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50+ Homes for Sale in Chatham, MA

50 results

Property at 2118 Main St, Chatham, MA 02633
1 / 33
Active
New

$1,399,000

2118 Main St, Chatham, MA 02633

4 bds
|
2.5 ba
|
2670 sqft
MLS® 73585978Single Family Residence
Gibson Sotheby's International Realty - Marcie Smith
Property at 764 Riverview Dr, Chatham, MA 02633
1 / 24
Active
New

$1,650,000

764 Riverview Dr, Chatham, MA 02633

3 bds
|
3 ba
|
1902 sqft
MLS® 73586414Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Dawn Marie Boynton
Property at 35 Crows Pond Rd, Chatham, MA 02633
1 / 29
Active
New

$3,995,000

35 Crows Pond Rd, Chatham, MA 02633

3 bds
|
4.5 ba
|
4400 sqft
MLS® 73584596Single Family Residence
Gibson Sotheby's International Realty - Betsy Hargreaves
Property at 9 Bassing Harbor, Chatham, MA 02633
1 / 42
Active

$3,299,900

9 Bassing Harbor, Chatham, MA 02633

3 bds
|
3.5 ba
|
3157 sqft
MLS® 73583875Single Family Residence
Christie's International Real Estate Atlantic Brokerage - Andrew Grattan
Property at 55 Winterset Drive, Chatham, MA 02633
1 / 38
Active
Price

$2,295,000

55 Winterset Drive, Chatham, MA 02633

4 bds
|
3.5 ba
|
4072 sqft
MLS® 73548377Single Family Residence
Coldwell Banker Realty - Concord - Janet Stuart

What's actually happening in Chatham right now?

Forget the national headlines. Get the hyper-local, street-level data on inventory, price drops, and true market value before you make an offer.

Property at 1114 Orleans Rd #8, Chatham, MA 02650
1 / 42
Active
Price

$1,325,000

1114 Orleans Rd #8, Chatham, MA 02650

2 bds
|
2.5 ba
|
2306 sqft
MLS® 73568802Condominium
Gibson Sotheby's International Realty - Betsy Hargreaves
Property at 20 Circle Drive, Chatham, MA 02659
1 / 42
Active
Price

$2,140,000

20 Circle Drive, Chatham, MA 02659

4 bds
|
3 ba
|
3102 sqft
MLS® 73571912Single Family Residence
Gibson Sotheby's International Realty - Barbara Carrollhorne
Property at 60 Harbor Hill Rd, Chatham, MA 02633
1 / 33
Active
Price

$2,850,000

60 Harbor Hill Rd, Chatham, MA 02633

4 bds
|
3.5 ba
|
3978 sqft
MLS® 73511079Single Family Residence
Shore Road Realty, LLC - Jacqueline Casey
Property at 41 Court St, Chatham, MA 02650
1 / 38
Active
Price

$2,295,000

41 Court St, Chatham, MA 02650

3 bds
|
2.5 ba
|
3504 sqft
MLS® 73477537Single Family Residence
Compass - The Nickerson Power Group
Property at 0 Court, Chatham, MA 02650
Active

$650,000

0 Court, Chatham, MA 02650

0 bds
|
0 ba
|
-- sqft
MLS® 73528474Residential
Compass - The Nickerson Power Group
Property at 800 Riverview Dr, Chatham, MA 02633
1 / 40
Active
New

$975,000

800 Riverview Dr, Chatham, MA 02633

3 bds
|
2 ba
|
1820 sqft
MLS® 73583012Single Family Residence
Compass - Shane Masaschi
Property at 336 Stage Island Rd, Chatham, MA 02633
1 / 42
Active
Price

$2,699,000

336 Stage Island Rd, Chatham, MA 02633

3 bds
|
2.5 ba
|
2205 sqft
MLS® 73513527Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 2653 Main St, Chatham, MA 02659
1 / 15
Active

$950,000

2653 Main St, Chatham, MA 02659

3 bds
|
2.5 ba
|
2252 sqft
MLS® 73583268Single Family Residence
Commercial Realty Advisors, Inc. - Kevin A. Pepe
Property at 231 Crowell Road, Chatham, MA 02633
1 / 27
Active
Price

$1,650,000

231 Crowell Road, Chatham, MA 02633

0 bds
|
1 ba
|
2586 sqft
MLS® 73258353Single Family Residence
John C. Ricotta & Associates, Inc. - Judith Smith
Property at 24 Kittys Ln, Chatham, MA 02659
1 / 41
Active

$775,000

24 Kittys Ln, Chatham, MA 02659

2 bds
|
1 ba
|
768 sqft
MLS® 73580015Single Family Residence
Compass - Shane Masaschi
Property at 2673 Main St, Chatham, MA 02659
1 / 42
Active

$849,000

2673 Main St, Chatham, MA 02659

4 bds
|
2 ba
|
1635 sqft
MLS® 73585326Single Family Residence
eXp Realty LLC - Barbara Garside
Property at 20 Stoughton Lane, Chatham, MA 02633
1 / 33
Active

$2,285,000

20 Stoughton Lane, Chatham, MA 02633

5 bds
|
4 ba
|
2478 sqft
MLS® 73582831Single Family Residence
William Raveis Real Estate & Homes Services - Elaine Lomenzo
Property at 31 Old Village Rd, Chatham, MA 02633
1 / 41
Active
Price

