9,636

Chatham, MA Homes

Section Image
  • /41

    $2,500,000 Sold Oct 24, 2025

    106 Stage Neck Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 3,834 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Below List Price
    • $652/SF
    • 152 Days On Market

    Current Estimated Value $2,535,227

    Last Listing Agent Jen Graham Christie's International Real Estate Atlantic Brokerage

    106 Stage Neck Rd, Chatham, MA 02633
    • /42

      Est $4,204,499 Not Listed For Sale

      107 School St, Chatham, MA 02633

      • 4 Beds
      • 5.5 Baths
      • 4,372 Sq Ft
      • Built 2014
      107 School St, Chatham, MA 02633

      Last Sold Summary

      • 11% Above List Price
      • $869/SF
      • 39 Days On Market

      Last Sold Price $3,800,000

      Last Listing Agent John Burke William Raveis Chatham

  • /71

    $2,195,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    9 Wadsworth Rd, South Chatham, MA 02659

    Proximity to Pleasant Street Beach - ChathamLocated in an area of substantial homes and offering water views along with exceptional proximity to Pleasant Street Beach, this 4-bedroom, 2.5-bath residence presents an outstanding Chatham opportunity.The home has been thoughtfully updated over the years, including recent interior repainting, refinished wood floors, and numerous additional

    LUXRECapeCod Gibson Sotheby's International Realty

    9 Wadsworth Rd, South Chatham, MA 02659
  • /73

    $2,685,000 Sold Jul 09, 2025

    7 Colonial Dr, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 3,056 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Above List Price
    • $879/SF
    • 13 Days On Market

    Current Estimated Value $2,489,655

    Last Listing Agent Pam Roberts Gibson Sotheby's International Realty

    7 Colonial Dr, Chatham, MA 02633
    • /23

      Est $555,478 Not Listed For Sale

      73 Main St Unit 8, Chatham, MA 02633

      • 1 Bed
      • 1 Bath
      • 551 Sq Ft
      • Built 1850
      73 Main St Unit 8, Chatham, MA 02633

      Last Sold Summary

      • 2% Above List Price
      • $989/SF
      • 34 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Meredyth Thomas Compass

  • /35

    $2,800,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    78 Indian Trail, Chatham, MA 02633

    Professional photos coming soon!Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in beautiful water views and unforgettable sunsets, with private stairs leading down to the water's edge of Bucks Creek

    Judith Smith John C Ricotta & Assoc.

    78 Indian Trail, Chatham, MA 02633
  • /48

    $582,500 Sold May 02, 2025

    1 Seastrand Way Unit 8, Chatham, MA 02633

    • 2 Beds
    • 1.5 Baths
    • 1,017 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $573/SF
    • 14 Days On Market

    Current Estimated Value $587,096

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    1 Seastrand Way Unit 8, Chatham, MA 02633
    • /31

      Not Listed For Sale

      90 Silver Leaf Ave, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 2,209 Sq Ft
      • Built 1850
      90 Silver Leaf Ave, Chatham, MA 02633

      Last Sold Summary

      • $1,200/SF
      • 25 Days On Market

      Last Sold Price $2,650,000

      Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

  • /42

    $3,795,000

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

    83 Old Mail Rd, North Chatham, MA 02650

    NEW CONSTRUCTION - NORTH CHATHAM, 02650. Zillow's February 2026 data showed just 6 homes for sale in the coveted 02650 North Chatham market, highlighting the rarity, higher pricing & prestige of this location. This newly built luxury residence pairs refined coastal design w/exceptional craftsmanship in one of Chatham's most sought-after settings. Thoughtfully designed for both everyday living &

    Shane Masaschi Compass

    83 Old Mail Rd, North Chatham, MA 02650
  • /28

    $795,000 Sold Jul 07, 2025

    96 Island View Ln, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 1975

    Last Sold Summary

    • 10% Below List Price
    • $475/SF
    • 20 Days On Market

    Current Estimated Value $849,862

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

    96 Island View Ln, South Chatham, MA 02659
    • /35

      Not Listed For Sale

      32 Little Beach Rd, Chatham, MA 02633

      • 5 Beds
      • 3.5 Baths
      • 1,713 Sq Ft
      • Built 1930
      32 Little Beach Rd, Chatham, MA 02633

      Last Sold Summary

      • $1,051/SF
      • 222 Days On Market

      Last Sold Price $1,800,000

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

  • /16

    $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
  • /94

    $3,020,000 Sold Jan 15, 2026

    404 Stage Harbor Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 2,905 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Above List Price
    • $1,040/SF
    • 5 Days On Market

    Current Estimated Value $2,975,383

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

    404 Stage Harbor Rd, Chatham, MA 02633
    • /53

      Est $2,464,831 Not Listed For Sale

      16 Windmill Ln, Chatham, MA 02633

      • 4 Beds
      • 1.5 Baths
      • 1,669 Sq Ft
      • Built 1920
      16 Windmill Ln, Chatham, MA 02633

