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14411 Hampshire Bay Circle

Winter Garden, FL 34787
  • $885,000
  • STATUS: Active
  • ON SITE: 62 Days
  • MLS #: O6413972
Price Reduced
UPDATED: 40 min ago
$885,000
  • 4
    BEDS
  • 0.3
    ACRES
  • 3
    BATHS
  • 2
    1/2 BATHS
  • 4,010
    SQFT
  • $221
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2005
County:

School Information

Elementary School:
Middle School:
High School:

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.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-07T15:00:07.483.
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14411 Hampshire Bay Circle Winter Garden, FL 34787

  • Price: $885,000
  • Status: Active
  • On Site: 62 Days
  • Updated: 40 min ago
  • MLS #: O6413972
4
Beds
3
Baths
2
½ Baths
0.3
Acres
4,010
SQFT
$221
$/SQFT
2005
Built
Neighborhood:
Bay Isle 48 17
County:
Orange
Area:
Winter Garden/Oakland
Elementary School:
Sunridge Elementary
Middle School:
Sunridge Middle
High School:
West Orange High
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.
Exterior Features

Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 3 Direction Faces North Exterior Features French DoorsIrrigation SystemOutdoor ShowerSidewalk Foundation Details Slab Lot Features City LotLevelSidewalk Lot Size Dimensions 100 x 130 Open Parking YN Yes Parking Features DrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces SideSplit Garage Patio And Porch Features CoveredPatioRear PorchScreened Pool Features GuniteIn GroundSalt WaterScreen EnclosureTile Pool Private Yn Yes Road Frontage Type Street PavedPrivate Road Road Surface Type PavedAsphalt Roof Shingle Spa Features In Ground Spa YN Yes Water Access Lake Water Access Yn Yes Water Body Name BLACK LAKE Water Extras Fishing Pier Water Extras Yn Yes Water View Yn No Waterfront Yn No

Interior Features

Additional Rooms Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityLoftMedia Room Appliances Built-In OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigerator Building Area Total 5049 Cooling Central Air Cooling YN Yes Fireplace Yn No Flooring CarpetLaminateTile Furnished Unfurnished Heating CentralElectricHeat Pump Heating YN Yes Interior Features Ceiling Fan(s)Crown MoldingHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s) Laundry Features InsideLaundry Room Levels Two Rooms Living Room Media Room Bedroom 3 (Ceiling Fan(s)En Suite BathroomExhaust FanJack & Jill BathroomLinen Closet) Dining Room Family Room (Ceiling Fan(s)) Bedroom 4 (Ceiling Fan(s)En Suite BathroomJack & Jill BathroomSplit VanitiesTub With ShowerWalk-In Closet(s)) Office (Ceiling Fan(s)) Balcony/Porch/Lanai Dinette Kitchen (Breakfast BarPantryKitchen IslandStone Counters) Bedroom 2 (Ceiling Fan(s)En Suite BathroomTub With ShowerWalk-In Closet(s)) Loft Balcony/Porch/Lanai ( Sewer Public Sewer Stories Total 2 Water Source Public Window Features Blinds

Property Features

Additional Lease Restrictions No short term rentals allowed. Buyer to confirm any lease restrictions through HOA and City Additional Parcels YN No Association Amenities GatedParkPlayground Association Approval Required Yn No Association Fee 546.25 Association Fee Frequency Quarterly Association Fee Includes Private RoadRecreational Facilities Association Fee Monthly Amount 182.08 Association Fee Requirement Required Association Yn Yes Builder Name Toll Orlando LP Cdd Yn No Community Features DockWater AccessAssociation Recreation - OwnedDeed RestrictionsIrrigation-Reclaimed WaterParkPlaygroundSidewalks Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventionalVA Loan Minimum Lease 1-2 Years New Construction Yn No Occupant Type Owner Ownership Fee Simple Pet Restrictions Buyer to confirm any pet restrictions through HOA and City Pets Allowed Yes Planned Unit Development Yn Yes Property Sub Type Single Family Residence Realtor Info As-Is Security Features Smoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 11923.59 Total Annual Fees 2185 Total Monthly Fees 182.08 Utilities BB/HS Internet AvailableCable AvailableElectricity ConnectedSewer ConnectedStreet LightsUnderground UtilitiesWater Connected Yrs Of Owner Prior To Leasing Re No Zoning R-1


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of STOCKWORTH REALTY GROUP: 407-909-5900.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-07T15:00:07.483.
 
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