Chatham, MA - homes for sale

43 of 43 results displayed

New
$6,500,000Active
10 beds 10 baths7,658 sq. ft.
150-154 Cross Street, Chatham, MA 02633
MLS# 22602857Listed by: COMPASS MASSACHUSETTS, LLC
New
$2,100,000Active
1 beds 2 baths1,479 sq. ft.
409 Main Street, Chatham, MA 02633
MLS# 22602838Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
New
$985,000Active
3 beds 2 baths1,392 sq. ft.
33 Jeanette Rd, Chatham, MA 02633
MLS# 73529488Listed by: Compass
$999,000Active
0.16 Acres
727 Main Street, Chatham, MA 02633
MLS# 22602638Listed by: KENNEDY REAL ESTATE
$1,350,000Pending
4 beds 2 baths1,951 sq. ft.
92 Hitching Post Road, Chatham, MA 02633
MLS# 22602644Listed by: HOME*LAND REALTY
$5,495,000Active
4 beds 4 baths2,932 sq. ft.
56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty
$1,199,900Active
2 beds 2 baths1,324 sq. ft.
99 Shane Drive, Chatham, MA 02633
MLS# 22602427Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$849,000Active
2 beds 1 baths864 sq. ft.
66 Snow Ln, Chatham, MA 02633
MLS# 73523077Listed by: Compass
$2,350,000Pending
3 beds 3 baths2,212 sq. ft.
320 Old Harbor Road, Chatham, MA 02633
MLS# 22602390Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,495,000Active
4 beds 6 baths5,372 sq. ft.
335 Stage Island Road, Chatham, MA 02633
MLS# 22602319Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$4,595,000Pending
5 beds 4 baths2,659 sq. ft.
92 Barcliff Avenue, Chatham, MA 02633
MLS# 22602315Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$1,800,000Pending
4 beds 2 baths1,236 sq. ft.
213 Main Street, Chatham, MA 02633
MLS# 22602308Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$490,000Pending
2 beds 1 baths496 sq. ft.
1340 Main Street #UNIT 9, Chatham, MA 02633
MLS# 22602247Listed by: COMPASS MASSACHUSETTS, LLC
$645,000Pending
2 beds 2 baths1,045 sq. ft.
99 Depot Road #APT 23, Chatham, MA 02633
MLS# 22602238Listed by: JOHN C RICOTTA & ASSOC.
$4,950,000Active
4 beds 5 baths5,371 sq. ft.
15 Bay Lane, Chatham, MA 02633
MLS# 22602178Listed by: COMPASS MASSACHUSETTS, LLC
$1,275,000Pending
3 beds 3 baths2,062 sq. ft.
58 Stepping Stones Road, Chatham, MA 02633
MLS# 22602135Listed by: NEW HOMES MARKETING, INC.
$2,995,000Active
3 beds 3 baths2,205 sq. ft.
336 Stage Island Road, Chatham, MA 02633
MLS# 22601983Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,995,000Pending
3 beds 4 baths3,014 sq. ft.
7 Squanto Drive, Chatham, MA 02633
MLS# 22601915Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$3,699,900Pending
3 beds 5 baths4,565 sq. ft.
29 Jessies Landing, Chatham, MA 02633
MLS# 22601788Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$3,600,000Active
4 beds 4 baths3,978 sq. ft.
60 Harbor Hill Road, Chatham, MA 02633
MLS# 22601737Listed by: SHORE ROAD REALTY
$1,650,000Active
3 beds 2 baths2,169 sq. ft.
48 Glover Square, Chatham, MA 02633
MLS# 22601653Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,995,000Active
5 beds 5 baths4,060 sq. ft.
70 Judges Way, Chatham, MA 02633
MLS# 22601572Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$450,000Pending
1 beds 1 baths578 sq. ft.
425 Main Street #UNIT D, Chatham, MA 02633
MLS# 22601604Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,850,000Active
3 beds 4 baths1,999 sq. ft.
32 Gladen Lane, Chatham, MA 02633
MLS# 22601360Listed by: COMPASS MASSACHUSETTS, LLC
$459,000Pending
1 beds 2 baths1,284 sq. ft.
912 Main Street #Unit 308, Chatham, MA 02633
MLS# 22600884Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$12,999,900Active
4 beds 7 baths6,234 sq. ft.
157 Bridge Street, Chatham, MA 02633
MLS# 22601380Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$699,000Active
2 beds 3 baths1,773 sq. ft.
6-894 Munson Meeting Way, Chatham, MA 02633
MLS# 22601278Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$735,000Active
2 beds 2 baths950 sq. ft.
22 Starfish Lane #UNIT 22, Chatham, MA 02633
MLS# 22600801Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$5,495,000Active
5 beds 5 baths3,225 sq. ft.
101 Morris Island Road, Chatham, MA 02633
MLS# 22601118Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$6,250,000Active
5 beds 6 baths5,620 sq. ft.
15 Windy Hill Way, Chatham, MA 02633
MLS# 22601111Listed by: JOHN C RICOTTA & ASSOC.
$4,500,000Active
4 beds 4 baths2,850 sq. ft.
346 Morris Island Road, Chatham, MA 02633
MLS# 22601006Listed by: COMPASS MASSACHUSETTS, LLC
$1,495,000Active
3 beds 2 baths1,530 sq. ft.
137 Shane Drive, Chatham, MA 02633
MLS# 22600988Listed by: COMPASS MASSACHUSETTS, LLC
$1,200,000Active
3 beds 3 baths1,804 sq. ft.
118 Wilfred Road, Chatham, MA 02633
MLS# 22600948Listed by: COMPASS
$4,250,000Active
4 beds 6 baths3,980 sq. ft.
222 Barcliff Avenue, Chatham, MA 02633
MLS# 22600932Listed by: COMPASS MASSACHUSETTS, LLC
$1,350,000Active
3 beds 2 baths2,278 sq. ft.
243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,350,000Active
3 beds 2 baths1,802 sq. ft.
32 Tip Cart Drive, Chatham, MA 02633
MLS# 22600918Listed by: COMPASS
$4,499,900Active
3 beds 7 baths5,820 sq. ft.
33 Crowell Road, Chatham, MA 02633
MLS# 22600794Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$1,995,000Active
3 beds 2 baths1,488 sq. ft.
50 Eldredge Square, Chatham, MA 02633
MLS# 22600669Listed by: COMPASS MASSACHUSETTS, LLC
$4,700,000Pending
5 beds 4 baths3,080 sq. ft.
85 Cedar Street, Chatham, MA 02633
MLS# 22504804Listed by: JOHN C RICOTTA & ASSOC.
$4,525,000Pending
4 beds 6 baths5,300 sq. ft.
230 Barcliff Avenue, Chatham, MA 02633
MLS# 22504396Listed by: COMPASS MASSACHUSETTS, LLC
$5,495,000Active
2 beds 3 baths1,850 sq. ft.
99 Uncle Alberts Drive Ext, Chatham, MA 02633
MLS# 22503829Listed by: COMPASS
$3,595,000Active
3 beds 5 baths3,640 sq. ft.
287 Cedar Street, Chatham, MA 02633
MLS# 22502029Listed by: COMPASS
$1,650,000Active
-- beds 1 baths2,586 sq. ft.
231 Crowell Road, Chatham, MA 02633
MLS# 22403062Listed by: JOHN C RICOTTA & ASSOC.

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.