9,675

Chatham, MA Homes

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  • /42

    $1,350,000

    • 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
  • /46

    $2,595,000

    Sold Jun 23, 2026

    8 Captains Walk, North Chatham, MA 02650

    • 4 Beds
    • 2.5 Baths
    • 3,479 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $746/SF
    • 15 Days On Market

    Current Estimated Value $2,647,165

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    8 Captains Walk, North Chatham, MA 02650
    • /26

      Est $2,610,110

      Not Listed For Sale

      10 Mill Hill Ln, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 2,174 Sq Ft
      • Built 1720
      10 Mill Hill Ln, Chatham, MA 02633

      Last Sold Summary

      • 44 Days On Market

  • /91

    $6,900,000

    $2M PRICE DROP Pending
    • 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
  • /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 $3,121,360

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

    404 Stage Harbor Rd, Chatham, MA 02633
    • /42

      Not Listed For Sale

      67 School St, Chatham, MA 02633

      • 4 Beds
      • 2 Baths
      • 1,595 Sq Ft
      • Built 1910
      67 School St, Chatham, MA 02633

      Last Sold Summary

      • 26 Days On Market

  • /48

    $2,995,000

    Open Fri 3:30PM - 5PM $205K PRICE DROP
    • 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
  • /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 $539,964

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

    912 Main St Unit 305, Chatham, MA 02633
    • /4

      Est $2,834,839

      Not Listed For Sale

      35 Mill Hill Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 2,016 Sq Ft
      • Built 1987
      35 Mill Hill Ln, Chatham, MA 02633

      Last Sold Summary

      • 3 Days On Market

  • /9

    $566,700

    Pending
    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft

    1761 Main St, Chatham, MA 02633

    Property is being offered via Real Estate Auction on Friday, June 26th at 2pm on-site. The actual selling price will be determined auction day. List price/estimated value seen is set at the real estate tax assessment. Pre-auction offers must be presented on the auction P&S and are subject to seller confirmation. 10% Buyer's Premium applies. 1+/- acre residential lot in highly desirable location

    Justin Manning JJManning Auctioneers

    1761 Main St, Chatham, MA 02633
  • /71

    $2,550,000

    Sold May 22, 2026

    16 Old Salt Works Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Above List Price
    • $1,051/SF
    • 6 Days On Market

    Current Estimated Value $2,520,774

    Last Listing Agent Chet Crabtree Christie's International Real Estate Atlantic Brokerage

    16 Old Salt Works Rd, Chatham, MA 02633
    • /42

      Est $4,268,898

      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

      • 39 Days On Market

  • /36

    $6,800,000

    $400K PRICE DROP
    • 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
  • /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 $1,394,896

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    134 Northgate Rd, North Chatham, MA 02650
    • /23

      Est $573,679

      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

      • 34 Days On Market

  • /32

    $995,000

    $105K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,476 Sq Ft

    35 Oak Ridge Cir, Chatham, MA 02633

    Nestled at the end of a cul-de-sac and abutting conservation land, this well-maintained 3-bedroom, 1.5-bath ranch offers the ideal combination of privacy, comfort, and timeless appeal. With 1,476 square feet of living space, this inviting home features hardwood floors throughout, an open floor plan, and a family room addition with a cathedral ceiling that fills the home with natural light. A

    Jack Farrell Compass

    35 Oak Ridge Cir, Chatham, MA 02633
  • /21

    $4,525,000

    Sold Jun 26, 2026

    230 Barcliff Ave, Chatham, MA 02633

    • 4 Beds
    • 6 Baths
    • 5,300 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Above List Price
    • $854/SF
    • 222 Days On Market

    Current Estimated Value $4,364,557

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    230 Barcliff Ave, Chatham, MA 02633
    • /38

      Est $2,424,695

      Not Listed For Sale

      16 Little Beach Rd, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 1,863 Sq Ft
      • Built 2018
      16 Little Beach Rd, Chatham, MA 02633

      Last Sold Summary

      • 356 Days On Market

  • /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
  • /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 $762,477

