Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
4 Beds
3 Baths
1,738 sqft

$8,950,000

166 Shore Road, Chatham MA, 02633

Price per sqft$5,149.60
Built in1940
Property size1,738 sqft
Property typeResidential

Overview

Pending

Listed Jul 27, 2026

Updated 2 days ago

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.

$59,545/mo

Est. mortgage payment based on a $8,950,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
22603612

Interior Features

Bedrooms
4
Bathrooms
3
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.12 Acres

Other Property Details

Taxes
$34,921
Tax Frequency
Annually
Waterfront
Yes

Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Guthrie Schofield Group

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Kristen Winn are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 9/17/2026. Neither the listing broker nor Kristen Winn shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.

Copyright© 2026 Cape Cod and Islands Multiple Listing Service, Inc. All rights reserved.

Powered by Luxury Presence