440 GRAND ISLAND DRIVE, OSTERVILLE MA, 02655

$7,750,000

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Cape Cod MLS #22502682

Status: Price Change
Year Built: 2013
Total Rooms: 16
Full Bathrooms: 9
Bedrooms: 7
Half Bathrooms: 2
Waterview: No
To Beach: Deeded Beach and Dock Rights mi.
Waterfront: No
Lot Size: 1.1 acres
Living Area: 11546 ft2
Price Change: 09/05/2025
Listing Date: 06/02/25 DOM: 449 days
Total Assessment: $7,293,500
Improvements Assessment: $5,010,900
Special Assessment: N/A
Annual Taxes: $59,471
Tax Year: 2026
Land Assessment: 0
Zoning: RF-1
Lead Paint: Unknown
Flood Zone: N/A

440 GRAND ISLAND DRIVE, OSTERVILLE MA, 02655

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


General Information:

VILLAGE: Osterville
STYLE: Single Family Residence
HEAT/COOLING: Forced Air, Oil, Propane
GARAGE: YES
BASEMENT:
Basement Type:
Convenient To: Conservation Area, Golf Course, House of Worship, Marina, Public Tennis, School, Shopping
Association: Yes - fee includes Road Maintenance, Security

Exterior Features:

Exterior Features: Private Yard
Pool: Y
Dock: N
Siding:
Roof: Shingle

Interior Features:

Fireplace: 6
Flooring: Carpet, Wood, Tile

Interior Features: Linen Closet, Pantry, Wet Bar, Breakfast Bar, Recessed Lighting, Walk-In Closet(s), Kitchen Island
Equipment/Appliances: Range Hood, Wall/Oven Cook Top, Wine Cooler, Microwave, Refrigerator, Washer, Water Heater, Indoor Grill, Countertop Range, Dishwasher

Mechanical Features:

Heating/Cooling: Forced Air, Oil, Propane
Utilities:

Listing Office Contact:


Listing Courtest of:
Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent: Robert Kinlin (508-420-1414)

440 GRAND ISLAND DRIVE OSTERVILLE MA 02655 Property Information Last Updated August 25, 2026 at 1:56:29 AM EDT.

 

CCIAOR MLS IDX listing courtesy of Berkshire Hathaway HomeServices Robert Paul Properties