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

    38 Andover Dr, Chatham, MA 02633
    • /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

      • 222 Days On Market

  • /64

    $995,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,367 Sq Ft

    127 Perch Pond Dr, Chatham, MA 02633

    Tucked away on a generous half-acre lot this inviting 4-bedroom, 2 bath home offers the perfect blend of comfort, style & Cape Cod charm. Step inside to discover an updated kitchen & refreshed baths complimented by a warm & inviting living room with gas fireplace. The dining area features sliders that open to a spacious deck creating a seamless indoor-outdoor flow, perfect for summer entertaining

    David Carter Compass Massachusetts, LLC

    127 Perch Pond Dr, Chatham, MA 02633
  • /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 $1,482,693

    Last Listing Agent Shane Masaschi Compass

    9 Bettys Path, Chatham, MA 02633
    • /53

      Est $2,814,280

      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

      • 32 Days On Market

  • /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
  • /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 $1,166,228

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    319 Riverview Dr, Chatham, MA 02633
    • /20

      Est $2,215,946

      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

      • 134 Days On Market

  • /42

    $12,950,000

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

    301 Whidah Rd, Chatham, MA 02650

    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 views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, Chatham, MA 02650
  • /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
    • /41

      Est $1,818,194

      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

      • 52 Days On Market

  • /46

    $1,399,000

    $96K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    137 Shane Dr, Chatham, MA 02633

    Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530

    Tom Riley Compass Massachusetts, LLC

    137 Shane Dr, 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 $2,444,608

    Last Listing Agent Catherine Baran Corcoran Property Advisors

    290 Old Comers Rd, Chatham, MA 02633
    • /44

      Est $1,977,779

      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

      • 114 Days On Market

  • /35

    $629,000

    Pending
    • 2 Beds
    • 1 Bath
    • 1,094 Sq Ft

    18 Quail Trail, South Chatham, MA 02659

    Charming 2 Bedroom, 1-bath Cape ideally sited on a corner lot close to shopping, restaurants, bike trial, and just minutes to Nantucket Sound beaches. Well cared for and brimming with potential, this sweet home is ready for a new owner to refresh and make it shine.

    David Carter Compass Massachusetts, LLC

    18 Quail Trail, South Chatham, MA 02659
  • /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 $953,754

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

    15 Sylvan Way, South Chatham, MA 02659
    • /36

      Est $2,176,105

      Not Listed For Sale

      84 Emery Ln, North Chatham, MA 02650

      • 3 Beds
      • 2.5 Baths
      • 2,270 Sq Ft
      • Built 1987
      84 Emery Ln, North Chatham, MA 02650

      Last Sold Summary

      • 0 Days On Market

  • /35

    $995,000

    $105K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,476 Sq Ft

    35 Oak Ridge Cir, Chatham, MA 02633

    Nestled at the end of a cul-de-sac and abutting conservation land, this well-maintained 3-bedroom, 1.5-bath ranch offers the ideal combination of privacy and comfort. With 1,476 square feet of living space, this inviting home features wood floors, an open floor plan, and a family room addition with a cathedral ceiling that fills the home with natural light. A formal living room with a

    David Doherty Compass

    35 Oak Ridge Cir, Chatham, MA 02633
  • /32

    $10,000,000

    Sold Sep 24, 2025

    108 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 9 Baths
    • 6,276 Sq Ft
    • Built 1920

    Last Sold Summary

    • 16% Below List Price
    • $1,593/SF
    • 67 Days On Market

    Last Listing Agent Frank Denauw Frank G. Denauw, Esq.

    108 Shore Rd, Chatham, MA 02633
    • /40

      Est $1,748,162

      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

      • 61 Days On Market

  • /6

    $5,750,000

    • 3 Beds
    • 6 Baths
    • 4,902 Sq Ft

    7 Cove Rd, Chatham, MA 02650

    Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre. The main level features an inviting open floor plan where a

    Chris Rhinesmith Compass

    7 Cove Rd, Chatham, MA 02650

Showing Results 41 - 80, Page 2 of 18

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