63 total properties
View 92 Indian Trail Chatham, MA MLS# 73457239
$3,200,000
3

Beds

3.0

Baths

2,004

Sq.Ft.

92 Indian Trail

Chatham, MA

Listed By: Judith Smith Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.
View 20 Jessies Landing Chatham, MA MLS# 22600591
  • Recently Listed
1 of 64
OPEN HOUSE: Saturday 3/7 11:00 AM - 1:00 PM
$3,299,900
4

Beds

3.1

Baths

2,940

Sq.Ft.

20 Jessies Landing

Chatham, MA

CapeCodIslands
View 287 Cedar Street Chatham, MA MLS# 22502029
  • Virtual Tour
1 of 63
$3,850,000
3

Beds

4.1

Baths

3,640

Sq.Ft.

287 Cedar Street

Chatham, MA

CapeCodIslands
The time to sell is now! THE TIME TO SELL IS NOW!
View 287 Cedar St Chatham, MA MLS# 73371097
  • Virtual Tour
1 of 42
$3,850,000
3

Beds

4.1

Baths

3,640

Sq.Ft.

287 Cedar St

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
View 230 Barcliff Avenue Chatham, MA MLS# 22504396
  • New Construction
1 of 10
$4,399,000
4

Beds

6.0

Baths

5,300

Sq.Ft.

230 Barcliff Avenue

Chatham, MA

CapeCodIslands
View 230 Barcliff Chatham, MA MLS# 73480794
  • Recently Listed
1 of 7
$4,399,000
4

Beds

5.1

Baths

5,300

Sq.Ft.

230 Barcliff

Chatham, MA

Listed By: Lori Fanning Smith Courtesy of COMPASS
View 85 Cedar Street Chatham, MA MLS# 22504804
$4,700,000
5

Beds

3.1

Baths

3,080

Sq.Ft.

85 Cedar Street

Chatham, MA

CapeCodIslands
View 85 Cedar Street Chatham, MA MLS# 73436313
$4,700,000
5

Beds

3.1

Baths

3,080

Sq.Ft.

85 Cedar Street

Chatham, MA

Listed By: Timothy Bailey Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.
View 14 Pond View Lane Chatham, MA MLS# 22503678
  • New Construction
1 of 30
$5,295,000
4

Beds

4.2

Baths

4,989

Sq.Ft.

14 Pond View Lane

Chatham, MA

CapeCodIslands
View 121 Queen Anne Road Chatham, MA MLS# 22600235
$5,400,000
4

Beds

4.3

Baths

3,702

Sq.Ft.

121 Queen Anne Road

Chatham, MA

CapeCodIslands
View 169 Tisquantum Chatham, MA MLS# 73477664
  • Recently Listed
1 of 38
$5,400,000
5

Beds

4.1

Baths

5,587

Sq.Ft.

169 Tisquantum

Chatham, MA

Listed By: Sandra Tanco Courtesy of KINLIN GROVER COMPASS
View 169 Tisquantum Road Chatham, MA MLS# 22600293
  • Recently Listed
1 of 43
$5,400,000
5

Beds

4.1

Baths

5,587

Sq.Ft.

169 Tisquantum Road

Chatham, MA

CapeCodIslands
View 99 Uncle Alberts Drive Ext Chatham, MA MLS# 22503829
$5,495,000
2

Beds

2.1

Baths

1,850

Sq.Ft.

99 Uncle Alberts Drive Ext

Chatham, MA

CapeCodIslands
View 99 Uncle Alberts Drive Ext Chatham, MA MLS# 73419421
$5,495,000
2

Beds

2.1

Baths

1,850

Sq.Ft.

99 Uncle Alberts Drive Ext

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
View 44 Buena Vista Road Chatham, MA MLS# 22503738
  • Virtual Tour
1 of 76
$6,900,000
7

Beds

6.1

Baths

6,521

Sq.Ft.

44 Buena Vista Road

Chatham, MA

CapeCodIslands
View 44 Buena Vista Rd Chatham, MA MLS# 73414794
  • Virtual Tour
1 of 42
$6,900,000
7

Beds

6.1

Baths

6,521

Sq.Ft.

44 Buena Vista Rd

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
View 150 Main Street Chatham, MA MLS# 73477178
  • Recently Listed
1 of 17
$6,950,000
7

Beds

2.1

Baths

2,552

Sq.Ft.

150 Main Street

Chatham, MA

Listed By: Paul E. Grover Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
View 150 Main Street Chatham, MA MLS# 22600447
  • Recently Listed
1 of 17
$6,950,000
7

Beds

2.1

Baths

2,552

Sq.Ft.

150 Main Street

Chatham, MA

CapeCodIslands
View 238 Cranberry Lane Chatham, MA MLS# 73358568
$7,200,000
5

Beds

2.1

Baths

1,896

Sq.Ft.

238 Cranberry Lane

Chatham, MA

Listed By: John Burke Courtesy of WILLIAM RAVEIS CHATHAM
View 246 Stage Island Road Chatham, MA MLS# 22600418
  • Recently Listed
1 of 46
$7,999,000
4

Beds

4.2

Baths

4,717

Sq.Ft.

246 Stage Island Road

Chatham, MA

CapeCodIslands

Information deemed reliable but not guaranteed.

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Data is updated as of 3/3/2026.

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