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For SaleMLS# 22502682

440 Grand Island Drive

Osterville, MA 02655
$7,250,000
7Beds
11Baths
11,546Sq Ft
3 carGarage
1.1 acres · Built 2013

Home For Sale in Osterville, MA

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

Property Type
Single Family Residence
Year Built
2013
Bedrooms
7
Bathrooms
9 full · 2 half
Sq Footage
11,546
Lot / Acres
1.1 acres
County
Barnstable
Rooms Total
16
Stories
2
Garage
3 car
Parking
6 spaces
Basement
Finished, Full
Flooring
Wood, Tile, Carpet
Fireplace
6
Roof
Shingle
Construction
Shingle Siding
HOA
yes
Annual Taxes
$59,471
Tax Year
2026
Assessed Value
$7,293,500

Features & Amenities

Countertop Range
Dishwasher
Indoor Grill
Microwave
Refrigerator
Range Hood
Wall/Oven Cook Top
Washer
Wine Cooler
Water Heater
Linen Closet
Pantry
Recessed Lighting
Walk-In Closet(s)
Wet Bar
Fenced/Enclosed
Interior Lot
Cleared
Level
Deck
Patio
Porch
Electric Dryer
Electric Dryer Hookup
Washer Hookup

Interior Details

Appliances
Countertop Range, Dishwasher, Indoor Grill, Microwave, Refrigerator, Range Hood, Wall/Oven Cook Top, Washer, Wine Cooler, Water Heater
Interior Features
Linen Closet, Pantry, Recessed Lighting, Walk-In Closet(s), Wet Bar
Laundry
Electric Dryer, Electric Dryer Hookup, Washer Hookup

Exterior & Location Details

Patio / Porch
Deck, Patio, Porch
Directions
Bridge Street to Oyster Harbors Gatehouse.

Listed by: Robert B Kinlin from Berkshire Hathaway HomeServices Robert Paul Properties

© 2026 Cape Cod & Islands Multiple Listing Service. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of CCIMLS. Information provided is deemed reliable but not guaranteed.

Location

440 Grand Island Drive

Osterville, MA 02655

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Alexander Malo
Alexander Malo
Wood Real Estate

Estimated Monthly Payment

$45,624

20% down · 7.1% rate · 30-yr fixed

Principal & Interest$38,978
Property Taxes$6,163
Insurance (est.)$483

Listing Details

MLS #22502682
StatusActive
List Price$7,250,000
Lot Size1.1 acres
Year Built2013

About Osterville

Median Price
$1.45M
Avg Days on Market
38
Explore Osterville
CCIMLS Data Distribution

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Wood Real Estate, Inc. are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Wood Real Estate, Inc. shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.