Chatham Real Estate | Cape Cod | On The Cape Real Estate

Raymond M. Hall, REALTOR® | (508) 221-2544 | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633

70 Judges Way - $5,750,000

$5,750,000

-8.0% from Original List Price of $6,250,000 · Jul 19

70 Judges Way
Chatham, MA 02633

5 Beds
4 Full Baths
1 Half Bath
4,060 sq ft

(Single Family Residence) Listed 04/19/26

Cape Cod MLS# 22601572

1772 Main Street - $699,999

$699,999

1772 Main Street
Chatham, MA 02633

0 Beds
0 Full Bath
1 Half Bath
600 sq ft

(Single Family Residence) Listed 04/13/26

Cape Cod MLS# 22601404

157 Bridge Street - $12,999,900

$12,999,900

157 Bridge Street
Chatham, MA 02633

4 Beds
5 Full Baths
2 Half Baths
6,234 sq ft

(Single Family Residence) Listed 04/11/26

Cape Cod MLS# 22601380

15 Windy Hill Way - $5,850,000

$5,850,000

-6.4% from Original List Price of $6,250,000 · Jun 24

15 Windy Hill Way
Chatham, MA 02633

5 Beds
5 Full Baths
1 Half Bath
5,620 sq ft

(Single Family Residence) Listed 04/01/26

Cape Cod MLS# 22601111

101 Morris Island Road - $4,995,000

$4,995,000

-16.7% from Original List Price of $5,995,000 · Jul 15

101 Morris Island Road
Chatham, MA 02633

5 Beds
4 Full Baths
1 Half Bath
3,225 sq ft

(Single Family Residence) Listed 04/01/26

Cape Cod MLS# 22601118

137 Shane Drive - $1,399,000

Pending/Continue to Show

$1,399,000

-6.4% from Original List Price of $1,495,000 · Jun 20

137 Shane Drive
Chatham, MA 02633

3 Beds
2 Full Baths
1,530 sq ft

(Single Family Residence) Listed 03/26/26

Cape Cod MLS# 22600988

346 Morris Island Road - $4,500,000

$4,500,000

346 Morris Island Road
Chatham, MA 02633

4 Beds
3 Full Baths
1 Half Bath
2,850 sq ft

(Single Family Residence) Listed 03/26/26

Cape Cod MLS# 22601006

222 Barcliff Avenue - $4,250,000

$4,250,000

+2.4% from Original List Price of $4,150,000 · Apr 29

222 Barcliff Avenue
Chatham, MA 02633

4 Beds
5 Full Baths
1 Half Bath
3,980 sq ft

(Single Family Residence) Listed 03/24/26

Cape Cod MLS# 22600932

243 Crowell Road - $1,280,000

$1,280,000

-5.2% from Original List Price of $1,350,000 · Jul 20

243 Crowell Road
Chatham, MA 02633

3 Beds
1 Full Bath
1 Half Bath
2,278 sq ft

(Single Family Residence) Listed 03/24/26

Cape Cod MLS# 22600915

32 Tip Cart Drive - $1,350,000

Pending/Continue to Show

$1,350,000

-6.9% from Original List Price of $1,450,000 · Jun 5

32 Tip Cart Drive
Chatham, MA 02633

3 Beds
2 Full Baths
1,802 sq ft

(Single Family Residence) Listed 03/23/26

Cape Cod MLS# 22600918

301 Whidah Road - $12,950,000

$12,950,000

301 Whidah Road
North Chatham (Chatham), MA 02650

5 Beds
6 Full Baths
1 Half Bath
7,259 sq ft

(Single Family Residence) Listed 03/19/26

Cape Cod MLS# 22600837

33 Crowell Road - $4,499,900

$4,499,900

33 Crowell Road
Chatham, MA 02633

3 Beds
5 Full Baths
2 Half Baths
5,820 sq ft

(Single Family Residence) Listed 03/17/26

Cape Cod MLS# 22600794