Chatham, MA Homes

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  $619,000

  • Land
  • 1.01 Acres
  • $612,871 per Acre

  1761 Main St, Chatham, MA 02633

  Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

  

  Kimberly Clark

  Bayside Realty Consultants

  (508) 719-6244

  1761 Main St, Chatham, MA 02633
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  $5,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  0000 Unspecified, Chatham, MA 02659

  If you're fond of sand dunes and salty air, quaint little villages here and there, you're sure to fall in love with old Cape Cod...This year-round charming Chatham rental is available and a steal starting now at $4500. monthly for annual renters, under 12 months the lease changes to Summer Rental rates: Chatham Cape recently updated with a BRAND NEW KITCHEN & BRAND NEW DECK, new floor, new

  

  Vena Priestly

  Rise Signature Homes

  (508) 690-5114

  0000 Unspecified, Chatham, MA 02659
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  $5,300,000 Sold Jan 14, 2026

  4 Ministers Ln, North Chatham, MA 02650

  • 5 Beds
  • 6.5 Baths
  • 5,143 Sq Ft
  • Built 2003

  Last Sold Summary

  • 12% Below List Price
  • $1,031/SF
  • 256 Days On Market

  Last Listing Agent Chris Rhinesmith Compass

  4 Ministers Ln, North Chatham, MA 02650
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  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,595 Sq Ft

  67 School St, Chatham, MA 02633

  67 School St, Chatham, MA 02633
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  $1,295,000

  • 2 Beds
  • 2.5 Baths
  • 2,295 Sq Ft

  5 Ridge Cove Ln Unit 5, Chatham, MA 02633

  Welcome to this meticulously maintained, light drenched townhome. Open great room, dining room and kitchen provide a seamless flow for entertaining or quietly enjoying the cozy gas fireplace. Kitchen boasts granite countertops, stainless appliances, viking range and hood and abundant cupboard space. A large center island is perfect for entertaining and preparation. Nestled on its own is the

  Christine Briscoe SeasCape Realty, Inc.

  5 Ridge Cove Ln Unit 5, Chatham, MA 02633
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  $2,250 total monthly price

  • 1 Bed
  • 1 Bath
  • 778 Sq Ft
  • Condo for Rent

  195 Stony Hill Rd Unit Condo-Apartment, Chatham, MA 02633

  195 Stony Hill Rd Unit Condo-Apartment, Chatham, MA 02633
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  $4,500,000 Sold Apr 23, 2025

  79 Barcliff Ave, Chatham, MA 02633

  • 3 Beds
  • 5 Baths
  • 3,724 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $1,208/SF
  • 3 Days On Market

  Current Estimated Value $4,552,689

  Last Listing Agent Doug Grattan Christie's International Real Estate Atlantic Brokerage

  79 Barcliff Ave, Chatham, MA 02633
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  Est $2,301,304 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,776 Sq Ft

  72 Old Field Bend, North Chatham, MA 02650

  72 Old Field Bend, North Chatham, MA 02650
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  /10

  $4,399,000 New Construction

  • 4 Beds
  • 6 Baths
  • 5,300 Sq Ft

  230 Barcliff Ave, Chatham, MA 02633

  Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The 5800 sf home will offer the best in new amenities with a

  Lori Fanning Smith Compass Massachusetts, LLC

  230 Barcliff Ave, Chatham, MA 02633
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  $20,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  101 Monomoyic Way, Chatham, MA 02633

  Furnished rental available June 1st to October 1st, 2026. Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that

  Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

  101 Monomoyic Way, Chatham, MA 02633
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  $1,282,500 Sold Oct 08, 2025

  591 Crowell Rd, North Chatham, MA 02650

  • 4 Beds
  • 3 Baths
  • 1,661 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $772/SF
  • 15 Days On Market

  Last Listing Agent Cheryle Young Today Real Estate

  591 Crowell Rd, North Chatham, MA 02650
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  Est $871,779 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  53 Partridge Path, Chatham, MA 02633

  53 Partridge Path, Chatham, MA 02633
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  $4,295,000

  • 3 Beds
  • 4.5 Baths
  • 5,154 Sq Ft

  83 Old Mail Rd, North Chatham, MA 02650

  NEW CONSTRUCTION: 83 Old Mail Rd is a stunning 3 BR, 4.5 bath, 5,154 sf retreat in North Chatham. This elegant home showcases exceptional craftsmanship & high-end finishes for refined coastal living. The chef's Thermador kitchen with quartz counters and waterfall island opens to a butler's pantry with custom sink & beverage fridge and a first-floor dining room with coffered ceiling. A

