View 38 Indian Trail Chatham, MA MLS# 22601752
  • Virtual Tour
1 of 72
$4,495,000
4

Beds

3.1

Baths

4,967

Sq.Ft.

38 Indian Trail

Chatham, MA

CapeCodIslands
View 60 Harbor Hill Road Chatham, MA MLS# 22601737
$3,390,000
4

Beds

3.1

Baths

3,978

Sq.Ft.

60 Harbor Hill Road

Chatham, MA

CapeCodIslands
View 70 Judges Way Chatham, MA MLS# 73506909
  • Virtual Tour
1 of 41
$5,995,000
5

Beds

4.1

Baths

4,060

Sq.Ft.

70 Judges Way

Chatham, MA

Listed By: Lori Jurkowski Courtesy of CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
The time to sell is now! THE TIME TO SELL IS NOW!
View 29 Jessies Landing Chatham, MA MLS# 22601788
  • New Construction
1 of 15
$3,699,900
3

Beds

4.1

Baths

4,565

Sq.Ft.

29 Jessies Landing

Chatham, MA

CapeCodIslands
View 48 Glover Square Chatham, MA MLS# 22601653
$1,585,000
3

Beds

2.0

Baths

2,169

Sq.Ft.

48 Glover Square

Chatham, MA

CapeCodIslands
View 61 Oak Hill Road Chatham, MA MLS# 22601667
$865,900
2

Beds

2.0

Baths

1,688

Sq.Ft.

61 Oak Hill Road

Chatham, MA

CapeCodIslands
View 70 Judges Way Chatham, MA MLS# 22601572
  • Virtual Tour
1 of 70
$5,995,000
5

Beds

4.1

Baths

4,060

Sq.Ft.

70 Judges Way

Chatham, MA

CapeCodIslands
View 1772 Main St Chatham, MA MLS# 73500740
$699,999
Studio

Beds

1.1

Baths

600

Sq.Ft.

1772 Main St

Chatham, MA

Listed By: Erin Terkelsen Courtesy of LPT REALTY, LLC
View 1772 Main Street Chatham, MA MLS# 22601404
$699,999
Studio

Beds

1.1

Baths

600

Sq.Ft.

1772 Main Street

Chatham, MA

CapeCodIslands
View 157 Bridge Street Chatham, MA MLS# 22601380
  • New Construction
1 of 20
$12,999,900
4

Beds

5.2

Baths

6,234

Sq.Ft.

157 Bridge Street

Chatham, MA

CapeCodIslands
View 109 Misty Meadow Ln # 4 Chatham, MA MLS# 73499320
$475,000
2

Beds

1.0

Baths

869

Sq.Ft.

109 Misty Meadow Ln # 4

Chatham, MA

Listed By: Guthrie Schofield Group Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
View 15 Windy Hill Way Chatham, MA MLS# 73495151
$5,850,000
5

Beds

5.1

Baths

5,620

Sq.Ft.

15 Windy Hill Way

Chatham, MA

Listed By: Timothy Bailey Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.
View 101 Morris Island Rd Chatham, MA MLS# 73494797
  • Virtual Tour
1 of 42
$5,495,000
4

Beds

4.1

Baths

3,225

Sq.Ft.

101 Morris Island Rd

Chatham, MA

Listed By: The Bohman Hartung Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 15 Windy Hill Way Chatham, MA MLS# 22601111
$5,850,000
5

Beds

5.1

Baths

5,620

Sq.Ft.

15 Windy Hill Way

Chatham, MA

CapeCodIslands
View 101 Morris Island Road Chatham, MA MLS# 22601118
  • Virtual Tour
1 of 77
OPEN HOUSE: Saturday 6/27 11:00 AM - 1:00 PM
$5,495,000
5

Beds

4.1

Baths

3,225

Sq.Ft.

101 Morris Island Road

Chatham, MA

CapeCodIslands
View 234 Round Cove Rd Chatham, MA MLS# 73494106
$2,150,000
3

Beds

2.1

Baths

2,481

Sq.Ft.

234 Round Cove Rd

Chatham, MA

Listed By: Guthrie Schofield Group Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
View 222 Barcliff Chatham, MA MLS# 73493426
$4,250,000
4

Beds

5.1

Baths

3,980

Sq.Ft.

222 Barcliff

Chatham, MA

Listed By: Lori Fanning Smith Courtesy of COMPASS
View 346 Morris Island Road Chatham, MA MLS# 73492591
$4,500,000
4

Beds

3.1

Baths

2,850

Sq.Ft.

346 Morris Island Road

Chatham, MA

Listed By: Chris Rhinesmith Courtesy of COMPASS
View 32 Tip Cart Dr Chatham, MA MLS# 73492178
  • Virtual Tour
1 of 31
$1,350,000
3

Beds

2.0

Baths

1,802

Sq.Ft.

32 Tip Cart Dr

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
View 137 Shane Dr Chatham, MA MLS# 73492122
$1,399,000
3

Beds

2.0

Baths

1,530

Sq.Ft.

137 Shane Dr

Chatham, MA

Listed By: Tom Riley Courtesy of COMPASS

About Chatham

Listings in Chatham, MA

125

Estimated median home price

$1,999,000
Chatham MA Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chatham, Massachusetts real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chatham, MA.

Homes for Sale by Price in Chatham, MA

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 1
$400K - 500K 4
$500K - 600K 0
$600K - 700K 6
$700K - 800K 6
$800K - 900K 7
$900K - 1M 5
$1M - Max 96

Homes for Sale by Type in Chatham, MA

Property Type Count
Single Family 104
Townhouse 0
Condo 6
Commercial 11
Rental 6
Lots and Land 4
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/25/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 6/25/2026.

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The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Weichert Realtors are marked with the BR Logo and detailed information about them includes the name of the listing broker company. Neither the listing broker nor Weichert Realtors shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

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Data is updated as of 6/25/2026. All properties are subject to prior sale, changes, or withdrawal.