IDX

Listed by Julie Bettosini, PA · Courtesy of STOCKWORTH REALTY GROUP· Agent MLS ID# MFR261069744 · Deemed reliable but not guaranteed. · Data last updated: Sep 12, 2026 · 6:06 PM

14411 HAMPSHIRE BAY CIR

Winter Garden, Orange, FL, 34787

Active

$870,000

$217/sqft

4Beds
5Baths
4,010Sq Ft
2005Built
99Days on Market

About this home

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.

Facts & Features

MFRO6413972
$870,000
Active
4
5
3
2
4,010 sqft
0.3000
2005
Residential
Single Family Residence
N/A

Community Information

14411 HAMPSHIRE BAY CIR
Bay Isle 48 17
Winter Garden
Orange
FL
34787
No

Amenities

Gated, Park, Playground
N/A
No
No
Yes

Interior

Ceiling Fans(s), High Ceilings, Open Floorplan, Split Bedroom, Walk-In Closet(s), Solid Wood Cabinets, Kitchen/Family Room Combo, Stone Counters, Thermostat, Crown Molding, Primary Bedroom Main Floor
Central, Electric, Heat Pump
Central Air
Laminate, Tile, Carpet
N/A
2
Built-In Oven, Cooktop, Dishwasher, Disposal, Microwave, Refrigerator, Electric Water Heater, Range Hood

Exterior

Sidewalk, Outdoor Shower
Block, Stucco
Slab
Shingle
N/A
City Limits, Paved, Level, Sidewalk, Private

School Information

Sunridge Elementary
Sunridge Middle
West Orange High

Additional Information

June 5, 2026
99
R-1
North
No

Mortgage Calculator

This calculator provides estimates for informational purposes only and is not a loan offer, pre-approval, or commitment to lend. Actual rates, payments, and loan terms vary by lender and are subject to credit approval, income/asset verification, and market conditions. Property tax and homeowners insurance shown are estimates and may differ. PMI applies when the down payment is under 20%. For an official Loan Estimate, contact a licensed mortgage lender. STOCKWORTH REALTY GROUP is a licensed real estate brokerage, not a mortgage lender. Equal Housing Opportunity.

99 days on market

Listing updated: Sep 12, 2026 · 6:06 PM

Listed by: Julie Bettosini, PA · 321-689-9594STOCKWORTH REALTY GROUP · 407-909-5900

Updated from Real Estate Market Data

Location

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