440 Grand Island Drive Osterville, MA $ 7,750,000
440 Grand Island Drive
$ 7,750,000
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440 Grand Island Drive

Osterville, MA, 02655
$ 7,750,000
Bedrooms7 Baths9.2 Sq 11,546

Monthly Estimate*

$ 48,350

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Single Family Home for sale in Osterville, MA

for $7,750,000 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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Single Family Active

Price

$ 7,750,000

Bedrooms

7

Full Bath

9

Half Bath

2

Property Type

Single Family

Taxes

$ 57,908

Style

Contemporary

Lot Size

1.1

Year Built

2013

Town/City

Osterville

County/Region

Barnstable

MLS | Web ID

22502682

Features
Interior
Interior Amenities Wet Bar Recessed Lighting Pantry Linen Closet
Basement Bulkhead Access Interior Entry Full Finished
Flooring Wood Carpet Tile
Total Fireplaces 6
Fireplace Features Gas
Kitchen Level First
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 2
Laundry Features Laundry Areas Sink Built-Ins First Floor
Total Bedrooms 7
Living Room Level First
Below Grade Finished Area Unit Type Square Feet
Kitchen Features Recessed Lighting Breakfast Bar Built-in Features Kitchen Island Pantry
Total Baths 11
Primary Bathroom Features Private Full Bath
Living Room Features Recessed Lighting Cathedral Ceiling(s)
Bedroom 4 Features Private Full Bath Closet
Bedroom 3 Features Private Full Bath Closet
Bedroom 2 Features Private Full Bath Closet
Dining Room Features Recessed Lighting Built-in Features
Kitchen Description Countertop(s): Granite Flooring: Wood
Primary Bedroom Features Office/Sitting Area Walk-In Closet(s) Recessed Lighting
Dining Room Level First
Bedroom 4 Level Second
Bedroom 3 Level Second
Second Bedroom Level Second
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General
Sewer Private Sewer
Cooling Central Air
Roof Shingle
Appliances Cooktop Wine Cooler Washer Wall/Oven Cook Top Range Hood Security System Refrigerator Microwave Indoor Grill Electric Dryer Dishwasher Electric Water Heater
Zoning RF-1
HOA Fee 4620
Garage Spaces 3
Patio/Porch Features Deck Porch Patio
Architectural Style Contemporary
Pool Features Pool Cover In Ground Heated Gunite
Construction Materials Shingle Siding
Year Built 2013
Stories Count 2
Township Barnstable
Property Subtype Single Family Residence
Tax Year 2025
Community Features Golf
Assoc Fee Paid Per Annually
County Barnstable
New Construction false
Property Type Residential
Association Amenities Road Maintenance Security
HOA true
Attached Garage true
Subdivision Name Oyster Harbors
Garage Y/N true
Total Rooms 16
Full Baths 9
Status Active
Directions Bridge Street to Oyster Harbors Gatehouse.
City Osterville
High School District Barnstable
Lot Size Units Acres
Lot Size Square Feet 47916
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 57908
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 dauco
Home Warranty Y/N false
Property Condition Actual
Virtual Tour https://vimeo.com/1010678229?share=copy#t=0 https://vimeo.com/1010678229?share=copy#t=0
Building Area Units Square Feet
Primary Bedroom Level First
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Barnstable
Elementary School District Barnstable
Tax Assessed Value 6978400
Waterview Y/N No
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Exterior
Fencing Fenced
Lot Features Conservation Area School House of Worship Near Golf Course Shopping Public Tennis Marina Level Cleared
Total Parking 6
Lot Size Area 1.1
Foundation Details Poured
Building Area Total 11546
Lot Size Acres 1.1
Road Surface Type Paved
Lot Size Source Assessor
Waterfront Y/N false
Door Features French Doors French
Road Responsibility Assoc Maintained
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* Excluded Features
List By
Robert B Kinlin

Listing Agent

Berkshire Hathaway Homeservices Robert Paul Properties

Broker

rkinlin@robertpaul.com

Email

Affordability Calculator

$53,176
Per Month
91%
9%
0%
Monthly Principal & Interest
$48,350
Monthly Property Taxes
$4,826
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% 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.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
9/5/2025$7,750,000 -3.13% Price Down
6/2/2025$8,000,000 Listed Price

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440 Grand Island Drive, Osterville, MA, 02655 is a Single Family Home for sale at $7,750,000 with 11,546 sqft and a lot size of 1.1. 440 Grand Island Drive has 7 bedrooms, 9.2 baths, and was built in 2013. The property's zip code is 02655 which is in Osterville, MA