9,677

Chatham, MA Homes

Section Image
  • 330 Champlain Rd, Chatham, MA 02633
    330 Champlain Rd, Chatham, MA 02633
    330 Champlain Rd, Chatham, MA 02633
    /42

    $2,199,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,520 Sq Ft

    330 Champlain Rd, Chatham, MA 02633

    Location! Location! On " The Loop" at 330 Champlain Rd you have an exceptional 42,518 Sq Ft lot near Stage Harbor & 2 town landings! This charming Colonial offers 2520 square feet of space in a coveted locale, great for summer or year round. The living room has an oversized wood burning fireplace hearth & is open plan to formal dining room, cathedral ceiling & slider to a private patio and

    Phyllis Power Compass

    330 Champlain Rd, Chatham, MA 02633
  • 65 Lantern Ln, South Chatham, MA 02659
    65 Lantern Ln, South Chatham, MA 02659
    65 Lantern Ln, South Chatham, MA 02659
    /41

    $825,000

    Sold Oct 08, 2025

    65 Lantern Ln, South Chatham, MA 02659

    • 3 Beds
    • 1 Bath
    • 1,251 Sq Ft
    • Built 1969

    Last Sold Summary

    • $659/SF
    • 7 Days On Market

    Current Estimated Value $858,964

    Last Listing Agent Erin Terkelsen Keller Williams Realty

    65 Lantern Ln, South Chatham, MA 02659
    • 912 Main St Unit 202, Chatham, MA 02633
      912 Main St Unit 202, Chatham, MA 02633
      912 Main St Unit 202, Chatham, MA 02633
      /10

      Est $437,038

      Not Listed For Sale

      912 Main St Unit 202, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,192 Sq Ft
      • Built 1999
      912 Main St Unit 202, Chatham, MA 02633

      Last Sold Summary

      • 1 Day On Market

  • 0 Court St, Chatham, MA 02650
    0 Court St, Chatham, MA 02650
    /2

    $650,000

    • Land
    • 20,908 Sq Ft
    • $1,354,167 per Acre

    0 Court St, Chatham, MA 02650

    Rare to find a 20,737 lot in an established neighborhood of beautiful homes, close to town center or Ryder's Cove...overlooking Frost Fish Creek conservation, birdlife, tranquility! Building lot has been engineered by Ryder and Wilcox, pre- existing sidelines are R20. This lot will be sold separately after the home at 41 Court Street is sold, listed $2,295,000. MLS#22600472 or it can be purchased

    Phyllis Power Compass

    0 Court St, Chatham, MA 02650
  • 292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    /29

    $1,875,000

    Sold Mar 24, 2026

    292 Stage Harbor Rd, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 1,834 Sq Ft
    • Built 2018

    Last Sold Summary

    • 18% Below List Price
    • $1,022/SF
    • 307 Days On Market

    Current Estimated Value $2,136,125

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

    292 Stage Harbor Rd, Chatham, MA 02633
    • 912 Main St Unit 101, Chatham, MA 02633
      912 Main St Unit 101, Chatham, MA 02633
      912 Main St Unit 101, Chatham, MA 02633
      /38

      Est $663,683

      Not Listed For Sale

      912 Main St Unit 101, Chatham, MA 02633

      • 2 Beds
      • 2.5 Baths
      • 1,550 Sq Ft
      • Built 1999
      912 Main St Unit 101, Chatham, MA 02633

      Last Sold Summary

      • 7 Days On Market

  • 19 Joshuas Way, Chatham, MA 02633
    19 Joshuas Way, Chatham, MA 02633
    19 Joshuas Way, Chatham, MA 02633
    /37

    $795,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 1,687 Sq Ft

    19 Joshuas Way, Chatham, MA 02633

    Tucked away on a cul-de-sac in W. Chatham this spacious 4 Bed, 3.5 Bath Cape offers potential in a peaceful setting. Set back from the road with canopy of trees, the property feels private & serene with seasonal views of a scenic cranberry bog & birdlife. The main level features an open sunny living/ dining area,2 picture windows and slider to wraparound deck, with hardwood floors & wood burning

