Chatham Homes For Sale

Chatham MA Homes For Sale

With the most shoreline in Massachusetts, Chatham has a wonderful inventory of single-family homes and many offer glimpses or panoramic views of water.  Chatham homes do come at a premium to similar property in neighboring towns, but the lure of this seaside village is highly appealing to so many.

Chatham architecture is dominated by traditional Cape-styling with weathered cedar shingles, white trim and cedar shake roofs on the more upscale homes.  Chatham is popular with boaters and there are many locations throughout town to moor a boat and even some luxury homes with private deepwater boat docks.  Many of the ponds in Chatham are developed with both modest cottages and newer upscale homes.

Chatham Homes For Sale

Price, High to Low
170 Properties Found.
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 #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 #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 #21900119
  • MLS® #: 21900119
  • 28 & 40 Old Wharf Road
  • Chatham, MA 02633
  • $5,500,000
  • 5 Bed, 7 Bath, 4040 SqFt, 0.84 Acres
  • Single Family
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Photo of Listing #21900449
  • MLS® #: 21900449
  • 28 Oyster Pond Lane
  • Chatham, MA 02633
  • $5,495,000
  • 5 Bed, 8 Bath, 6098 SqFt, 1.45 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 #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 #21808822
  • MLS® #: 21808822
  • 255 Seapine Road
  • North Chatham, MA 02650
  • $4,699,000
  • 4 Bed, 5 Bath, 5507 SqFt, 1.29 Acres
  • Single Family
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Photo of Listing #21805829
  • MLS® #: 21805829
  • 141 Cotchpinicut Road
  • North Chatham, MA 02650
  • $4,500,000
  • 8 Bed, 8 Bath, 4193 SqFt, 1.03 Acres
  • Single Family
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Photo of Listing #21900804
  • MLS® #: 21900804
  • 617 Fox Hill Road
  • Chatham, MA 02633
  • $4,500,000
  • 4 Bed, 7 Bath, 7722 SqFt, 0.99 Acres
  • Single Family
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Photo of Listing #21807585
  • MLS® #: 21807585
  • 58 Pond Street
  • Chatham, MA 02633
  • $4,500,000
  • 5 Bed, 5 Bath, 4031 SqFt, 0.36 Acres
  • Single Family
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Photo of Listing #21802947
  • MLS® #: 21802947
  • 581 Shore Road
  • Chatham, MA 02633
  • $3,999,999
  • 5 Bed, 7 Bath, 4030 SqFt, 0.5 Acres
  • Single Family
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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.