440 Grand Island Dr, Osterville, MA 02655
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
440 Grand Island Dr,Barnstable, MA 02655
$7,750,000
- 7 Beds
- 11 Baths
- 11,546 sq. ft.
- Single family
- Active
Listed by: robert kinlin
Office: berkshire hathaway homeservices robert paul properties
MLS#:73383981
Source:MLSPIN
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....
Contact an agent
Home facts
- Year built:2013
- Listing ID #:73383981
- Updated:August 25, 2026 at 11:02 AM
Rooms and interior
- Bedrooms:7
- Total bathrooms:11
- Full bathrooms:9
- Half bathrooms:2
- Rooms Total:16
- Flooring:Carpet, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet, Flooring - Wood, Marble, Tile, Wood
- Dining Description:Closet/Cabinets - Custom Built, Coffered Ceiling(s), Recessed Lighting, Wood
- Kitchen Description:Breakfast Bar / Nook, Countertops - Upgraded, Dishwasher, Flooring - Wood, Indoor Grill, Kitchen Island, Microwave, Oven, Pantry, Plumbed For Ice Maker, Range, Range Hood, Refrigerator, Second Dishwasher, Wine Refrigerator
- Basement Description:Finished, Full, Interior Entry
- Living area:11,546 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Fireplace, Fireplace(s), Oil
- Central air:Yes
Structure and exterior
- Roof:Wood
- Year built:2013
- Building area:11,546 sq. ft.
- Lot area:1.1 Acres
- Lot Features:Cleared, Level
- Architectural Style:Contemporary
- Exterior Features:Balcony, Patio, Porch, Professional Landscaping, Screened
- Foundation Description:Concrete Perimeter
Utilities
- Water:Public
- Sewer:Private Sewer
Finances and disclosures
- Price:$7,750,000
- Price per sq. ft.:$671.23
- Tax amount:$59,471 (2026)
Features and amenities
- Appliances:Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Laundry features:Closet/Cabinets - Custom Built, Dryer, Electric Dryer Hookup, First Floor, Flooring - Marble, Washer, Washer Hookup
- Amenities:Elevator, Wet Bar, Wine Cellar
- Pool features:Pool - Inground Heated, Private Pool
Parking
- Total parking spaces:9
- Parking description:Attached, Garage Door Opener, Garage Faces Side, Off Street, Storage
- Garage:Yes
- Garage spaces:3
New listings near 440 Grand Island Dr
- New
$659,000Active3 beds 1 baths1,156 sq. ft.112 Osterville West Barnstable Road, Osterville, MA 02655
MLS# 22603898Listed by: KINLIN GROVER COMPASS - New
$3,000,000Active0.83 Acres264 Sea View Avenue, Osterville, MA 02655
MLS# 22604115Listed by: SOTHEBY'S INTERNATIONAL REALTY - Open Sat, 10am to 12pmNew
$1,100,000Active2 beds 2 baths2,010 sq. ft.51 Falling Leaf Lane, Osterville, MA 02655
MLS# 22604062Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES - New
$795,000Active3 beds 2 baths1,248 sq. ft.111 Westwind, Barnstable, MA 02655
MLS# 73565006Listed by: Compass - New
$2,700,000Active4 beds 3 baths2,050 sq. ft.72 Hathaway Rd Road, Osterville, MA 02655
MLS# 22603965Listed by: THE FOLEY COMPANY
$18,500,000Active7 beds 11 baths10,104 sq. ft.47 Sunset Point, Barnstable, MA 02655
MLS# 73563501Listed by: Berkshire Hathaway HomeServices Robert Paul Properties
$18,500,000Active7 beds 11 baths10,104 sq. ft.47 Sunset Point, Osterville, MA 02655
MLS# 22603952Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,250,000Active3 beds 4 baths2,721 sq. ft.35 Blue Heron Drive, Osterville, MA 02655
MLS# 22603916Listed by: THE FOLEY COMPANY
$3,350,000Active4 beds 4 baths3,686 sq. ft.141 Hollingsworth Rd, Barnstable, MA 02655
MLS# 73560747Listed by: Compass
$4,950,000Active5 beds 8 baths5,970 sq. ft.313 Bridge Street, Osterville, MA 02655
MLS# 22603652Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES