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Chatham town, MA - single-family homes for sale
84 of 84 results displayed
- New
$4,995,000Active5 beds 6 baths4,763 sq. ft.65 Harbor View Road, Chatham, MA 02633
MLS# 22604593Listed by: COMPASS MASSACHUSETTS, LLC - New
$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 - New
$1,200,000Active4 beds 2 baths2,050 sq. ft.122 Forest Beach Rd, Chatham, MA 02659
MLS# 73575812Listed by: Berkshire Hathaway HomeServices Robert Paul Properties - New
$875,000Active3 beds 2 baths2,167 sq. ft.31 Old Village Road, South Chatham, MA 02659
MLS# 22604510Listed by: COMPASS - New
$975,000Active3 beds 2 baths1,410 sq. ft.1455 Old Queen Anne Rd, Chatham, MA 02633
MLS# 73570542Listed by: Christie's International Real Estate Atlantic Brokerage - New
$5,250,000Active4 beds 5 baths4,000 sq. ft.106 Barcliff Avenue, Chatham, MA 02633
MLS# 22604428Listed by: EXP REALTY, LLC - New
$4,000,000Active5 beds 3 baths2,303 sq. ft.64 Harbor View, Chatham, MA 02633
MLS# 73571777Listed by: Gibson Sotheby's International Realty 
$1,295,000Pending5 beds 2 baths2,046 sq. ft.700 Crowell Road, North Chatham, MA 02650
MLS# 22604398Listed by: COMPASS MASSACHUSETTS, 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
$2,240,000Active4 beds 3 baths3,102 sq. ft.20 Circle Drive, South Chatham, MA 02659
MLS# 22604370Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$2,600,000Active3 beds 3 baths2,160 sq. ft.10 Mill Hill Lane, Chatham, MA 02633
MLS# 73570905Listed by: Gibson Sotheby's International Realty
$2,499,000Active2 beds 2 baths1,547 sq. ft.72 Ridgevale Road, Chatham, MA 02633
MLS# 22604319Listed by: COMPASS
$4,950,000Active3 beds 4 baths3,441 sq. ft.103 Aunt Nabby's Lane, Chatham, MA 02633
MLS# 22604310Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$1,340,000Pending3 beds 3 baths2,155 sq. ft.116 Vineyard Avenue, Chatham, MA 02633
MLS# 22604274Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES- Open Sat, 1 to 3pm
$1,495,000Active3 beds 2 baths1,415 sq. ft.87 Cranberry Lane, Chatham, MA 02633
MLS# 22604234Listed by: COMPASS MASSACHUSETTS, LLC 
$1,795,000Active3 beds 3 baths2,719 sq. ft.23 Taylors Pond Rd, Chatham, MA 02633
MLS# 73569230Listed by: Compass
$3,495,000Pending3 beds 4 baths3,838 sq. ft.40 Middle Road, North Chatham, MA 02650
MLS# 22604203Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$6,990,000Active5 beds 6 baths4,248 sq. ft.108 Queen Anne Road, Chatham, MA 02633
MLS# 22603964Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$5,900,000Active4 beds 6 baths5,254 sq. ft.48 Hillcrest Road, North Chatham, MA 02650
MLS# 22604112Listed by: COMPASS MASSACHUSETTS, LLC
$810,000Pending1 beds 2 baths1,468 sq. ft.24 Deep Water Lane, South Chatham, MA 02659
MLS# 22603631Listed by: TODAY REAL ESTATE
$2,995,000Pending5 beds 4 baths1,969 sq. ft.156 Chatham Bars Avenue, Chatham, MA 02633
MLS# 22603979Listed by: EXP REALTY, LLC
$1,695,000Active2 beds 4 baths2,331 sq. ft.43 Tobey Turtle, Chatham, MA 02659
MLS# 73561031Listed by: John C. Ricotta & Associates, Inc.
$1,695,000Active2 beds 4 baths2,331 sq. ft.43 Tobey Turtle Road, Chatham, MA 02633
MLS# 22603842Listed by: JOHN C RICOTTA & ASSOC.
