440 Grand Island Drive, Osterville, MA, 02655

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$7,750,000
177 Days On Site

440 Grand Island Drive
Osterville, MA 02655

For Sale|Single Family Residence|Active
7
Beds
11
Total Baths
9
Full Baths
2
Partial Baths
11,546
SqFt
$671
/SqFt
2013
Built
Subdivision:
Oyster Harbors
County:
Barnstable
Listing courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties
440 Grand Island Drive440 Grand Island Drive440 Grand Island Drive440 Grand Island Drive
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Monthly Payment (Est.)

$35,359
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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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Listing Snapshot
Price 
$7,750,000
Days On Site 
177 Days
Bedrooms 
7
Inside Area (SqFt) 
11,546 sqft
Total Baths 
11
Full Baths 
9
Partial Baths 
2
Lot Size 
1.1 Acres
Year Built 
2013
MLS® Number 
22502682
Status 
Active
Property Tax 
$57,908
HOA/Condo/Coop Fees 
$385 monthly
Sq Ft Source 
Plans
Friends & Family
Recent Activity
13 hours agoListing updated with changes from the MLS®
3 months agoPrice changed to $7,750,000
6 months agoListing first seen on site
General Features
Acres 
1.1
Attached Garage 
Yes
Garage 
Yes
Garage Spaces 
3
Land Lease 
No
Parking 
Attached
Parking Spaces 
6
Property Sub Type 
Single Family Residence
Sewer 
Private Sewer
SqFt Total 
11546
Style 
Contemporary
Zoning 
RF-1
Interior Features
Appliances 
DryerCooktopWine CoolerWasherRange HoodRefrigeratorMicrowaveIndoor GrillDishwasherElectric Water Heater
Basement 
Interior EntryFullFinished
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Gas
Fireplaces 
6
Flooring 
WoodCarpetTile
Heating 
Interior 
Wet BarRecessed LightingPantryWalk-In Closet(s)Breakfast Bar
Laundry Features 
Sink
Bedroom 2 
Level - SecondDescription - Flooring: Carpet
Bedroom 3 
Level - SecondDescription - Flooring: Carpet
Bedroom 4 
Level - SecondDescription - Flooring: Carpet,Door(s): French
Dining Room 
Level - FirstDescription - Flooring: Wood
Kitchen 
Level - FirstDescription - Countertop(s): Granite,Flooring: Wood
Living Room 
Level - FirstDescription - Fireplace(s): Gas,Flooring: Wood,Door(s): French
Master Bedroom 
Level - FirstDescription - Flooring: Carpet,Door(s): French
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Exterior Features
Construction Details 
Shingle Siding
Fencing 
Fenced
Lot Features 
On Golf CourseNear Golf CourseLevelCleared
Patio And Porch 
DeckPorchPatio
Pool Features 
Pool CoverIn GroundHeatedGunitePrivate
Private Pool 
Yes
Roof 
Shingle
Windows/Doors 
French Doors
Community Features
Association Amenities 
Security
Association Dues 
4620
Community Features 
Golf
HOA Fee Frequency 
Annually
MLS Area 
Mid-Cape
Roads 
Paved
School District 
Barnstable
Township 
Barnstable
Schools
School District
Barnstable
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties



Listing information is provided by Participants of the Cape Cod Islands Association of REALTORS MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2025, Cape Cod Islands Association of REALTORS MLS.
Last checked: 2025-11-27 06:00 AM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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