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

Pleasant Bay Homes For Sale September 29, 2023
11
Listed
198
Avg. DOM
N/A
Avg. $ / Sq.Ft.
$5,300,000
Med. List Price
11 Properties
7
Beds
5F11/2
Baths
3.7
Acres
1940
Year Built
570
Days on Site
22200926
MLS
One of the finest oceanfront properties to exist in all of New England, ''High Scatteree'' sits proudly on nearly 3.7 acres and is sited to enjoy commanding water views. Behind tall and established...
$12,900,000
Neighborhood: North Hill
8
Beds
6
Baths
2.94
Acres
1940
Year Built
261
Days on Site
22300106
MLS
Magnificent eight bedroom mansion from days gone by designed by Architect Edward Sears Read. Perched on a hill overlooking Chatham Harbor, North Beach, and the Atlantic Ocean beyond. Almost 300 feet...
5
Beds
6F11/2
Baths
0.78
Acres
2003
Year Built
156
Days on Site
22301578
MLS
This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and...
2
Beds
2
Baths
1.83
Acres
1963
Year Built
57
Days on Site
22303217
MLS
Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom,...
Open 10/1
21 Captains Cove Lane North Chatham,  MA 02650
5
Beds
7F11/2
Baths
0.86
Acres
2015
Year Built
109
Days on Site
22302262
MLS
This exceptional 5 bedroom coastal retreat & boater's delight offers the best of waterfront living; complete with a private deep water dock on Ryder's Cove! Beautifully constructed by Eastward Homes,...
5
Beds
3
Baths
0.8
Acres
1958
Year Built
29
Days on Site
22204503
MLS
Your very own paradise in Chatham in exclusive Eastward Point Assoc. 180 degrees of beautiful waterfront views. Sandy beach on Pleasant Bay and association dock on Crows Pond. This 5 bedroom 3 bath...
5
Beds
5
Baths
0.54
Acres
1973
Year Built
157
Days on Site
22301536
MLS
The ultimate in seaside living has arrived! Complete with a NEW dock (1/2 shared interest), 13 Captains Cove Lane is a true boater's paradise, where your dreams of fishing, paddle boarding, & a...
1
Beds
1F11/2
Baths
0.1
Acres
1900
Year Built
360
Days on Site
22205317
MLS
CHATHAM - Possible potential for a 1031 tax free exchange. Move to Chatham and own your first floor commercial space and live above it right on Main Street in a beautiful apartment ! Offering the...
Open 9/30
119 Rowland Drive Chatham,  MA 02633
3
Beds
2F11/2
Baths
1.5
Acres
1979
Year Built
445
Days on Site
22203316
MLS
One of the best views in Chatham! Waterfront with a permitted pier on Ryders Cove, encompassing 1.5 acres and 175 feet of salt waterfront. Settle in and enjoy in the marvelous scenery of the salt...
4
Beds
3
Baths
1.27
Acres
1976
Year Built
24
Days on Site
22301106
MLS
A charming Cape home on a very private, well-maintained 1.27 acres of flat land. This home was renovated in 2004 with a more contemporary look and is located in the highly desired North Chatham...
3
Beds
2F11/2
Baths
2012
Year Built
16
Days on Site
22303947
MLS
Welcome to this charming three bedroom, three bath townhome ideally nestled on a quiet lane in town just off Main Street. This lovely residence offers a perfect blend of comfort, style, and...