9,489

Chatham, MA Homes

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  • /48

    $1,340,000

    • 3 Beds
    • 2.5 Baths
    • 2,155 Sq Ft

    116 Vineyard Ave, Chatham, MA 02633

    Nestled in a private, nature-rich setting, this exceptional property blends coastal charm, thoughtful architectural design, and high-end modern amenities. Renovated and expanded by renowned architects Polhemus, Savery & DaSilva in 2005 this home has a terrific location! Neighborhood features a town landing on Oyster River, perfect for boats or kayaks, and an easement path leads to pond views and

    Allison Beavan William Raveis Real Estate & Home Services

    116 Vineyard Ave, Chatham, MA 02633
  • /42

    $846,000

    Sold Oct 21, 2025

    29 Wilfred Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Above List Price
    • $551/SF
    • 2 Days On Market

    Current Estimated Value $876,558

    Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty

    29 Wilfred Rd, Chatham, MA 02633
    • /35

      Not Listed For Sale

      2550 Main St, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 2,490 Sq Ft
      • Built 1954
      2550 Main St, Chatham, MA 02633

      Last Sold Summary

      • 116 Days On Market

      Last Listing Agent Ward Brown, III William Raveis Real Estate & Home Services

  • /13

    $689,000

    • 2 Beds
    • 2 Baths
    • 1,083 Sq Ft

    212 Orleans Rd Unit D, North Chatham, MA 02650

    Beautifully appointed, fully furnished, and turnkey, this exceptional end-unit 2-bedroom, 2-bath second-floor condominium is located in the desirable Nickerson Corners community in North Chatham, offering effortless Cape Cod living in a quiet, well-maintained association. Ideally situated just moments from Chatham Harbor and downtown Chatham, this exceptional location provides easy access to

    Jim Peterson Peterson Realty Inc.

    212 Orleans Rd Unit D, North Chatham, MA 02650
  • /58

    $730,000

    Sold Jul 22, 2026

    260 Tanglewood Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Below List Price
    • $506/SF
    • 35 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    260 Tanglewood Dr, Chatham, MA 02633
    • /59

      Not Listed For Sale

      189 Bay View Rd, Chatham, MA 02633

      • 5 Beds
      • 5 Baths
      • 3,240 Sq Ft
      • Built 1950
      189 Bay View Rd, Chatham, MA 02633

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Robin Thayer Gibson Sotheby's International Realty

  • /47

    $4,950,000

    • 3 Beds
    • 4 Baths
    • 3,441 Sq Ft

    103 Aunt Nabbys Ln, Chatham, MA 02633

    Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    103 Aunt Nabbys Ln, Chatham, MA 02633
  • /36

    $670,000

    Sold Jun 30, 2026

    216 Orleans Rd Unit E, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 996 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $569,245

    Last Listing Agent Ella Leavitt Compass

    216 Orleans Rd Unit E, North Chatham, MA 02650
    • /36

      Not Listed For Sale

      11 Uncle Deanes Rd, South Chatham, MA 02659

      • 3 Beds
      • 2 Baths
      • 1,098 Sq Ft
      • Built 1965
      11 Uncle Deanes Rd, South Chatham, MA 02659

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /38

    $2,295,000

    $655K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,504 Sq Ft

    41 Court St, North Chatham, MA 02650

    Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments

    Phyllis Power Compass

    41 Court St, North Chatham, MA 02650
  • /41

    $898,000

    Sold Oct 30, 2025

    306 Old Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $535/SF
    • 14 Days On Market

    Current Estimated Value $915,886

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    306 Old Queen Anne Rd, Chatham, MA 02633
    • /73

      Not Listed For Sale

      5 Hillcrest Ln, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 3,532 Sq Ft
      • Built 1952
      5 Hillcrest Ln, Chatham, MA 02633

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Kathleen Phelan Compass Massachusetts, LLC

  • /29

    $950,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,201 Sq Ft

    268 Barn Hill Rd, Chatham, MA 02633

    This charming seasonal cottage is in a coveted location close to beautiful Hardings Beach on Nantucket Sound and Barn Hill town landing with iconic oyster shanties and access to the Oyster River, Stage Harbor for kayaking & paddleboarding. 2 marinas are also nearby for boating fun not to mention all the local dining options and bike trail. This adorable quintessential Cape Cod cottage has updated

    Phyllis Power Compass

    268 Barn Hill Rd, Chatham, MA 02633
  • /47

    $490,000

    Sold Jun 24, 2026

    1340 Main St Unit 9, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 496 Sq Ft
    • Built 1929

    Last Sold Summary

    • $988/SF
    • 1 Day On Market

    Current Estimated Value $454,893

    Last Listing Agent Tom Riley Compass Massachusetts, LLC

    1340 Main St Unit 9, Chatham, MA 02633
    • /24

      Not Listed For Sale

      25 Eddie Ln, Chatham, MA 02633

      • 2 Beds
      • 2.5 Baths
      • 1,786 Sq Ft
      • Built 1964
      25 Eddie Ln, Chatham, MA 02633