      Last Sold Summary

      • 19% Above List Price
      • $1,243/SF
      • 32 Days On Market

      Last Sold Price $2,075,000

      Last Listing Agent Robin Thayer Gibson Sotheby's International Realty

  • /4

    $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
  • /30

    $507,000 Sold Jul 25, 2025

    912 Main St Unit 305, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft
    • Built 1999

    Last Sold Summary

    • 15% Above List Price
    • $392/SF
    • 5 Days On Market

    Current Estimated Value $493,887

    Last Listing Agent Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 305, Chatham, MA 02633
    • /53

      Not Listed For Sale

      43 Morris Island Rd, Chatham, MA 02633

      • 5 Beds
      • 7 Baths
      • 5,861 Sq Ft
      • Built 2006
      43 Morris Island Rd, Chatham, MA 02633

      Last Sold Summary

      • $1,962/SF
      • 296 Days On Market

      Last Sold Price $11,500,000

      Last Listing Agent Jeffrey Marcus Sotheby's International Realty

  • /23

    $949,000 Pending

    • 4 Beds
    • 1 Bath
    • 1,547 Sq Ft

    66 Ethelma Dr, Chatham, MA 02633

    66 Ethelma Drive is a rare pond front opportunity in Chatham, MA, set along the shores of Emery Pond just minutes from downtown Chatham, Cape Cod beaches, restaurants, shops and close to the bike path. This 4-bedroom, 1-bath home offers 1,547 sq ft on approximately half an acre and presents exceptional potential for renovation, reconstruction, or a custom waterfront build. For buyers seeking

    Shane Masaschi Compass

    66 Ethelma Dr, Chatham, MA 02633
  • /34

    $674,000 Sold Oct 31, 2025

    38 Andover Dr, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 1,244 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $542/SF
    • 6 Days On Market

    Current Estimated Value $713,671

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

    38 Andover Dr, Chatham, MA 02633
    • /20

      Est $2,176,449 Not Listed For Sale

      32 Cranberry Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft
      • Built 1976
      32 Cranberry Ln, Chatham, MA 02633

      Last Sold Summary

      • 7% Above List Price
      • $944/SF
      • 134 Days On Market

      Last Sold Price $2,025,000

      Last Listing Agent William Storff Compass

  • /25

    $689,000 Pending

    • 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
  • /43

    $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 $1,588,676

    Last Listing Agent Shane Masaschi Compass

    9 Bettys Path, Chatham, MA 02633
    • /45

      Est $3,568,361 Not Listed For Sale

      48 Salt Marsh Way, North Chatham, MA 02650

      • 5 Beds
      • 3 Baths
      • 2,448 Sq Ft
      • Built 1790
      48 Salt Marsh Way, North Chatham, MA 02650

      Last Sold Summary

      • 8% Above List Price
      • $1,348/SF
      • 96 Days On Market

      Last Sold Price $3,300,000

      Last Listing Agent Phyllis Power Kinlin Grover Compass

  • /50

    $1,200,000

    • 3 Beds
    • 3 Baths
    • 1,804 Sq Ft

    118 Wilfred Rd, Chatham, MA 02633

    PONDFRONT: Welcome to 118 Wilfred Road, a charming Cape-style home tucked into one of Chatham's beloved ponds settings. With 3 bedrooms, 3 baths, and 1,804 square feet, this inviting residence captures the essence of relaxed Cape Cod living. Enjoy sweeping views of Black Pond, White Pond and Emery Pond and take advantage of an exceptional location less than 0.2 miles from White Pond, a cherished

    Shane Masaschi Compass

    118 Wilfred Rd, Chatham, MA 02633
  • /34

    $5,250,000 Sold May 09, 2025

    372 Fox Hill Rd, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 2,214 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $2,371/SF
    • 3 Days On Market

    Current Estimated Value $5,369,267

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    372 Fox Hill Rd, Chatham, MA 02633
    • /41

      Est $1,718,718 Not Listed For Sale

      39 Windward Passage, North Chatham, MA 02650

      • 3 Beds
      • 2.5 Baths
      • 2,205 Sq Ft
      • Built 1980
      39 Windward Passage, North Chatham, MA 02650

      Last Sold Summary

      • 7% Above List Price
      • $726/SF
      • 52 Days On Market

      Last Sold Price $1,600,000

      Last Listing Agent Jack Tobin Berkshire Hathaway HomeServices Robert Paul Properties

  • /25

    $450,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula “It’s All About Me,” Unit D at 425 Main Street offers a rare blend of privacy, comfort, and true in-town living. One of only two residences on the second floor, it features a discreet private entrance and an open, light-filled layout with recent upgrades, including luxury vinyl flooring and refreshed finishes. The well-appointed kitchen flows into a spacious living and