$2,395,000Pending3 beds 3 baths1,638 sq. ft.10 Kingsbury Way, Chatham, MA 02633
MLS# 22603840Listed by: COMPASS MASSACHUSETTS, LLC- Open Sat, 10 to 11am
$1,795,000Active2 beds 2 baths1,398 sq. ft.71 Rowland Drive, North Chatham, MA 02650
MLS# 22603834Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES 
$3,595,000Pending3 beds 4 baths3,922 sq. ft.48 Hunter Rise, Chatham, MA 02633
MLS# 22603757Listed by: COMPASS MASSACHUSETTS, LLC
$1,175,000Active3 beds 3 baths1,884 sq. ft.190 Heritage Lane, Chatham, MA 02633
MLS# 22603647Listed by: COMPASS
$1,495,000Pending3 beds 3 baths1,771 sq. ft.124 Pleasant Street, South Chatham, MA 02659
MLS# 22603654Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,500,000Active4 beds 5 baths4,689 sq. ft.66 Ethelma Drive, Chatham, MA 02633
MLS# 22603629Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$1,230,000Pending3 beds 3 baths2,294 sq. ft.72 Smith Street, Chatham, MA 02633
MLS# 22603611Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$8,950,000Active4 beds 3 baths1,738 sq. ft.166 Shore Road, Chatham, MA 02633
MLS# 22603612Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$950,000Pending3 beds 1 baths1,201 sq. ft.268 Barn Hill Road, Chatham, MA 02633
MLS# 22603601Listed by: COMPASS
$9,995,000Active3 beds 3 baths3,079 sq. ft.153 Shore Road, Chatham, MA 02633
MLS# 22603522Listed by: EXP REALTY, LLC
$4,250,000Active3 beds 4 baths3,071 sq. ft.600 Fox Hill Rd, Chatham, MA 02633
MLS# 73552814Listed by: Compass
$725,000Pending4 beds 4 baths1,687 sq. ft.19 Joshuas Way, Chatham, MA 02633
MLS# 22603514Listed by: COMPASS
$1,350,000Pending3 beds 1 baths1,056 sq. ft.50 Pine Ridge Road, Chatham, MA 02633
MLS# 22603455Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$799,900Pending4 beds 2 baths1,680 sq. ft.42 Indian Hill Road, Chatham, MA 02633
MLS# 22603376Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$2,295,000Active4 beds 4 baths4,066 sq. ft.55 Winterset Drive, Chatham, MA 02633
MLS# 22603375Listed by: COLDWELL BANKER REALTY
$1,469,000Active5 beds 10 baths11,000 sq. ft.558 Fox Hill Road, Chatham, MA 02633
MLS# 22603353Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$1,374,900Pending3 beds 3 baths2,302 sq. ft.88 Indian Hill Road, Chatham, MA 02633
MLS# 22603249Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,795,000Pending3 beds 4 baths3,514 sq. ft.44 Baileys Path, Chatham, MA 02633
MLS# 22603263Listed by: COMPASS MASSACHUSETTS, LLC
$5,900,000Active4 beds 5 baths4,394 sq. ft.95 Cotchpinicut, Chatham, MA 02633
MLS# 73544856Listed by: William Raveis Chatham
$5,900,000Active4 beds 5 baths4,394 sq. ft.95 Cotchpinicut Road, Chatham, MA 02633
MLS# 22603274Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,275,000Pending3 beds 2 baths2,070 sq. ft.240 Riverview Drive, Chatham, MA 02633
MLS# 22603060Listed by: JOHN C RICOTTA & ASSOC.
$975,000Active3 beds 3 baths3,384 sq. ft.65 Captain Kendrick Drive, Chatham, MA 02633
MLS# 22602982Listed by: EXP REALTY, LLC
$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
$5,900,000Active6 beds 8 baths6,183 sq. ft.50 Sylvan Way, Chatham, MA 02659
MLS# 73533378Listed by: Berkshire Hathaway HomeServices Robert Paul Properties
$1,250,000Active3 beds 2 baths2,176 sq. ft.35 Duncan Lane, Chatham, MA 02633
MLS# 73531412Listed by: Alliance Realty Advisors, Inc.
