440 Grand Island Drive
Osterville, MA, 02655 $ 7,250,000
Bedrooms7 Baths9.2 Sq 11,546 Monthly Estimate*
$ 45,777
for $7,250,000 with 7 bedrooms and 9 full baths, 2 half baths. This 11,546 square foot home was built in 2013 on a lot size of 1.1.
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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FeaturesGeneralHeating Oil Propane
Cooling Central Air
Roof Shingle
Appliances Countertop Range Dishwasher Indoor Grill Microwave Refrigerator Range Hood Wall/Oven Cook Top Washer Wine Cooler Water Heater
HOA Fee 4620
Garage Spaces 3
Patio/Porch Features Deck Patio Porch
Security Features Security System
Construction Materials Shingle Siding
Year Built 2013
Stories Count 2
Property Subtype Single Family Residence
Tax Year 2026
Assoc Fee Paid Per Annually
County Barnstable
Property Type Residential
Association Amenities Road Maintenance Security Beach Access Boat Dock Golf Course
HOA true
Attached Garage true
Subdivision Name Oyster Harbors
Garage Y/N true
Other Structures Guest House
Total Rooms 16
Full Baths 9
Status Active
Directions Bridge Street to Oyster Harbors Gatehouse.
City Osterville
MLS Area Barnstable
Lot Size Units Acres
Lot Size Square Feet 47916
Tax Annual Amount 59471
Showing Instructions Total square footage bedroom and bathroom counts reflect both the main house and the guest house. Contact Robert Kinlin at 508.648.2739 rkinlin@robertpaul.com or Donna Aucoin at 508.737.0465 daucoin@robertpaul.com. Please give 24 hours notice.
Virtual Tour https://vimeo.com/1010678229?share=copy#t=0
Building Area Units Square Feet
Standard Status Active
Tax Assessed Value 7293500
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InteriorInterior Amenities Linen Closet Pantry Recessed Lighting Walk-In Closet(s) Wet Bar
Basement Finished Full
Flooring Wood Tile Carpet
Total Fireplaces 6
Air Conditioning Y/N true
Heating Y/N true
Half Baths 2
Laundry Features Electric Dryer Electric Dryer Hookup Washer Hookup
Total Bedrooms 7
Total Baths 11
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ExteriorParking Features Direct Access Garage Door Opener Off Street
Lot Features Fenced/Enclosed Interior Lot Cleared Level
Water Source Public
Total Parking 6
Lot Size Area 1.1
Building Area Total 11546
Lot Size Acres 1.1
Waterfront Y/N false
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* Excluded FeaturesList ByRobert B KinlinListing Agent
Berkshire Hathaway Homeservices Robert Paul PropertiesBroker
rkinlin@robertpaul.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $45,777
- Monthly Property Taxes
- $4,956
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Osterville, MA
Average List Price $4,607,129
Percent of Sale Price 36%
About Osterville, MA 3,556 Population
-11% Since 2002
$ 73,497 Median Income
54.53 Median Age
14% Households with Children
Trends Information provided by ATTOM Data Solutions.
0 Elementary School
0 Middle School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/1/2026 | $7,250,000 | | Listed Price |