14411 Hampshire Bay Circle, Winter Garden, FL 34787 (MLS # O6413972)

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PRICE $895,000 dsIDX morgage calculator
BEDS 4
BATHS 5
HOME SIZE 4,010 sqft
LOT SIZE 13,068 sqft

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.

DAYS ON MARKET 1 LAST UPDATED 6/5/2026
TRACT BAY ISLE 48 17 YEAR BUILT 2005
COMMUNITY 34787 - Winter Garden/Oakland GARAGE SPACES 3.0
COUNTY Orange STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
Elementary School SunRidge Elementary
Jr. High School SunRidge Middle
High School West Orange High


ADDITIONAL DETAILS
AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
AREA 34787 - Winter Garden/Oakland
CONSTRUCTION Block, Stucco
EXTERIOR Outdoor Shower
GARAGE Yes
HEAT Central, Electric, Heat Pump
HOA DUES 546.25
INTERIOR Crown Molding, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s)
LOT 0.3 acre(s)
LOT DESCRIPTION Level, Paved, Private
LOT DIMENSIONS 100x130
PARKING Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Garage, Attached
POOL Yes
POOL DESCRIPTION Gunite, In Ground, Salt Water, Screen Enclosure, Tile, Private
SEWER Public Sewer
STORIES 2
SUBDIVISION BAY ISLE 48 17
TAXES 11923.59
UTILITIES Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
WATER Public
WATER ACCESS BLACK LAKE
WATERFRONT DESCRIPTION Lake Privileges
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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Listing provided by Julie Bettosini, PA, STOCKWORTH REALTY GROUP, 407-909-5900
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 6/5/26 10:57 PM PDT.

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