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I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

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  1. Home
  2. Listings
  3. 166 Shore Road, Chatham, MA 02633
Active
30 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

166 Shore Road, Chatham, MA 02633

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$5150/sqft
Local Avg (Chatham)$1143/sqft
351% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Chatham, MA.

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

Population

4,512

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$85K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

15.9%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Barnstable County

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)

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.

Full Chatham, MA market report ZIP 02633 market data
Listing Provided By

Listing Agent: Provided by MLS PIN

Listing Office: Provided by MLS PIN

MLS® Number: 73556482

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