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440 Grand Island Drive

Osterville, MA 02655
  • $7,250,000
  • STATUS: Active
  • ON SITE: 491 Days
  • MLS #: 22502682
UPDATED: 76 min ago
$7,250,000
  • 7
    BEDS
  • 1.1
    ACRES
  • 9
    BATHS
  • 2
    1/2 BATHS
  • 11,546
    SQFT
  • $628
    $/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 © 2026 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: 2026-10-07T14:25:35.1.
www.capecodrealestategroup.com/homes/164464309
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440 Grand Island Drive Osterville, MA 02655

  • Price: $7,250,000
  • Status: Active
  • On Site: 491 Days
  • Updated: 76 min ago
  • MLS #: 22502682
7
Beds
9
Baths
2
½ Baths
1.1
Acres
11,546
SQFT
$628
$/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

Attached Garage YN Yes Construction Materials Shingle Siding Foundation Details Poured Garage YN Yes Parking Features Direct AccessGarage Door OpenerOff Street Parking Total 6 Patio And Porch Features DeckPatioPorch Private Pool Yes Private Pool Description CoveredGuniteHeatedIn Ground Roof Shingle Separate Living Quarters Yes

Interior Features

Appliances Countertop RangeDishwasherIndoor GrillMicrowaveRefrigeratorRange HoodWall/Oven Cook TopWasherWine CoolerWater Heater Basement FinishedFull Basement Description Bulkhead AccessFinishedFullInterior Access Bedroom2 Private Full BathCloset Bedroom2 Flooring Carpet Bedroom2 Level Second Floor Bedroom3 Private Full BathCloset Bedroom3 Flooring Carpet Bedroom3 Level Second Floor Bedroom4 Private Full BathCloset Bedroom4 Flooring Carpet Bedroom4 Level Second Floor Cooling Central Air Cooling YN Yes Dining Room Recessed LightingBuilt-Ins Dining Room Flooring Wood Dining Room Level First Floor Fireplaces Total 6 Flooring WoodTileCarpet Foyer ClosetCathedral Ceiling Heat Forced Air Heating OilPropane Heating YN Yes Interior Features Linen ClosetPantryRecessed LightingWalk-In Closet(s)Wet Bar Kitchen Recessed LightingPantryLaundry AreasKitchen IslandBuilt-InsBreakfast Bar Kitchen Countertops Granite Kitchen Flooring Wood Kitchen Level First Floor Laundry Features Electric DryerElectric Dryer HookupWasher Hookup Laundry Room Laundry AreasBuilt-InsSink Laundry Room Flooring Tile Laundry Room Level First Floor Living Room Recessed LightingCathedral Ceiling Living Room Fireplace Gas Living Room Flooring Wood Living Room Level First Floor Other Room1 Level Basement Other Room1 Room Type Exercise Room Other Room2 Level First Floor Other Room2 Room Type Home Office Other Room3 Level First Floor Other Room3 Room Type Sun Room Other Room4 Level Basement Other Room4 Room Type Game Room Primary Bedroom Office/Sitting AreaPrivate Full BathRecessed LightingWalk-in Closet Primary Bedroom Flooring Carpet Primary Bedroom Level First Floor Rooms Total 16 Separate Living Quarters Bedrooms 2 Separate Living Quarters Full Bath 3

Property Features

Association Amenities Road MaintenanceSecurityBeach AccessBoat DockGolf Course Association Fee 4620 Association Fee Frequency Annually Association YN Yes Convenient To Conservation AreaMarinaPublic TennisShoppingGolf CourseHouse of WorshipSchool FEMAFlood Zone X Fence Fenced Golf Course Front No Golf Course View No Lot Features Fenced/EnclosedInterior LotClearedLevel Membership Required Yes Miles To Beach Comments Deeded Beach and Dock Rights Other Structures Guest House Property Sub Type Single Family Residence Region Mid-Cape Renovated No Security Features Security System Separate Living Quarters Description DetachedSecond FloorFirst Floor Special Listing Conditions None Tax Annual Amount 59471 Tax Assessed Value 7293500 Tax Year 2026 Water Source Public Waterfront YN No Year Round Yes

Cape Cod & Islands MLS logo Listing information © 2026 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 © 2026 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: 2026-10-07T14:25:35.1.
 
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1645 Falmouth Rd BLD F Suite D6
Centerville MA, 02632