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • /29

    $1,050,000 Sold Jan 09, 2026

    319 Riverview Dr, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,202 Sq Ft
    • Built 1984

    Last Sold Summary

    • 19% Below List Price
    • $477/SF
    • 180 Days On Market

    Current Estimated Value $1,105,361

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    319 Riverview Dr, Chatham, MA 02633
    • /16

      Not Listed For Sale

      356 Stony Hill Rd, North Chatham, MA 02650

      • 4 Beds
      • 5.5 Baths
      • 4,581 Sq Ft
      • Built 2023
      356 Stony Hill Rd, North Chatham, MA 02650

      Last Sold Summary

      • $895/SF
      • 65 Days On Market

      Last Sold Price $4,100,000

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /48

    $1,350,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 2,278 Sq Ft

    243 Crowell Rd, Chatham, MA 02633

    Comfortable Cape style 3 bedroom home, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Set back from the road on a level, grassy front lawn, Updated chef's kitchen, newer A/C splits, fenced, sunny back yard with deck. Free standing 2 car garage on over .6 acre lot. Unfinished second floor offers expansion potential with previously permitted plan. Large unfinished

    Michael Hall William Raveis Real Estate & Home Services

    243 Crowell Rd, Chatham, MA 02633
  • /48

    $2,950,000 Sold Dec 02, 2025

    314 Cockle Cove Rd, Chatham, MA 02659

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $946/SF
    • 13 Days On Market

    Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    314 Cockle Cove Rd, Chatham, MA 02659
    • /44

      Est $1,849,802 Not Listed For Sale

      504 Stony Hill Rd, North Chatham, MA 02650

      • 5 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 1946
      504 Stony Hill Rd, North Chatham, MA 02650

      Last Sold Summary

      • 3% Above List Price
      • $945/SF
      • 114 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent LUXRECapeCod Gibson Sotheby's International Realty

  • /15

    $675,000 Pending

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft

    39 Meadow Brook Rd, Chatham, MA 02650

    Location! Location! Location! This Freshly painted charming North Chatham gem, remodeled in 2024, offers 768 sq/ft of living space and is located conveniently to the Cape Cod Rail trail, for recreational fun. Enjoy single story living in this 2 bedroom 1 bath home with hardwood floors and a fireplace. There is a 768 sq/ft walkout basement currently used as a single car garage which also has great

    Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    39 Meadow Brook Rd, Chatham, MA 02650
  • /50

    $1,200,000 Sold Apr 30, 2025

    54 Rowland Dr, North Chatham, MA 02650

    • 4 Beds
    • 3.5 Baths
    • 2,062 Sq Ft
    • Built 1970

    Last Sold Summary

    • 33% Below List Price
    • $582/SF
    • 282 Days On Market

    Current Estimated Value $1,420,067

    Last Listing Agent Barbara Garside eXp Realty, LLC

    54 Rowland Dr, North Chatham, MA 02650
    • /40

      Est $1,690,147 Not Listed For Sale

      98 Orleans Rd, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 3,428 Sq Ft
      • Built 1997
      98 Orleans Rd, Chatham, MA 02633

      Last Sold Summary

      • 9% Above List Price
      • $454/SF
      • 61 Days On Market

      Last Sold Price $1,557,500

      Last Listing Agent Jason Saphire www.HomeZu.com

  • /88

    $6,900,000

    • 7 Beds
    • 6.5 Baths
    • 6,521 Sq Ft

    44 Buena Vista Rd, Chatham, MA 02633

    Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

    Shane Masaschi Compass

    44 Buena Vista Rd, Chatham, MA 02633
  • /40

    $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 $2,486,553

    Last Listing Agent Catherine Baran Corcoran Property Advisors

    290 Old Comers Rd, Chatham, MA 02633
    • /43

      Est $1,563,027 Not Listed For Sale

      17 Menekish Ln, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 2,124 Sq Ft
      • Built 1984
      17 Menekish Ln, Chatham, MA 02633

      Last Sold Summary

      • 12% Above List Price
      • $659/SF
      • 136 Days On Market

      Last Sold Price $1,400,000

      Last Listing Agent Daren Marvin Sotheby's International Realty

  • /52

    $12,950,000

    • 5 Beds
    • 6.5 Baths
    • 7,259 Sq Ft

    301 Whidah Rd, North Chatham, MA 2650

    Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping vistas and invite natural light to pour in throughout the home. Indoor and outdoor spaces flow effortlessly, from sun-drenched rooms to generous

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, North Chatham, MA 2650
  • /36

    $899,000 Sold Jan 02, 2026

    15 Sylvan Way, South Chatham, MA 02659

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft
    • Built 2002

    Last Sold Summary

    • 16% Below List Price
    • $511/SF
    • 70 Days On Market

    Current Estimated Value $897,671

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

    15 Sylvan Way, South Chatham, MA 02659

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home