9,489

Chatham, MA Homes

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  • /41

    $2,450,000

    Sold Oct 31, 2025

    252 N Skyline Dr, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 3,275 Sq Ft
    • Built 2007

    Last Sold Summary

    • 3% Above List Price
    • $748/SF
    • 3 Days On Market

    Current Estimated Value $2,372,761

    Last Listing Agent Phyllis Power Compass

    252 N Skyline Dr, Chatham, MA 02633
    • /47

      Est $2,878,842

      Not Listed For Sale

      47 Quasson Rd, Chatham, MA 02633

      • 4 Beds
      • 4 Baths
      • 2,399 Sq Ft
      • Built 1956
      47 Quasson Rd, Chatham, MA 02633

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Kristin Muller John C Ricotta & Assoc.

  • /50

    $2,240,000

    • 4 Beds
    • 3 Baths
    • 3,102 Sq Ft

    20 Circle Dr, South Chatham, MA 02659

    A meticulously maintained and beautifully decorated beach home awaits you in the quaint village of South Chatham. Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm. Nestled near Forest Beach, Mill Creek, the Cape Cod Rail Trail, tennis court and conservation areas, this home

    Barbara Carroll-Horne Gibson Sotheby's International Realty

    20 Circle Dr, South Chatham, MA 02659
  • /33

    $695,000

    Sold Apr 21, 2026

    1 Seastrand Way Unit 1, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1983

    Last Sold Summary

    • $536/SF
    • 11 Days On Market

    Current Estimated Value $680,296

    Last Listing Agent Phyllis Power Compass

    1 Seastrand Way Unit 1, Chatham, MA 02633
    • /59

      Est $7,882,378

      Not Listed For Sale

      504 Old Harbor Rd, North Chatham, MA 02650

      • 8 Beds
      • 6 Baths
      • 4,615 Sq Ft
      • Built 1940
      504 Old Harbor Rd, North Chatham, MA 02650

      Last Sold Summary

      • 165 Days On Market

      Last Listing Agent Phyllis Power Compass

  • /40

    $4,295,000

    $455K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,967 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings & dramatic walls of glass fill the home with natural light and frame spectacular sunsets. Multiple sliders open to an expansive wraparound deck for effortless indoor-outdoor living. Chefs kitchen, dual living areas, and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    38 Indian Trail, Chatham, MA 02633
  • /40

    $815,000

    Sold Sep 01, 2026

    66 Snow Ln, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1962

    Last Sold Summary

    • 9% Below List Price
    • $943/SF
    • 78 Days On Market

    Current Estimated Value $820,561

    Last Listing Agent Shane Masaschi Compass

    66 Snow Ln, Chatham, MA 02633
    • /36

      Est $3,508,073

      Not Listed For Sale

      525 Shore Rd, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 3,436 Sq Ft
      • Built 1996
      525 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Peggy Rowland Sotheby's International Realty

  • /38

    $789,000

    $106K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    49 Duck Marsh Ln, Chatham, MA 02633

    Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

    Tim Bailey John C. Ricotta & Associates, Inc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • /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 $848,544

    Last Listing Agent Erin Terkelsen LPT Realty, LLC

    65 Lantern Ln, South Chatham, MA 02659
    • /42

      Est $8,466,870

      Not Listed For Sale

      552 Shore Rd, Chatham, MA 02633

      • 7 Beds
      • 6.5 Baths
      • 5,868 Sq Ft
      • Built 1930
      552 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 327 Days On Market

      Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  • /42

    $12,950,000

    Pending
    • 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
  • /47

    $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

    Current Estimated Value $3,411,210

    Last Listing Agent Jill Boudreau eXp Realty, LLC

    174 Seapine Rd, North Chatham, MA 02650
    • /37

      Est $2,799,358

      Not Listed For Sale

      47 Gladen Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 3,203 Sq Ft
      • Built 1987
      47 Gladen Ln, Chatham, MA 02633

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent John Hopkins Frank A Sullivan Real Estate

  • /40

    $4,950,000

    • 4 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    15 Bay Ln, Chatham, MA 02633

    Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native

    Chris Rhinesmith Compass

    15 Bay Ln, Chatham, MA 02633
  • /34

    $1,330,000

    Sold Feb 06, 2026

    56 Skyline Dr, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 2,392 Sq Ft
    • Built 1979

    Last Sold Summary

    • 17% Below List Price
    • $556/SF
    • 120 Days On Market

    Current Estimated Value $1,323,390

    Last Listing Agent Janet Stuart Coldwell Banker Realty

    56 Skyline Dr, Chatham, MA 02633
    • /42

      Est $3,829,830

      Not Listed For Sale

      38 Sandy Shoes Ln, Chatham, MA 02633

      • 7 Beds
      • 5 Baths
      • 3,203 Sq Ft
      • Built 1930
      38 Sandy Shoes Ln, Chatham, MA 02633

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Team Real Market Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /31

    $1,295,000

    Pending
    • 5 Beds
    • 2 Baths
    • 2,046 Sq Ft

    700 Crowell Rd, North Chatham, MA 02650

    Crisp 5BR, 2 full bath Cape Cod home set on level .49 acre lot with covered side porch and private rear yard awaits in sought after North Chatham location. Updated over the years and beautifully maintained, this home offers generous interior living spaces. Enjoy gathering with friends and family in the living room with vaulted beamed ceilings with skylights, adjacent dining area with room for

    Lori Fanning Smith Compass Massachusetts, LLC

    700 Crowell Rd, North Chatham, MA 02650
  • /51

    $1,550,000

    Sold Dec 02, 2025

    97 Round Cove Rd, Chatham, MA 02633

    • 3 Beds
    • 4 Baths
    • 2,388 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Below List Price
    • $649/SF
    • 34 Days On Market

