117 total properties
View 1772 Main Street Chatham, MA MLS# 22601404
$699,999
Studio

Beds

1.1

Baths

600

Sq.Ft.

1772 Main Street

Chatham, MA

CapeCodIslands
View 157 Bridge Street Chatham, MA MLS# 22601380
  • New Construction
1 of 20
$12,999,900
4

Beds

5.2

Baths

6,234

Sq.Ft.

157 Bridge Street

Chatham, MA

CapeCodIslands
View 15 Windy Hill Way Chatham, MA MLS# 73495151
$5,850,000
5

Beds

5.1

Baths

5,620

Sq.Ft.

15 Windy Hill Way

Chatham, MA

Listed By: Timothy Bailey Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 15 Windy Hill Way Chatham, MA MLS# 22601111
$5,850,000
5

Beds

5.1

Baths

5,620

Sq.Ft.

15 Windy Hill Way

Chatham, MA

CapeCodIslands
View 101 Morris Island Road Chatham, MA MLS# 22601118
  • Virtual Tour
1 of 77
$4,995,000
5

Beds

4.1

Baths

3,225

Sq.Ft.

101 Morris Island Road

Chatham, MA

CapeCodIslands
View 222 Barcliff Chatham, MA MLS# 73493426
$4,250,000
4

Beds

5.1

Baths

3,980

Sq.Ft.

222 Barcliff

Chatham, MA

Listed By: Lori Fanning Smith Courtesy of COMPASS
View 346 Morris Island Road Chatham, MA MLS# 73492591
$4,500,000
4

Beds

3.1

Baths

2,850

Sq.Ft.

346 Morris Island Road

Chatham, MA

Listed By: Chris Rhinesmith Courtesy of COMPASS
View 137 Shane Drive Chatham, MA MLS# 22600988
$1,399,000
3

Beds

2.0

Baths

1,530

Sq.Ft.

137 Shane Drive

Chatham, MA

CapeCodIslands
View 346 Morris Island Road Chatham, MA MLS# 22601006
$4,500,000
4

Beds

3.1

Baths

2,850

Sq.Ft.

346 Morris Island Road

Chatham, MA

CapeCodIslands
View 234 Round Cove Road Chatham, MA MLS# 22601089
$2,150,000
3

Beds

2.1

Baths

2,481

Sq.Ft.

234 Round Cove Road

Chatham, MA

CapeCodIslands
View 243 Crowell Road Chatham, MA MLS# 22600915
$1,280,000
3

Beds

1.1

Baths

2,278

Sq.Ft.

243 Crowell Road

Chatham, MA

CapeCodIslands
View 222 Barcliff Avenue Chatham, MA MLS# 22600932
  • New Construction
1 of 29
$4,250,000
4

Beds

5.1

Baths

3,980

Sq.Ft.

222 Barcliff Avenue

Chatham, MA

CapeCodIslands
View 32 Tip Cart Drive Chatham, MA MLS# 22600918
  • Virtual Tour
1 of 33
$1,350,000
3

Beds

2.0

Baths

1,802

Sq.Ft.

32 Tip Cart Drive

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 33 Crowell Road Chatham, MA MLS# 22600794
  • New Construction
1 of 11
$4,499,900
3

Beds

5.2

Baths

5,820

Sq.Ft.

33 Crowell Road

Chatham, MA

CapeCodIslands
View 1772 Main St Chatham, MA MLS# 73486416
$699,999
1.0

Baths

600

Sq.Ft.

1772 Main St

Chatham, MA

Listed By: Erin Terkelsen Courtesy of LPT REALTY, LLC
View Address not provided Chatham, MA MLS# 22600731
$699,999
600

Sq.Ft.

Address not provided

Chatham, MA

CapeCodIslands
View 856 Main Street Chatham, MA MLS# 73484112
$1,499,000

856 Main Street

Chatham, MA

Listed By: Nat Santoro Courtesy of KINLIN GROVER COMPASS COMMERCIAL
View 856 Main Street Chatham, MA MLS# 22600313
$1,499,000
2,015

Sq.Ft.

856 Main Street

Chatham, MA

CapeCodIslands
View 33 Duck Marsh Ln Chatham, MA MLS# 73460325
  • Virtual Tour
1 of 36
$829,000
3

Beds

2.0

Baths

1,192

Sq.Ft.

33 Duck Marsh Ln

Chatham, MA

Listed By: Darci Sequin Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY

Information deemed reliable but not guaranteed.

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Data is updated as of 9/1/2026.

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Data is updated as of 9/1/2026. All properties are subject to prior sale, changes, or withdrawal.