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Chatham town, MA - homes for sale
91 of 91 results displayed
- New
$6,500,000Active10 beds 10 baths7,658 sq. ft.150-154 Cross Street, Chatham, MA 02633
MLS# 22602857Listed by: COMPASS MASSACHUSETTS, LLC - New
$2,100,000Active1 beds 2 baths1,479 sq. ft.409 Main Street, Chatham, MA 02633
MLS# 22602838Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY - New
$1,299,000Active4 beds 3 baths2,391 sq. ft.68 Chippingstone Road, Chatham, MA 02633
MLS# 22602848Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE 
$1,150,000Pending3 beds 3 baths2,178 sq. ft.251 Joshua Jethro Road, Chatham, MA 02633
MLS# 22602576Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY- New
$985,000Active3 beds 2 baths1,392 sq. ft.33 Jeanette Road, Chatham, MA 02633
MLS# 22602639Listed by: COMPASS - New
$5,900,000Active6 beds 8 baths6,183 sq. ft.50 Sylvan Way, Chatham, MA 02659
MLS# 73533378Listed by: Berkshire Hathaway HomeServices Robert Paul Properties - New
$1,475,000Active3 beds 3 baths2,264 sq. ft.367 Deer Meadow Lane, Chatham, MA 02633
MLS# 22602782Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY - New
$2,400,000Active4 beds 3 baths2,317 sq. ft.7 Fox Hill Rd, Chatham, MA 02633
MLS# 73531982Listed by: Gibson Sotheby's International Realty - New
$1,350,000Active3 beds 2 baths2,176 sq. ft.35 Duncan Lane, Chatham, MA 02633
MLS# 73531412Listed by: Alliance Realty Advisors, Inc. 
$1,350,000Pending4 beds 2 baths1,951 sq. ft.92 Hitching Post Road, Chatham, MA 02633
MLS# 22602644Listed by: HOME*LAND REALTY
$1,049,000Pending3 beds 2 baths1,673 sq. ft.149 Island View Lane, South Chatham, MA 02659
MLS# 22602562Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$5,495,000Active4 beds 4 baths2,932 sq. ft.56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty
$895,000Active3 beds 2 baths1,896 sq. ft.304 Round Cove Road, Chatham, MA 02633
MLS# 73529549Listed by: Venture
$1,495,000Active4 beds 3 baths2,384 sq. ft.333 Old Comers Road, Chatham, MA 02633
MLS# 22602619Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$799,000Active2 beds 2 baths1,563 sq. ft.7 Aunt Matties Rd, Chatham, MA 02633
MLS# 73524655Listed by: Greer Real Estate, LLC
$1,650,000Pending3 beds 3 baths3,190 sq. ft.700 Riverview Drive, Chatham, MA 02633
MLS# 22602435Listed by: KINLIN GROVER COMPASS
$1,349,000Pending3 beds 3 baths2,268 sq. ft.36 Pursel Drive, North Chatham, MA 02650
MLS# 22602433Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$1,199,900Active2 beds 2 baths1,324 sq. ft.99 Shane Drive, Chatham, MA 02633
MLS# 22602427Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$1,800,000Active4 beds 2 baths1,238 sq. ft.213 Main St, Chatham, MA 02633
MLS# 73523164Listed by: Gibson Sotheby's International Realty
$849,000Active2 beds 1 baths864 sq. ft.66 Snow Ln, Chatham, MA 02633
MLS# 73523077Listed by: Compass
$1,175,000Pending3 beds 2 baths1,528 sq. ft.40 Sam Ryder Road, Chatham, MA 02633
MLS# 22602414Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$2,350,000Pending3 beds 3 baths2,212 sq. ft.320 Old Harbor Road, Chatham, MA 02633
MLS# 22602390Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,495,000Active4 beds 6 baths5,372 sq. ft.335 Stage Island Road, Chatham, MA 02633
MLS# 22602319Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$4,595,000Pending5 beds 4 baths2,659 sq. ft.92 Barcliff Avenue, Chatham, MA 02633
MLS# 22602315Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$1,999,000Active3 beds 3 baths3,514 sq. ft.70 Uncle Deane's Rd, Chatham, MA 02659
MLS# 73519558Listed by: Shining Sea Realty
$1,999,000Active3 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
$950,000Active3 beds 3 baths2,252 sq. ft.2653 Main St, Chatham, MA 02659
MLS# 73517271Listed by: William Raveis Real Estate & Homes Services
$2,250,000Pending3 beds 2 baths2,220 sq. ft.148 Seapine Road, North Chatham, MA 02650
MLS# 22602140Listed by: COMPASS MASSACHUSETTS, LLC
$1,275,000Pending3 beds 3 baths2,062 sq. ft.58 Stepping Stones Road, Chatham, MA 02633
MLS# 22602135Listed by: NEW HOMES MARKETING, INC.
