440 Grand Island Dr

Taxes: $59,471 (2026)

About this home

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 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail defines elegant living and entertaining spaces, from the chef’s kitchen with granite islands and fireside sitting room to the spectacular sunroom with a bar, kitchen, and retractable screens. The main-level primary suite is a serene retreat, while four additional en-suite bedrooms and a sitting room await upstairs. The lower level includes a wine cellar, media room, gym, and game room. Outside, lush landscaping surrounds the resort-style pool and expansive lounging areas. Complete with beach and dock rights, this estate is an extraordinary offering in one of Cape Cod’s most prestigious settings.

Property details

Sewer

On-Site

Style

Modified

Water

City/Town Water

Cooling

Central Air

Heating

Central Heat, Individual

Type

Detached

Flooring

Wood, Tile, Wall to Wall Carpet, Marble

Road type

Paved

Appliances

Range, Wall Oven, Dishwasher, Microwave, Indoor Grill, Countertop Range, Refrigerator, Washer, Dryer, Refrigerator - Wine Storage, Vent Hood

Master Bath

Yes

Roof

Membrane

Garage

Attached, Garage Door Opener, Storage, Side Entry

Lot

Cleared, Level

Parking

1-10 Spaces

Basement

Full, Finished, Interior Access, Exterior Access

Exterior

Porch, Porch - Screened, Patio, Balcony, Pool - Inground Heated, Professional Landscaping, Fenced Yard, Guest House

Interior

Security System, Cable Available, Wetbar, French Doors, Elevator