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Active

166 Shore Road

Chatham, MA 02633

Offered at$8,950,000

Residential · Active · MLS #73556482
Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties | Guthrie Schofield Group

4Bedrooms
3Bathrooms
1,738Square feet
1940Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
6
Heating
Forced Air
Cooling
Central Air
Fireplaces
1

Building

Style
Single Family Residence
Year built
1940
Parking
4
Foundation
Concrete Perimeter
Roof
Wood

Land & utilities

Lot size
1.12 acres
Water
Public
Sewer
Private Sewer
Waterfront
Y
Zoning
R40

Financial

Annual taxes
$34,921
Assessment year
2026

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$5,495,397

Estimated range $3,420,937$7,569,857

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Chatham

MetricThis propertyChatham
List price$8,950,000$2,850,000214% above local
Price / sq ft$5,150$1,145350% above local
Days on market389158% below local
Explore homes in Chatham

Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.

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Common questions

About 166 Shore Road

Can I schedule a private showing?

Yes. Request a tour of 166 Shore Road and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.