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: 133
Average Price: $2,003,851
Highest Listing Price: $19,995,000
Lowest Listing Price: $315,000

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Chatham Homes For Sale

Price, High to Low
211 Properties Found.
Photo of Listing #21306159
  • MLS® #: 21306159
  • 97 Tilipi Run
  • Chatham, MA 02633
  • $19,995,000
  • 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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Photo of Listing #21717503
  • MLS® #: 21717503
  • 72 Main Street
  • Chatham, MA 02633
  • $5,000,000
  • 5 Bed, 5 Bath, 2905 SqFt, 1.17 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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Photo of Listing #21802938
  • MLS® #: 21802938
  • 114 Cranberry Lane
  • North Chatham, MA 02650
  • $4,995,000
  • 5 Bed, 9 Bath, 6072 SqFt, 1.42 Acres
  • Single Family
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Photo of Listing #21803466
  • MLS® #: 21803466
  • 155 & 157 Bridge Street
  • Chatham, MA 02633
  • $4,995,000
  • 8 Bed, 9 Bath, 7720 SqFt, 2.83 Acres
  • Single Family
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Photo of Listing #21803306
  • MLS® #: 21803306
  • 369 Old Harbor Road
  • Chatham, MA 02633
  • $4,950,000
  • 18 Bed, 22 Bath, 9161 SqFt, 1.77 Acres
  • Single Family
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Photo of Listing #21713971
  • MLS® #: 21713971
  • 141 Cotchpinicut Road
  • Chatham, MA 02633
  • $4,900,000
  • 8 Bed, 7 Bath, 4193 SqFt, 1.03 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

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

North Chatham: Hot Real Estate Market

The real estate market is hot in many areas of the country right now, and North Chatham is certainly no exception. In fact, just declared North Chatham as number ten on the list of places with the nation’s hottest luxury neighborhoods.The website credits some of this to wealthy northeasterners in search of a destination outside of the big city. With high demand right now and a limited supply of homes to work with, it’s meant a big boost in home prices. Right now, the median ho... Read More

Famous Chatham Residents

Famous in its own right, it just so happens that Chatham also gets to lay claim to several famous names and faces. In fact, you’ll find that several notable people can be traced to the Chatham area, some who currently own homes in the area and some that have moved on, but left their mark on the area.Harry Connick, Jr.One such resident is musician and actor Harry Connick, Junior. If you think perhaps you’ve crossed paths with the famous entertainer before on the Cape, you may just be right... Read More

Handcrafted Cape Cod Boats

There’s no doubt that boating is a big part of a Cape Cod lifestyle, and for many that means looking local when it comes to the design and purchase of a boat, as well. That’s why you’ll find many boats handcrafted right on Cape Cod, and designed to sail the local waters.E.M. Crosby BoatworksWith an impressive eight generations of quality workmanship to its name, E.M. Crosby Boatworks in West Barnstable is a family-owned boatbuilding company, and traces its legacy of family boat building b... Read More

First Night Chatham

The countdown is on to ring in the New Year with First Night Chatham. The annual event is packed with family fun, from the annual town photo at noon to the traditional Countdown Cod drop at the strike of midnight.With non-stop fun and entertainment, this year’s event promises two fireworks displays, the return of the popular Noise Parade and at least 70 planned performers, entertaining the crowds at nearly two-dozen different venues in Chatham.Now in its 26th year, a full lineup of perfor... 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 05/22/2018. All properties are subject to prior sale, changes or withdrawal.