440 Grand Island Dr, Osterville, MA 02655

Osterville
Local realty services provided by:ERA The Castelo 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 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail defines elegant living and entertaining spaces, from the chef’s kitchen with granite islands and fireside sitting room to the spectacular sunroom with a bar, kitchen, and retractable screens. The main-level primary suite is a serene retreat, while four additional en-suite bedrooms and a sitting room await upstairs. The lower level includes a wine cellar, media room, gym, and game room. Outside, lush landscaping surrounds the resort-style pool and expansive lounging areas. Complete with beach and dock rights, this estate is an extraordinary offering in one of Cape Cod’s most prestigious settings.

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Home facts

  • Year built:2013
  • Listing ID #:73383981
  • Updated:March 19, 2026 at 10:23 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
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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