Main Street Chatham

Main Street Chatham MA

Main Street in Chatham is an iconic roadway and the anchor of Chatham Village.  Lined with eclectic shops, fine dining restaurants and historic sites, Main Street Chatham is one of the most visited and beloved locations on Cape Cod.  Long-time favorites along Main Street in Chatham include Marion’s Pie Shop, the Orpheum Theatre, the Chatham Squire and the Chatham Penny Candy Store.

In recent years, a number of condo units have been built in buildings along Main Street.  Many of these are within biking or walking distance of multiple Chatham Beaches.

The section of Chatham from the Harwich town line running through downtown to Stage Harbor Road is also known as Massachusetts Route 28.   The section of Main Street east of Stage Harbor Road is a local road and not a numbered state highway.

Main Street Homes And Condos For Sale

Price, High to Low
15 Properties Found.
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 #21807675
  • MLS® #: 21807675
  • 907 Main Street
  • Chatham, MA 02633
  • $1,998,000
  • 2846 SqFt, 1.06 Acres
  • Income/Multi Family
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Photo of Listing #21802133
  • MLS® #: 21802133
  • 136 Main Street
  • Chatham, MA 02633
  • $1,695,000
  • 5 Bed, 4 Bath, 1681 SqFt, 0.27 Acres
  • Single Family
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Photo of Listing #21802299
  • MLS® #: 21802299
  • 595 Main Street 10
  • Chatham, MA 02633
  • $1,595,000
  • 3 Bed, 3 Bath, 2148 SqFt
  • Single Family
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Photo of Listing #21806603
  • MLS® #: 21806603
  • 595 Main Street
  • Chatham, MA 02633
  • $1,595,000
  • 3 Bed, 3 Bath, 2800 SqFt
  • Single Family
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Photo of Listing #21510790
  • MLS® #: 21510790
  • 80 Main Street
  • Chatham, MA 02633
  • $1,499,000
  • 5 Bed, 4 Bath, 1332 SqFt, 0.32 Acres
  • Single Family
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Photo of Listing #21710183
  • MLS® #: 21710183
  • 410 Main Street
  • Chatham, MA 02633
  • $995,000
  • 1008 SqFt, 0.26 Acres
  • Income/Multi Family
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Photo of Listing #21710142
  • MLS® #: 21710142
  • 859 Main Street
  • Chatham, MA 02633
  • $795,000
  • 1920 SqFt, 0.63 Acres
  • Income/Multi Family
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Photo of Listing #21716023
  • MLS® #: 21716023
  • 759 Main Street
  • Chatham, MA 02633
  • $649,900
  • 4 Bed, 4 Bath, 2269 SqFt, 0.14 Acres
  • Single Family
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Photo of Listing #21805691
  • MLS® #: 21805691
  • 1068 Main Street
  • Chatham, MA 02633
  • $539,000
  • 2 Bed, 2 Bath, 1467 SqFt
  • Single Family
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Photo of Listing #21808899
  • MLS® #: 21808899
  • 2337 Main Street
  • South Chatham, MA 02659
  • $499,000
  • 3 Bed, 2 Bath, 1540 SqFt, 0.46 Acres
  • Single Family
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Photo of Listing #21710337
  • MLS® #: 21710337
  • 912 Main Street 303
  • Chatham, MA 02633
  • $425,000
  • 2 Bed, 2 Bath, 1649 SqFt
  • Single Family
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Blog Posts About Main Street

Marion’s Pie Shop: A Chatham Legacy

You’ll find generations of history packed into each slice of pie at one of Chatham’s most famous locations.  Marion’s Pie Shop is truly a Chatham Legacy when it comes to Cape Cod food.  Around since 1947, Marion first began by baking chicken pot pies right in her own kitchen.  Fast-forward more than 67 years and this charming little pie shop now has its own location, and its own special menu.The bakery now includes a number of fresh fruit pies as well as a selection of savory pies.  Baked... 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 12/15/2018. All properties are subject to prior sale, changes or withdrawal.