50+ Homes for Sale in Chatham, MA

51 results

51 homes are for sale in Chatham, MA (median list price $1,695,000), as of November 5, 2026.

Property at 55 Winterset Drive, Chatham, MA 02633
1 / 24
Active
Price drop
Open

$2,295,000

Price reduced by

55 Winterset Drive, Chatham, MA 02633

4 bds
|
3.5 ba
|
4072 sqft

$564/sqft · 117 days on market

MLS® 73548377Single Family Residence
Coldwell Banker Realty - Concord - Janet Stuart
Property at 106 Barcliff Ave, Chatham, MA 02633
1 / 35
Active Under Contract

$5,250,000

106 Barcliff Ave, Chatham, MA 02633

4 bds
|
4.5 ba
|
4000 sqft

$1,313/sqft · 63 days on market

MLS® 73571701Single Family Residence
eXp Realty LLC - Corporate Office - Jill Boudreau
Property at 35 Crows Pond Rd, Chatham, MA 02633
1 / 42
Active Under Contract

$3,995,000

35 Crows Pond Rd, Chatham, MA 02633

3 bds
|
4.5 ba
|
4400 sqft

$908/sqft · 33 days on market

MLS® 73584596Single Family Residence
Gibson Sotheby's International Realty - Betsy Hargreaves

$810,000

24 Deep Water Ln, Chatham, MA 02633

1 bds
|
2 ba
|
768 sqft

$1,055/sqft · 80 days on market

MLS® 73557769Single Family Residence
Today Real Estate, Inc. - Karen St. Amand
Property at 2673 Main St, Chatham, MA 02659
1 / 42
Active
Price drop

$829,000

Price reduced by

2673 Main St, Chatham, MA 02659

4 bds
|
2 ba
|
1635 sqft

$507/sqft · 41 days on market

MLS® 73585326Single Family Residence
eXp Realty LLC - Barbara Garside

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.

$475,000

109 Misty Meadow #4, Chatham, MA 02650

2 bds
|
1 ba
|
957 sqft

$496/sqft · 3 days on market

MLS® 73598199Condominium
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group

$3,999,000

Price reduced by

169 Tisquantum Rd, Chatham, MA 02633

5 bds
|
4.5 ba
|
5887 sqft

$679/sqft · 44 days on market

MLS® 73581092Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group

$5,900,000

48 Hillcrest, Chatham, MA 02633

4 bds
|
5.5 ba
|
5254 sqft

$1,123/sqft · 6 days on market

MLS® 73596909Single Family Residence
Compass - William Storff
Property at 336 Stage Island Rd, Chatham, MA 02633
1 / 42
Active
Price drop
Open

$2,699,000

Price reduced by

336 Stage Island Rd, Chatham, MA 02633

3 bds
|
2.5 ba
|
2205 sqft

$1,224/sqft · 183 days on market

MLS® 73513527Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 12 Pond St, Chatham, MA 02633
1 / 42
Active
Price drop

$6,575,000

Price reduced by

12 Pond St, Chatham, MA 02633

4 bds
|
4 ba
|
4512 sqft

$1,457/sqft · 43 days on market

MLS® 73582098Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 41 Court St, Chatham, MA 02650
1 / 38
Active Under Contract
Price drop

$2,295,000

Price reduced by

41 Court St, Chatham, MA 02650

3 bds
|
2.5 ba
|
3504 sqft

$655/sqft · 262 days on market

MLS® 73477537Single Family Residence
Compass - The Nickerson Power Group

$699,999

25 Clifford Pl, Chatham, MA 02633

3 bds
|
2 ba
|
1624 sqft

$431/sqft · 8 days on market

MLS® 73596255Single Family Residence
Coldwell Banker Realty - Easton - Catherine Walsh

$589,000

193 Heritage Ln, Chatham, MA 02633

3 bds
|
1 ba
|
1008 sqft

$584/sqft · 9 days on market

MLS® 73595531Single Family Residence
Chatelain Real Estate - Ned Chatelain

$779,000

49 Duck Marsh Lane, Chatham, MA 02633

3 bds
|
2 ba
|
1437 sqft

$542/sqft · 9 days on market

MLS® 73595488Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group

$995,000

20 Cedar Swamp Lane, Chatham, MA 02633

2 bds
|
1 ba
|
710 sqft

$1,401/sqft · 17 days on market

MLS® 73592561Single Family Residence
Sotheby's International Realty - Ellen Valentgas

$9,495,000

153 Shore Rd, Chatham, MA 02633

3 bds
|
2.5 ba
|
3079 sqft

$3,084/sqft · 13 days on market

MLS® 73594589Single Family Residence
eXp Realty LLC - Sarah Keith

$1,175,000

789 Riverview Drive, Chatham, MA 02633

2 bds
|
3 ba
|
1764 sqft

$666/sqft · 13 days on market

MLS® 73594614Single Family Residence
John C. Ricotta & Associates, Inc. - Timothy Bailey

