There are multiple listings for this address:
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
Price:
$870,000
MLS #:
O6413972
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ISLE 48 17
Neighborhood:
34787wintergardenoakland
Listed Date:
Jun 5, 2026
Finished Sq Ft:
4,010
Total Sq Ft:
5,049
Lot Size:
13,000 sqft / 0.30 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
SunRidge Elementary
Middle School:
SunRidge Middle
High School:
West Orange High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central, Electric, Heat Pump
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)
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Association Amenities
Gated, Park, Playground
Attached Garage YN
1
Community Features
Dock, Water Access, Association Recreation – Owned, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Covered Spaces
3
Direction Faces
North
Exterior Features
French Doors, Irrigation System, Outdoor Shower, Sidewalk
Garage Spaces
3
Lot Features
City Lot, Level, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
Patio And Porch Features
Covered, Patio, Rear Porch, Screened
Security Features
Smoke Detector(s)
Spa Features
In Ground
Window Features
Blinds
Financial
HOA Name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
HOA Phone
407-392-1533
Map
Community
- Address14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL
- SubdivisionBAY ISLE 48 17
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 29, 2026
826
Single Family Listed
112
Avg DOM
279
Avg $ / SqFt
$758,304
Avg List Price
Property Summary
- Located in the BAY ISLE 48 17 subdivision, 14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $870,000 and features 4 beds, 4 baths, and has approximately 4,010 square feet of living space, and was originally constructed in 2005. The current price per square foot is $217. The average price per square foot for Single Family listings in WINTER GARDEN is $279. The average listing price for Single Family in WINTER GARDEN is $758,304. To schedule a showing of MLS#o6413972 at 14411 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of STOCKWORTH REALTY GROUP. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 14411 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL
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
Price:
$6,000
MLS #:
O6430003
Status:
Active
Beds:
4
Baths:
4
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
BAY ISLE 48 17
Neighborhood:
34787wintergardenoakland
Listed Date:
Aug 4, 2026
Finished Sq Ft:
4,010
Total Sq Ft:
5,049
Lot Size:
13,000 sqft / 0.30 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
SunRidge Elementary
Middle School:
SunRidge Middle
High School:
West Orange High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central, Electric, Heat Pump
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)
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Association Amenities
Gated, Park, Playground
Attached Garage YN
1
Community Features
Dock, Water Access, Association Recreation – Owned, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Covered Spaces
3
Direction Faces
North
Exterior Features
French Doors, Irrigation System, Outdoor Shower, Sidewalk
Garage Spaces
3
Lot Features
City Lot, Level, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
Patio And Porch Features
Covered, Patio, Rear Porch, Screened
Security Features
Smoke Detector(s)
Spa Features
In Ground
Window Features
Blinds
Financial
HOA Name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
HOA Phone
407-392-1533
Map
Community
- Address14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL
- SubdivisionBAY ISLE 48 17
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Rental in WINTER GARDEN as of Aug 29, 2026
826
Rental Listed
112
Avg DOM
279
Avg $ / SqFt
$758,304
Avg List Price
Property Summary
- Located in the BAY ISLE 48 17 subdivision, 14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL is a Rental for sale in WINTER GARDEN, FL, 34787. It is listed for $6,000 To schedule a showing of MLS#o6430003 at 14411 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
