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:
$895,000
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, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Construction Materials
Block, Stucco
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, Split Garage
Patio And Porch Features
Covered, Patio, Rear Porch, Screened
Roof
Shingle
Security Features
Smoke Detector(s)
Spa Features
In Ground
Window Features
Blinds
Financial
HOA Fee
$546
HOA Fee Frequency
Quarterly
HOA Includes
Private Road, Recreational Facilities
HOA Name
Bay Isle at Black Lake Homeowners Assn: c/o HMI
HOA Phone
407-392-1533
Tax Year
2025
Taxes
$11,924
Map
Community
- Address14411 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL
- SubdivisionBAY ISLE 48 17
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
- .
- 30 NORTH PARK
- ACREAGE
- ACREAGE & UNREC
- ADDITION TO MARY JEAN SUB
- ALEXANDER RIDGE
- AMBERLEIGH
- AMBERLEIGH 47/7
- ARROWHEAD LAKES
- AVALON COVE
- AVALON ESTATES
- AVALON HILLS SUB
- AVALON RESERVE
- AVALON RESERVE – VILLAGE 1
- AVALON RESERVE VILLAGE 1
- AVALON RIDGE
- AVALON WOODS
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE-PH I B D & G
- BLACK LAKE
- BLACK LAKE PARK PH 01
- BLACK LAKE PARK PH 02
- BLACK LAKE PRESERVE
- BRADFORD CREEK
- BRADFORD CRK PH I
- BRADFORD CRK PH II
- BRAY J W F ADD 01
- BRONSON’S LANDING
- BRONSONS LNDGS F & M
- BURCHSHIRE
- CANOPY OAKS PHASE 1
- CARRIAGE POINTE
- CARRIAGE POINTE A-I & L
- CITRUS COVE UNIT 01
- COBBLESTONE/WINTER GARDEN
- COURTLEA OAKS
- COVINGTON CHASE
- COVINGTON CHASE PH 2C
- COVINGTON PARK A B D E F G & J
- CROWN POINT SPGS
- CROWN POINT SPRINGS, UNIT 2
- CYPRESS RESERVE PH 1
- CYPRESS RESERVE PH 2
- CYPRESS RESERVE PHASE 2
- DANIEL CROSSING
- DANIELS CROSSING
- DANIELS LANDING
- DANIELS LANDING A-J
- DANIELS LNDG
- DANIELS LNDG A-J
- DEER ISLAND PH 02
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 2
- DEL WEBB OASIS PH 3
- DEL WEBB OASIS PHASE 2
- DEL WEBB OASIS PHASE 3
- ELLMAN PARK
- EMERALD ACRES
- ENCLAVE/HAMLIN
- ENCORE AT OVATION
- ENCORE AT OVATION – PHASE 4B 111/103 LOT 410
- ENCORE AT OVATION-PH 3
- ENCORE/OVATION PH 3
- ENCORE/OVATION-PH 2
- ENCORE/OVATION-PH 3
- ENCORE/OVATION-PH 4B
- ESTATES AT LAKEVIEW
- ESTS/LAKEVIEW PRESERVE
- FRIES WINTER GARDEN
- FULLERS CROSSING PH 01 44/14
- FULLERS LNDG B
- FULLERS XING PH 03 A-G
- GARDEN HEIGHTS
- GARDEN WEST
- GROVE PK/STONE CREST A-E
- GROVE RES & SPA HOTEL CONDO 3
- GROVE RES & SPA HOTEL CONDO IV
- GROVE RESIDENCE & SPA HOTEL
- GROVE RESIDENCE & SPA HOTEL CONDO
- GROVE RESIDENCE & SPA HOTEL CONDO 1
- GROVE RESIDENCE & SPA HOTEL CONDO 3
- GROVE RESIDENCE & SPA HOTEL CONDO I
- GROVE RESIDENCE & SPA HOTEL CONDO II
- GROVE RESIDENCE & SPA HOTEL CONDO IL
- GROVE RESIDENCE Y SPA HOTEL CONDO II
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT & SPA HOTEL CONDO IV
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDO 1
- GROVE RESORT AND SPA HOTEL CONDO II
- GROVE RESORT AND SPA HOTEL CONDOMINIUM
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 1
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 2
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 2 201903961
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM U
- GROVE RESORT AND WATER PARK
- GROVEHURST A-D
- HAMILTON GARDENS
- HAMILTON GARDENS PH 2A & 2B
- HAMLIN MEADOWS AT HAMLIN
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN RIDGE
- HARVEST AT OVATION
- HARVEST AT OVATION PHASE 2
- HARVEST/OVATION
- HAWKSMOOR PH 1
- HAWKSMOOR PH 2
- HAWKSMOOR PH 3
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PH 2
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK
