Refine Search

14411 Hampshire Bay Circle , Winter Garden, FL 34787

$895,000

72 Total Photos [Click to View All]

Property Description

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.

14411 Hampshire Bay Circle | MLS# O6413972

This single family home located at 14411 Hampshire Bay Circle , Winter Garden, FL 34787 is currently listed for sale with an asking price of $895,000. This property was built in 2005 and has 4 bedrooms and 3 full and 2 partial baths with 4010 sq. ft. Hampshire Bay Circle is located in the BAY ISLE 48 17 subdivision. Search BAY ISLE 48 17 real estate on www.signwithsanford.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 3 car attached
Heating: Central, Electric, Heat Pump
Lot Size: 0.30 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $11,923
Year Built: 2005
Square Feet: 4,010

Amenities

Ceiling Fans(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)
French Doors
Outdoor Shower
Sidewalk

Feature Descriptions

Additional Rooms: Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Loft, Media Room
Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Association Amenities: Gated, Park, Playground
Body of Water: BLACK LAKE
Builder: Toll Orlando LP
Community Features: Association Recreation - Owned, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks, Street Lights
Directions: 429 to exit for 535/Stoneybrook Parkway head north and first Left onto Winter Garden/Vineland Road, through roundabout to first left at Bay Isle. Through gate turn left and home around curve on left.
Exterior: Block, Stucco
Flood Zone Code: X
Flooring: Carpet, Laminate, Tile
Foundation: Slab
HOA Fee: 546.25/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, VA Loan
Lot: City Limits, Level, Sidewalk, Paved, Private
Lot Dimensions: 0.3
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Garage
Parking Notes: Driveway, Electric Vehicle Charging Station(s), Gara
Patio/Porch: Covered, Patio, Rear Porch, Screened
Pets Allowed: Yes
Pets Restrictions: Buyer to confirm any pet restrictions through HOA and City
Pool: Gunite, In Ground, Salt Water, Screen Enclosure, Tile
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: Appointment Only
Spa: In Ground
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access: Lake
Water Access Y/N: Yes
Waterfront Features: Fishing Pier
Windows: Blinds
Zoning: R-1

Room Sizes

Living Room: 16x11
Office: 13x12
Primary Bedroom: 17x16
Dining Room: 12x12
Kitchen: 19x14
Dinette: 10x9
Family Room: 18x16
Bedroom 2: 13x13
Bedroom 3: 14x12
Bedroom 4: 13x13
Loft: 21x12
Media Room: 21x13
Laundry: 8x7
Balcony/Porch/Lanai: 13x10
Balcony/Porch/Lanai: 19x18

Local Schools

High School: West Orange High
Middle School: SunRidge Middle
Elementary School: SunRidge Elementary

Listed By / Shown By

Listed By

Agency Name: STOCKWORTH REALTY GROUP
Agency Contact: 407-909-5900

Shown By

Agent Name: The Sanford Group
Agent Phone: Cell: (904) 868-9651
Agency Title: Watson Realty Corp., REALTORS ®

IDX logo

Estimate Your Payment

Estimated Payment

$ 5,808.52 per month $4,553.90 Principal & Interest $993.58 Property Tax $261.04 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 06/06/2026. The listing information on this page last changed on 06/06/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 06/06/2026 2:15:24 AM EST) or GAMLS (last updated Fri 06/05/2026 11:15:12 PM EST) or Stellar MLS (last updated Sat 06/06/2026 1:58:59 AM EST) or SPC MLS (last updated Fri 06/05/2026 11:21:23 PM EST) or Martin MLS (last updated Fri 06/05/2026 11:38:10 PM EST) or Indian River MLS (last updated Fri 06/05/2026 11:30:17 PM EST) or Daytona MLS (last updated Fri 06/05/2026 11:36:50 PM EST) or Northeast Florida MLS (last updated Sat 06/06/2026 12:19:00 AM EST) or Beaches MLS (last updated Sat 06/06/2026 2:09:16 AM EST) or BORMLS (last updated Fri 06/05/2026 11:16:13 PM EST) or Amelia/Nassau MLS (last updated Fri 06/05/2026 11:25:15 PM EST) or Dixie Gilchrist Levy MLS (last updated Fri 06/05/2026 11:42:16 PM EST) or NFLMLS (last updated Fri 06/05/2026 9:05:05 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that 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, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information 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/agent presenting the information.



Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder

Pixel