    Current Estimated Value $1,548,790

    Last Listing Agent Day - Logan Group Kinlin Grover Compass

    97 Round Cove Rd, Chatham, MA 02633
    • /5

      Est $2,407,079

      Not Listed For Sale

      48 Bay Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 1,953 Sq Ft
      • Built 1953
      48 Bay Ln, Chatham, MA 02633

      Last Sold Summary

      • 54 Days On Market

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

  • /39

    $8,950,000

    $3M PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,738 Sq Ft

    166 Shore Rd, Chatham, MA 02633

    The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    166 Shore Rd, Chatham, MA 02633
  • /45

    $6,995,000

    Sold Nov 21, 2025

    13 Captain Knowles Way, Chatham, MA 02633

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft
    • Built 2025

    Last Sold Summary

    • $1,227/SF
    • 147 Days On Market

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

    13 Captain Knowles Way, 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

      • 39 Days On Market

      Last Listing Agent Phyllis Power Compass

  • /42

    $3,595,000

    Pending
    • 3 Beds
    • 4 Baths
    • 2,856 Sq Ft

    48 Hunter Rise, Chatham, MA 2633

    Stunning custom home built by Eastward Companies in 2020, ideally situated in Chatham's sought-after Hunter Rise neighborhood just moments from Harding's Beach. Thoughtfully designed with exceptional craftsmanship and timeless finishes, this home features an open-concept floor plan filled with natural light, white oak floors, and custom details throughout. The living room showcases a shiplap

    Chris Rhinesmith Compass

    48 Hunter Rise, Chatham, MA 2633
  • /50

    $2,325,000

    Sold Oct 30, 2025

    94 Ocean Port Ln, Chatham, MA 02633

    • 3 Beds
    • 4 Baths
    • 3,226 Sq Ft
    • Built 2014

    Last Sold Summary

    • 2% Below List Price
    • $721/SF
    • 13 Days On Market

    Current Estimated Value $2,532,350

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

    94 Ocean Port Ln, Chatham, MA 02633
    • /23

      Not Listed For Sale

      30 Mill Hill Ln, Chatham, MA 02633

      • 7 Beds
      • 3 Baths
      • 2,460 Sq Ft
      • Built 1840
      30 Mill Hill Ln, Chatham, MA 02633

      Last Sold Summary

      • 238 Days On Market

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /60

    $1,495,000

    Pending
    • 3 Beds
    • 3 Baths
    • 1,771 Sq Ft

    124 Pleasant St, South Chatham, MA 02659

    This is the South Chatham beach house everyone is looking for! Fully renovated and turnkey, 124 Pleasant Street is ready for immediate enjoyment -- as a private retreat of your own, or as a proven, guest-favorite rental. A short walk to Pleasant Street Beach, this South Chatham location grows only more desirable year over year. The living room, anchored by a fireplace, flows into the dining room

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    124 Pleasant St, South Chatham, MA 02659
  • /27

    $349,999

    Sold Feb 02, 2026

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $503/SF
    • 76 Days On Market

    Current Estimated Value $363,674

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    • /4

      Est $3,131,653

      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

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /22

    $1,795,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft

    71 Rowland Dr, North Chatham, MA 02650

    Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    71 Rowland Dr, North Chatham, MA 02650
  • /29

    $3,400,000

    Sold Dec 30, 2025

    450 Main St, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 7,396 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $460/SF
    • 55 Days On Market

    Current Estimated Value $3,551,666

    Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, 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

      Last Listing Agent John Burke William Raveis Chatham

  • /6

    $5,750,000

    Pending
    • 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
  • /68

    $2,200,000

    Sold Apr 23, 2026

    9 Wadsworth Rd, South Chatham, MA 02659

    • 4 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Built 2001

    Last Sold Summary

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

    Current Estimated Value $2,104,331

    Last Listing Agent LUXRECapeCod Gibson Sotheby's International Realty

    9 Wadsworth Rd, South Chatham, MA 02659
    • /2

      Est $550,622

      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

  • /27

    $468,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 576 Sq Ft

    19 Captain Richards Way, Chatham, MA 02633

    Beautifully remodeled in 2023, this charming 2 bedroom, 1.5 bath Seasonal Cottage is just 0.8 miles from Hardings Beach . Thoughtfully updated and move-in ready, it features a private deck, spacious patio and outdoor shower; perfect for enjoying the Cape lifestyle. Ideally located just minutes from Chatham's acclaimed restaurants, boutiques, and beaches, this turnkey property baosts strong rental

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    19 Captain Richards Way, Chatham, MA 02633
  • /42

    $6,230,000

    Sold Jul 17, 2026

    44 Buena Vista Rd, Chatham, MA 02633

    • 7 Beds
    • 6.5 Baths
    • 6,521 Sq Ft
    • Built 1925

    Last Sold Summary

    • 27% Below List Price
    • $955/SF
    • 240 Days On Market

    Last Listing Agent Shane Masaschi Compass

    44 Buena Vista Rd, Chatham, MA 02633
    • /38

      Est $2,328,648

      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

      • 357 Days On Market

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /2

    $5,900,000

    • 6 Beds
    • 8 Baths
    • 6,183 Sq Ft

    50 Sylvan Way, South Chatham, MA 02659

    The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    50 Sylvan Way, South Chatham, MA 02659
  • /49

    $2,830,000

    Sold Jan 30, 2026

    86 Champlain Rd, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 4,361 Sq Ft
    • Built 1998

    Last Sold Summary

    • 28% Below List Price
    • $649/SF
    • 188 Days On Market

    Current Estimated Value $3,544,905

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

    86 Champlain Rd, Chatham, MA 02633

Showing Results 81 - 120, Page 3 of 18

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