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440 Grand Island Drive

Osterville, MA 02655
  • $8,000,000
  • STATUS: Active
  • ON SITE: 15 Days
  • MLS #: 22502682
UPDATED: 59 min ago
$8,000,000
  • 7
    BEDS
  • 1.1
    ACRES
  • 9
    BATHS
  • 2
    1/2 BATHS
  • 11,546
    SQFT
  • $693
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2013
County:
Area:

School Ratings & Info

School District:

Description

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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Cape Cod & Islands MLS logo © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' 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 is not guaranteed accurate by the MLS or Cape Cod Real Estate Group. Data last updated: 2025-06-18T20:25:22.873.
www.capecodrealestategroup.com/homes/164464309
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440 Grand Island Drive Osterville, MA 02655

  • Price: $8,000,000
  • Status: Active
  • On Site: 15 Days
  • Updated: 59 min ago
  • MLS #: 22502682
7
Beds
9
Baths
2
½ Baths
1.1
Acres
11,546
SQFT
$693
$/SQFT
2013
Built
Neighborhood:
Oyster Harbors
County:
Barnstable
Area:
Barnstable
School District:
Barnstable
Property Description
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.
Exterior Features

Carport No Construction Materials Shingle Siding Dock No Fencing Fenced Foundation Details Poured Lot Features Conservation AreaSchoolHouse of WorshipNear Golf CourseShoppingPublic TennisMarinaLevelCleared Open Parking No Parking Total 6 Pool Features Pool CoverIn GroundHeatedGunite Pool Private Yes Roof Shingle Separate Living Quarters Description DetachedFirst FloorSecond Floor Water Front No Water View No

Interior Features

Appliances CooktopWasherWall/Oven Cook TopRefrigeratorMicrowaveIndoor GrillDishwasherElectric Water Heater Attached Garage Yes Basement Yes Basement1 Bulkhead AccessInterior EntryFullFinished Cooling True Cooling Features Central Air Door Features French DoorsFrench Fireplace Features Gas Fireplace YN Yes Fireplaces Total 6 Flooring WoodCarpetTile Garage Yes Heating Yes Interior Features Wet BarRecessed LightingPantryLinen Closet Laundry Features Laundry AreasSinkBuilt-InsFirst Floor Master Bedroom Level First Rooms Total 16

Property Features

Association Yes Association Amenities Road MaintenanceSecurity Association Fee 4620 Association Fee Frequency Annually Community Features Golf Flood Insurance Required No Flood Zone X Improvement Assessments 4163400 Land Assessments 2222100 Land Lease No Lead Paint Unknown Membership Required Yes New Construction No Nitrogen Sensitive Area Yes Other Assessments 592900 Property Attached No Property Sub Type Single Family Residence Road Responsibility Assoc Maintained Road Surface Type Paved Sewer Private Sewer Special List Conditions None Tax Annual Amount 57908 Tax Assessed Value 6978400 Tax Book Number C217695 Tax Year 2025 Warranty Available False Year Built Description Actual Year Round Yes Zoning RF-1

Cape Cod & Islands MLS logo Listing information © 2025 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties: rkinlin@robertpaul.com


Cape Cod & Islands MLS logo © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' 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 is not guaranteed accurate by the MLS or Cape Cod Real Estate Group. Data last updated: 2025-06-18T20:25:22.873.
 
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1645 Falmouth Rd BLD F Suite D6
Centerville MA, 02632