
166 Shore Road Chatham — Photo 1 of 39
Recent Drop: $3,050,000
$8,950,000
Investment Analysis — 166 Shore Road
Chatham, MA 02633
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 4-bedroom in 02633 carries an estimated $3,400/mo in gross rent — about a -0.04% cap rate and $-3,913/yr in estimated NOI at the $8,950,000 list price. Adjust every assumption in the calculator below.
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.
ADU Potential
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater
Geography
Property History
$8,950,000
Was $12,000,000
Aug 7, 2026
MLS® 73556482
$12,000,000
Jul 27, 2026
MLS® 73556482
Listing Agent: Guthrie Schofield Group
Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties
MLS® Number: 73556482