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

  • /42

    $889,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 3 Baths
    • 1,618 Sq Ft

    96 Stage Coach Dr, South Chatham, MA 02659

    Lovingly maintained, this classic Chatham ranch reflects true pride of ownership. A traditional layout offers three bedrooms, including a primary with en suite bath, and easy, comfortable living throughout. Recently refreshed with full interior paint and beautifully staged, the home feels bright, welcoming, and move-in ready. Set on a generous lot with adjacent green space, the property offers

    Dawn Lee Gibson Sotheby's International Realty

    96 Stage Coach Dr, South Chatham, MA 02659
  • /42

    $1,350,000

    Sold Jun 05, 2026

    134 Northgate Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 2,329 Sq Ft
    • Built 1982

    Last Sold Summary

    • 3% Below List Price
    • $580/SF
    • 20 Days On Market

    Current Estimated Value $1,362,930

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    134 Northgate Rd, North Chatham, MA 02650
    • /42

      Not Listed For Sale

      70 Sears Point Rd, Chatham, MA 02633

      • 5 Beds
      • 4 Baths
      • 2,992 Sq Ft
      • Built 1940
      70 Sears Point Rd, Chatham, MA 02633

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Tony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  • /9

    $4,499,900

    New Construction Pending
    • 3 Beds
    • 7 Baths
    • 4,450 Sq Ft

    1 Peirce Path, South Chatham, MA 02659

    South of Route 28 and moments from the shimmering shores of Nantucket Sound, this new residence by Eastward Companies captures the essence of refined coastal living. Gracefully sited on over two-thirds of an acre, the home's striking Dutch Gambrel architecture evokes timeless Cape heritage while delivering over 4,450 square feet of sophisticated, modern design across three impeccably finished

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    1 Peirce Path, South Chatham, MA 02659
  • /61

    $2,400,000

    Sold Oct 30, 2025

    290 Old Comers Rd, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 3,603 Sq Ft
    • Built 2005

    Last Sold Summary

    • 26% Below List Price
    • $666/SF
    • 246 Days On Market

    Current Estimated Value $2,320,410

    Last Listing Agent Catherine Baran Corcoran Property Advisors

    290 Old Comers Rd, Chatham, MA 02633
    • /48

      Not Listed For Sale

      88 Fox Hill Rd, North Chatham, MA 02650

      • 4 Beds
      • 3 Baths
      • 2,716 Sq Ft
      • Built 1984
      88 Fox Hill Rd, North Chatham, MA 02650

      Last Sold Summary

      • 149 Days On Market

      Last Listing Agent Tony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  • /41

    $1,450,000

    $45K PRICE DROP Pending
    • 2 Beds
    • 3.5 Baths
    • 1,770 Sq Ft

    739 Main St Unit 739, Chatham, MA 2633

    Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers baseball games, band concerts, a sandy beach at Oyster Pond, and much more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen,

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    739 Main St Unit 739, Chatham, MA 2633
  • /52

    $1,750,000

    Sold Oct 09, 2025

    10 Pursel Dr, North Chatham, MA 02650

    • 3 Beds
    • 2 Baths
    • 2,366 Sq Ft
    • Built 1971

    Last Sold Summary

    • 12% Below List Price
    • $740/SF
    • 84 Days On Market

    Current Estimated Value $1,809,745

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    10 Pursel Dr, North Chatham, MA 02650
    • /25

      Not Listed For Sale

      409 Orleans Rd Unit A, North Chatham, MA 02650

      • 2 Beds
      • 1.5 Baths
      • 1,038 Sq Ft
      • Built 1987
      409 Orleans Rd Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Marie Kelly Berkshire Hathaway HomeServices Robert Paul Properties

  • /55

    $1,175,000

    $24K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,884 Sq Ft

    190 Heritage Ln, Chatham, MA 02633

    In Town Location! Experience the best of Chatham living in this beautifully reimagined 3-bedroom, 2.5-bath home, ideally located close to Chatham Village, beaches, White Pond & the bike path. Thoughtfully updated inside and out, the home features a stunning new kitchen with quartz countertops & an AGA professional range, refinished hardwood floors, custom cabinetry, recessed lighting, fresh

    Shane Masaschi Compass

    190 Heritage Ln, Chatham, MA 02633
  • /52

    $7,000,000

    Sold Dec 18, 2025

    30 Tisquantum Rd, Chatham, MA 02633

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft
    • Built 1973

    Last Sold Summary

    • 18% Below List Price
    • $1,626/SF
    • 129 Days On Market

    Current Estimated Value $6,967,161

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum Rd, Chatham, MA 02633
    • /40

      Not Listed For Sale

      2388 Main St, South Chatham, MA 02659

      • 5 Beds
      • 4 Baths
      • 2,400 Sq Ft
      • Built 1910
      2388 Main St, South Chatham, MA 02659

      Last Sold Summary

      • 193 Days On Market

      Last Listing Agent W&W Boston/Cape Cod Connection Compass Massachusetts, LLC

  • /40

    $1,250,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    35 Duncan Ln, Chatham, MA 02633

    Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove.

