Pleasant Bay Chatham

Pleasant Bay marks Chatham’s northern boundary and provides miles of pristine sand and sheltered water from the Atlantic.  It’s the largest bay contiguous to the Cape Cod National Seashore and provides world-class windsurfing, canoeing, boating, fishing and other water activities.  

The Town of Chatham operates several landings ideal for boat launches and smaller swimming beaches.   Many residents moor their boats in Pleasant Bay and enjoy accessing the open waters of the Atlantic via Chatham Harbor.  The raw beauty of the wide open spaces provide the perfect backdrop for treasured homes used for entertaining and family gatherings.

Pleasant Bay Homes For Sale

Price, High to Low
55 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
Add as Favorite
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
Add as Favorite
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
Add as Favorite
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
Add as Favorite
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
Add as Favorite
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
Add as Favorite
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
Add as Favorite
Photo of Listing #21802245
  • MLS® #: 21802245
  • 24 Andrew Mitchell Lane
  • North Chatham, MA 02650
  • $3,990,000
  • 6 Bed, 8 Bath, 5700 SqFt
  • Single Family
Add as Favorite
Photo of Listing #21900121
  • MLS® #: 21900121
  • 40 Old Wharf Road
  • North Chatham, MA 02650
  • $3,800,000
  • 3 Bed, 3 Bath, 2433 SqFt, 0.59 Acres
  • Single Family
Add as Favorite
Photo of Listing #21607014
  • MLS® #: 21607014
  • 34 Salt Marsh Way
  • North Chatham, MA 02650
  • $3,600,000
  • 4 Bed, 6 Bath, 7940 SqFt, 2.54 Acres
  • Single Family
Add as Favorite
Photo of Listing #21801587
  • MLS® #: 21801587
  • 439 Shore Road
  • Chatham, MA 02633
  • $3,495,000
  • 4 Bed, 5 Bath, 4522 SqFt, 0.55 Acres
  • Single Family
Add as Favorite
Photo of Listing #21806918
  • MLS® #: 21806918
  • 789 Fox Hill Road
  • Chatham, MA 02633
  • $3,495,000
  • 3 Bed, 2 Bath, 1275 SqFt, 0.47 Acres
  • Single Family
Add as Favorite

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 02/23/2019. All properties are subject to prior sale, changes or withdrawal.