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Property Details: MLS #22603612
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.
Price: $12,000,000   |  Bedrooms: 4   |  Bathrooms: 3/0
166 Shore Road , Chatham, MA   02633
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GENERAL INFORMATION
Waterview: Yes - Y
Waterfront: Y
Miles to Beach:
Beach Description:
Beach Ownership:
Convenient To:
Association: No
Yearly Association Fee: $0

Lot Size (SQFT):

49000
Lot Size (Acres): 1.12
Living Area (SQFT): 1738
Lot Description:
Basement Type:

Year Built: 1940


EXTERIOR
Style: Single Family Residence
Pool:
Dock: N
Exterior Features:
Siding:
Roof:


INTERIOR

Total Rooms: 6
Bedrooms: 4
Full Bathrooms: 3
Half Bathrooms: 0
Fireplace:
Flooring:
Interior Features:
Equipment/Appliances:


MECHANICAL
Heating/Cooling: YES/
Utilities:
Hot Water:


TAX/LEGAL INFORMATION
Listing Date: July 27, 2026
Special Listing Conditions:
Improvements Assessment: $9,108,400.00
Title Reference: /
Annual Betterment:
Total Assessment: $9,108,400.00
Assessors Parcel:
Special Assessment:
Annual Taxes: $34,921.00
Tax Year: 2026
Land Assessment: $1,200.00
To Be Assessed:
Mass Use:

Asbestos:

Flood Zone:
Lead Paint:
Underground Fuel:
Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent: Guthrie Schofield Group (774-487-8554)


MLS Broker Reciprocity Listing
MLS Broker Reciprocity Disclaimer
Courtesy of Orleans Village Properties, LLC. All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Orleans Village Properties, LLC include the name of the listing broker. Neither the listing company nor Orleans Village Properties, LLC shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Orleans Village Properties, LLC has chosen to display only certain towns and/or types or styles of properties. Copyright 2002 - 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

SITE ACCESSIBILITY: Orleans Village Properties, LLC is committed to providing an accessible website. If you have difficulty accessing content, have difficulty viewing a file on the website, or notice any accessibility problems, please contact us to specify the nature of the accessibility issue and any assistive technology you use. We will strive to provide the content you need in the format you require.

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This site was last updated July 31, 2026 at 1:55:56 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

Orleans Village Properties, LLC has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.
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Orleans Village Properties, LLC
220 Main Street
PO Box 1551
East Orleans, MA 02643
Call: 508-255-1700
Text: 508-254-8001