    John Habeeb Alliance Realty Advisors, Inc.

    35 Duncan Ln, Chatham, MA 02633
  • /25

    $1,050,000

    Sold Jan 30, 2026

    144 Barn Hill Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1978

    Last Sold Summary

    • 16% Below List Price
    • $684/SF
    • 29 Days On Market

    Current Estimated Value $1,175,833

    Last Listing Agent Chris Rhinesmith Compass

    144 Barn Hill Rd, Chatham, MA 02633
    • /16

      Not Listed For Sale

      38 Patuxet Trail, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 513 Sq Ft
      • Built 1953
      38 Patuxet Trail, Chatham, MA 02633

      Last Sold Summary

      • 232 Days On Market

      Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

  • /48

    $2,995,000

    $205K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 2,700 Sq Ft

    26 Hardings Beach Rd, Chatham, MA 02633

    Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms. Just a short distance from Nantucket Sound and Hardings Beach, this craftsman-renovated home offers a spacious open floor plan highlighted by vaulted, beamed ceilings and expansive windows that showcase ever-shifting views of the tidal

    The Bohman Hartung Group Gibson Sotheby's International Realty

    26 Hardings Beach Rd, Chatham, MA 02633
  • /83

    $3,250,000

    Sold Aug 06, 2026

    87 Squanto Dr, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 3,902 Sq Ft
    • Built 2010

    Last Sold Summary

    • $833/SF
    • 1 Day On Market

    Current Estimated Value $3,275,509

    Last Listing Agent Julie Chapin William Raveis Real Estate & Home Services

    87 Squanto Dr, Chatham, MA 02633
    • /39

      Not Listed For Sale

      32 Cranberry Ln, North Chatham, MA 02650

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft
      • Built 1976
      32 Cranberry Ln, North Chatham, MA 02650

      Last Sold Summary

      • 310 Days On Market

      Last Listing Agent Bill Storff Compass Massachusetts, LLC

  • /36

    $6,800,000

    $400K PRICE DROP Pending
    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, Chatham, MA 02633

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean

    John Burke William Raveis Chatham

    238 Cranberry Ln, Chatham, MA 02633
  • /37

    $1,354,321

    Sold Sep 30, 2025

    96 Uncle Abners Path, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,863 Sq Ft
    • Built 1981

    Last Sold Summary

    • 13% Above List Price
    • $473/SF
    • 11 Days On Market

    Current Estimated Value $1,331,455

    Last Listing Agent Timothy Bailey John C Ricotta & Assoc.

    96 Uncle Abners Path, Chatham, MA 02633
    • /41

      Not Listed For Sale

      55 Twine Field Dr, Chatham, MA 02659

      • 3 Beds
      • 4 Baths
      • 2,760 Sq Ft
      • Built 1988
      55 Twine Field Dr, Chatham, MA 02659

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jen Whitaker Gibson Sotheby's International Realty

  • /87

    $3,495,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 3,838 Sq Ft

    40 Middle Rd, North Chatham, MA 02650

    Set in North Chatham's prestigious Harbor Coves Association, this Eastward-built residence carries true pedigree. As you arrive, you're welcomed by an inviting farmer's porch, leading into an open-concept great room where vaulted ceilings and recessed lighting create an airy, sun-filled feel throughout. The kitchen, living, and dining spaces flow seamlessly, appointed with custom cabinetry and

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    40 Middle Rd, North Chatham, MA 02650
  • /39

    $1,511,258

    Sold Oct 01, 2025

    9 Bettys Path, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,008 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Below List Price
    • $753/SF
    • 175 Days On Market

    Current Estimated Value $1,394,512

    Last Listing Agent Shane Masaschi Compass

    9 Bettys Path, Chatham, MA 02633
    • /11

      Not Listed For Sale

      281 Orleans Rd Unit 5, North Chatham, MA 02650

      • 1 Bed
      • 1 Bath
      • 604 Sq Ft
      • Built 1985
      281 Orleans Rd Unit 5, North Chatham, MA 02650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Isaac Sargent Compass Massachusetts, LLC

  • /33

    $899,000

    Pending
    • 2 Beds
    • 2 Baths
    • 2,127 Sq Ft

    1068 Main St Unit 1068, Chatham, MA 02633

    Welcome to "the Perch"! This 3 level townhome is located in the coastal town of Chatham! This serene setting overlooks Perch Pond where nature abounds.The complex is located close to downtown shops & restaurants, local beaches & the Old Colony Rail Trail. There is a finished lower level w/ great room and a sleeping area (2 queen beds) as well as 2 bedroom suites incl a first floor option. If you

    Kristin Coletti William Raveis R.E. & Home Services

    1068 Main St Unit 1068, Chatham, MA 02633

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