- HICKORY HAMMOCK EMERALD POINTE
- HICKORY HAMMOCK PH 1A
- HICKORY HAMMOCK PH 1B
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2A
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE 110/69 LOT 19
- HIGHLANDS AT SUMMERLAKE GROVES
- HIGHLANDS/SUMMERLAKE GROVE
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS #1
- HIGHLANDS/SUMMERLAKE GRVS PH 1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HILLCREST
- HORIZON ISLE
- HORIZON ISLES
- INDEPENDENCE
- INDEPENDENCE COMMUNITY
- INDEPENDENCE, SIGNATURE LAKES
- ISLAND POINTE SUB
- ISLES LAKE HANCOCK
- ISLES OF LAKE HANCOCK
- J L DILLARD SUB 3
- JOE LOUIS PARK
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- K HOVNANIAN WINDING BAY PRESERVE
- KING BAY
- LAKE APOPKA SOUND
- LAKE AVALON GROVES
- LAKE AVALON GROVES REP
- LAKE AVALON GROVES REP 02
- LAKE AVALON GRVS 2ND REP
- LAKE AVALON HEIGHTS
- LAKE HANCOCK PRESERVE
- LAKE ROBERTS LNDG E
- LAKE STAR AT OVATION
- LAKESHORE PRESERVE
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 4
- LAKESHORE PRESERVE PH 5
- LAKESIDE AT HAMLIN
- LAKESIDE/HAMLIN
- LAKEVIEW POINTE/HORIZON WEST
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW PRESERVE PHASE 2
- LAKEVIEW RESERVE 46/149
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LIFT STATION/COBBLESTONE/WINTE
- LOVELESS J S ADD 01
- MAGNOLIA WOOD
- MAGNOLIA WOOD FIFTH ADD
- MANNS FIRST ADD
- MARY JEAN SUB
- MCALLISTER LNDG
- MCALLISTER LNDG PH 2
- MERCHANTS SUB
- MEZZANO
- MT PARK ORANGE GROVE
- NORTHLAKE AT OVATION
- NORTHLAKE AT OVATION PHASE 1 109/122 LOT 135
- NORTHLAKE AT OVATION PHASE 2 & 3
- NORTHLAKE AT OVATION PHASE 2 & 3 119/60 LOT 194
- NORTHLAKE/OVATION PH 1
- OAK PARK AT WINTER GARDEN
- OAKLAND PARK
- OAKLAND PARKB-1
- OAKLAND PARKB-2
- OAKS/BRANDY LAKE 01 REP A & B
- OAKS/BRANDY LAKE O
- ORANGE COVE
- ORANGE GROVE SUB
- ORCHARD
- ORCHARD A1-A26 B1 B2 C D1-D4
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 2 SIGNATURE LAKES
- ORCHARD HILLS PH 3
- ORCHARD PK/STILLWATER XING
- ORCHARD PK/STILLWATER XING PH
- OSPREY RANCH
- OSPREY RANCH PH 1
- OSPREY RANCH-PH 1
- OVERLOOK 2 AT HAMLIN
- OVERLOOK 2/HAMLIN PH 1 & 6
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERLOOK AT HAMLIN/WEST LAKE HANCOCK ESTATES
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PALISADES CONDO
- PANTHER VIEW
- PARK PLACE
- PARK PLACE/WINTER GARDEN
- PARKVIEW AT HAMLIN
- PROMINENT POINTE PHASE 2
- RAVENNA
- RAVENNA PH 1
- REGAL POINTE PH 02 47/133
- REGENCY OAKS F
- REGENCY OAKS PH 02 A-C
- RESERVE AT CARRIAGE POINTE
- RESERVE CARRIAGE POINTE
- ROPER RESERVE
- SANCTUARY/HAMLIN
- SANCTUARY/TWIN WATERS
- SAVANNAH RIDGE SUB
- SCHENLEY PARK
- SERENADE AT OVATION
- SHADOW LAWN
- SHOREFRONT COVE
- SHOWALTER PARK
- SIGNATURE LAKES
- SIGNATURE LAKES PARCEL 1A
- SIGNATURE LAKES PARCEL 1D
- SIGNATURE LAKES PH 02 A B H I J
- SIGNATURE LAKES PH 2
- SIGNATURE LAKES PH 2A
- SIGNATURE LAKES PH 3B-2 & 3B-3
- SIGNATURE LAKES PH 3B-4, 3B-5
- SIGNATURE LAKES PH 3B-4, 3B-5 & 3B-7 83/27 LOT 184
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PHASE 3B-6 83/8 LOT 1807
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LAKES-PCL 01D PH 02
- SIGNATURE LAKES, INDEPENDENCE
- SIGNATURE LKS-PCL 01A
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 01
- SIGNATURE LKS-PCL 01D PH 02
- SILVERLEAF
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN PHASE 3A
- SILVERLEAF OAKS AT HAMLIN PHASE 3A 115/63 LOT 499
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE BUNGALOWS
- SILVERLEAF RESERVE/HAML PH 2A
- SILVERLEAF RESERVE/HAMLIN PH 2
- SIPLIN HEIGHTS
- SOLOMON SUB
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- STONE CREEK 44/131