    Phyllis Power Compass

    19 Joshuas Way, Chatham, MA 02633
  • 92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    /78

    $4,700,000

    Sold Jun 22, 2026

    92 Barcliff Ave, Chatham, MA 02633

    • 5 Beds
    • 3.5 Baths
    • 2,659 Sq Ft
    • Built 1870

    Last Sold Summary

    • 2% Above List Price
    • $1,768/SF
    • 6 Days On Market

    Current Estimated Value $4,283,720

    Last Listing Agent Mina O'Keefe Gibson Sotheby's International Realty

    92 Barcliff Ave, Chatham, MA 02633
    • 920 Main St, Chatham, MA 02633
      920 Main St, Chatham, MA 02633
      920 Main St, Chatham, MA 02633
      /40

      Est $1,412,501

      Not Listed For Sale

      920 Main St, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 2,408 Sq Ft
      • Built 2005
      920 Main St, Chatham, MA 02633

      Last Sold Summary

      • 48 Days On Market

  • 42 Indian Hill Rd, Chatham, MA 02633
    42 Indian Hill Rd, Chatham, MA 02633
    42 Indian Hill Rd, Chatham, MA 02633
    /42

    $799,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    42 Indian Hill Rd, Chatham, MA 02633

    Nestled on a picturesque, level parcel accented by tranquil water features, this beautifully maintained four-bedroom, two-bath residence offers an exceptional opportunity to embrace the quintessential Cape Cod lifestyle. Thoughtfully designed for comfortable year-round living and effortless entertainment, the home combines classic charm with modern conveniences in a highly desirable location. The

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    42 Indian Hill Rd, Chatham, MA 02633
  • 150 Barcliff Ave, Chatham, MA 02633
    150 Barcliff Ave, Chatham, MA 02633
    150 Barcliff Ave, Chatham, MA 02633
    /42

    $4,125,000

    Sold Oct 10, 2025

    150 Barcliff Ave, Chatham, MA 02633

    • 6 Beds
    • 4 Baths
    • 3,808 Sq Ft
    • Built 1840

    Last Sold Summary

    • 2% Below List Price
    • $1,083/SF
    • 132 Days On Market

    Current Estimated Value $3,990,477

    Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    150 Barcliff Ave, Chatham, MA 02633
    • 199 Crowell Rd, Chatham, MA 02633
      199 Crowell Rd, Chatham, MA 02633
      199 Crowell Rd, Chatham, MA 02633
      /40

      Est $857,994

      Not Listed For Sale

      199 Crowell Rd, Chatham, MA 02633

      • 2 Beds
      • 3 Baths
      • 1,368 Sq Ft
      • Built 1995
      199 Crowell Rd, Chatham, MA 02633

      Last Sold Summary

      • 44 Days On Market

  • 239 Northgate Rd, Chatham, MA 02633
    239 Northgate Rd, Chatham, MA 02633
    239 Northgate Rd, Chatham, MA 02633
    /45

    $1,150,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,021 Sq Ft

    239 Northgate Rd, Chatham, MA 02633

    Tucked away in a private North Chatham setting with deeded rights to Lovers Lake just a short distance away, this extensively renovated 2,000 sq. ft. home offers the ideal blend of comfort, style, and turnkey ease. Thoughtfully updated throughout, the home features a renovated kitchen and bathrooms, air conditioning, and inviting living spaces designed for year-round enjoyment. The main level

    The Bohman Hartung Group Gibson Sotheby's International Realty

    239 Northgate Rd, Chatham, MA 02633
  • 2548 Main St, South Chatham, MA 2659
    2548 Main St, South Chatham, MA 2659
    2548 Main St, South Chatham, MA 2659
    /41

    $3,619,000

    Sold Jul 01, 2026

    2548 Main St, South Chatham, MA 2659

    • 4 Beds
    • 5.5 Baths
    • 4,942 Sq Ft
    • Built 2026

    Last Sold Summary

    • 10% Below List Price
    • $732/SF
    • 264 Days On Market

    Current Estimated Value $4,168,000

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

    2548 Main St, South Chatham, MA 2659
    • 14 Windsong Landing, Chatham, MA 02633
      14 Windsong Landing, Chatham, MA 02633
      14 Windsong Landing, Chatham, MA 02633
      /22

