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: 134
Average Price: $1,819,408
Highest Listing Price: $17,500,000
Lowest Listing Price: $315,000

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Chatham Homes For Sale

Price, High to Low
194 Properties Found.
Photo of Listing #21306159
  • MLS® #: 21306159
  • 97 Tilipi Run
  • Chatham, MA 02633
  • $17,500,000
  • 6 Bed, 10 Bath, 10974 SqFt, 1.9 Acres
  • Single Family
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Photo of Listing #21607479
  • MLS® #: 21607479
  • 67 Wilkey Way
  • Chatham, MA 02633
  • $13,500,000
  • 6 Bed, 9 Bath, 7040 SqFt, 1.26 Acres
  • Single Family
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Photo of Listing #21801182
  • MLS® #: 21801182
  • 150 -154 Cross Street
  • Chatham, MA 02633
  • $11,700,000
  • 10 Bed, 10 Bath, 8000 SqFt, 1.3 Acres
  • Single Family
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Photo of Listing #21607303
  • MLS® #: 21607303
  • 75 Tilipi Run
  • Chatham, MA 02633
  • $9,900,000
  • 6 Bed, 6 Bath, 6043 SqFt, 1.45 Acres
  • Single Family
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Photo of Listing #21407880
  • MLS® #: 21407880
  • 74 Sears Point Road
  • Chatham, MA 02633
  • $6,750,000
  • 5 Bed, 4 Bath, 2597 SqFt, 6.63 Acres
  • Single Family
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Photo of Listing #21714366
  • MLS® #: 21714366
  • 113 Seapine Road
  • Chatham, MA 02633
  • $5,695,000
  • 4 Bed, 6 Bath, 5850 SqFt, 0.62 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

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

Biking in Chatham

Exploring Cape Cod doesn’t necessarily always mean out on the water. While boating is, of course, a popular pastime, it’s not the only way to see all that the region has to offer.Chatham, in particular, is a great location to view on two wheels. With that in mind, there are plenty of bike trails in Chatham to take on, most notably the Chatham branch of the Cape Cod Rail Trail. Often used by bicyclists, the trail winds through a generally wooded area of Chatham, often crossing over existin... Read More

Chatham Light Shines Bright

Volunteers are gearing up for another summer season highlighting the bright history of Chatham Light. The historic lighthouse often hosts tours during the summer season, offering up the opportunity to get a close-up view of this early 19th century landmark.The Cape’s second lighthouse, Chatham Light was first constructed in the early 1800s, easily distinguished by its two fixed white lights. Originally consisting of two wooden towers and a keeper house, the lighthouse was no match for Mot... Read More

Nauset Beach Dispute Resolved

After about a year of talks, including a partial impasse that’s lasted for the past several months, the two Cape Cod towns at odds over Nauset Beach patrols and revenue just signed off on a short-term agreement. Until now, selectmen from Chatham and Orleans hadn’t been able to come to an agreement at all. The newly signed, one-year agreement means Chatham will now patrol its own portion of the barrier beach and keep 25-percent of permit revenue paid by non-residents for off-road vehicle... 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 Old Cape Sotheby's International Realty are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Old Cape Sotheby's International Realty shall be responsible for any typographical errors, misinformation or misprints and shall be held totally harmless. This site was last updated 07/20/2018. All properties are subject to prior sale, changes or withdrawal.