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

558 Fox Hill Road, Chatham
  • Single Family
  • 5 Beds
  • 10 Baths
  • 10,058 SqFt

558 Fox Hill Road, Chatham

$9,995,000
108 Shore Road, Chatham
  • Single Family
  • 7 Beds
  • 8 Baths
  • 6,276 SqFt

108 Shore Road, Chatham

$9,900,000
166 Shore Road, Chatham
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,801 SqFt

166 Shore Road, Chatham

$4,950,000 ↑ $750,000
255 Seapine Road, North Chatham
  • Single Family
  • 4 Beds
  • 5 Baths
  • 5,507 SqFt

255 Seapine Road, North Chatham

$4,699,000
19 Old Wharf Road, North Chatham
  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,820 SqFt

19 Old Wharf Road, North Chatham

$4,500,000 ↓ $350,000
617 Fox Hill Road, Chatham
  • Single Family
  • 4 Beds
  • 7 Baths
  • 7,722 SqFt

617 Fox Hill Road, Chatham

$4,250,000 ↓ $250,000
581 Shore Road, Chatham
  • Single Family
  • 5 Beds
  • 7 Baths
  • 4,030 SqFt

581 Shore Road, Chatham

$3,999,999
676and 684 Orleans Road, North Chatham
  • Single Family
  • 7 Beds
  • 7 Baths
  • 5,230 SqFt

676and 684 Orleans Road, North Chatham

$3,999,000
Lot 2 Whidah Road, Chatham
  • Single Family
  • 5 Beds
  • 6 Baths
  • 4,496 SqFt

Lot 2 Whidah Road, Chatham

$3,995,000
24 Andrew Mitchell Lane, North Chatham
  • Single Family
  • 6 Beds
  • 8 Baths
  • 5,700 SqFt

24 Andrew Mitchell Lane, North Chatham

$3,890,000 ↓ $100,000
34 Salt Marsh Way, North Chatham
  • Single Family
  • 5 Beds
  • 6 Baths
  • 7,940 SqFt

34 Salt Marsh Way, North Chatham

$3,600,000 ↓ $1,900,000
16 Aunt Lydias Way, Chatham
  • Single Family
  • 5 Beds
  • 6 Baths
  • 6,311 SqFt

16 Aunt Lydias Way, Chatham

$3,495,000

Cape Cod img src Islands Association of Realtors LogoThe 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 08/18/2019. All properties are subject to prior sale, changes or withdrawal.

What's Your Home Worth? Find out now, for Free.

Let's Go