View 65 Harbor View Road Chatham, MA MLS# 22604593
$4,995,000
5

Beds

5.1

Baths

4,763

Sq.Ft.

65 Harbor View Road

Chatham, MA

CapeCodIslands
View 216 Orleans Rd # D Chatham, MA MLS# 73571094
$619,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

216 Orleans Rd # D

Chatham, MA

Listed By: Kathleen Phelan Courtesy of COMPASS
View 22 Moonpenny Lane Chatham, MA MLS# 22604577
  • Virtual Tour
1 of 59
$4,250,000
4

Beds

4.1

Baths

4,298

Sq.Ft.

22 Moonpenny Lane

Chatham, MA

CapeCodIslands
The time to sell is now! THE TIME TO SELL IS NOW!
View 72 Ridgevale Rd So Chatham, MA MLS# 73574801
$2,499,000
2

Beds

2.0

Baths

1,547

Sq.Ft.

72 Ridgevale Rd So

Chatham, MA

Listed By: Shane Masaschi Courtesy of COMPASS
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 231 Crowell Road Chatham, MA MLS# 73258353
$1,650,000
1.0

Baths

2,586

Sq.Ft.

231 Crowell Road

Chatham, MA

Listed By: Judith Smith Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.
View 2653 Main St Chatham, MA MLS# 73571994
$950,000
2,252

Sq.Ft.

2653 Main St

Chatham, MA

Listed By: Kevin A. Pepe Courtesy of COMMERCIAL REALTY ADVISORS, INC.
View 20 Circle Drive Chatham, MA MLS# 73571912
  • Virtual Tour
1 of 42
$2,140,000
4

Beds

3.0

Baths

3,102

Sq.Ft.

20 Circle Drive

Chatham, MA

Listed By: Barbara Carroll-Horne Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 2653 Main Street Chatham, MA MLS# 22604441
$950,000
2,252

Sq.Ft.

2653 Main Street

Chatham, MA

CapeCodIslands
View 106 Barcliff Ave Chatham, MA MLS# 73571701
$5,250,000
4

Beds

4.1

Baths

4,000

Sq.Ft.

106 Barcliff Ave

Chatham, MA

Listed By: Jill Boudreau Courtesy of EXP REALTY LLC - CORPORATE OFFICE
View 64 Harbor View Road Chatham, MA MLS# 22604409
$4,000,000
5

Beds

3.0

Baths

2,303

Sq.Ft.

64 Harbor View Road

Chatham, MA

CapeCodIslands
View 106 Barcliff Avenue Chatham, MA MLS# 22604428
  • New Construction
1 of 35
OPEN HOUSE: Saturday 10/24 11:00 AM - 12:30 PM
$5,250,000
4

Beds

4.1

Baths

4,000

Sq.Ft.

106 Barcliff Avenue

Chatham, MA

CapeCodIslands
View 5 Kingsbury Way Chatham, MA MLS# 22604381
$2,995,000
3

Beds

3.1

Baths

2,405

Sq.Ft.

5 Kingsbury Way

Chatham, MA

CapeCodIslands
View 72 Ridgevale Road Chatham, MA MLS# 22604319
  • Virtual Tour
1 of 51
$2,499,000
2

Beds

2.0

Baths

1,547

Sq.Ft.

72 Ridgevale Road

Chatham, MA

CapeCodIslands
View 87 Cranberry Lane Chatham, MA MLS# 22604234
  • Virtual Tour
1 of 47
$1,495,000
3

Beds

2.0

Baths

1,238

Sq.Ft.

87 Cranberry Lane

Chatham, MA

CapeCodIslands
View 210 Orleans Road # C Chatham, MA MLS# 73568884
$675,000
2

Beds

2.0

Baths

996

Sq.Ft.

210 Orleans Road # C

Chatham, MA

Listed By: John Burke Courtesy of WILLIAM RAVEIS CHATHAM
View 1114 Orleans Rd # 8 Chatham, MA MLS# 73568802
$1,325,000
2

Beds

2.1

Baths

2,306

Sq.Ft.

1114 Orleans Rd # 8

Chatham, MA

Listed By: Betsy Hargreaves Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 48 Hillcrest Road Chatham, MA MLS# 22604112
$5,900,000
4

Beds

5.1

Baths

5,254

Sq.Ft.

48 Hillcrest Road

Chatham, MA

CapeCodIslands
View 156 Chatham Bars Avenue Chatham, MA MLS# 22603979
$2,995,000
5

Beds

3.1

Baths

1,969

Sq.Ft.

156 Chatham Bars Avenue

Chatham, MA

CapeCodIslands
View 43 Tobey Turtle Chatham, MA MLS# 73561031
  • Virtual Tour
1 of 42
$1,695,000
2

Beds

3.1

Baths

2,331

Sq.Ft.

43 Tobey Turtle

Chatham, MA

Listed By: Timothy Bailey Courtesy of JOHN C. RICOTTA & ASSOCIATES, INC.

About Chatham

Listings in Chatham, MA

115

Estimated median home price

$2,295,000
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 0
$500K - 600K 1
$600K - 700K 3
$700K - 800K 0
$800K - 900K 10
$900K - 1M 5
$1M - Max 95

Homes for Sale by Type in Chatham, MA

Property Type Count
Single Family 94
Townhouse 0
Condo 3
Commercial 15
Rental 7
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/21/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 10/21/2026.

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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 10/21/2026. All properties are subject to prior sale, changes, or withdrawal.