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Listing: 1 of 1 Updated 22 minutes ago

440 Grand Island Drive Osterville, MA 02655

7bd. 9fb. 2pb. Single Family $8,000,000



Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.


General Information for 440 Grand Island Drive Osterville, MA 02655

Town Barnstable
Village Osterville
County Barnstable
Stories 2
SQFT 11,546
Status Available
Listing Number 22502682 (CCIMLS)

Rooms Information for 440 Grand Island Drive Osterville, MA 02655

Family Room 0X0
Fireplace(s): Gas
Flooring: Wood
Door(s): French
Recessed Lighting
Cathedral Ceiling(s)
Kitchen Features 0X0
Countertop(s): Granite
Flooring: Wood
Recessed Lighting
Breakfast Bar
Built-in Features
Kitchen Island
Pantry
Dining Room 0X0
Flooring: Wood
Recessed Lighting
Built-in Features
Laundry Laundry Areas
Sink
Built-Ins
First Floor
Bedroom 0X0
Flooring: Carpet
Door(s): French
Office/Sitting Area
Walk-In Closet(s)
Recessed Lighting
Master Bath Features Private Full Bath
Bedroom 1 0X0
Flooring: Carpet
Door(s): French
Office/Sitting Area
Walk-In Closet(s)
Recessed Lighting
Bedroom 2 0X0
Flooring: Carpet
Private Full Bath
Closet
Bedroom 3 0X0
Flooring: Carpet
Private Full Bath
Closet
Bedroom 4 0X0
Flooring: Carpet
Door(s): French
Private Full Bath
Closet

Interior Information for 440 Grand Island Drive Osterville, MA 02655

Basement Bulkhead Access
Interior Entry
Full
Finished
Interior Features Wet Bar
Recessed Lighting
Pantry
Linen Closet
Fireplace Yes
Appliances Cooktop
Washer
Wall/Oven Cook Top
Refrigerator
Microwave
Indoor Grill
Dishwasher
Electric Water Heater

Exterior Information for 440 Grand Island Drive Osterville, MA 02655

Lot Size 1.10 acres
Lot Description Conservation Area
School
House of Worship
Near Golf Course
Shopping
Public Tennis
Marina
Level
Cleared
Construction Shingle Siding
Garage 3 Car Garage
Parking Spaces: 6
Lot Conservation Area
School
House of Worship
Near Golf Course
Shopping
Public Tennis
Marina
Level
Cleared
Sewer Private Sewer
Pool Pool Cover
In Ground
Heated
Gunite

Neighborhood Information for 440 Grand Island Drive Osterville, MA 02655

Neighborhood Amenities Road Maintenance
Security

Schools information for 440 Grand Island Drive Osterville, MA 02655

Elementary Barnstable
Middle Barnstable
High Barnstable
General Area Public, Private School and College Information

Miscellaneous Information for 440 Grand Island Drive Osterville, MA 02655

Year Built 2013
Association Fee 4620
Taxes $57,908 /Yr

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Listing provided courtesy of robert b kinlin, berkshire hathaway homeservices robert paul properties

Market Snapshot as of June 12, 2025 (Last 30 days)

Condo Data
Units 6,956
Avg Price $992,963
Avg Days Listed 97
Total New Listings 1
House Data
Units 12,541
Avg Price $1,308,534
Avg Days Listed 80
Total New Listings 15
Multi-Family Data
Units 1,946
Avg Price $1,274,040
Avg Days Listed 106
Total New Listings 0

Average Price by Property Type
Units by Property Type
Average Days on Market by Property Type

Recent Home Sales In This Zip Code (02655)

For a more detailed market analyis one of our real estate agents can provide you with a full report.

Address Closing Date List Price Closing Price % of List Price
42 Pond Street
Osterville, MA 02655
01/03/2025 $1,348,000 $1,300,000 96%
21 Nathans Way
Osterville, MA 02655
12/16/2024 $2,950 $2,950 100%
146 Wintergreen Circle
Osterville, MA 02655
12/16/2024 $799,000 $780,000 98%
3040 Falmouth Rd. A1
Osterville, MA 02655
12/15/2024 $1,800 $1,800 100%
16 Second Avenue 5A
Osterville, MA 02655
12/06/2024 $649,000 $610,000 94%
920 Main Street 4
Osterville, MA 02655
12/05/2024 $633,000 $595,000 94%
920A Main Street 17
Osterville, MA 02655
11/27/2024 $85,000 $75,000 88%
17 Chine Way
Osterville, MA 02655
11/26/2024 $1,295,000 $1,275,000 98%
82 Blanid Road
Osterville, MA 02655
11/26/2024 $1,500,000 $1,500,000 100%
298 Starboard Lane
Osterville, MA 02655
11/21/2024 $2,695,000 $2,500,000 93%
39 Tower Hill Road 1A 1A
Osterville, MA 02655
11/19/2024 $630,000 $610,000 97%
33 Waterfield Road
Osterville, MA 02655
11/18/2024 $1,050,000 $1,050,000 100%
28 Bayview Road
Osterville, MA 02655
11/15/2024 $4,150,000 $4,150,000 100%
34 Rebecca Lane
Osterville, MA 02655
11/04/2024 $544,000 $540,000 99%
201 Old Mill Road
Osterville, MA 02655
11/01/2024 $2,399,000 $2,250,000 94%
92 Concord Lane
Osterville, MA 02655
10/31/2024 $3,500 $3,500 100%
22 Marion Way
Osterville, MA 02655
10/31/2024 $850,000 $845,000 99%
263 Tower Hill Road
Osterville, MA 02655
10/28/2024 $1,195,000 $1,250,000 105%
65 Deerfield Road
Osterville, MA 02655
10/24/2024 $940,000 $890,000 95%
13 South Street
Osterville, MA 02655
10/20/2024 $2,500 $2,500 100%
39 Tower Hill Road 5A
Osterville, MA 02655
10/11/2024 $689,000 $660,000 96%
42 Yawl Road
Osterville, MA 02655
10/11/2024 $628,000 $628,000 100%
812 Main Street
Osterville, MA 02655
10/07/2024 $1,000 $1,000 100%
51 Poplar Drive
Osterville, MA 02655
10/03/2024 $749,000 $749,000 100%
104 Great Bay Road
Osterville, MA 02655
06/25/2024 $7,995,000 $8,250,000 103%

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Listing: 1 of 1 Updated 22 minutes ago

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