View a Virtual Tour of 440 Grand Island Drive, Osterville, MA440 Grand Island Drive, Osterville, MA
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
440 Grand Island Drive, Osterville, MA
Listing Courtest of:
Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent: Robert Kinlin (508-420-1414)
Listing provided courtesy of Berkshire Hathaway HomeServices Robert Paul Properties
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This site was last updated 04/18/2026. All properties are subject to prior sale, changes, or withdrawal.
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