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14039 Hampshire Bay Circle

Winter Garden, FL 34787

4 beds
4 baths
3,801 sqft
~1/2 acre lot
$243 per sqft
2006 build
– on site

Fully renovated and designed with modern efficiency in mind, this home offers unparalleled comfort and style. Nestled in one of the most desirable locations in town, this home is part of the exclusive Bay Isle gated community, where residents enjoy access to a serene private lake, a private park, a playground, sidewalks, and the added security of a gated entrance. The HOA conveniently covers grounds maintenance, private roads, recreational facilities, and security.Water Filter installed through all house Paid off. Located just one block from Winter Garden Mall and a new hospital, and only minutes from top amusement parks and the airport, the location is second to none. This premium corner-lot property boasts a fully paved, oversized courtyard, ample parking, rain gutters, an irrigation system, and professional outdoor lighting. Inside, the home features an open layout with a kitchen/family room combo, a living/dining room combo, an extended loft, a theater room, and an enclosed lanai perfect for entertaining or relaxing. Elegant interior details include crown molding, high ceilings, solid wood cabinets, solid surface countertops, custom window treatments, walk-in closets, and a wet bar. The roof was replaced in 2021, and the property features three A/C units, including one brand new, ensuring reliability and energy efficiency. With 4 spacious bedrooms, including two master suites and a guest suite with a private entrance, and 3.5 beautifully appointed bathrooms, this home is thoughtfully designed to meet every need. Located just one block from Winter Garden Mall and a new hospital, and only minutes from top amusement parks and the airport, the home offers unbeatable convenience. As part of the sought-after Bay Isle community, you’ll enjoy access to a private park, Lake, a playground, sidewalks, and the peace of mind that comes with gated security. The HOA takes care of grounds maintenance, private roads, recreational facilities, and security. Nestled in one of the most desirable locations in town, this home is a rare opportunity to live in style and comfort.

Listing courtesy of STELLAR_MLS / SUMMERHILL REALTY GROUP LLC

Last checked: Checking… • Last updated May 5, 2025 •

MLS# O6274785 —

The Building

Year Built:

2006
New Construction:

false
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Roof:

Shingle
Foundation Details:

Slab
Building Area Total:

4590
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Eating Space In Kitchen
Flooring:

Porcelain Tile
Fireplace:

false

Room Dimensions

Living Area:

3801
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

Take Winter Garden Vineland Rd to Hampshire Bay Cir Use the left lane to turn left onto Winter Garden Vineland Rd Slight left to stay on Winter Garden Vineland Rd At the traffic circle, take the 2nd exit and stay on Winter Garden Vineland Rd Turn left onto Bristol Isle Ln Turn right onto Hampshire Bay Cir
Latitude:

28.528594
Longitude:

-81.591184
Coordinates:

-81.591184, 28.528594

The Property

Parcel Number:

342227016200420
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.4
Lot Size Area:

17609
Lot Size SqFt:

17609
Lot Size Units:

Square Feet
Total Acres:

1/4 to less than 1/2
Zoning:

R-1
Direction Faces:

Southeast
View:

false
Exterior Features:

French Doors
Water Source:

Public
Road Surface Type:

Asphalt
Flood Zone Code:

x
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

42
Tax Block:

N/A
Tax Legal Description:

BAY ISLE 48/16 LOT 42
Tax Book Number:

NA
Tax Annual Amount:

$11,068.48

Beds

Bedrooms Total:

4

Baths

Total Baths:

3.5
Total Baths:

4
Full Baths:

3
Half Baths:

1

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6274785
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Available
Sewer:

Public Sewer

Appliances

Appliances:

Convection Oven
Laundry Features:

Laundry Room

The Community

Subdivision Name:

BAY ISLE 48 17
Senior Community:

false
Community Features:

Water Access
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Pets Allowed:

Yes
Association:

true
Association Fee:

141
Association Fee Frequency:

Monthly
Association Fee Includes:

Maintenance Grounds
Association Fee Requirement:

Required
Monthly HOA Amount:

141
Ownership:

Fee Simple
Association Approval Required:

true

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

2
Carport:

false
Covered Spaces:

2

Monthly cost estimate

Asking price

$924,900

Expense	Monthly cost
Mortgage	$4,952
Taxes	$922
Insurance	$254
HOA fees	$141
Utilities	$216 See report
Total	$6,485/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

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Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
5/4/25 May 4, 2025	Price Changed	STELLAR_MLS	$924,900	-0.1%
4/15/25 Apr 15, 2025	Price Changed	STELLAR_MLS	$925,900	-0.5%
4/11/25 Apr 11, 2025	Price Changed	STELLAR_MLS	$930,900	-0.2%

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This house located in Glynwood, Winter Garden, FL 34787 is currently for sale for $924,900. 14039 Hampshire Bay Circle is a 3,801 square foot house with 4 beds and 4 baths that has been on Estately for 105 days. 14039 Hampshire Bay Circle is in the Glynwood neighborhood of Winter Garden and has a WalkScore® of 34, making it car-dependent. This house is in the attendance area of Sunridge Middle School, Cornerstone Charter Academy High School, Sunridge Elementary School, Cornerstone Charter Academy K-8, and West Orange High School.

Listing Courtesy of: STELLAR_MLS and SUMMERHILL REALTY GROUP LLC.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.