440 Grand Island Drive, Osterville, MA 02655
Local realty services provided by:CENTURY 21 North East
440 Grand Island Drive,Osterville, MA 02655
$7,750,000
- 7 Beds
- 11 Baths
- 11,546 sq. ft.
- Single family
- Active
Listed by: robert b kinlin
Office: berkshire hathaway homeservices robert paul properties
MLS#:22502682
Source:CAPECOD
Price summary
- Price:$7,750,000
- Price per sq. ft.:$671.23
- Monthly HOA dues:$385
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 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....
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Home facts
- Year built:2013
- Listing ID #:22502682
- Added:378 day(s) ago
- Updated:June 16, 2026 at 02:52 PM
Rooms and interior
- Bedrooms:7
- Total bathrooms:11
- Rooms Total:16
- Basement Description:Bulkhead Access, Finished, Full, Interior Access
- Living area:11,546 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Forced Air
Structure and exterior
- Year built:2013
- Building area:11,546 sq. ft.
- Lot area:1.1 Acres
- Lot Features:Cleared, Fenced/Enclosed, Interior Lot, Level
- Construction Materials:Shingle Siding
Finances and disclosures
- Price:$7,750,000
- Price per sq. ft.:$671.23
- Tax amount:$59,471
Features and amenities
- Amenities:Linen Closet, Pantry, Recessed Lighting, Walk-In Closet(s), Wet Bar
Parking
- Parking description:Direct Access, Garage Door Opener, Off Street
- Garage spaces:3
Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor CENTURY 21 North East shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. CAPECOD Member Broker: Jim D’AmicoNew listings near 440 Grand Island Drive
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