Single Family for Sale in Chatham MA

Favorite

38 photos

153 Shore Rd Chatham MA 02633

$9,495,000

Beds: 3

Baths: 2.5

Sq Ft: 3,079

Days on Market: 8

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Open: Saturday 11:30 am - 1 pm

Favorite

42 photos

12 Pond St Chatham MA 02633

$6,575,000

-$300,000

Beds: 4

Baths: 4

Sq Ft: 4,512

Days on Market: 38

Open: 10/31/26 11:30 AM - 1 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 150-154 Cross Street Chatham MA 02633

Favorite

28 photos

150-154 Cross Street Chatham MA 02633

$6,500,000

Beds: 10

Baths: 8.5

Sq Ft: 7,658

Days on Market: 141

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Favorite

1 photos

50 Sylvan Way Chatham MA 02659

$5,900,000

Beds: 6

Baths: 7

Sq Ft: 6,183

Days on Market: 143

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 95 Cotchpinicut Chatham MA 02633

Favorite

41 photos

95 Cotchpinicut Chatham MA 02633

$5,900,000

Beds: 4

Baths: 5

Sq Ft: 4,394

Days on Market: 117

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

New Listing

Favorite

40 photos

48 Hillcrest Chatham MA 02633

$5,900,000

Beds: 4

Baths: 5.5

Sq Ft: 5,254

Days on Market: 1

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 15 Windy Hill Way Chatham MA 02633

Favorite

42 photos

15 Windy Hill Way Chatham MA 02633

$5,850,000

Beds: 5

Baths: 5.5

Sq Ft: 5,620

Days on Market: 213

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 160 Woodland Way Chatham MA 02650

Favorite

4 photos

160 Woodland Way Chatham MA 02650

$5,800,000

Beds: 3

Baths: 5

Sq Ft: 4,902

Days on Market: 11

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Favorite

42 photos

70 Judges Way Chatham MA 02633

$5,450,000

Beds: 5

Baths: 4.5

Sq Ft: 4,060

Days on Market: 192

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 106 Barcliff Ave Chatham MA 02633

Open: Saturday 11 am - 12:30 pm

Favorite

35 photos

106 Barcliff Ave Chatham MA 02633

$5,250,000

Beds: 4

Baths: 4.5

Sq Ft: 4,000

Days on Market: 58

Open: 10/31/26 11 AM - 12:30 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 56 Stage Island Road Chatham MA 02633

Favorite

42 photos

56 Stage Island Road Chatham MA 02633

$4,995,000

Beds: 4

Baths: 4

Sq Ft: 2,932

Days on Market: 150

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Favorite

42 photos

48 Sylvan Way Chatham MA 02659

$4,500,000

Beds: 6

Baths: 6

Sq Ft: 5,721

Days on Market: 249

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 22 Moonpenny Ln Chatham MA 02633

Favorite

42 photos

22 Moonpenny Ln Chatham MA 02633

$4,250,000

Beds: 4

Baths: 4.5

Sq Ft: 4,298

Days on Market: 48

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 169 Tisquantum Rd Chatham MA 02633

Open: Sunday 1:30 pm - 3 pm

Favorite

42 photos

169 Tisquantum Rd Chatham MA 02633

$3,999,000

-$496,000

Beds: 5

Baths: 4.5

Sq Ft: 5,887

Days on Market: 39

Open: 11/1/26 1:30 PM - 3 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 35 Crows Pond Rd Chatham MA 02633

Open: Saturday 11 am - 1 pm

Favorite

42 photos

35 Crows Pond Rd Chatham MA 02633

$3,995,000

Beds: 3

Baths: 4.5

Sq Ft: 4,400

Days on Market: 28

Open: 10/31/26 11 AM - 1 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 92 Indian Trail Chatham MA 02633

Favorite

41 photos

92 Indian Trail Chatham MA 02633

$3,200,000

Beds: 3

Baths: 3

Sq Ft: 2,004

Days on Market: 344

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 78 Indian Trail Chatham MA 02633

Favorite

42 photos

78 Indian Trail Chatham MA 02633

$2,800,000

Beds: 3

Baths: 2

Sq Ft: 1,160

Days on Market: 344

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 336 Stage Island Rd Chatham MA 02633

Open: Sunday 1 pm - 3 pm

Favorite

42 photos

336 Stage Island Rd Chatham MA 02633

$2,699,000

Beds: 3

Baths: 2.5

Sq Ft: 2,205

Days on Market: 178

Open: 11/1/26 1 PM - 3 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Favorite

38 photos

41 Court St Chatham MA 02650

$2,295,000

Beds: 3

Baths: 2.5

Sq Ft: 3,504

Days on Market: 257

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 55 Winterset Drive Chatham MA 02633

Favorite

39 photos

55 Winterset Drive Chatham MA 02633

$2,295,000

Beds: 4

Baths: 3.5

Sq Ft: 4,072

Days on Market: 112

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 20 Stoughton Lane Chatham MA 02633

Favorite

33 photos

20 Stoughton Lane Chatham MA 02633

$2,285,000

Beds: 5

Baths: 4

Sq Ft: 2,478

Days on Market: 36

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 20 Lords Pond Lane Chatham MA 02633

Favorite

42 photos

20 Lords Pond Lane Chatham MA 02633

$2,199,900

Beds: 3

Baths: 3.5

Sq Ft: 2,576

Days on Market: 44

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 312 Round Cove Rd Chatham MA 02633

Open: Saturday 1:30 pm - 3 pm

Favorite

42 photos

312 Round Cove Rd Chatham MA 02633

$2,199,000

Beds: 3

Baths: 2.5

Sq Ft: 2,848

Days on Market: 18

Open: 10/31/26 1:30 PM - 3 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 20 Circle Drive Chatham MA 02659

Open: Sunday 12 pm - 1 pm

Favorite

42 photos

20 Circle Drive Chatham MA 02659

$2,140,000

Beds: 4

Baths: 3

Sq Ft: 3,102

Days on Market: 57

Open: 11/1/26 12 PM - 1 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Favorite

42 photos

409 Main St Chatham MA 02633

$2,100,000

Beds: 1

Baths: 1.5

Sq Ft: 1,479

Days on Market: 141

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 71 Rowland Drive Chatham MA 02650

Favorite

22 photos

71 Rowland Drive Chatham MA 02650

$1,795,000

Beds: 3

Baths: 2

Sq Ft: 1,398

Days on Market: 84

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 43 Tobey Turtle Chatham MA 02659

Favorite

42 photos

43 Tobey Turtle Chatham MA 02659

$1,695,000

Beds: 2

Baths: 3.5

Sq Ft: 2,331

Days on Market: 84

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 231 Crowell Road Chatham MA 02633

Favorite

27 photos

231 Crowell Road Chatham MA 02633

$1,650,000

Beds: 0

Baths: 1

Sq Ft: 2,586

Days on Market: 863

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 764 Riverview Dr Chatham MA 02633

Favorite

26 photos

764 Riverview Dr Chatham MA 02633

$1,650,000

Beds: 3

Baths: 3

Sq Ft: 1,902

Days on Market: 27

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Photo of 70 Uncle Deane's Rd Chatham MA 02659

Open: Saturday 11 am - 12:30 pm

Favorite

42 photos

70 Uncle Deane's Rd Chatham MA 02659

$1,599,000

Beds: 3

Baths: 3

Sq Ft: 3,514

Days on Market: 170

Open: 10/31/26 11 AM - 12:30 PM

Updated 7 Minutes Ago

FavoriteUn-FavoriteTrip MapRequest InfoAppointment

Bedrooms

Bathrooms

Previous Levels