Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$7,750,000

440 Grand Island Drive, Osterville, MA 02655

7 Beds 9 Full Baths 2 Half Baths 11,546 Sq Ft 1.10 acres 3 Car Garage
MLS# 22502682 · Residential / (Single Family Residence)
Listed: 06/02/25 (listing data as of 07/30/26 at 3:09 pm)

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

Property Details

Property TypeResidential
(Single Family Residence)
StatusActive
MLS Number22502682
Year Built2013
Annual Taxes$59,471 (2026)
Total Assessment$7,293,500
Square Footage11,546
Price/Sq Ft$671/sq ft
Separate Living QuartersYes
Additional Finished Space4,700 sqft
Lot Size1.10 acres
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 Market423
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
  • Carpet Flooring
  • Office/Sitting Area
  • Private Full Bath
  • Recessed Lighting
  • French Door Access
  • Walk-in Closet

Bedroom 2

  • Second Floor
  • Closet
  • Carpet Flooring
  • Private Full Bath

Bedroom 3

  • Second Floor
  • Closet
  • Carpet Flooring
  • Private Full Bath

Bedroom 4

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

Living Area Details

Living Room

  • First Floor
  • Cathedral Ceiling
  • Gas Fireplace
  • Wood Flooring
  • Recessed Lighting
  • French Door Access

Dining Room

  • First Floor
  • Built-Ins
  • Wood Flooring
  • Recessed Lighting

Kitchen

  • Pantry
  • First Floor
  • Breakfast Bar
  • Built-Ins
  • Wood Flooring
  • Laundry Areas
  • Recessed Lighting

Appliances

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

Exercise Room

  • Basement

Home Office

  • First Floor

Sun Room

  • First Floor

Laundry Room

  • First Floor
  • Built-Ins
  • Tile Flooring
  • Laundry Areas
  • Sink

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

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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 07/30/2026. 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.