$4,200,000Active3 beds 3 baths2,418 sq. ft.30 Indian Trail, Chatham, MA 02633
MLS# 22602056Listed by: COMPASS MASSACHUSETTS, LLC
$2,995,000Active3 beds 3 baths2,205 sq. ft.336 Stage Island Road, Chatham, MA 02633
MLS# 22601983Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$750,000Active3 beds 2 baths1,442 sq. ft.260 Tanglewood Dr, Chatham, MA 02659
MLS# 73513211Listed by: Kinlin Grover Compass
$899,000Active3 beds 3 baths1,618 sq. ft.96 Stage Coach Drive, Chatham, MA 02659
MLS# 73512654Listed by: Gibson Sotheby's International Realty
$899,000Active3 beds 3 baths1,618 sq. ft.96 Stage Coach Drive, South Chatham, MA 02659
MLS# 22601955Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$2,995,000Pending3 beds 4 baths3,014 sq. ft.7 Squanto Drive, Chatham, MA 02633
MLS# 22601915Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$2,800,000Pending3 beds 3 baths266 Seapine Road, North Chatham, MA 02650
MLS# 22601837Listed by: COMPASS MASSACHUSETTS, LLC
$3,695,000Active3 beds 5 baths5,154 sq. ft.83 Old Mail Rd, Chatham, MA 02650
MLS# 73509367Listed by: Compass
$4,495,000Active4 beds 4 baths4,967 sq. ft.38 Indian Trail, Chatham, MA 02633
MLS# 22601752Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$3,699,900Pending3 beds 5 baths4,565 sq. ft.29 Jessies Landing, Chatham, MA 02633
MLS# 22601788Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$1,650,000Active3 beds 2 baths1,531 sq. ft.48 Glover Sq, Chatham, MA 02633
MLS# 73508434Listed by: Gibson Sotheby's International Realty
$895,000Pending2 beds 2 baths1,716 sq. ft.58 Tirrells Way, South Chatham, MA 02659
MLS# 22601749Listed by: COMPASS
$3,695,000Active3 beds 5 baths5,154 sq. ft.83 Old Mail Road, North Chatham, MA 02650
MLS# 22601738Listed by: COMPASS MASSACHUSETTS, LLC
$3,600,000Active4 beds 4 baths3,978 sq. ft.60 Harbor Hill Road, Chatham, MA 02633
MLS# 22601737Listed by: SHORE ROAD REALTY
$1,250,000Pending3 beds 2 baths2,257 sq. ft.35 Pine Tree Road, South Chatham, MA 02659
MLS# 22601708Listed by: GIBSON SOTHEBY'S INTERNATIONAL 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
$865,900Pending2 beds 2 baths1,688 sq. ft.61 Oak Hill Road, Chatham, MA 02633
MLS# 22601667Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$5,995,000Active5 beds 5 baths4,060 sq. ft.70 Judges Way, Chatham, MA 02633
MLS# 22601572Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$2,975,000Pending5 beds 6 baths4,822 sq. ft.35 Northgate Road, North Chatham, MA 02650
MLS# 22601580Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$2,699,000Pending4 beds 3 baths3,479 sq. ft.8 Captains Walk, North Chatham, MA 02650
MLS# 22601552Listed by: COMPASS MASSACHUSETTS, LLC
$2,850,000Active3 beds 4 baths1,999 sq. ft.32 Gladen Lane, Chatham, MA 02633
MLS# 22601360Listed by: COMPASS MASSACHUSETTS, LLC
$760,000Active2 beds 2 baths864 sq. ft.21 Quail Trail, South Chatham, MA 02659
MLS# 22601292Listed by: NAUSET MANAGEMENT
$699,999Active-- beds 1 baths600 sq. ft.1772 Main Street, Chatham, MA 02633
MLS# 22601404Listed by: LPT REALTY
$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
$950,000Active3 beds 3 baths2,252 sq. ft.2653 Main Street, South Chatham, MA 02659
MLS# 22601168Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$5,495,000Active5 beds 5 baths3,225 sq. ft.101 Morris Island Road, Chatham, MA 02633
MLS# 22601118Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$6,250,000Active5 beds 6 baths5,620 sq. ft.15 Windy Hill Way, Chatham, MA 02633
MLS# 22601111Listed by: JOHN C RICOTTA & ASSOC.