      Est $1,933,465

      Not Listed For Sale

      14 Windsong Landing, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 1983
      14 Windsong Landing, Chatham, MA 02633

      Last Sold Summary

      • 5 Days On Market

  • 150 Cross St, Chatham, MA 02633
    150 Cross St, Chatham, MA 02633
    150 Cross St, Chatham, MA 02633
    /34

    $6,500,000

    • 10 Beds
    • 10 Baths
    • 7,658 Sq Ft

    150 Cross St, Chatham, MA 02633

    Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500

    Chris Rhinesmith Compass Massachusetts, LLC

    150 Cross St, Chatham, MA 02633
  • 785 Old Harbor Rd, North Chatham, MA 02650
    785 Old Harbor Rd, North Chatham, MA 02650
    785 Old Harbor Rd, North Chatham, MA 02650
    /40

    $4,600,000

    Sold Dec 11, 2025

    785 Old Harbor Rd, North Chatham, MA 02650

    • 5 Beds
    • 5 Baths
    • 4,200 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $1,095/SF
    • 60 Days On Market

    Current Estimated Value $4,720,136

    Last Listing Agent Phyllis Power Compass

    785 Old Harbor Rd, North Chatham, MA 02650
    • 67 Capri Ln, Chatham, MA 02633
      67 Capri Ln, Chatham, MA 02633
      67 Capri Ln, Chatham, MA 02633
      /29

      Est $3,659,816

      Not Listed For Sale

      67 Capri Ln, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 3,560 Sq Ft
      • Built 2023
      67 Capri Ln, Chatham, MA 02633

      Last Sold Summary

      • 35 Days On Market

  • 169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    /53

    $4,900,000

    $500K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,587 Sq Ft

    169 Tisquantum Rd, Chatham, MA 02633

    Located in Chatham's Quitnesset neighborhood on Morris Island, ideally situated between the Association's private deeded beach and the trails of the protected Monomoy National Wildlife Refuge, this elegant and spacious home embodies the quintessential Cape Cod lifestyle. Step into the sunlit foyer leading to a soaring great room with a fireplace and a chef's kitchen designed for entertaining.

    Sandra Tanco Kinlin Grover Compass

    169 Tisquantum Rd, Chatham, MA 02633
  • 40 Florence Dr, South Chatham, MA 02659
    40 Florence Dr, South Chatham, MA 02659
    40 Florence Dr, South Chatham, MA 02659
    /53

    $870,000

    Sold Jul 31, 2025

    40 Florence Dr, South Chatham, MA 02659

    • 3 Beds
    • 1.5 Baths
    • 1,362 Sq Ft
    • Built 1960

    Last Sold Summary

    • 8% Below List Price
    • $639/SF
    • 65 Days On Market

    Current Estimated Value $911,660

    Last Listing Agent Melanie Cauchon Melanie Cauchon Real Estate

    40 Florence Dr, South Chatham, MA 02659
    • 51 Oyster Bay Ln, Chatham, MA 02633
      51 Oyster Bay Ln, Chatham, MA 02633
      /2

      Est $2,568,508

      Not Listed For Sale

      51 Oyster Bay Ln, Chatham, MA 02633

      • 4 Beds
      • 4 Baths
      • 3,037 Sq Ft
      • Built 1986
      51 Oyster Bay Ln, Chatham, MA 02633

  • 92 Hitching Post Rd, Chatham, MA 02633
    92 Hitching Post Rd, Chatham, MA 02633
    92 Hitching Post Rd, Chatham, MA 02633
    /33

    $1,350,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,951 Sq Ft

    92 Hitching Post Rd, Chatham, MA 02633

    Fabulous Downtown Chatham! Stroll to Veterans Field for a Cape League ball game or have a front row seat for the New Years Eve fireworks! Then continue down Main Street for all of the wonderful shops, drinks and dining. This well-loved home has been in the same family for generations and is now ready for new owners to make their special memories. Substantial and well built, the property could use