$4,995,000Active4 beds 4 baths2,932 sq. ft.56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty LLC
$1,899,000Active3 beds 3 baths3,514 sq. ft.70 Uncle Deane's Rd, Chatham, MA 02659
MLS# 73519558Listed by: Shining Sea Realty
$1,899,000Active3 beds 3 baths3,514 sq. ft.70 Uncle Deane's Road, South Chatham, MA 02659
MLS# 22602219Listed by: SHINING SEA REALTY
$4,950,000Active4 beds 5 baths5,371 sq. ft.15 Bay Lane, Chatham, MA 02633
MLS# 22602178Listed by: COMPASS MASSACHUSETTS, LLC
$4,200,000Active3 beds 3 baths2,418 sq. ft.30 Indian Trail, Chatham, MA 02633
MLS# 22602056Listed by: COMPASS MASSACHUSETTS, LLC
$2,850,000Active3 beds 3 baths2,205 sq. ft.336 Stage Island Road, Chatham, MA 02633
MLS# 22601983Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$889,000Pending3 beds 3 baths1,618 sq. ft.96 Stage Coach Drive, South Chatham, MA 02659
MLS# 22601955Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$4,295,000Active4 beds 4 baths4,967 sq. ft.38 Indian Trail, Chatham, MA 02633
MLS# 73509923Listed by: Christie's International Real Estate Atlantic Brokerage
$2,950,000Active4 beds 4 baths3,978 sq. ft.60 Harbor Hill Road, Chatham, MA 02633
MLS# 22601737Listed by: SHORE ROAD REALTY
$4,499,900Pending3 beds 7 baths4,450 sq. ft.1 Peirce Path, South Chatham, MA 02659
MLS# 22601418Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$1,585,000Pending3 beds 2 baths2,169 sq. ft.48 Glover Square, Chatham, MA 02633
MLS# 22601653Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,750,000Active5 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
$4,995,000Pending5 beds 5 baths3,225 sq. ft.101 Morris Island Road, Chatham, MA 02633
MLS# 22601118Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,850,000Active5 beds 6 baths5,620 sq. ft.15 Windy Hill Way, Chatham, MA 02633
MLS# 22601111Listed by: JOHN C RICOTTA & ASSOC.
$2,150,000Pending3 beds 3 baths2,481 sq. ft.234 Round Cove Road, Chatham, MA 02633
MLS# 22601089Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,500,000Active4 beds 4 baths2,850 sq. ft.346 Morris Island Road, Chatham, MA 02633
MLS# 22601006Listed by: COMPASS MASSACHUSETTS, LLC
$4,250,000Active4 beds 6 baths3,980 sq. ft.222 Barcliff Avenue, Chatham, MA 02633
MLS# 22600932Listed by: COMPASS MASSACHUSETTS, LLC
$1,280,000Active3 beds 2 baths2,278 sq. ft.243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,350,000Pending3 beds 2 baths1,802 sq. ft.32 Tip Cart Drive, Chatham, MA 02633
MLS# 22600918Listed by: COMPASS
$5,750,000Pending3 beds 6 baths4,902 sq. ft.7 Cove Road, North Chatham, MA 02650
MLS# 22600844Listed by: COMPASS MASSACHUSETTS, LLC
$12,950,000Pending5 beds 7 baths7,259 sq. ft.301 Whidah Road, North Chatham, MA 02650
MLS# 22600837Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$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
$4,500,000Active6 beds 7 baths5,721 sq. ft.48 Sylvan Way, South Chatham, MA 02659
MLS# 22600543Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$2,295,000Active3 beds 3 baths3,504 sq. ft.41 Court Street, North Chatham, MA 02650
MLS# 22600472Listed by: COMPASS
$829,000Active3 beds 2 baths1,192 sq. ft.33 Duck Marsh Lane, Chatham, MA 02633
MLS# 22505803Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$3,200,000Active3 beds 3 baths2,004 sq. ft.92 Indian Trail, Chatham, MA 02633
MLS# 73457239Listed by: John C. Ricotta & Associates, Inc.
$2,700,000Active3 beds 2 baths1,160 sq. ft.78 Indian Trail, Chatham, MA 02633
MLS# 22505704Listed by: JOHN C RICOTTA & ASSOC.
$789,000Active3 beds 2 baths1,425 sq. ft.49 Duck Marsh, Chatham, MA 02633
MLS# 73435928Listed by: John C. Ricotta & Associates, Inc.
$5,495,000Active2 beds 3 baths1,850 sq. ft.99 Uncle Alberts Drive Ext, Chatham, MA 02633
MLS# 22503829Listed by: COMPASS
$3,595,000Active3 beds 5 baths3,640 sq. ft.287 Cedar Street, Chatham, MA 02633
MLS# 22502029Listed by: COMPASS
$6,800,000Pending5 beds 3 baths1,896 sq. ft.238 Cranberry Lane, North Chatham, MA 02650
MLS# 22501564Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,650,000Active-- beds 1 baths2,586 sq. ft.231 Crowell Road, Chatham, MA 02633
MLS# 73258353Listed by: John C. Ricotta & Associates, Inc.
$825,000Active4 beds 2 baths1,493 sq. ft.714 Crowell Rd, Chatham, MA 02650
MLS# 73183473Listed by: Redfin Corp.
$815,000Active3 beds 2 baths1,617 sq. ft.1842 Main St, Chatham, MA 02633
MLS# 73147241Listed by: Keller Williams Realty
Local realty services provided by:CENTURY 21 North East, CENTURY 21 Custom Home Realty
Neighborhoods near Chatham town, MA
Zip codes near Chatham town, 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.