View 196 Shore Road Chatham, MA MLS# 22504216
$25,000,000
13,388

Sq.Ft.

196 Shore Road

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 301 Whidah Road Chatham, MA MLS# 73489042
$12,950,000
5

Beds

6.1

Baths

7,259

Sq.Ft.

301 Whidah Road

Chatham, MA

Listed By: Paul E. Grover Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 166 Shore Road Chatham, MA MLS# 22603612
  • Recently Listed
1 of 103
$12,000,000
4

Beds

3.0

Baths

1,738

Sq.Ft.

166 Shore Road

Chatham, MA

CapeCodIslands
View 166 Shore Road Chatham, MA MLS# 73556482
  • Recently Listed
1 of 39
$12,000,000
4

Beds

3.0

Baths

1,738

Sq.Ft.

166 Shore Road

Chatham, MA

Listed By: Guthrie Schofield Group Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
View 153 Shore Road Chatham, MA MLS# 22603522
  • Recently Listed
1 of 59
$9,995,000
3

Beds

2.1

Baths

3,079

Sq.Ft.

153 Shore Road

Chatham, MA

CapeCodIslands
View 238 Cranberry Lane Chatham, MA MLS# 73358568
$6,800,000
5

Beds

2.1

Baths

1,896

Sq.Ft.

238 Cranberry Lane

Chatham, MA

Listed By: John Burke Courtesy of WILLIAM RAVEIS CHATHAM
View 150-154 Cross Street Chatham, MA MLS# 22602857
$6,500,000
10

Beds

7.3

Baths

7,658

Sq.Ft.

150-154 Cross Street

Chatham, MA

CapeCodIslands
View 150-154 Cross Street Chatham, MA MLS# 73535185
$6,500,000
10

Beds

7.3

Baths

7,658

Sq.Ft.

150-154 Cross Street

Chatham, MA

Listed By: Chris Rhinesmith Courtesy of COMPASS
View 50 Sylvan Way Chatham, MA MLS# 73533378
$5,900,000
6

Beds

6.2

Baths

6,183

Sq.Ft.

50 Sylvan Way

Chatham, MA

Listed By: Guthrie Schofield Group Courtesy of BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
View 95 Cotchpinicut Road Chatham, MA MLS# 22603274
$5,900,000
4

Beds

5.0

Baths

4,394

Sq.Ft.

95 Cotchpinicut Road

Chatham, MA

CapeCodIslands
View 95 Cotchpinicut Chatham, MA MLS# 73544856
  • Virtual Tour
1 of 41
$5,900,000
4

Beds

5.0

Baths

4,394

Sq.Ft.

95 Cotchpinicut

Chatham, MA

Listed By: John Burke Courtesy of WILLIAM RAVEIS CHATHAM
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 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 70 Judges Way Chatham, MA MLS# 22601572
  • Virtual Tour
1 of 62
$5,750,000
5

Beds

4.1

Baths

4,060

Sq.Ft.

70 Judges Way

Chatham, MA

CapeCodIslands
View 70 Judges Way Chatham, MA MLS# 73506909
  • Virtual Tour
1 of 42
$5,750,000
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
View 99 Uncle Alberts Drive Ext Chatham, MA MLS# 22503829
$5,495,000
2

Beds

2.1

Baths

1,850

Sq.Ft.

99 Uncle Alberts Drive Ext

Chatham, MA

CapeCodIslands
View 99 Uncle Alberts Drive Ext Chatham, MA MLS# 73419421
$5,495,000
2

Beds

2.1

Baths

1,850

Sq.Ft.

99 Uncle Alberts Drive Ext

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
View 56 Stage Island Road Chatham, MA MLS# 73529657
  • Virtual Tour
1 of 41
$5,250,000
4

Beds

4.0

Baths

2,932

Sq.Ft.

56 Stage Island Road

Chatham, MA

Listed By: James Lowenstern Courtesy of EXP REALTY LLC
View 101 Morris Island Road Chatham, MA MLS# 22601118
  • Virtual Tour
1 of 77
$4,995,000
5

Beds

4.1

Baths

3,225

Sq.Ft.

101 Morris Island Road

Chatham, MA

CapeCodIslands

About Chatham

Listings in Chatham, MA

130

Estimated median home price

$2,247,000
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 1
$100K - 200K 0
$200K - 300K 0
$300K - 400K 1
$400K - 500K 3
$500K - 600K 0
$600K - 700K 8
$700K - 800K 5
$800K - 900K 4
$900K - 1M 6
$1M - Max 102

Homes for Sale by Type in Chatham, MA

Property Type Count
Single Family 104
Townhouse 0
Condo 7
Commercial 15
Rental 6
Lots and Land 4
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 8/6/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 8/7/2026.

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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 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 or leasing 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 or leasing. 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.

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.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 8/7/2026. All properties are subject to prior sale, changes, or withdrawal.