$895,000

14411 HAMPSHIRE BAY CIR, Winter Garden, FL 34787

Active
4
Beds
5
Baths
4,010
Sq Ft
$223
Per Sq Ft
2005
Built
1
Days Listed

About This Property

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.

Property Details

TypeSingle Family Residence
Garage3 spaces
Lot0.30 ac
Stories2
PoolYes
WaterfrontNo
SubdivisionBAY ISLE 48 17
HOAYes · $546/mo
Tax/yr$11,924
HeatingCentral, Electric, Heat Pump
CoolingCentral Air
FlooringCarpet, Laminate, Tile
RoofShingle

Schools

ElementarySunRidge Elementary
MiddleSunRidge Middle
High SchoolWest Orange High

Listed by STOCKWORTH REALTY GROUP · MLS# MFRO6413972

Similar Homes in 34787

View all Homes For Sale in 34787 →

Recently Sold in 34787

408 S BOYD ST
$750,000
408 S BOYD ST, 34787
3 bd · 3 ba · 2,295 sqft
Sold Jun 2026
8911 SONOMA COAST DR
$940,000
8911 SONOMA COAST DR, 34787
5 bd · 5 ba · 3,227 sqft
Sold Jun 2026
7245 HALF MOON LAKE DR
$2,950
7245 HALF MOON LAKE DR, 34787
3 bd · 3 ba · 1,825 sqft
Sold Jun 2026

Properties displayed may be listed or sold by various participants in the MLS


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. Data deemed reliable but not guaranteed. Last updated: 2026-06-06.
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.
Schedule a Showing
Rise Team · LPT Realty, LLC
Mike Valdes
Mike Valdes
Rise Team · LPT Realty
(813) 548-5618
Browse More
Property photo