    Betsy & Gerry Ciarcia Home*Land Realty

    92 Hitching Post Rd, Chatham, MA 02633
  • 21 Gramps Way, South Chatham, MA 02659
    21 Gramps Way, South Chatham, MA 02659
    21 Gramps Way, South Chatham, MA 02659
    /58

    $1,244,000

    Sold Aug 26, 2025

    21 Gramps Way, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 3,080 Sq Ft
    • Built 1987

    Last Sold Summary

    • $404/SF
    • 5 Days On Market

    Current Estimated Value $1,381,006

    Last Listing Agent Cheryle Young Today Real Estate

    21 Gramps Way, South Chatham, MA 02659
    • 356 Stage Harbor Rd, Chatham, MA 02633
      356 Stage Harbor Rd, Chatham, MA 02633
      356 Stage Harbor Rd, Chatham, MA 02633
      /65

      Not Listed For Sale

      356 Stage Harbor Rd, Chatham, MA 02633

      • 5 Beds
      • 5.5 Baths
      • 4,000 Sq Ft
      • Built 2024
      356 Stage Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 94 Days On Market

  • 92 Absegami Run, Chatham, MA 02633
    92 Absegami Run, Chatham, MA 02633
    92 Absegami Run, Chatham, MA 02633
    /54

    $3,600,000

    Sold Jun 03, 2026

    92 Absegami Run, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 3,199 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $1,125/SF
    • 4 Days On Market

    Current Estimated Value $3,658,730

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

    92 Absegami Run, Chatham, MA 02633
    • 88 Champlain Rd, Chatham, MA 02633
      88 Champlain Rd, Chatham, MA 02633
      88 Champlain Rd, Chatham, MA 02633
      /62

      Est $4,755,334

      Not Listed For Sale

      88 Champlain Rd, Chatham, MA 02633

      • 4 Beds
      • 5.5 Baths
      • 4,112 Sq Ft
      • Built 2003
      88 Champlain Rd, Chatham, MA 02633

      Last Sold Summary

      • 14 Days On Market

  • 425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    /25

    $440,000

    Sold Jun 24, 2026

    425 Main St Unit D, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Below List Price
    • $761/SF
    • 26 Days On Market

    Current Estimated Value $448,960

    Last Listing Agent Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
    • 270 Stage Island Rd, Chatham, MA 02633
      270 Stage Island Rd, Chatham, MA 02633
      /2

      Est $6,773,821

      Not Listed For Sale

      270 Stage Island Rd, Chatham, MA 02633

      • 5 Beds
      • 5 Baths
      • 4,000 Sq Ft
      • Built 1984
      270 Stage Island Rd, Chatham, MA 02633

  • 144 Barn Hill Rd, Chatham, MA 02633
    144 Barn Hill Rd, Chatham, MA 02633
    144 Barn Hill Rd, Chatham, MA 02633
    /24

    $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
    • 37 Days On Market

    Current Estimated Value $1,183,468

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    144 Barn Hill Rd, Chatham, MA 02633
    • 48 Strong Island Rd, Chatham, MA 02633
      48 Strong Island Rd, Chatham, MA 02633
      48 Strong Island Rd, Chatham, MA 02633
      /82

      Est $3,774,254

      Not Listed For Sale

      48 Strong Island Rd, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 3,929 Sq Ft
      • Built 1985
      48 Strong Island Rd, Chatham, MA 02633

      Last Sold Summary

      • 41 Days On Market

  • 41 Woodland Rd, South Chatham, MA 02659
    41 Woodland Rd, South Chatham, MA 02659
    41 Woodland Rd, South Chatham, MA 02659
    /22

    $860,000

    Sold Dec 30, 2025

    41 Woodland Rd, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • Built 1960

    Last Sold Summary

    • 8% Above List Price
    • $517/SF
    • 4 Days On Market

    Current Estimated Value $924,335

    Last Listing Agent Phyllis Power Compass

    41 Woodland Rd, South Chatham, MA 02659
    • 27 Strong Island Rd, Chatham, MA 02633
      27 Strong Island Rd, Chatham, MA 02633
      27 Strong Island Rd, Chatham, MA 02633
      /43