  Shane Masaschi Compass

  83 Old Mail Rd, North Chatham, MA 02650
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  $615,300 Sold May 27, 2025

  369 Orleans Rd Unit A, Chatham, MA 2633

  • 2 Beds
  • 2.5 Baths
  • 1,283 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $480/SF
  • 18 Days On Market

  Current Estimated Value $629,465

  Last Listing Agent David Colville HomeSmart First Class Realty

  369 Orleans Rd Unit A, Chatham, MA 2633
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  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  22 Cahoons Hollow, Chatham, MA 02633

  22 Cahoons Hollow, Chatham, MA 02633
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  $2,499,000

  • 3 Beds
  • 4 Baths
  • 3,090 Sq Ft

  2 Seapine Rd, North Chatham, MA 02650

  Offered fully furnished, this light-filled contemporary Cape in North Chatham blends coastal elegance with casual sophistication. The main level features a welcoming den, an inviting living room with a fireplace, and a stylish kitchen and dining area that open to a sunny deck, ideal for seamless indoor-outdoor living. The serene first floor primary suite offers comfort and privacy. Upstairs, two

  Jack Bohman Gibson Sotheby's International Realty

  2 Seapine Rd, North Chatham, MA 02650
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  /31

  $1,450,000 Sold Jul 03, 2025

  450 Old Harbor Rd, Chatham, MA 02633

  • 2 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1830

  Last Sold Summary

  • 24% Below List Price
  • $960/SF
  • 265 Days On Market

  Current Estimated Value $1,701,413

  Last Listing Agent Barbara Garside eXp Realty, LLC

  450 Old Harbor Rd, Chatham, MA 02633
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft

  25 Bobbie's Ln, Chatham, MA 02659

  25 Bobbie's Ln, Chatham, MA 02659
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  $5,400,000 Pending

  • 4 Beds
  • 7 Baths
  • 3,702 Sq Ft

  121 Queen Anne Rd, Chatham, MA 02633

  Set in one of Chatham’s most coveted in-town locations, this refined coastal residence offers a rare combination of setting, privacy, and enduring quality. With expansive views over Oyster Pond and private water access just across the street, the home enjoys a meaningful connection to the water alongside immediate proximity to downtown—an increasingly scarce pairing. Thoughtfully designed and

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  121 Queen Anne Rd, Chatham, MA 02633
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  $1,520,000 Sold Aug 15, 2025

  457 Training Field Rd, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 3,027 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $502/SF
  • 8 Days On Market

  Current Estimated Value $1,535,060

  Last Listing Agent Shane Masaschi Compass

  457 Training Field Rd, Chatham, MA 02633
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  Est $3,141,439 Not Listed For Sale

  • 3 Beds
  • 5.5 Baths
  • 4,197 Sq Ft

  21 Hunter Rise, Chatham, MA 02633

  21 Hunter Rise, Chatham, MA 02633
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  $1,970,000

  • 3 Beds
  • 4.5 Baths
  • 1,834 Sq Ft

  292 Stage Harbor Rd, Chatham, MA 02633

  Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower

  Ward Brown William Raveis Real Estate & Home Services

  292 Stage Harbor Rd, Chatham, MA 02633
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  $1,415,000 Sold Jan 12, 2026

  200 Hardings Beach Rd, Chatham, MA 02633

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 1964

  Last Sold Summary

  • 5% Below List Price
  • $777/SF
  • 75 Days On Market

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  200 Hardings Beach Rd, Chatham, MA 02633
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  Est $4,394,520 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,751 Sq Ft

  110 Sea Shells Dr, South Chatham, MA 02659

  110 Sea Shells Dr, South Chatham, MA 02659
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  /90

  $4,700,000

  • 5 Beds
  • 3.5 Baths
  • 3,080 Sq Ft

  85 Cedar St, Chatham, MA 02633

  ** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room

  Tim Bailey John C Ricotta & Assoc.

