Date
Details
Price
Change
Source
8/04/2026
Listed
$6,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$6,000
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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.
Full Property Details
Full Property Details for 14411 Hampshire Bay Cir
General
- Rent: $6,000
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6430003
- Updated: 8/5/2026
- Added to Site: 18 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 15
- Interior Features: Ceiling Fan(s), Crown Molding, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Laminate, Tile
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Gated, Park, Playground
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Salt Water, Screen Enclosure, Tile
- Spa: Yes
- Spa Description: In Ground
- Security/Safety: Smoke Detector(s)
Exterior
- Exterior Features: French Doors, Irrigation System, Outdoor Shower, Sidewalk
- Deck/Patio: Covered, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: BAY ISLE 48 17
- Driving 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.
- Direction Faces: North
School Information
- Elementary School: SunRidge Elementary
- Middle School: SunRidge Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Dock, Water Access, Association Recreation - Owned, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
- Optional Amenities: Gated, Park, Playground
- Association: Yes
- Assoc. Name: Bay Isle at Black Lake Homeowners Assn: c/o HMI
- Pet Restrictions: Buyer to confirm any pet restrictions through HOA and City
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric, Heat Pump
Utilities
- Sewer: Public Sewer
- Water District: BLACK LAKE
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Sewer Connected, Street Lights, Underground Utilities, Water Connected
Structural Information
- Builder: Toll Orlando LP
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 4,010
- Sq. Ft. Source: Public Records
- Year Built: 2005
Lot Features
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 13,000
- Lot Size: 13000
- Lot Dimensions: 100 x 130
- Frontage: Street Paved, Private Road
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Name: BLACK LAKE
Financial Considerations
- Lease Price: $6,000
- Assoc Fee Desc.: Required
- Application Fee: $150
Disclosures and Reports
- Flood Zone Info: X
- APN: 342227016200050
- Property ID: 342227016200050
Listed by Stockworth Realty Group
Schools
Schools serving 14411 Hampshire Bay Cir
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Sunridge Elementary School 14455 Sunridge Boulevard, Winter Garden, FL 34787 | PK-5 | 1 mi |
SunRidge Middle School 14955 Sunridge Boulevard, Winter Garden, FL 34787 | 6-8 | 1 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 14411 Hampshire Bay Cir
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- Single Family
- Active
- 4Beds
- 5Total Baths
- 4,099Sq. Ft.
Listed by Crown Realty Company
- Single Family
- Active
- Updated 5 hours ago
- 4Beds
- 5Total Baths
- 3,002Sq. Ft.
Listed by Dtb Florida Realty, Inc.
- Single Family
- Active
- 4Beds
- 4Total Baths
- 3,062Sq. Ft.
Listed by Windermere International Realty
- Single Family
- Active
- 4Beds
- 4Total Baths
- 3,739Sq. Ft.
Listed by Mila Realty
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- Single Family
- Active
- Updated 2 days ago
- 2Beds
- 1Total Bath
- 1,492Sq. Ft.
Listed by Elite Evolution Properties
- Single Family
- Active
- Updated 11 hours ago
- 4Beds
- 3Total Baths
- 2,718Sq. Ft.
Listed by Wra Business & Real Estate
- Townhouse
- Active
- Updated 3 days ago
- 3Beds
- 3Total Baths
- 1,685Sq. Ft.
Listed by Exp Realty Llc
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- Condo
- Active
- Updated 6 hours ago
- 3Beds
- 3Total Baths
- 1,568Sq. Ft.
Listed by West Orlando Property Management Realty, Llc
- Single Family
- Active
- Updated 1 day ago
- 5Beds
- 5Total Baths
- 3,705Sq. Ft.
Listed by Wra Business & Real Estate
- Single Family
- Active
- Updated 5 days ago
- 3Beds
- 2Total Baths
- 1,495Sq. Ft.
Listed by Florida Connexion Properties
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 1,974Sq. Ft.
Listed by Cani Property Management
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- Single Family
- Closed
- 4Beds
- 4Total Baths
- 4,272Sq. Ft.
Listed and Sold by Ms Land & Building Llc
- Single Family
- Closed
- 5Beds
- 4Total Baths
- 4,045Sq. Ft.
Listed by Stellar Non-Member Office
Sold by Keller Williams Classic
Sold by Keller Williams Classic
- Single Family
- Closed
- Updated 9 days ago
- 6Beds
- 4Total Baths
- 3,210Sq. Ft.
Listed by Robert Sullivan
Sold by Stellar Non-Member Office
Sold by Stellar Non-Member Office
- Single Family
- Closed
- 5Beds
- 4Total Baths
- 2,591Sq. Ft.
Listed by Era Grizzard Real Estate
Sold by Corcoran Premier Realty
Sold by Corcoran Premier Realty
14411 Hampshire Bay Circle, Winter Garden, FL 34787 (MLS# O6430003) is a Single Family property with 4 bedrooms, 3 full bathrooms and 2 partial bathrooms. 14411 Hampshire Bay Circle is currently listed for rent at $6,000 and was received on August 04, 2026. Want to learn more about 14411 Hampshire Bay Circle? Do you have questions about finding other real estate for sale or rent in Winter Garden? You can browse all Winter Garden rentals or contact a Coldwell Banker agent to request more information.