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440 Grand Island Drive

Osterville, MA 02655

7 beds
11 baths
11,546 sqft
~1 acre lot
$692 per sqft
2013 build
– on site

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.

Listing courtesy of CCI / Robert B Kinlin / Berkshire Hathaway HomeServices Robert Paul Properties

Last checked: Checking… • Last updated Jun 3, 2025 •

MLS# 22502682 —

This home is listed in more than one place. See it here.

The Building

Year Built:

2013
New Construction:

false
Construction Materials:

Shingle Siding
Roof:

Shingle
Foundation Details:

Poured
Stories:

2
Basement:

Bulkhead Access
Door Features:

French Doors
Building Area Units:

Square Feet
Building Area Total:

11546
Building Area Source:

Plans
Below Grade Finished Area Units:

Square Feet

Interior

Interior Features:

Wet Bar
Living Room Level:

First
Kitchen Features:

Recessed Lighting, Breakfast Bar, Built-in Features, Kitchen Island, Pantry
Kitchen Description:

Countertop(s): Granite,Flooring: Wood
Rooms Total:

16
Living Room Features:

Recessed Lighting, Cathedral Ceiling(s)
Kitchen Level:

First
Living Room Description:

Fireplace(s): Gas,Flooring: Wood,Door(s): French
Dining Room Features:

Recessed Lighting, Built-in Features
Dining Room Description:

Flooring: Wood
Dining Room Level:

First
Laundry Features:

Laundry Areas
Fireplace:

true
Fireplaces Total:

6
Fireplace Features:

Gas
Flooring:

Wood

Room Dimensions

Living Area Units:

Square Feet

Location

Directions:

Bridge Street to Oyster Harbors Gatehouse.
Coordinates:

-70.418099, 41.613708
Latitude:

41.613708
Longitude:

-70.418099

The Property

Property Type:

Residential
Property Subtype:

Single Family Residence
Property Condition:

Actual
Property Attached:

false
Parcel Number:

051014002
Lot Features:

Conservation Area
Lot Size Acres:

1.1
Lot Size SqFt:

47916
Lot Size Area:

1.1
Lot Size Units:

Acres
Lot Size Source:

Assessor
Zoning:

RF-1
Fencing:

Fenced
Waterfront:

false
Road Surface Type:

Paved
Road Responsibility:

Assoc Maintained
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2025
Tax Annual Amount:

57908
Tax Assessed Value:

6978400

Beds

Bedrooms Total:

7
Master Bedroom Level:

First
Master Bedroom Features:

Office/Sitting Area, Walk-In Closet(s), Recessed Lighting
Master Bedroom Description:

Flooring: Carpet,Door(s): French
Bedroom 2 Level:

Second
Bedroom 2 Features:

Private Full Bath, Closet
Bedroom 2 Description:

Flooring: Carpet
Bedroom 3 Level:

Second
Bedroom 3 Features:

Private Full Bath, Closet
Bedroom 3 Description:

Flooring: Carpet
Bedroom 4 Level:

Second
Bedroom 4 Features:

Private Full Bath, Closet
Bedroom 4 Description:

Flooring: Carpet,Door(s): French

Baths

Total Baths:

10
Total Baths:

11
Full Baths:

9
Half Baths:

2
Master Bath Features:

Private Full Bath

The Listing

Home Warranty:

false
Virtual Tour URL Branded:

https://vimeo.com/1010678229?share=copy#t=0
Virtual Tour URL Unbranded:

https://vimeo.com/1010678229?share=copy#t=0

Heating & Cooling

Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Sewer:

Private Sewer

Appliances

Appliances:

Cooktop

Schools

Elementary School District:

Barnstable
Middle Or Junior School District:

Barnstable
High School District:

Barnstable

The Community

Subdivision Name:

Oyster Harbors
Community Features:

Golf
Association:

true
Association Amenities:

Road Maintenance
Association Fee Frequency:

Annually
Association Fee:

4620
Pool Private:

true
Pool Features:

Pool Cover

Parking

Parking Total:

6
Garage:

true
Garage Spaces:

3
Attached Garage:

true
Carport:

false
Open Parking:

false

Monthly cost estimate

Asking price

$8,000,000

Expense	Monthly cost
Mortgage	$42,837
Taxes	$4,825
Insurance	$2,200
HOA fees	$385
Utilities	$503 See report
Total	$50,750/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
6/2/25 Jun 2, 2025	Listed / Active	CCI	$8,000,000	90.5% (13.7% / YR)
10/29/18 Oct 29, 2018		CCI	$4,200,000	12.0% (1.4% / YR)
7/1/10 Jul 1, 2010		CCI	$3,750,000	265.9% (85.4% / YR)

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This house located in Mid Cape, Barnstable, MA 02655 is currently for sale for $8,000,000. 440 Grand Island Drive is a 11,546 square foot house with 7 beds and 11 baths that has been on Estately for 5 days. 440 Grand Island Drive is in the Mid Cape neighborhood of Barnstable and has a WalkScore® of 8, making it car-dependent.

This site was last updated on 06/07/2025. All properties are subject to prior sale, changes, or withdrawal.