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For salePrice cut: $3.05M (8/7)
$8,950,000
4beds
1,738sqft

166 Shore Road, Chatham, MA 02633

4beds
1,738sqft
Single family residence
Built in 1940
1.12 Acres
No data
$5,150 price/sqft

What's special

Shiplap-clad great roomWell-appointed guest spaces

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.

36 days
|
7,741
|
276
|
Source: CCIMLS,MLS#: 22603612MLS Logo
Travel times

Sunrise

Aerial

Living Room

Dining Room

Kitchen

Primary Bedroom

Primary Bathroom

Den

Guest Bedroom

Guest Bedroom

Bathroom

Zillow last checked:

Listing updated:

Listed by:

Guthrie Schofield Group 774-487-8554,

Berkshire Hathaway HomeServices Robert Paul Properties

Source: CCIMLS,MLS#: 22603612MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 3
  • Full bathrooms: 3
Heating
  • Natural Gas
Cooling
  • Central Air
Appliances
  • Included: Natural Gas, Water Heater
Features
  • Flooring: Wood, Tile
  • Basement: Partial
Interior area
  • Total structure area: 1,738
  • Total interior livable area: 1,738 sqft

Property

Features
  • Stories: 2
  • Exterior features: Outdoor Shower, Garden, Underground Sprinkler System
  • On waterfront: Yes
  • Waterfront features: Waterview, Waterfront, Ocean Front
  • Body of water: Atlantic Ocean,Salt
Lot
  • Size: 1.12 Acres
Details
  • Parcel number: CHAT M:0016E B:016A L:00K20
  • Special conditions: None

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Shingle Siding
  • Roof: Wood
Condition
  • Year built: 1940

Utilities & green energy

  • Water: Public

Community & HOA

Location
  • Region: Chatham

Financial & listing details

  • Price per square foot: $5,150/sqft
  • Tax assessed value: $9,108,400
  • Annual tax amount: $34,921
  • Date on market: 7/27/2026
  • Cumulative days on market: 16 days

Price history

DateEventPrice
8/7/2026Price change$8,950,000-25.4%$5,150/sqft
Source: MLS PIN #73556482 Report a problem
7/27/2026Listed for sale$12,000,000+200.4%$6,904/sqft
Source: CCIMLS #22603612 Report a problem
6/16/2020Listing removed$3,995,000$2,299/sqft
Source: Robert Paul Properties #22001703 Report a problem
3/16/2020Listed for sale$3,995,000-19.3%$2,299/sqft
Source: Robert Paul Properties #72634151 Report a problem
1/30/2020Listing removed$4,950,000$2,848/sqft
Source: Robert Paul Properties #21902961 Report a problem
5/28/2019Price change$4,950,000+17.9%$2,848/sqft
Source: Robert Paul Properties #21902961 Report a problem
4/29/2019Listed for sale$4,200,000-6.6%$2,417/sqft
Source: Robert Paul Properties, Inc. #21902961 Report a problem
11/11/2015Listing removed$4,499,000$2,589/sqft
Source: Robert Paul Properties #21505002 Report a problem
5/26/2015Listed for sale$4,499,000+55.1%$2,589/sqft
Source: Robert Paul Properties, Inc. #21505002 Report a problem
8/18/2003Sold$2,900,000+590.5%$1,669/sqft
Source: Public Record Report a problem
1/26/1998Sold$420,000$242/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$30,684 +3%$8,842,600 +6%
2024$29,783 +31.1%$8,342,700 +42.5%
2023$22,723 +42.6%$5,856,500 +69.8%
2022$15,931 $3,448,200
2021$15,931 -11.3%$3,448,200 -7.5%
2020$17,969 +6.7%$3,728,000 +7.3%
2019$16,846 +0.2%$3,473,500 +0.6%
2018$16,815 -0.3%$3,452,700 +2.9%
2017$16,874 +23.4%$3,354,700 +23.2%
2016$13,672 +3.4%$2,723,500 +2.8%
2015$13,219 -1.7%$2,649,000 +0%
2014$13,454 -2.1%$2,648,400 -3.1%
2013$13,744 +27.1%$2,732,500 +12.5%
2012$10,811 +4%$2,429,400
2011$10,398 -12.3%$2,429,400 -21.7%
2010$11,850 +3%$3,102,200 +0.9%
2009$11,502 +7.2%$3,075,300 +5.1%
2008$10,734 $2,924,700
2007$10,734 +2.1%$2,924,700 +3.8%
2006$10,510 +11.1%$2,817,600 +34%
2005$9,464 $2,103,200
2004$9,464 +35.1%$2,103,200 +91.6%
2003$7,004 +2.5%$1,097,800 +10%
2001$6,836 +54.7%$998,000 +117.4%
1998$4,420 $459,000

Find assessor info on the county website

Monthly payment

Est. payment
$50,704/mo
Principal & interest
$46154
Property taxes
$4550
More affordability toolsChevron Right

Estimated market value

$8,391,400

$7.97M - $8.81M

$4,787/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 02633

Nearby schools

Chatham Elementary School
Grades PK-40.7 miles
8/10
GreatSchools® Rating
Test Score Rating
8/10
Monomoy Regional Middle School
Grades 5-71.4 miles
7/10
GreatSchools® Rating
Test Score Rating
7/10
Student Progress Rating
7/10
Monomoy Regional High School
Grades 8-126.2 miles
5/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
6/10
Student Progress Rating
1/10