440 Grand Island Drive, Osterville, MA 02655

bedrooms 7
bathrooms 10
|House
NZD $12,717,066
USD $7,250,000
Published on: 03 Jun 2025
Last updated on: 21 Oct 2026
440 Grand Island Drive, Osterville, MA 02655
440 Grand Island Drive, Osterville, MA 02655
440 Grand Island Drive, Osterville, MA 02655
+68
440 Grand Island Drive, Osterville, MA 02655
  • 68
Property ID: 110099909924
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Residential, Osterville, MA

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 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 Details

Basic Info

Property Type
House
Listing Status
Active
Land Size
4,451.55 m2
Building Size
1,072.66 m2
Year Built
2013
Rooms
7 bedroom(s), 10 bathroom(s)
Num Floors
2
County
Barnstable
Parcel ID
051-014-002
Provider
Cape Cod & Islands Association of REALTORS®, Inc.
Subdivision
Oyster Harbors
Brokerage Office Name
Robert Paul Properties, Inc.
Brokerage Office Phone
(508) 863-4663
Neighbourhoods
Oyster Harbors
Address
440 Grand Island Drive, Osterville, MA 02655

Tax History

YearTax amount
2026USD $59471NZD $104,317*

*Converted price in your currency provided by Open Exchange Rates. Exchange rates are subject to continuous change. Neither realestate.co.nz nor its affiliates guarantee that the conversion reflects current conversion rates and are not responsible for any inaccuracies. realestate.co.nz recommends that you independently verify any information before relying on it.

Contact Agent
Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
867 Main Street , Osterville, MA 02655
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Robert B Kinlin
867 Main Street , Osterville, MA 02655
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      Property ID: 110099909924

      Original Property ID: 3yd-CCIAORMA-22502682
      Data provided by Cape Cod & Islands Association of REALTORS®, Inc., MLS #: 22502682
      * THIS SERVICE MAY CONTAIN TRANSLATIONS POWERED BY GOOGLE. GOOGLE DISCLAIMS ALL WARRANTIES RELATED TO THE TRANSLATIONS, EXPRESS OR IMPLIED, INCLUDING ANY WARRANTIES OF ACCURACY, RELIABILITY, AND ANY IMPLIED WARRANTIES OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT.
      Copyright © 2026 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.