440 Grand Island Drive, Osterville, MA 02655

Description

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.

Property Information

Property Features

Interior:

Wet Bar, Recessed Lighting, Pantry, Walk-In Closet(s), Breakfast Bar

Appliances:

Dryer, Cooktop, Wine Cooler, Washer, Range Hood, Refrigerator, Microwave, Indoor Grill, Dishwasher, Electric Water Heater

Cooling:

Central Air

Flooring:

Wood, Carpet, Tile

Fireplace:

Gas

Basement:

Interior Entry, Full, Finished

Pool:

Pool Cover, In Ground, Heated, Gunite, Private

Parking:

Attached

Laundry:

Sink

Patio:

Deck, Porch, Patio

Fencing:

Fenced

Lot Features:

On Golf Course, Near Golf Course, Level, Cleared

Construction:

Shingle Siding

Roof:

Shingle

Community:

Golf

Sewer:

Private Sewer

Rooms

• Bedroom 2Second
• Bedroom 3Second
• Bedroom 4Second
• Dining RoomFirst
• KitchenFirst
• Living RoomFirst
• Master BedroomFirst

HOA & Tax

HOA:

$4,620/Annually

Annual Tax:

$59,471 (2026)

Assessed Value:

$7,293,500

Parcel #:

051014002

Directions

Bridge Street to Oyster Harbors Gatehouse.

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