17144 Phil C Peters Rd
Winter Garden, FL 34787

4

5

6,526 SqFt

2.5 Acres

16788 Muskgrass Dr, WINTER GARDEN
$1,600,000

MLS#MFRO6388174

16788 Muskgrass Dr
Winter Garden, FL 34787

4

5

3

5,833 SqFt

0.17 Acres

2015 Sandy Garden Ln, WINTER GARDEN
Reduced
$765,000
$799,900

Carriage Pointe

2015 Sandy Garden Ln
Winter Garden, FL 34787

4

5

3

5,632 SqFt

0.24 Acres

720 Lake Brim Dr, WINTER GARDEN
Reduced
$1,850,000
$1,899,000

Oakland Park

720 Lake Brim Dr
Winter Garden, FL 34787

4

4

2

5,626 SqFt

0.21 Acres

15198 E Oakland Ave, WINTER GARDEN
Under Contract
$1,850,000

Oakland Park

15198 E Oakland Ave
Winter Garden, FL 34787

4

4

3

5,294 SqFt

0.37 Acres

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.

Currency