Home in 14411 Hampshire Bay Cir Winter Garden for sale with MLS# O6413972

Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities - all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows - a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding - flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience - theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage - two bays connected to the main home, a third independently accessed - provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake - offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

📅 View days on the market

Days on the market

14411 Hampshire Bay Cir, Winter Garden, FL 34787

Price
Price:
$885,000.00
Previous Asking Price:
$895,000.00
Original List Price:
$895,000.00
List Price per Sq Ft (Calculated, Approx.):
$220.7
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6413972
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
5
Full Bath:
3
Half Bath:
2
Additional Rooms:
Den/library/office, Inside Utility, Loft, Media Room, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Breakfast Room Separate
Measures
Living Area:
4,010 Sqft
Built-Up Area:
5,049 Sqft
Lot Area:
13,000 Sqft
Lot Size Dimensions and Info:
100x130
Building Area Source:
Public Records
Living Area Source:
Public Records
Lot Features:
Paved, Level, City Limits, Sidewalk, Private
Lot Size Acres:
0.3
Property Features
Waterfront:
No
Private Pool
Swimming Pool Features:
Gunite, In Ground, Salt Water, Screen Enclosure, Tile
Spa
Spa Features:
In Ground
Security:
Smoke Detector(s)
Furnished:
Unfurnished
Appliances:
Dishwasher, Disposal, Microwave, Refrigerator, Cooktop, Built-in Oven, Electric Water Heater, Range Hood
Interior:
High Ceilings, Walk-In Closet(s), Ceiling Fans(s), Kitchen/family Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Solid Wood Cabinets, Crown Molding, Primary Bedroom Main Floor
Exterior:
Outdoor Shower, Sidewalk, French Doors
Patio and Porch:
Patio, Screened, Covered, Rear Porch
Windows:
Blinds
Laundry:
Inside, Laundry Room
Air Conditioning System:
Central Air
Heating System:
Central, Electric, Heat Pump
Vegetation and Trees:
Trees/landscaped, Mature Landscaping
Property Entrance Faces:
North
Road Responsibility:
Private Maintained Road
Other Equipment:
Irrigation Equipment
Water Access
Water Access Features:
Lake
Water Extras
Water Extra Details:
Fishing Pier
Construction
Year Built:
2005
Roof:
Shingle
Builder Name:
Toll Orlando LP
Levels:
Two
Construction Materials:
Block, Stucco
Flooring:
Carpet, Tile, Laminate
Number of stories:
2
Foundation Details:
Slab
Flood Zone Code:
X
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$11,923.59
Tax Year:
2025
Association Fee:
$546.25
Association Fee Frequency:
Quarterly
Total Annual Fees:
$2,185.00
Total Monthly Fees:
$182.08
Parking
Garage
Garage Spaces:
3
Attached Garage
Parking Features:
Driveway, Garage, Garage Door Opener, Electric Vehicle Charging Station(s), Garage Faces Side
Utilities
Sewer:
Public Sewer
Utilities Available:
Cable Available, Underground Utilities, Electricity Connected, Sewer Connected, Water Connected, Broadband/High Speed Internet Available
Water Source:
Public
Community
Association
Minimum Lease Term:
1-2 Years
Pets Allowed?
Amenities Provided by the Homeowner's Association (HOA):
Playground, Gated, Park
Subdivision Name:
BAY ISLE 48 17
Community Features:
Sidewalks, Street Lights, Park, Playground, Association Recreation - Owned, Irrigation-reclaimed Water, Deed Restrictions
Association Fee Includes:
Recreational Facilities, Private Road
Senior Community:
No
Association Fee Required:
Required
Planned Unit Development
Association Management:
Bay Isle at Black Lake Homeowners Assn: c/o HMI
Association Phone:
407-392-1533
Terms
Listing Terms Considered by Seller:
Cash, Conventional, VA Loan
Occupant Type:
Owner
Buyer Possession:
Close Of Escrow
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
BAY ISLE 48/16 LOT 5
Real Estate Folio Number (Parcel Number):
34-22-27-0162-00-050
Zoning:
R-1
Title to the property is held by owner as:
Fee Simple
Public Schools Assigned
Elementary School:
Sunset
High School:
West Orange High
Middle Or Junior School:
Sunridge Middle
Listing History
Originally published on:
June 6, 2026 2:41 am
Active on the market since:
June 5, 2026
Listing Agreement executed on:
June 5, 2026
Price change occurred on:
July 24, 2026 11:53 pm
Listing Status Last Changed On:
June 6, 2026 2:41 am
Photos updated on:
June 6, 2026 2:43 am
Last Modified:
July 24, 2026 11:54 pm
Additional Information
Courtesy of:
STOCKWORTH REALTY GROUP
Attribution:
407-909-5900
Road Surface Type:
Asphalt
Location
Street Name:
HAMPSHIRE BAY
Street Number:
14411
City:
WINTER GARDEN
State:
Florida
Zip Code:
34787
County:
Orange
Latitude:
N28° 31' 32.8''
Longitude:
W82° 24' 27.2''
Property Map

Want to schedule an in-person or virtual tour? Have questions?

Want to schedule an in-person or virtual tour? Have questions?
Schedule a Tour or Ask a Question


Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $114,988
Median Home Value $475,000
Median Rent $1,994/mo
Median Age 37
Population 93,064
Mortgage Calculator

Please note: Monthly HOA / Condo Fees Not Included. The calculator shows the listing price as home value. Update all fields at your convenience.

Calculate Your Mortgage Payment

$.00
$.00
6.5
30

Taxes and Insurance

$.00
$.00
%

Financial Analysis

%

%

$

$

$

$

$
Ver la Propiedad Ver la propiedad 14411 Hampshire Bay Cir
Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. 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. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House information, if any, 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 or agent presenting the information. The data is deemed reliable but is not guaranteed by MLS GRID. Use of MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS and as amended from time to time. Some IDX listings have been excluded from this website. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available. Based on information submitted to MLS GRID as of July 24, 2026, 11:54 PM.