Privately sited within the prestigious Oyster Harbors golf

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Home For Sale

440 Grand Island Drive

Osterville, Massachusetts 02655

Barnstable County

Community: Oyster Harbors

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$7,750,000 7 br, 10.0 bath 11546 sq. ft. 1.100 acres

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 entertainingpleting 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.

Interior:
  • Bedrooms: 7
  • Baths: 10.0
  • Sq Ft: 11546
  • Year Built: 2013
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 2
  • Heat/AC: Propane (Heating), Oil, Forced Air
  • Garage: Open, Off Street
Exterior:
  • Lot Size: 1.100 acre
  • Lot Dimensions: 
  • View Types: 
  • Yard: 
  • Siding: Shingle Siding
  • Roof: Shingle
  • Property Taxes: $57,908
  • Swimming Pool: Yes
  • MLS #: 22502682
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Contact Information:
Beach Home For Sale in Osterville, Massachusetts
Listing Agent: Robert B Kinlin, Robert Paul Properties, Inc., 508-420-1414, 508-420-1414 Listing Site, Listing Status: Active
Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc.. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6250809
Viewed 113 times.
Updated: Oct 15, 2025

This property is a Home located at 440 Grand Island Drive, Osterville, Massachusetts 02655, and is currently For Sale at $7,750,000. This Home has 7 bedrooms, 10.0 baths, 11546 sq ft.