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40+ Houses for Sale in Chatham, MA

41 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 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 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

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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 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
Property at 43 Tobey Turtle, Chatham, MA 02659
1 / 42
Active
Price

$1,695,000

43 Tobey Turtle, Chatham, MA 02659

2 bds
|
3.5 ba
|
2331 sqft
MLS® 73561031Single Family Residence
John C. Ricotta & Associates, Inc. - Timothy Bailey
Property at 22 Moonpenny Ln, Chatham, MA 02633
1 / 42
Active

$4,250,000

22 Moonpenny Ln, Chatham, MA 02633

4 bds
|
4.5 ba
|
4298 sqft
MLS® 73576453Single Family Residence
Christie's International Real Estate Atlantic Brokerage - Lori Jurkowski
Property at 56 Stage Island Road, Chatham, MA 02633
1 / 42
Active
Price

$4,995,000

56 Stage Island Road, Chatham, MA 02633

4 bds
|
4 ba
|
2932 sqft
MLS® 73529657Single Family Residence
eXp Realty LLC - James Lowenstern
Property at 72 Ridgevale Rd So, Chatham, MA 02633
1 / 42
Active

$2,499,000

72 Ridgevale Rd So, Chatham, MA 02633

2 bds
|
2 ba
|
1547 sqft
MLS® 73574801Single Family Residence
Compass - Shane Masaschi
Property at 106 Barcliff Ave, Chatham, MA 02633
1 / 35
Active

$5,250,000

106 Barcliff Ave, Chatham, MA 02633

4 bds
|
4.5 ba
|
4000 sqft
MLS® 73571701Single Family Residence
eXp Realty LLC - Corporate Office - Jill Boudreau
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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Houses for sale in Chatham, MA: market at a glance

As of October 4, 2026, there are 41 single-family 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 (all home types) was $1,800,000, down 3.4% from a year earlier.

Houses for sale
41
Median list price
$2,295,000
Median sale price (July 2026, all home types)
$1,800,000
Median days on market (July 2026, all home types)
34 days
  • Chatham market report

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 single-family homes are for sale in Chatham, MA?

As of October 4, 2026, there are 41 single-family homes for sale in Chatham, MA.

What is the median single-family home price in Chatham, MA?

The median list price of single-family homes for sale in Chatham, MA is $2,295,000. Homes (all home types) 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 (all home types) in Chatham, MA that sold in July 2026 had a median of 34 days on market. Single-family homes currently for sale show a median of about 6 days on market.