Chatham Loop Real Estate

Chatham Loop

The Chatham Loop is an exclusive section of Chatham that circles Mill Pond and Little Mill Pond and is defined as Main Street, Bridge Street, and Stage Harbor Road. The Chatham Loop passes near the elite Sears Point, Harbor Hill, Stage Harbor and Oyster Pond River neighborhoods.  Many residents enjoy the ultimate combination of beach-front properties with an easy walk to town as well as deep-water access to the Nantucket Sound. 

The Loop was one of the first parts of Chatham to be settled when William Nickerson purchased the Stage Neck area of the Loop from the Monomoyick Indian Tribe.  Samuel Smith of Eastham was another early settler in the Tom’s Neck area east of Mill Pond.  While farming was the initial industry in the Loop area, fishing and whaling grew in importance in early 19th century.  Historic landmarks including the Captain Fred Eldridge House located at 154 Champlain Road and the Atwood House at 347 Stage Harbor Road are lasting monuments to early life in the Chatham Loop.

Chatham Loop Area Homes

Price, High to Low
19 Properties Found.
Photo of Listing #21900934
  • MLS® #: 21900934
  • 373 Bridge Street
  • Chatham, MA 02633
  • $6,995,000
  • 6 Bed, 10 Bath, 10000 SqFt, 1.54 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 #21806729
  • MLS® #: 21806729
  • 173 Main Street
  • Chatham, MA 02633
  • $3,995,000
  • 4 Bed, 6 Bath, 4309 SqFt, 0.39 Acres
  • Single Family
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Photo of Listing #21712414
  • MLS® #: 21712414
  • 257 Stage Harbor Road
  • Chatham, MA 02633
  • $2,995,000
  • 4 Bed, 5 Bath, 4820 SqFt, 0.5 Acres
  • Single Family
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Photo of Listing #21712807
  • MLS® #: 21712807
  • 34 Holway Street
  • Chatham, MA 02633
  • $2,495,000
  • 3 Bed, 2 Bath, 1962 SqFt, 0.97 Acres
  • Single Family
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Photo of Listing #21808296
  • MLS® #: 21808296
  • 107 School Street
  • Chatham, MA 02633
  • $2,495,000
  • 5 Bed, 6 Bath, 3809 SqFt, 0.33 Acres
  • Single Family
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Photo of Listing #21900312
  • MLS® #: 21900312
  • 203 Cross Street
  • Chatham, MA 02633
  • $2,495,000
  • 4 Bed, 4 Bath, 3183 SqFt, 0.64 Acres
  • Single Family
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Photo of Listing #21808819
  • MLS® #: 21808819
  • 372 Stage Harbor Road
  • Chatham, MA 02633
  • $2,395,000
  • 5 Bed, 5 Bath, 3500 SqFt, 1 Acre
  • Single Family
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Photo of Listing #21900092
  • MLS® #: 21900092
  • 38 Mill Pond Road
  • Chatham, MA 02633
  • $2,049,000
  • 5 Bed, 3 Bath, 2579 SqFt, 0.25 Acres
  • Single Family
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Photo of Listing #21606985
  • MLS® #: 21606985
  • 43 Hallet Lane
  • Chatham, MA 02633
  • $1,995,000
  • 3 Bed, 4 Bath, 2196 SqFt, 0.15 Acres
  • Single Family
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Photo of Listing #21800964
  • MLS® #: 21800964
  • 47 Chase Street
  • Chatham, MA 02633
  • $1,995,000
  • 4 Bed, 4 Bath, 4258 SqFt, 0.36 Acres
  • Single Family
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Photo of Listing #21900395
  • MLS® #: 21900395
  • 59 Hardings Lane
  • Chatham, MA 02633
  • $1,850,000
  • 3 Bed, 2 Bath, 1968 SqFt, 0.7 Acres
  • Single Family
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Blog Posts About The Chatham Loop

Visit the Atwood House Museum in Chatham

If you’re hoping to learn more about the history of Chatham, there is perhaps no better place to go on Cape Cod then the Atwood House Museum.  Since the mid 1920’s, this museum has served to not only protect the area’s history, but also to preserve and teach it to generations to come.The museum has its own unique history, as well.  Part of the museum is the oldest structure still standing in Chatham.  It was once the home of Captain Joseph Atwood, and built around 1752.  The Chatham Histo... Read More

Just what is the Chatham Loop?

How would you like to live in a place that offers stunning views of Chatham Harbor and Nauset Beach, deep-water access to the open waters of the Atlantic and Nantucket Sound and within a short walk to town.  That’s possible when you set your sites upon the Chatham Loop.So, what exactly is Chatham Loop?  The answer to that goes back decades, and even centuries.  The Loop dates back to the time when settler William Nickerson first purchased the area of Stage Neck from the Monomoyick Indians.... 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 02/22/2019. All properties are subject to prior sale, changes or withdrawal.