- STONE CREEK UNIT 4
- STONE CRK A-1 & A-2
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UT 04 48 48
- STONEYBROOK WEST UT 04 REP 49 121
- STOREY GROVE
- STOREY GROVE 50
- STOREY GROVE PH 1A-1
- STOREY GROVE PH 1B-1
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-4
- STOREY GROVE PH 1B-4A
- STOREY GROVE PH 2
- STOREY GROVE PH 3
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GROVE PHASE 4
- STOREY GRV PH 2
- STORY ROAD BUS PARK
- SUBURBAN SHORES
- SUMMERLAKE
- SUMMERLAKE GRVS
- SUMMERLAKE GRVS PH 2
- SUMMERLAKE PD PH 01A
- SUMMERLAKE PD PH 1A
- SUMMERLAKE PD PH 1B
- SUMMERLAKE PD PH 1B A REP
- SUMMERLAKE PD PH 1B-A REP
- SUMMERLAKE PD PH 2A & 2B
- SUMMERLAKE PD PH 2C 2D 2E
- SUMMERLAKE PD PH 2C-2E
- SUMMERLAKE PD PH 3A
- SUMMERLAKE PD PH 3B
- SUMMERLAKE PD PH 3C
- SUMMERLAKE PD PH 4B
- SUMMERLAKE PD PHASES 2C, 2D, 2E 83/145 LOT 9 BLK I
- SUMMERLAKE RESERVE
- THE GROVE RESORT
- THE GROVE RESORT AND SPA
- THE GROVE RESORT AND SPA CONDOMINIUM
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES OF WINTER GARDEN CONDO
- TOWNHOMES WINTER GARDEN
- TRADITIONS SUB
- TRIBUTE AT OVATION
- TRIBUTE AT OVATION WAY
- TRIBUTE OF OVATION
- TRIBUTE/OVATION
- TROYNELLE BY LAKE APOPKA
- TROYNELLE/BIG LAKE APOPKA
- TUCKER OAKS
- TUCKER OAKS CONDO PH 1
- TUCKER OAKS CONDO PH 7
- TUSCANY
- TUSCANY PH 02
- TWINWATERS
- TWINWATERS HOMEOWNERS’ ASSOCIATION, INC.
- VERDE PARK PH 1
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VILLAGE GROVE PHASE 2
- VILLAS AT TUCKER OAKS
- VININGS ADD WINTER GARDEN
- WALKERS GROVE
- WALKERS GROVE TWNHMS
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2C-1
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B & 3C
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 3B 3C 3D
- WATERLEIGH PH 3B-3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PH 5
- WATERLEIGH PHASE 5 116/135 LOT 228
- WATERMARK
- WATERMARK PH 1A
- WATERMARK PH 1B
- WATERMARK PH 2A
- WATERMARK PH 2B
- WATERMARK PH 2B1
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PHASE 4A
- WATERSIDE ON JOHNS LAKE
- WATERSIDE ON JOHNS LAKE PH 1
- WATERSIDE/JOHNS LAKE PH 2A
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 1
- WATERSIDE/JOHNS LK-PH 2A
- WEST LAKE HANCOCK ESTATES
- WESTCHESTER PLACE
- WESTFIELD III-PH A
- WESTFIELD LAKES PH 04 A-F
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR 1ST ADD
- WESTPOINT TWNHMS A & B
- WESTSIDE TOWNHOMES
- WESTSIDE TWNHMS
- WINCEY GROVES
- WINCEY GROVES PHASE 2
- WINCEY GRVS PH 1
- WINDING BAY II LLC
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS
- WINDTREE GARDENS CONDO PH 01
- WINDTREE GARDENS CONDO PH 02
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 05
- WINDTREE GARDENS PHASE 5
- WINTER GARDEN MANOR
- WINTER GARDEN SHORES REP
- WINTER GARDEN TRLS 01-3
- WINTER GROVE
- WINTERMERE POINTE
- WINTERMERE POINTE PH 02 46/141
- WINTERMERE POINTE PHASE 2
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Jun 09, 2026
831
Single Family Listed
105
Avg DOM
281
Avg $ / SqFt
$768,876
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 $895,000 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 $223. The average price per square foot for Single Family listings in WINTER GARDEN is $281. The average listing price for Single Family in WINTER GARDEN is $768,876. To schedule a showing of MLS#o6413972 at 14411 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
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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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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