$2,150,000Active3 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
$1,495,000Active3 beds 2 baths1,530 sq. ft.137 Shane Drive, Chatham, MA 02633
MLS# 22600988Listed by: COMPASS MASSACHUSETTS, LLC
$1,200,000Active3 beds 3 baths1,804 sq. ft.118 Wilfred Road, Chatham, MA 02633
MLS# 22600948Listed by: COMPASS
$4,250,000Active4 beds 6 baths3,980 sq. ft.222 Barcliff Avenue, Chatham, MA 02633
MLS# 22600932Listed by: COMPASS MASSACHUSETTS, LLC
$1,350,000Active3 beds 2 baths2,278 sq. ft.243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,350,000Active3 beds 2 baths1,802 sq. ft.32 Tip Cart Drive, Chatham, MA 02633
MLS# 22600918Listed by: COMPASS- Open Sat, 10am to 1pm
$1,650,000Active2 beds 2 baths1,810 sq. ft.39 Jedidiah Way, Chatham, MA 02633
MLS# 22600861Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES 
$5,750,000Active3 beds 6 baths4,902 sq. ft.7 Cove Road, Chatham, MA 02650
MLS# 73489258Listed by: Compass
$12,950,000Active5 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
$2,650,000Pending3 beds 3 baths2,969 sq. ft.104 Seapine Road, North Chatham, MA 02650
MLS# 22600761Listed by: JOHN C RICOTTA & ASSOC.
$1,995,000Active3 beds 2 baths1,488 sq. ft.50 Eldredge Square, Chatham, MA 02633
MLS# 22600669Listed by: COMPASS MASSACHUSETTS, LLC
$4,999,000Active6 beds 7 baths5,721 sq. ft.48 Sylvan Way, South Chatham, MA 02659
MLS# 22600543Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$4,900,000Active5 beds 5 baths5,587 sq. ft.169 Tisquantum Road, Chatham, MA 02633
MLS# 22600293Listed by: KINLIN GROVER COMPASS
$2,295,000Active3 beds 3 baths3,504 sq. ft.41 Court Street, North Chatham, MA 02650
MLS# 22600472Listed by: COMPASS
$9,995,000Active6 beds 6 baths6,547 sq. ft.197 Woodland Way, North Chatham, MA 02650
MLS# 22600461Listed by: COMPASS MASSACHUSETTS, LLC
$842,000Active3 beds 2 baths1,192 sq. ft.33 Duck Marsh Lane, Chatham, MA 02633
MLS# 22505803Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$3,695,000Active3 beds 5 baths5,154 sq. ft.83 Old Mail Road, North Chatham, MA 02650
MLS# 22505756Listed by: COMPASS
$2,800,000Active3 beds 2 baths1,160 sq. ft.78 Indian Trail, Chatham, MA 02633
MLS# 73457238Listed by: John C. Ricotta & Associates, Inc.
$3,200,000Active3 beds 3 baths2,004 sq. ft.92 Indian Trail, Chatham, MA 02633
MLS# 73457239Listed by: John C. Ricotta & Associates, Inc.
$789,000Active3 beds 2 baths1,425 sq. ft.49 Duck Marsh, Chatham, MA 02633
MLS# 73435928Listed by: John C. Ricotta & Associates, Inc.
$4,700,000Pending5 beds 4 baths3,080 sq. ft.85 Cedar Street, Chatham, MA 02633
MLS# 22504804Listed by: JOHN C RICOTTA & ASSOC.
$3,999,900Active3 beds 5 baths4,393 sq. ft.2550 Main Street, South Chatham, MA 02659
MLS# 22504680Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$3,999,900Pending4 beds 6 baths4,942 sq. ft.2548 Main Street, South Chatham, MA 02659
MLS# 22504678Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$4,525,000Pending4 beds 6 baths5,300 sq. ft.230 Barcliff Avenue, Chatham, MA 02633
MLS# 22504396Listed by: COMPASS MASSACHUSETTS, LLC
$5,495,000Active2 beds 3 baths1,850 sq. ft.99 Uncle Alberts Drive Ext, Chatham, MA 02633
MLS# 22503829Listed by: COMPASS
$6,900,000Pending7 beds 7 baths6,521 sq. ft.44 Buena Vista Road, Chatham, MA 02633
MLS# 22503738Listed by: COMPASS
$3,595,000Active3 beds 5 baths3,640 sq. ft.287 Cedar Street, Chatham, MA 02633
MLS# 22502029Listed by: COMPASS
$6,800,000Active5 beds 3 baths1,896 sq. ft.238 Cranberry Lane, Chatham, MA 02633
MLS# 73358568Listed by: William Raveis Chatham
$1,469,000Active5 beds 10 baths11,000 sq. ft.558 Fox Hill Road, North Chatham, MA 02650
MLS# 22505606Listed by: CORCORAN PROPERTY ADVISORS
$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 Signature Properties
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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.