$815,000

31 Old Village Rd, Chatham, MA 02633

3 bds
|
1.5 ba
|
2167 sqft
MLS® 73574852Single Family Residence
Compass - Shane Masaschi
Property at 12 Pond St, Chatham, MA 02633
1 / 42
Active

$6,875,000

12 Pond St, Chatham, MA 02633

4 bds
|
4 ba
|
4512 sqft
MLS® 73582098Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 32 Tip Cart Dr, Chatham, MA 02633
1 / 27
Active

$1,295,000

32 Tip Cart Dr, Chatham, MA 02633

3 bds
|
2 ba
|
1802 sqft
MLS® 73581150Single Family Residence
Compass - Shane Masaschi
Property at 169 Tisquantum Rd, Chatham, MA 02633
1 / 42
Active

$4,495,000

169 Tisquantum Rd, Chatham, MA 02633

5 bds
|
4.5 ba
|
5887 sqft
MLS® 73581092Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 95 Cotchpinicut, Chatham, MA 02633
1 / 41
Active Under Contract

$5,900,000

95 Cotchpinicut, Chatham, MA 02633

4 bds
|
5 ba
|
4394 sqft
MLS® 73544856Single Family Residence
William Raveis Chatham - John Burke
Property at 71 Rowland  Drive, Chatham, MA 02650
1 / 22
Active
Price

$1,795,000

71 Rowland Drive, Chatham, MA 02650

3 bds
|
2 ba
|
1398 sqft
MLS® 73561027Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Dawn Marie Boynton
Property at 222 Barcliff, Chatham, MA 02633
1 / 26
Active Under Contract

$4,250,000

222 Barcliff, Chatham, MA 02633

4 bds
|
5.5 ba
|
3980 sqft
MLS® 73493426Single Family Residence
Compass - Lori Fanning Smith
Property at 99 Uncle Alberts Drive Ext, Chatham, MA 02633
1 / 34
Active Under Contract
Price

$5,495,000

99 Uncle Alberts Drive Ext, Chatham, MA 02633

2 bds
|
2.5 ba
|
1850 sqft
MLS® 73419421Single Family Residence
Compass - Shane Masaschi
Property at 64 Harbor View, Chatham, MA 02633
1 / 16
Active Under Contract

$4,000,000

64 Harbor View, Chatham, MA 02633

5 bds
|
3 ba
|
2303 sqft
MLS® 73571777Single Family Residence
Gibson Sotheby's International Realty - The Bohman Hartung Group
Property at 20 Lords Pond Lane, Chatham, MA 02633
1 / 42
Active

$2,199,900

20 Lords Pond Lane, Chatham, MA 02633

3 bds
|
3.5 ba
|
2576 sqft
MLS® 73579550Single Family Residence
Christie's International Real Estate Atlantic Brokerage - Andrew Grattan
Property at 108 Queen Anne Road, Chatham, MA 02633
1 / 21
Active Under Contract
Price

$6,499,000

108 Queen Anne Road, Chatham, MA 02633

5 bds
|
5 ba
|
4000 sqft
MLS® 73569424Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Dawn Marie Boynton
Property at 39 Jedidiah Way, Chatham, MA 02633
1 / 38
Active

$1,495,000

39 Jedidiah Way, Chatham, MA 02633

2 bds
|
2 ba
|
1810 sqft
MLS® 73577973Single Family Residence
Christie's International Real Estate Atlantic Brokerage - Andrew Grattan
Property at 70 Uncle Deane's Rd, Chatham, MA 02659
1 / 42
Active
Price

$1,799,000

70 Uncle Deane's Rd, Chatham, MA 02659

3 bds
|
3 ba
|
3514 sqft
MLS® 73519558Single Family Residence
Shining Sea Realty - Patrick Davison
Page 1 of 2

Brokerage Information

Gundersheim Group Real Estate

10 Lincoln St, Newton, MA, 02461

(617) 997-8272

Market Area Served

Boston, Somerville, Newton, Brookline, Wellesley, Needham and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Melanie Gundersheim

Buy or sell in Boston, Newton, Needham, Brookline, Wellesley, and Somerville with clear guidance, local insight, and a calm, strategic process.

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Homes for sale in Chatham, MA: market at a glance

As of October 4, 2026, there are 50 homes for sale in Chatham, MA, with a median list price of $2,295,000. In July 2026, the median sale price for homes in Chatham, MA was $1,800,000, down 3.4% from a year earlier.

Homes for sale
50
Median list price
$2,295,000
Median sale price (July 2026)
$1,800,000
Median days on market (July 2026)
34 days
  • Chatham market report
  • Chatham single-family homes for sale
  • Chatham condos for sale

Homes for sale near Chatham

  • West Chatham, MA
  • North Chatham, MA
  • South Chatham, MA
  • Harwich, MA
  • Brewster, MA
  • Orleans, MA
  • East Orleans, MA
  • West Harwich, MA

Common questions about Chatham, MA real estate

How many homes are for sale in Chatham, MA?

As of October 4, 2026, there are 50 homes for sale in Chatham, MA, including 46 single-family homes and 3 condos.

What is the median home price in Chatham, MA?

The median list price of homes for sale in Chatham, MA is $2,295,000. Homes that sold in July 2026 had a median sale price of $1,800,000, down 3.4% from a year earlier.

How long do homes take to sell in Chatham, MA?

Homes in Chatham, MA that sold in July 2026 had a median of 34 days on market. Homes currently for sale show a median of about 15 days on market.

What types of homes are for sale in Chatham, MA?

The homes for sale in Chatham, MA include 46 single-family homes and 3 condos.