Chatham Real Estate

Chatham is an upscale resort town occupying the southeast “elbow” of Cape Cod. Originally a prosperous fishing and whaling center, Chatham still is home to many 18th century buildings which add to its charm. Some of the most sought after properties are renovated captains’ homes that take advantage of the harbor and ocean views.

The town offers six saltwater beaches fronting Nantucket Sound and the Atlantic Ocean and is perhaps best known for the Chatham Lighthouse Beach.

Real Estate Statistics

Total Listings: 122
Average Price: $1,794,721
Highest Listing Price: $14,950,000
Lowest Listing Price: $325,000

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Chatham Homes For Sale

Price, High to Low
198 Properties Found.
Photo of Listing #21808394
  • MLS® #: 21808394
  • 97 Tilipi Run
  • Chatham, MA 02633
  • $14,950,000
  • 6 Bed, 10 Bath, 11284 SqFt, 1.9 Acres
  • Single Family
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Photo of Listing #21806851
  • MLS® #: 21806851
  • 558 Fox Hill Road
  • Chatham, MA 02633
  • $9,995,000
  • 5 Bed, 10 Bath, 10058 SqFt, 2.74 Acres
  • Single Family
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Photo of Listing #21808188
  • MLS® #: 21808188
  • 103 Shore Road
  • Chatham, MA 02633
  • $9,995,000
  • 5 Bed, 10 Bath, 6923 SqFt, 1.33 Acres
  • Single Family
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Photo of Listing #21808231
  • MLS® #: 21808231
  • 108 Shore Road
  • Chatham, MA 02633
  • $9,900,000
  • 7 Bed, 8 Bath, 6276 SqFt, 1.62 Acres
  • Single Family
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Photo of Listing #21407880
  • MLS® #: 21407880
  • 74 Sears Point Road
  • Chatham, MA 02633
  • $5,995,000
  • 5 Bed, 4 Bath, 2597 SqFt, 6.63 Acres
  • Single Family
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Photo of Listing #21802665
  • MLS® #: 21802665
  • 24 Captain Sears Way
  • Chatham, MA 02633
  • $4,999,999
  • 5 Bed, 6 Bath, 5896 SqFt, 0.96 Acres
  • Single Family
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Chatham Community Summary

This pristine expanse of sand is famed for nature walks out to Monomoy Island as well as views of the daily migration routes of Chatham seals.   At the heart of the beach, is the much photographed Chatham Light -- an active lighthouse at the Coast Guard Station that aids in the navigation of Chatham Waters.

Chatham is also well known for its pedestrian-friendly downtown which provides a myriad of shops, galleries, restaurants and inns.  During the summer, residents enjoy concerts in the gazebo on Main Street.  Distinctive boutiques specializing in antiques, resort clothing,  fine art, jewelry, and nautical treasures provide nearly one mile of shopping.  Seafood restaurants are also popular destinations fueled by the abundance of fresh catch.  The elegant Chatham Bars Inn provides spectacular water views and a Gatsby-like setting for tourists and residents alike.  

For many residents, Chatham is a year-round community offering a “First Night” during the holiday season as well as the “Spring Fling” fashion show in May to benefit various charitable organizations.
Chatham is bordered by Harwich to the west, Pleasant Bay and Orleans to the north, the Atlantic Ocean to the east and Nantucket Sound to the south.  Villages include Chatham proper, Chatham Port, North Chatham, West Chatham, and South Chatham.   Approximately 34 miles east of the Sagamore Bridge, Chatham is 85 miles southeast of Boston.

Blog Posts About Chatham

Cape Seals Getting Feisty

Photo: Allison Richards Cape Cod is known for its stunning scenery and abundant marine life, but it seems some of the Cape’s seals are getting a bit feisty as of late. There have been two recent reports of seals coming in contact with children along the Cape this summer, including a girl who was bitten on her hands in mid-August at Ryder’s Cove. Just one day later a young boy was also bitten.Apparently in the first incident the teenager was preparing to board a boat at the town landing ... Read More

Where to go for Spa Services in Chatham

Cape Cod isn’t just a place to go relax out on the sand and the water. It’s also a place to enjoy true relaxation from one of the many spas that dot the area. Particularly in Chatham you’ll find plenty of options for indulging in pure relaxation.Chatham Bars InnThe Chatham Bars Inn takes the entire experience up a notch with its inspirational spa suites. The resort personalizes the spa treatment to each guest, from music to aromatherapy and products. The rejuvenating experience takes adva... Read More

Chatham Bars Inn is a Cape Institution

Photo: Leslie_atFlickr A true Cape institution, Chatham Bars Inn serves up more than a century of charm and history on Cape Cod. This luxury resort is the epitome of elegance, a world-renowned destination that continues to draw in guests to rave reviews.Originally designed as a hunting lodge for wealthy vacationers from the Boston area, the site transformed itself into a real destination. In fact, some of the prominent names in American history have once stayed here, from William Rockef... Read More

Communities Unite to Protect Pleasant Bay

Several Cape Cod communities are banding together to help protect Pleasant Bay now, and for years to come. The towns of Chatham, Brewster, Orleans and Harwich all share its watershed. Just recently they joined together, gaining issuance of the first Watershed Permit ever in the state. While it may seem that everything came together in recent weeks, it’s actually been a work in progress for a couple of decades.That’s when the four towns first adopted a Pleasant Bay Resource Management Plan... Read More

Chatham amp; Harwich Music Strolls

Family-friendly entertainment is on tap all summer long with live music strolls in both Chatham and in Harwich Port. While the tradition has been a long-standing one in Harwich, the fun just spread to Chatham this summer season. Dubbed Mondays on Main, the new Chatham addition brings musicians, bands and other types of live entertainment to Main Street. The Monday evening event stretches for eight weeks this summer, from locations including the Chatham Wine Bar to the rotary, and features... Read More

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. Summary or thumbnail real estate listings held by brokerage firms other than Robert Paul Properties are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Robert Paul Properties shall be responsible for any typographical errors, misinformation or misprints and shall be held totally harmless. This site was last updated 11/18/2018. All properties are subject to prior sale, changes or withdrawal.