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47 Days on market
166 Shore Road Chatham — Photo 1 of 39

166 Shore Road Chatham — Photo 1 of 39

Recent Drop: $3,050,000

$12,000,000
$8,950,000

$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.

View Standard Listing

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

Original Price$12,000,000
Annual Taxes$34,921

Parking

Garage0
Off-Street4

Interior Specifications

Total Rooms6
Fireplaces1
Flooring--
BasementPartial, Bulkhead

Climate & Utilities

HeatingForced Air
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
RoofWood
FoundationConcrete Perimeter
ZoningR40

Property & Lot

Acres1.12
SqFt Lot48,787
Lot Features--

Amenities & Appliances

Gas Water Heater

Geography

Property History

Price Drop
$8,950,000

Was $12,000,000

Aug 7, 2026

MLS® 73556482

Listed
$12,000,000

Jul 27, 2026

MLS® 73556482

Listing Provided By

Listing Agent: Guthrie Schofield Group

Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties

MLS® Number: 73556482