
166 Shore Road Chatham — Photo 1 of 39
Recent Drop: $3,050,000
$8,950,000
Chatham, MA 02633
Beds
4
Baths
3
SqFt
1,738
Style
Single Family
Built
1940
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.
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Chatham, MA.
Gas Water Heater
Was $12,000,000
Aug 7, 2026
MLS® 73556482
Jul 27, 2026
MLS® 73556482
4,512
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$85K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
15.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
513 housing units permitted in the last 12 months (-50% vs the prior 12 months) — 128 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 869 sq ft (the lesser of 900 sq ft or half the 1,738 sq ft principal dwelling). Lot size: 48,787 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Provided by MLS PIN
Listing Office: Provided by MLS PIN
MLS® Number: 73556482
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