      Est $2,753,431

      Not Listed For Sale

      27 Strong Island Rd, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 2,764 Sq Ft
      • Built 1960
      27 Strong Island Rd, Chatham, MA 02633

      Last Sold Summary

      • 58 Days On Market

  • 28 Charles St, South Chatham, MA 02659
    28 Charles St, South Chatham, MA 02659
    28 Charles St, South Chatham, MA 02659
    /23

    $550,000

    Sold Apr 03, 2026

    28 Charles St, South Chatham, MA 02659

    • 4 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1967

    Last Sold Summary

    • $385/SF
    • 6 Days On Market

    Current Estimated Value $577,194

    Last Listing Agent Shane Masaschi Compass

    28 Charles St, South Chatham, MA 02659
    • 789 Fox Hill Rd, Chatham, MA 02633
      789 Fox Hill Rd, Chatham, MA 02633
      789 Fox Hill Rd, Chatham, MA 02633
      /41

      Est $2,683,800

      Not Listed For Sale

      789 Fox Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 1.5 Baths
      • 1,275 Sq Ft
      • Built 1950
      789 Fox Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 1,761 Days On Market

  • 2590 Main St, South Chatham, MA 02659
    2590 Main St, South Chatham, MA 02659
    2590 Main St, South Chatham, MA 02659
    /65

    $749,900

    Sold Jul 31, 2025

    2590 Main St, South Chatham, MA 02659

    • 5 Beds
    • 3 Baths
    • 2,184 Sq Ft
    • Built 1834

    Last Sold Summary

    • 4% Below List Price
    • $343/SF
    • 97 Days On Market

    Current Estimated Value $755,869

    Last Listing Agent Richard Waystack William Raveis Real Estate & Home Services

    2590 Main St, South Chatham, MA 02659
    • 771 Fox Hill Rd, Chatham, MA 02633
      771 Fox Hill Rd, Chatham, MA 02633
      771 Fox Hill Rd, Chatham, MA 02633
      /41

      Est $6,739,878

      Not Listed For Sale

      771 Fox Hill Rd, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 3,439 Sq Ft
      • Built 2012
      771 Fox Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 0 Days On Market

  • 0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    /7

    $250,000

    Sold May 19, 2026

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

    • Land
    • 31,363 Sq Ft
    • $347,222 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 991 Days On Market

    Last Listing Agent Shane Masaschi Compass

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    • 66 Woodland Way, North Chatham, MA 02650
      66 Woodland Way, North Chatham, MA 02650
      66 Woodland Way, North Chatham, MA 02650
      /30

      Est $3,561,976

      Not Listed For Sale

      66 Woodland Way, North Chatham, MA 02650

      • 3 Beds
      • 4.5 Baths
      • 2,971 Sq Ft
      • Built 2018
      66 Woodland Way, North Chatham, MA 02650

      Last Sold Summary

      • 9 Days On Market

  • 7 Bearberry Ln, South Chatham, MA 02659
    7 Bearberry Ln, South Chatham, MA 02659
    7 Bearberry Ln, South Chatham, MA 02659
    /56

    $900,000

    Sold Sep 23, 2025

    7 Bearberry Ln, South Chatham, MA 02659

    • 3 Beds
    • 3 Baths
    • 1,328 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $678/SF
    • 16 Days On Market

    Current Estimated Value $992,558

    Last Listing Agent Richard Robbins Compass

    7 Bearberry Ln, South Chatham, MA 02659
    • 121 Middle Rd, North Chatham, MA 02650
      121 Middle Rd, North Chatham, MA 02650
      121 Middle Rd, North Chatham, MA 02650
      /38

      Est $1,904,130

      Not Listed For Sale

      121 Middle Rd, North Chatham, MA 02650

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft
      • Built 1974
      121 Middle Rd, North Chatham, MA 02650

      Last Sold Summary

      • 9 Days On Market

Showing Results 281 - 320, Page 8 of 18

Massachusetts Barnstable County

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