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Chatham, MA - single-family homes for sale
28 of 28 results displayed
- New
$9,495,000Active3 beds 3 baths3,079 sq. ft.153 Shore Rd, Chatham, MA 02633
MLS# 73594589Listed by: eXp Realty LLC - New
$995,000Active2 beds 1 baths710 sq. ft.20 Cedar Swamp Lane, Chatham, MA 02633
MLS# 22605308Listed by: SOTHEBY'S INTERNATIONAL REALTY 
$2,500,000Pending2 beds 3 baths1,568 sq. ft.155 Stage Island Road, Chatham, MA 02633
MLS# 22605288Listed by: NAUSET MANAGEMENT
$1,275,000Active4 beds 4 baths3,805 sq. ft.41 Taylor Ln, Rowley, MA 01969
MLS# 73583059Listed by: RE/MAX Bentley's
$3,100,000Pending3 beds 4 baths4,053 sq. ft.26 Chatham Heights Road, Chatham, MA 02633
MLS# 22604867Listed by: COMPASS MASSACHUSETTS, LLC
$6,875,000Active4 beds 5 baths4,512 sq. ft.12 Pond Street, Chatham, MA 02633
MLS# 22604827Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$3,100,000Pending3 beds 4 baths2,209 sq. ft.90 Silver Leaf Avenue, Chatham, MA 02633
MLS# 22604797Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,900,000Active4 beds 6 baths5,254 sq. ft.48 Hillcrest Road, Chatham, MA 02633
MLS# 22604112Listed by: COMPASS MASSACHUSETTS, LLC
$4,250,000Active4 beds 5 baths4,298 sq. ft.22 Moonpenny Lane, Chatham, MA 02633
MLS# 22604577Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$5,250,000Active4 beds 5 baths4,000 sq. ft.106 Barcliff Avenue, Chatham, MA 02633
MLS# 22604428Listed by: EXP REALTY, LLC
$2,995,000Pending3 beds 4 baths2,405 sq. ft.5 Kingsbury Way, Chatham, MA 02633
MLS# 22604381Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$9,495,000Active3 beds 3 baths3,079 sq. ft.153 Shore Road, Chatham, MA 02633
MLS# 22603522Listed by: EXP REALTY, LLC
$2,295,000Active4 beds 4 baths4,066 sq. ft.55 Winterset Drive, Chatham, MA 02633
MLS# 22603375Listed by: COLDWELL BANKER REALTY
$6,500,000Active10 beds 10 baths7,658 sq. ft.150-154 Cross Street, Chatham, MA 02633
MLS# 22602857Listed by: COMPASS MASSACHUSETTS, LLC
$2,100,000Active1 beds 2 baths1,479 sq. ft.409 Main Street, Chatham, MA 02633
MLS# 22602838Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$4,995,000Active4 beds 4 baths2,932 sq. ft.56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty LLC
$2,699,000Active3 beds 3 baths2,205 sq. ft.336 Stage Island Road, Chatham, MA 02633
MLS# 22601983Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,850,000Active4 beds 4 baths3,978 sq. ft.60 Harbor Hill Rd, Chatham, MA 02633
MLS# 73511079Listed by: Shore Road Realty, LLC
$5,450,000Active5 beds 5 baths4,060 sq. ft.70 Judges Way, Chatham, MA 02633
MLS# 22601572Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$12,999,900Active4 beds 7 baths6,234 sq. ft.157 Bridge Street, Chatham, MA 02633
MLS# 22601380Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$5,850,000Active5 beds 6 baths5,620 sq. ft.15 Windy Hill Way, Chatham, MA 02633
MLS# 22601111Listed by: JOHN C RICOTTA & ASSOC.
$4,500,000Pending4 beds 4 baths2,850 sq. ft.346 Morris Island Road, Chatham, MA 02633
MLS# 22601006Listed by: COMPASS MASSACHUSETTS, LLC
$4,250,000Pending4 beds 6 baths3,980 sq. ft.222 Barcliff Avenue, Chatham, MA 02633
MLS# 22600932Listed by: COMPASS MASSACHUSETTS, LLC
$1,175,000Active3 beds 2 baths2,278 sq. ft.243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,295,000Pending3 beds 2 baths1,802 sq. ft.32 Tip Cart Drive, Chatham, MA 02633
MLS# 22600918Listed by: COMPASS
$4,499,900Active3 beds 7 baths5,820 sq. ft.33 Crowell Road, Chatham, MA 02633
MLS# 22600794Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$5,495,000Pending2 beds 3 baths1,850 sq. ft.99 Uncle Alberts Drive Ext, Chatham, MA 02633
MLS# 22503829Listed by: COMPASS
$1,650,000Active-- beds 1 baths2,586 sq. ft.231 Crowell Road, Chatham, MA 02633
MLS# 22403062Listed by: JOHN C RICOTTA & ASSOC.
Local realty services provided by:CENTURY 21 Elite Realty, Inc., CENTURY 21 North East
Neighborhoods near Chatham, MA
Zip codes near Chatham, MA
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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.
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.