Sell Your Home
Get a free home valuation
Contact
Tell us about your needs

14411 HAMPSHIRE BAY CIRCLE

House For Sale
$895,000

BTC: 14.57654723

ETH: 512.60022910

1 days
4 bds
3 ba
4,010 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Driveway / Electric Vehicle Charging Station(s) / Garage Door Opener / Garage Faces Side / Split Garage
Year Built:
2005
Lot:
0.30 Acres
Heating:
Central / Electric / Heat Pump
Price/sqft:
$223
Cooling:
Central Air
HOA:
$546

Valuation

Our model vs. what's actually selling nearby.
Estimate
$850,000
$537K – $1.2M
Confidence Low
List vs. estimate
$45K above estimate
List $895,000 · +5.3%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$223
-17.8% vs. city median $271
Based on
17 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$11,923
2025
HOA
$546/qtr
Private Road, Recreational Facilities
Pool
Gunite
Garage
3 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Carpet

    • Laminate

    • Tile

    Heating

    • Central

    • Electric

    • Heat Pump

    Cooling

    • Central Air

    Appliances

    • Built-In Oven

    • Cooktop

    • Dishwasher

    • Disposal

    • Electric Water Heater

    • Microwave

    • Range Hood

    • Refrigerator

    Other interior features

    • Ceiling Fan(s)

    • Crown Molding

    • High Ceilings

    • Kitchen/Family Room Combo

    • Open Floorplan

    • Primary Bedroom Main Floor

    • Solid Wood Cabinets

    • Split Bedroom

    • Stone Counters

    • Thermostat

    • Walk-In Closet(s)

    Bedrooms and bathrooms

    • Bedrooms: 4

    • Bathrooms: 2

    • Full bathrooms: 3

  • Parking

    • Driveway

    • Electric Vehicle Charging Station(s)

    • Garage Door Opener

    • Garage Faces Side

    • Split Garage

    Property

    • Levels: Two

    • Pool Private: Yes

    • Exterior Features: French Doors / Irrigation System / Outdoor Shower / Sidewalk

    Lot

    • Lot: 0.30 Acres

    Other Property Information

    • Parcel Number: 342227016200050

    • Zoning: R-1

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • BB/HS Internet Available

    • Cable Available

    • Electricity Connected

    • Sewer Connected

    • Street Lights

    • Underground Utilities

    • Water Connected

  • Other financial information

    • HOA: $546

    • HOA Frequency: Quarterly

    • Annual tax amount: $11,924

  • Source details

    • MLS ID: O6413972

    Other facts

    • Construction Materials: Block / Stucco

    • Foundation Details: Slab

    • Laundry Features: Inside / Laundry Room

    • Lot Features: City Lot / Level / Sidewalk

    • Patio And Porch Features: Covered / Patio / Rear Porch / Screened

    • Pool Features: Gunite / In Ground / Salt Water / Screen Enclosure / Tile

    • Window Features: Blinds

    • Direction Faces: North

    • Water Body Name: BLACK LAKE

    • Garage Spaces: 3

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 4010

    • Water Source: Public

    • Lot Size Dimensions: 100 x 130

    • Subdivision Name: BAY ISLE 48 17

Private inquiry
Talk to the advisor on this listing.
Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

More like this

New
For Sale
$764,900
House
4 bds · 4 ba · 3,167 sqft
BLACK LAKE PRESERVE, WINTER GARDEN
14378 BLACK LAKE PRESERVE STREET
New
For Sale
$1,080,000
House
4 bds · 3 ba · 3,881 sqft
TWINWATERS, WINTER GARDEN
1651 AMSEL FALLS PARK TERRACE
New
For Sale
$1,050,000
House
4 bds · 3 ba · 2,667 sqft
OAKLAND PARKB-1, WINTER GARDEN
1219 SADDLEBACK DRIVE
New
For Sale
$635,000
House
4 bds · 2 ba · 2,596 sqft
JOHN LAKE POINTE, WINTER GARDEN
745 MARSH REED DRIVE
New
For Sale
$774,900
House
4 bds · 3 ba · 2,814 sqft
CYPRESS RESERVE PH 1, WINTER GARDEN
13959 JOMATT LOOP
New
For Sale
$840,000
House
7 bds · 4 ba · 4,688 sqft
BELLE MEADE PH 02 H, WINTER GARDEN
15130 OVATION DRIVE
New
For Sale
$799,000
Commercial
0 room(s) · 1,448 sqft
WINTER GARDEN EXECUTIVE CENTRE, WINTER GARDEN
213 S DILLARD STREET UNIT 230
For Sale
$1,000,000
House
4 bds · 3 ba · 3,828 sqft
CYPRESS RESERVE PH 1, WINTER GARDEN
13822 JOMATT LOOP

Market around this address

Live counts in the same area.
View all

The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: STOCKWORTH REALTY GROUP