Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$7,250,000
-9.4% from original list of $8,000,000 · September 1, 2026

440 Grand Island Drive, Osterville, MA 02655

7 bedrooms 9 Full Baths 2 Half Baths 11,546 Sq Ft 1.10 acres 3 Car Garage
MLS# 22502682 · Residential / (Single Family Residence)
Listed: 12/19/25 (listing data as of 09/25/26 at 2:05 am)
  • Primary Suite
  • Chef's Kitchen
  • Built-Ins
  • Finished Lower Level
  • Front Porch
  • 1st Floor Primary Bedroom
  • Private Pool
  • Central A/C
  • 6 Fireplaces

About This Property

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.

Property Details

Property TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22502682
Year Built2013
Annual Taxes$59,471 (2026)
Total Assessment$7,293,500
Square Footage11,546
Price/Sq Ft$628/sq ft
Separate Living QuartersYes
Additional Finished Space4,700 sqft
Lot Size1.10 acres
Total Rooms16
Bedrooms7
Full Baths9
Half Baths2
Heat Source Forced Air, Oil, Propane
Add'l Heating Forced Air
Cooling A/C Central Air
Association Fee $4,620.00 (Annually)
Association Fee Includes Road Maintenance, Security
Garage Spaces3
Days on Market280
WaterfrontNo
Private PoolYes
Private Pool Description Covered, Gunite, Heated, In Ground
Fireplaces6
Lot Features Cleared, Fenced/Enclosed, Interior Lot, Level

Bedroom Details

Primary Bedroom

  • First Floor
  • Walk-In Closet(s)
  • French Door
  • Recessed Lighting
  • Private Full Bath
  • Office/Sitting Area
  • Carpet Flooring

Bedroom 2

  • Second Floor
  • Private Full Bath
  • Carpet Flooring

Bedroom 3

  • Second Floor
  • Private Full Bath
  • Carpet Flooring

Bedroom 4

  • Second Floor
  • French Door
  • Private Full Bath
  • Carpet Flooring

Living Area Details

Living Room

  • First Floor
  • French Door
  • Recessed Lighting
  • Wood Flooring
  • Gas Fireplace
  • Cathedral Ceiling(s)

Dining Room

  • First Floor
  • Recessed Lighting
  • Wood Flooring
  • Built-in Features

Kitchen

  • First Floor
  • Kitchen Island
  • Wood Flooring
  • Granite Counters
  • Built-in Features
  • Breakfast Bar
  • Recessed Lighting
  • Pantry
  • Laundry Areas

Appliances

  • Countertop Range
  • Dishwasher
  • Electric Dryer
  • Indoor Grill
  • Microwave
  • Range Hood
  • Refrigerator
  • Security System
  • Wall/Oven Cook Top
  • Washer
  • Wine Cooler

Foyer

  • Cathedral Ceiling(s)

Sunroom

  • First Floor

Game Room

  • Basement Floor

Laundry

  • First Floor
  • Laundry Areas
  • Tile Flooring
  • Built-in Features

Exercise Room

  • Basement Floor

Office

  • First Floor

Sep Living Qtrs Info

Baths - Full 3
Beds 2
Baths - Total 3

Convenient To

  • Conservation Area
  • Golf Course
  • House of Worship
  • Marina
  • Public Tennis
  • School
  • Shopping

Exterior Features

  • Private Yard

Interior Features

  • Electric Dryer Hookup
  • Elevator
  • Linen Closet
  • Pantry
  • Recessed Lighting
  • Walk-In Closet(s)
  • Washer Hookup
  • Wet Bar

Location

Nearby Listings

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Listing Courtesy of: Robert B Kinlin / Berkshire Hathaway HomeServices Robert Paul Properties

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 09/25/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.