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Chatham town, MA - single-family homes for sale
92 of 92 results displayed
- Open Sat, 11am to 2pmNew
$1,230,000Active3 beds 3 baths2,294 sq. ft.72 Smith St, Chatham, MA 02633
MLS# 73555753Listed by: Gibson Sotheby's International Realty - New
$4,500,000Active4 beds 5 baths4,689 sq. ft.66 Ethelma Drive, Chatham, MA 02633
MLS# 22603629Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES - New
$12,000,000Active4 beds 3 baths1,738 sq. ft.166 Shore Road, Chatham, MA 02633
MLS# 22603612Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES - New
$950,000Active3 beds 2 baths1,201 sq. ft.268 Barn Hill Rd, Chatham, MA 02633
MLS# 73554911Listed by: Compass - New
$695,000Active2 beds 1 baths992 sq. ft.40 Uncle Abners Path, Chatham, MA 02633
MLS# 73550743Listed by: Compass - New
$9,995,000Active3 beds 3 baths3,079 sq. ft.153 Shore Road, Chatham, MA 02633
MLS# 22603522Listed by: EXP REALTY, LLC - New
$795,000Active4 beds 4 baths1,687 sq. ft.19 Joshuas Way, Chatham, MA 02633
MLS# 22603514Listed by: COMPASS - New
$4,250,000Active3 beds 4 baths3,071 sq. ft.600 Fox Hill Road, Chatham, MA 02633
MLS# 22603504Listed by: COMPASS MASSACHUSETTS, LLC 
$699,900Active2 beds 1 baths572 sq. ft.22 Country Lane, South Chatham, MA 02659
MLS# 22603469Listed by: SOTHEBY'S INTERNATIONAL REALTY, INC.
$1,350,000Active3 beds 1 baths1,056 sq. ft.50 Pine Ridge Rd, Chatham, MA 02633
MLS# 73551106Listed 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
$2,390,000Active4 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
$2,199,000Active4 beds 3 baths2,520 sq. ft.330 Champlain Rd, Chatham, MA 02633
MLS# 73543021Listed by: Compass
$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
$2,995,000Active4 beds 4 baths2,700 sq. ft.26 Hardings Beach Road, Chatham, MA 02633
MLS# 22603172Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$995,000Pending3 beds 2 baths1,476 sq. ft.35 Oakridge Circle, Chatham, MA 02633
MLS# 22603135Listed by: COMPASS
$995,000Active4 beds 2 baths2,367 sq. ft.127 Perch Pond Road, Chatham, MA 02633
MLS# 73542198Listed by: Compass
$1,275,000Active3 beds 2 baths2,070 sq. ft.240 Riverview Drive, Chatham, MA 02633
MLS# 22603060Listed by: JOHN C RICOTTA & ASSOC.
$1,069,000Active3 beds 3 baths3,384 sq. ft.65 Captain Kendrick Drive, Chatham, MA 02633
MLS# 22602982Listed by: EXP REALTY, LLC
$1,150,000Pending3 beds 3 baths2,021 sq. ft.239 Northgate Road, Chatham, MA 02633
MLS# 22602979Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$3,250,000Pending3 beds 4 baths3,902 sq. ft.87 Squanto Drive, Chatham, MA 02633
MLS# 22602966Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$5,900,000Active6 beds 8 baths50 Sylvan Way, South Chatham, MA 02659
MLS# 22602789Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$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
$1,199,000Active4 beds 3 baths2,391 sq. ft.68 Chippingstone Road, Chatham, MA 02633
MLS# 22602848Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$1,475,000Pending3 beds 3 baths2,264 sq. ft.367 Deer Meadow Lane, Chatham, MA 02633
MLS# 22602782Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$1,350,000Active3 beds 2 baths2,176 sq. ft.35 Duncan Lane, Chatham, MA 02633
MLS# 73531412Listed by: Alliance Realty Advisors, Inc.
$2,400,000Active4 beds 3 baths2,317 sq. ft.7 Fox Hill Road, Chatham, MA 02633
MLS# 22602702Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$5,250,000Active4 beds 4 baths2,932 sq. ft.56 Stage Island Road, Chatham, MA 02633
MLS# 73529657Listed by: eXp Realty LLC
$799,000Pending2 beds 2 baths1,563 sq. ft.7 Aunt Matties Road, Chatham, MA 02633
MLS# 22602367Listed by: GREER REAL ESTATE, LLC
$1,199,900Pending2 beds 2 baths1,324 sq. ft.99 Shane Drive, Chatham, MA 02633
MLS# 22602427Listed by: CHRISTIE'S INTERNATIONAL REAL ESTATE ATLANTIC BROKERAGE
$849,000Active2 beds 1 baths864 sq. ft.66 Snow Ln, Chatham, MA 02633
MLS# 73523077Listed by: Compass
$4,395,000Active4 beds 6 baths5,372 sq. ft.335 Stage Island Road, Chatham, MA 02633
MLS# 22602319Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$1,800,000Pending4 beds 2 baths1,236 sq. ft.213 Main Street, Chatham, MA 02633
MLS# 22602308Listed 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
$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
$889,000Active3 beds 3 baths1,618 sq. ft.96 Stage Coach Drive, Chatham, MA 02659
MLS# 73512654Listed by: Gibson Sotheby's International Realty
$889,000Active3 beds 3 baths1,618 sq. ft.96 Stage Coach Drive, South Chatham, MA 02659
MLS# 22601955Listed by: GIBSON SOTHEBY'S INTERNATIONAL REALTY
$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
$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- Open Sat, 12 to 2pm
$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
$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
$4,995,000Active5 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
$1,350,000Active3 beds 2 baths1,802 sq. ft.32 Tip Cart Dr, Chatham, MA 02633
MLS# 73492178Listed by: Compass
$1,399,000Active3 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
$1,280,000Active3 beds 2 baths2,278 sq. ft.243 Crowell Road, Chatham, MA 02633
MLS# 22600915Listed by: WILLIAM RAVEIS REAL ESTATE & HOME SERVICES
$1,650,000Active2 beds 2 baths1,810 sq. ft.39 Jedidiah Way, Chatham, MA 02633
MLS# 22600861Listed by: BERKSHIRE HATHAWAY HOMESERVICES ROBERT PAUL PROPERTIES
$5,750,000Pending3 beds 6 baths4,902 sq. ft.7 Cove Road, North Chatham, MA 02650
MLS# 22600844Listed by: COMPASS MASSACHUSETTS, LLC
$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
$1,995,000Active3 beds 2 baths1,488 sq. ft.50 Eldredge Square, Chatham, MA 02633
MLS# 22600669Listed by: COMPASS MASSACHUSETTS, LLC
$4,750,000Active6 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
$829,000Active3 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
$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.
$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
$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
$6,800,000Active5 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# 22403062Listed by: JOHN C RICOTTA & ASSOC.
$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 Tassinari & Associates, Inc, CENTURY 21 Custom Home Realty
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Zip codes near Chatham town, MA
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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.
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.