Chatham, MA - single-family homes for sale

34 of 34 results displayed

New
$5,250,000Active
4 beds 5 baths4,000 sq. ft.
106 Barcliff Avenue, Chatham, MA 02633
MLS# 22604428Listed by: EXP REALTY, LLC
$2,995,000Pending
3 beds 4 baths2,405 sq. ft.
5 Kingsbury Way, Chatham, MA 02633
MLS# 22604381Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
New
$2,600,000Active
3 beds 3 baths2,160 sq. ft.
10 Mill Hill Lane, Chatham, MA 02633
MLS# 73570905Listed by: Gibson Sotheby's International Realty
New
$4,950,000Active
3 beds 4 baths3,441 sq. ft.
103 Aunt Nabby's Lane, Chatham, MA 02633
MLS# 22604310Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$1,340,000Pending
3 beds 3 baths2,155 sq. ft.
116 Vineyard Avenue, Chatham, MA 02633
MLS# 22604274Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$6,990,000Active
5 beds 6 baths4,248 sq. ft.
108 Queen Anne Road, Chatham, MA 02633
MLS# 22603964Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,995,000Pending
5 beds 4 baths1,969 sq. ft.
156 Chatham Bars Avenue, Chatham, MA 02633
MLS# 22603979Listed by: EXP REALTY, LLC
$2,395,000Pending
3 beds 3 baths1,638 sq. ft.
10 Kingsbury Way, Chatham, MA 02633
MLS# 22603840Listed by: COMPASS MASSACHUSETTS, LLC
Open Sun, 10:30am to 12pm
$1,175,000Active
3 beds 3 baths1,884 sq. ft.
190 Heritage Lane, Chatham, MA 02633
MLS# 22603647Listed by: COMPASS
$4,500,000Active
4 beds 5 baths4,689 sq. ft.
66 Ethelma Dr, Chatham, MA 02633
MLS# 73556459Listed by: Berkshire Hathaway HomeServices Robert Paul Properties
$4,500,000Active
4 beds 5 baths4,689 sq. ft.
66 Ethelma Drive, Chatham, MA 02633
MLS# 22603629Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$1,230,000Pending
3 beds 3 baths2,294 sq. ft.
72 Smith Street, Chatham, MA 02633
MLS# 22603611Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$8,950,000Active
4 beds 3 baths1,738 sq. ft.
166 Shore Road, Chatham, MA 02633
MLS# 22603612Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$9,995,000Active
3 beds 3 baths3,079 sq. ft.
153 Shore Road, Chatham, MA 02633
MLS# 22603522Listed by: EXP REALTY, LLC
$2,390,000Active
4 beds 4 baths4,066 sq. ft.
55 Winterset Drive, Chatham, MA 02633
MLS# 22603375Listed by: COLDWELL BANKER REALTY
$6,500,000Active
10 beds 10 baths7,658 sq. ft.
150-154 Cross Street, Chatham, MA 02633
MLS# 22602857Listed by: COMPASS MASSACHUSETTS, LLC
$2,100,000Active
1 beds 2 baths1,479 sq. ft.
409 Main Street, Chatham, MA 02633
MLS# 22602838Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$4,995,000Active
4 beds 4 baths2,932 sq. ft.
56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty LLC
$4,950,000Active
4 beds 5 baths5,371 sq. ft.
15 Bay Lane, Chatham, MA 02633
MLS# 22602178Listed by: COMPASS MASSACHUSETTS, LLC
Open Sat, 2 to 4pm
$2,850,000Active
3 beds 3 baths2,205 sq. ft.
336 Stage Island Road, Chatham, MA 02633
MLS# 22601983Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,950,000Active
4 beds 4 baths3,978 sq. ft.
60 Harbor Hill Road, Chatham, MA 02633
MLS# 22601737Listed by: SHORE ROAD REALTY
$1,585,000Pending
3 beds 2 baths2,169 sq. ft.
48 Glover Square, Chatham, MA 02633
MLS# 22601653Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,750,000Active
5 beds 5 baths4,060 sq. ft.
70 Judges Way, Chatham, MA 02633
MLS# 22601572Listed 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
$4,995,000Pending
5 beds 5 baths3,225 sq. ft.
101 Morris Island Road, Chatham, MA 02633
MLS# 22601118Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,850,000Active
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
$4,250,000Active
4 beds 6 baths3,980 sq. ft.
222 Barcliff Avenue, Chatham, MA 02633
MLS# 22600932Listed by: COMPASS MASSACHUSETTS, LLC
$1,280,000Active
3 beds 2 baths2,278 sq. ft.
243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,350,000Pending
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
$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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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.