  85 Cedar St, Chatham, MA 02633
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  $1,200,000 Sold Feb 24, 2025

  1174 Old Queen Anne Rd, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft
  • Built 1995

  Last Sold Summary

  • 20% Below List Price
  • $742/SF
  • 256 Days On Market

  Last Listing Agent Paul McCormick Gibson Sotheby's International Realty

  1174 Old Queen Anne Rd, Chatham, MA 02633
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  Est $3,058,679 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,399 Sq Ft

  47 Quasson Rd, Chatham, MA 02633

  47 Quasson Rd, Chatham, MA 02633
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  $3,850,000

  • 3 Beds
  • 4.5 Baths
  • 3,640 Sq Ft

  287 Cedar St, Chatham, MA 02633

  NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

  Shane Masaschi Compass

  287 Cedar St, Chatham, MA 02633
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  /40

  $900,000 Sold Jul 11, 2025

  100 Potonumecot Rd, Chatham, MA 02633

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $670/SF
  • 16 Days On Market

  Current Estimated Value $937,222

  Last Listing Agent Andy Falconio Kinlin Grover Compass

  100 Potonumecot Rd, Chatham, MA 02633
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  Est $3,277,519 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,449 Sq Ft

  114 Main St, Chatham, MA 02633

  114 Main St, Chatham, MA 02633
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  $2,499,000 Pending

  • Land
  • 2.46 Acres
  • $1,015,854 per Acre

  0 Crows Pond Rd, Chatham, MA 02633

  2.46 acre waterfront lot in Chatham with 220 feet of frontage directly on salt water Crow's Pond. Land is set on a bluff and has direct water access to Ryders Cove, Pleasant Bay, Chatham Harbor and the Atlantic Ocean. Near Eastward Ho! Country Club. Paved driveway has been installed and there is town water already on the property. Custom build the home of your dreams. Site plan and covenants are

  Jen Pappalardo Christie's International Real Estate Atlantic Brokerage

  0 Crows Pond Rd, Chatham, MA 02633
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  $1,320,000 Sold Jun 12, 2025

  67 The Cornfield, Chatham, MA 02633

  • 4 Beds
  • 2.5 Baths
  • 2,238 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $590/SF
  • 78 Days On Market

  Current Estimated Value $1,371,944

  Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  67 The Cornfield, Chatham, MA 02633
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  Est $7,605,718 Not Listed For Sale

  • 8 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  504 Old Harbor Rd, North Chatham, MA 02650

  504 Old Harbor Rd, North Chatham, MA 02650
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  $749,999 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  23 Shane Dr, Chatham, MA 02633

  Welcome to 23 Shane Dr, where coastal elegance meets everyday comfort. This charming single-level home offers 3 spacious bedrooms and 2 baths, perfectly blending modern convenience with classic character. Imagine relaxing by the cozy fireplace, or enjoying a good book from the built-in bookshelves that add a touch of sophistication to your living space. In addition to bright and airy bedrooms,

  Samantha Edwards Compass

  23 Shane Dr, Chatham, MA 02633
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  $2,000,000 Sold Sep 08, 2025

  55 Meadowview Rd S, Chatham, MA 02633

  • 4 Beds
  • 3 Baths
  • 1,897 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Above List Price
  • $1,054/SF
  • 9 Days On Market

  Last Listing Agent INSPIRE Team Keller Williams Realty

  55 Meadowview Rd S, Chatham, MA 02633
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  Est $2,655,169 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,203 Sq Ft

  47 Gladen Ln, Chatham, MA 02633

  47 Gladen Ln, Chatham, MA 02633
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  $315,000

  • Land
  • 1.07 Acres
  • $294,393 per Acre

  2386 Main St, South Chatham, MA 02659

  This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

  Judith Smith John C Ricotta & Assoc.

  2386 Main St, South Chatham, MA 02659
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  $3,350,000 Sold Dec 11, 2025

  174 Seapine Rd, North Chatham, MA 02650

  • 4 Beds
  • 3.5 Baths
  • 3,899 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Below List Price
  • $859/SF
  • 88 Days On Market

  Last Listing Agent Jill Boudreau eXp Realty, LLC

  174 Seapine Rd, North Chatham, MA 02650
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  Est $4,109,863 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 3,203 Sq Ft

  38 Sandy Shoes Ln, Chatham, MA 02633

  38 Sandy Shoes Ln, Chatham, MA 02633
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  /25

  $749,000 Open Sat 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  132 Stage Coach Dr, South Chatham, MA 02659

  This well-maintained 2-bedroom, 2-bath home in South Chatham, MA offers a rare combination of privacy, location, and potential. Located in a quiet residential neighborhood and abutting acres of conservation land, the property provides a peaceful, natural setting that feels far removed from town while still being close to everything Chatham is known for.The home is move-in ready and awaiting your

  John Delellis Keller Williams Realty

  132 Stage Coach Dr, South Chatham, MA 02659

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