AndrewGoldberg
Buy
Property SearchSearch all available MLS listingsSet AlertsGet notified about new listingsNeighborhood GuidesExplore local communities & data
Boston, MA
Newton, MA
Medford, MA
Brookline, MA
Cambridge, MA
Somerville, MA
View All Neighborhoods →
Featured PropertiesBrowse our exclusive local listings
65 Chestnut St
50 Brooks Street
4 Edward Cody Ln
View All Featured →
Plan a TourBuild an open house tour from homes you’ve viewed
Sell
Home ValuationGet a free, instant estimateMy ListingsBrowse my active market properties
Insights
Resources
ResourcesHelpful guides and toolsLocal EventsEvents & local favorites near you
About
Meet the AgentMy background and experienceClient StoriesRead reviews from past clients
Contact Me
Buy
Property Search
Set Alerts
Neighborhood Guides
Boston, MA
Back BayBeacon HillSeaport DistrictSouth EndNorth EndSouth BostonFenway-KenmoreCharlestownDorchesterJamaica PlainAllstonRoslindaleWest RoxburyEast BostonMission HillBay VillageBrightonRoxbury
Newton, MA
Medford, MA
Brookline, MA
Cambridge, MA
Somerville, MA
View All Neighborhoods →
Featured Properties
65 Chestnut St
50 Brooks Street
4 Edward Cody Ln
View All Featured →
Plan a Tour
Sell
Home Valuation
My Listings
Insights
Resources
Resources
Local Events
About
Meet the Agent
Client Stories
Contact Me

Homes for Sale in Chatham, MA – Page 2

51 results

Property at 336 Stage Island Rd, Chatham, MA 02633
1 / 42
Active
Price
Open

$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 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 169 Tisquantum Rd, Chatham, MA 02633
1 / 42
Active
Open

$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

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 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 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 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 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 210 Orleans Road #C, Chatham, MA 02650
1 / 22
Active

$675,000

210 Orleans Road #C, Chatham, MA 02650

2 bds
|
2 ba
|
996 sqft
MLS® 73568884Condominium
William Raveis Chatham - John Burke
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 106 Barcliff Ave, Chatham, MA 02633
1 / 35
Active
Open

$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
Property at 48 Sylvan Way, Chatham, MA 02659
1 / 42
Active
Price

$4,500,000

48 Sylvan Way, Chatham, MA 02659

6 bds
|
6 ba
|
5721 sqft
MLS® 73479712Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 78 Indian Trail, Chatham, MA 02633
1 / 42
Active

$2,800,000

78 Indian Trail, Chatham, MA 02633

3 bds
|
2 ba
|
1160 sqft
MLS® 73457238Single Family Residence
John C. Ricotta & Associates, Inc. - Judith Smith
Property at 92 Indian Trail, Chatham, MA 02633
1 / 41
Active

$3,200,000

92 Indian Trail, Chatham, MA 02633

3 bds
|
3 ba
|
2004 sqft
MLS® 73457239Single Family Residence
John C. Ricotta & Associates, Inc. - Judith Smith
Property at 558 Fox Hill Rd, Chatham, MA 02633
1 / 33
Active

$1,469,000

558 Fox Hill Rd, Chatham, MA 02633

5 bds
|
8 ba
|
11000 sqft
MLS® 73548115Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Property at 15 Windy Hill Way, Chatham, MA 02633
1 / 42
Active
Price

$5,850,000

15 Windy Hill Way, Chatham, MA 02633

5 bds
|
5.5 ba
|
5620 sqft
MLS® 73495151Single Family Residence
John C. Ricotta & Associates, Inc. - Timothy Bailey
Property at 150-154 Cross Street, Chatham, MA 02633
1 / 28
Active

$6,500,000

150-154 Cross Street, Chatham, MA 02633

10 bds
|
8.5 ba
|
7658 sqft
MLS® 73535185Single Family Residence
Compass - Chris Rhinesmith
Property at 409 Main St, Chatham, MA 02633
1 / 42
Active

$2,100,000

409 Main St, Chatham, MA 02633

1 bds
|
1.5 ba
|
1479 sqft
MLS® 73535300Single Family Residence
Gibson Sotheby's International Realty - Rick Smith
Property at 50 Sylvan Way, Chatham, MA 02659
Active

$5,900,000

50 Sylvan Way, Chatham, MA 02659

6 bds
|
7 ba
|
6183 sqft
MLS® 73533378Single Family Residence
Berkshire Hathaway HomeServices Robert Paul Properties - Guthrie Schofield Group
Page 2 of 2

Brokerage Information

Commonwealth Standard Realty Advisors

10 Lincoln St, Newton, MA, 02461

(617) 256-7438

Market Area Served

Boston, Brookline, Cambridge, Medford, Somerville, Newton 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.

Andrew Goldberg

I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

Explore

  • Home
  • About
  • Home Search
  • Set Alerts
  • My Active Listings
  • Featured Listings
  • Home Valuation
  • Plan a Tour
  • Insights
  • Testimonials
  • Resources
  • Contact
  • Privacy Policy

Contact

  • 10 Lincoln St, Newton, MA, 02461
  • (617) 256-7438
  • andrew@commonwealthstandard.com

Brokerage

Commonwealth Standard Realty Advisors

© 2026 Andrew Goldberg. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.