Thomas D. Brown Real Estate Associates
Rentals 508-349-2700
300 Route 6
PO Box 2003
Truro, MA 02666

440 Grand Island Drive Osterville Barnstable MA 02655 MLS #22502682

MLS #22502682 image #0
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.
Current real estate data for Single Family in Barnstable as of May 17, 2026
208
Single Family Listed
84
Avg DOM
621
Avg $ / SqFt
$1,907,470
Avg List Price

Property Details

Price:
$7,750,000
MLS #:
22502682
Status:
Active
Beds:
7
Baths:
10
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Oyster Harbors
Listed Date:
Jun 2, 2025
Finished Sq Ft:
11,546
Total Sq Ft:
11,546
Lot Size:
47,916 sqft / 1.10 acres (approx)
Year Built:
2013
ContemporaryPoolOyster HarborsBarnstable

Schools

School District:
Barnstable

Interior

Appliances
Cooktop, Wine Cooler, Washer, Wall/Oven Cook Top, Range Hood, Security System, Refrigerator, Microwave, Indoor Grill, Electric Dryer, Dishwasher, Electric Water Heater
Bathrooms
9 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Fireplaces Total
6
Flooring
Wood, Carpet, Tile
Interior Features
Wet Bar, Recessed Lighting, Pantry, Linen Closet
Laundry Features
Laundry Areas, Sink, Built-Ins, First Floor

Exterior

Architectural Style
Contemporary
Association Amenities
Road Maintenance, Security
Attached Garage YN
1
Community Features
Golf
Construction Materials
Shingle Siding
Fencing
Fenced
Garage Spaces
3
Lot Features
Conservation Area, School, House of Worship, Near Golf Course, Shopping, Public Tennis, Marina, Level, Cleared
Parking Spots
6
Parking Total
6
Patio And Porch Features
Deck, Porch, Patio
Roof
Shingle
Stories
2

Financial

HOA Fee
$4,620
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$59,471

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Property Summary

    Located in the Oyster Harbors subdivision, 440 Grand Island Drive Osterville Barnstable MA is a Single Family for sale in Barnstable, MA, 02655. It is listed for $7,750,000 and features 7 beds, 10 baths, and has approximately 11,546 square feet of living space, and was originally constructed in 2013. The current price per square foot is $671. The average price per square foot for Single Family listings in Barnstable is $621. The average listing price for Single Family in Barnstable is $1,907,470. To schedule a showing of MLS#22502682 at 440 Grand Island Drive Osterville in Barnstable, MA, contact your Thomas D Brown R E Associates agent at 508-487-1112.

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Raised in Orleans and now a resident of Truro, Lucy is extremely familiar with life on the Outer Cape. She is experienced in real estate sales on Cape Cod and has been involved in construction, development and real estate for over thirty-five years here on the Outer Cape. She presently handles all facets of marketing for both Brown Associates and Cape Vacation Rentals. Degree in Sales & Marketing; formerly associated with Nickerson Realty Corp. where she handled all phases of land development, a…

More About Lucy
440 Grand Island Drive Osterville
Barnstable, MA