$5,800,000

160 Woodland Way, Chatham, MA 02650

3 bds
|
5 ba
|
4902 sqft

$1,183/sqft · 16 days on market

MLS® 73593924Single Family Residence
Compass - Chris Rhinesmith

$739,000

235 Morton Rd, Chatham, MA 02659

3 bds
|
1.5 ba
|
1428 sqft

$518/sqft · 14 days on market

MLS® 73594309Single Family Residence
Gibson Sotheby's International Realty - Natalia Weiner
Property at 800 Riverview Dr, Chatham, MA 02633
1 / 40
Active Under Contract
Price drop

$875,000

Price reduced by

800 Riverview Dr, Chatham, MA 02633

3 bds
|
2 ba
|
1820 sqft

$481/sqft · 33 days on market

MLS® 73583012Single Family Residence
Compass - Shane Masaschi
Property at 15 Eddie Ln, Chatham, MA 02633
1 / 14
Active Under Contract

$599,999

15 Eddie Ln, Chatham, MA 02633

2 bds
|
1 ba
|
1296 sqft

$463/sqft · 24 days on market

MLS® 73589780Single Family Residence
Coldwell Banker Realty - Easton - Catherine Walsh
Property at 2118 Main St, Chatham, MA 02633
1 / 26
Active
Price drop
Open

$1,275,000

Price reduced by

2118 Main St, Chatham, MA 02633

4 bds
|
2.5 ba
|
2670 sqft

$478/sqft · 34 days on market

MLS® 73585978Single Family Residence
Gibson Sotheby's International Realty - Marcie Smith
Property at 35 Duncan Lane, Chatham, MA 02633
1 / 38
Active
Price drop

$1,195,000

Price reduced by

35 Duncan Lane, Chatham, MA 02633

3 bds
|
2 ba
|
2176 sqft

$549/sqft · 151 days on market

MLS® 73531412Single Family Residence
Alliance Realty Advisors, Inc. - John Habeeb

$870,000

304 Round Cove Rd, Chatham, MA 02633

3 bds
|
2 ba
|
1896 sqft

$459/sqft · 23 days on market

MLS® 73590218Single Family Residence
Venture - Kimberly Arena

$5,900,000

95 Cotchpinicut, Chatham, MA 02633

4 bds
|
5 ba
|
4394 sqft

$1,343/sqft · 122 days on market

MLS® 73544856Single Family Residence
William Raveis Chatham - John Burke
Property at 70 Uncle Deane's Rd, Chatham, MA 02659
1 / 42
Active
Price drop
Open

$1,599,000

Price reduced by

70 Uncle Deane's Rd, Chatham, MA 02659

3 bds
|
3 ba
|
3514 sqft

$455/sqft · 175 days on market

MLS® 73519558Single Family Residence
Shining Sea Realty - Patrick Davison

$2,199,000

312 Round Cove Rd, Chatham, MA 02633

3 bds
|
2.5 ba
|
2848 sqft

$772/sqft · 23 days on market

MLS® 73590086Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group

$619,000

Price reduced by

216 Orleans Rd #D, Chatham, MA 02650

2 bds
|
2 ba
|
1000 sqft

$619/sqft · 57 days on market

MLS® 73571094Condominium
Compass - Kathleen Phelan

$1,650,000

764 Riverview Dr, Chatham, MA 02633

3 bds
|
3 ba
|
1902 sqft

$868/sqft · 32 days on market

MLS® 73586414Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Sharon Mabile
Property at 70 Judges Way, Chatham, MA 02633
1 / 42
Active
Price drop
Open

$5,450,000

Price reduced by

70 Judges Way, Chatham, MA 02633

5 bds
|
4.5 ba
|
4060 sqft

$1,342/sqft · 197 days on market

MLS® 73506909Single Family Residence
Christie's International Real Estate Atlantic Brokerage - Lori Jurkowski

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

As of November 5, 2026, there are 51 homes for sale in Chatham, MA, with a median list price of $1,695,000. In August 2026, the median sale price for homes in Chatham, MA was $1,355,500, down 22.5% from a year earlier.

Homes for sale
51
Median list price
$1,695,000
Median sale price (August 2026)
$1,355,500
Median days on market (August 2026)
44 days
Median sale price, Sep 2025 – Aug 2026

Common questions about Chatham, MA real estate

How many homes are for sale in Chatham, MA?

As of November 5, 2026, there are 51 homes for sale in Chatham, MA, including 47 single-family homes and 4 condos.

What is the median home price in Chatham, MA?

The median list price of homes for sale in Chatham, MA is $1,695,000. Homes that sold in August 2026 had a median sale price of $1,355,500, down 22.5% from a year earlier.

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

Homes in Chatham, MA that sold in August 2026 had a median of 44 days on market. Homes currently for sale show a median of about 32 days on market.

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

The homes for sale in Chatham, MA include 47 single-family homes and 4 condos.