9,489

Chatham, MA Homes

Section Image
    • /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

      • 223 Days On Market

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

  • /68

    $2,395,000

    Pending
    • 2 Beds
    • 4 Baths
    • 2,294 Sq Ft

    15 Shattuck Place Unit 15, Chatham, MA 2633

    New listing in one of the most coveted neighborhoods in Chatham Village! This exquisitely renovated property was transformed by Eastward Companies into a light-filled coastal retreat on three levels and received the Chatham Preservation Award in 2015. The first level offers an elegant open floor plan with Chef's kitchen, living room w/gas fireplace, and adjacent dining area. Gorgeous red birch

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    15 Shattuck Place Unit 15, Chatham, MA 2633
  • /32

    $950,000

    Sold Sep 01, 2026

    35 Oak Ridge Cir, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,476 Sq Ft
    • Built 1978

    Last Sold Summary

    • 14% Below List Price
    • $644/SF
    • 22 Days On Market

    Current Estimated Value $1,080,857

    Last Listing Agent Jack Farrell Compass

    35 Oak Ridge Cir, Chatham, MA 02633
    • /2

      Est $2,656,057

      Not Listed For Sale

      16 Windmill Ln, Chatham, MA 02633

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

  • /41

    $5,495,000

    $405K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    99 Uncle Alberts Drive Extension, Chatham, MA 2633

    Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

    Shane Masaschi Compass

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • /4

    $4,400,000

    Sold Sep 26, 2025

    169 Woodland Way, North Chatham, MA 02650

    • 3 Beds
    • 4 Baths
    • 4,994 Sq Ft
    • Built 1960

    Last Sold Summary

    • $881/SF
    • 0 Days On Market

    Current Estimated Value $4,225,982

    Last Listing Agent Kimberly Howard Christie's International Real Estate Atlantic Brokerage

    169 Woodland Way, North Chatham, MA 02650
    • /20

      Est $2,104,965

      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

      Last Listing Agent William Storff Compass

  • /80

    $2,395,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,638 Sq Ft

    10 Kingsbury Way, Chatham, MA 02633

    Location! Location! Location! Perfectly situated across from Oyster Pond Beach and just around the corner from downtown Chatham, this beautifully renovated Cape Cod cottage offers the ideal blend of charm, comfort, and convenience. Classic cedar shingles, a shell driveway, vibrant hydrangeas, and a welcoming front porch create timeless curb appeal. Inside, the open-concept floor plan is filled

    Tom Riley Compass Massachusetts, LLC

    10 Kingsbury Way, Chatham, MA 02633
  • /32

    $775,000

    Sold Jun 05, 2026

    35 Bobbie's Ln, Chatham, MA 02659

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • 11% Above List Price
    • $673/SF
    • 6 Days On Market

    Last Listing Agent Richard Waystack Keller Williams Realty

    35 Bobbie's Ln, Chatham, MA 02659
    • /44

      Est $1,859,364

      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

      Last Listing Agent LUXRECapeCod Gibson Sotheby's International Realty

  • /58

    $1,374,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    88 Indian Hill Rd N, Chatham, MA 02633

    Welcome to 88 Indian Hill Road, where stunning curb appeal and timeless Cape Cod charm welcomes you home. Perfectly situated on a prominent, beautifully landscaped large lot, this sprawling Cape has been meticulously maintained and thoughtfully designed for both everyday living and entertainment. The private, tranquil grounds are a true highlight, featuring flowering ornamental trees, lush

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    88 Indian Hill Rd N, Chatham, MA 02633
  • /39

    $1,050,000

    Sold May 15, 2026

    298 Chippingstone Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft
    • Built 1972

    Last Sold Summary

    • $489/SF
    • 3 Days On Market

    Current Estimated Value $1,048,227

    Last Listing Agent Robert Bantick Keller Williams Realty

    298 Chippingstone Rd, Chatham, MA 02633
    • /37

      Est $2,069,319

      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

      • 1 Day On Market

      Last Listing Agent Phyllis Power Compass

  • /36

    $829,000

    $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    33 Duck Marsh Ln, Chatham, MA 02633

    Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural

    Darci Sequin Gibson Sotheby's International Realty

    33 Duck Marsh Ln, 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 $443,393

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
    • /24

      Est $1,750,922

      Not Listed For Sale

      98 Orleans Rd, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 2,112 Sq Ft
      • Built 1997
      98 Orleans Rd, Chatham, MA 02633

      Last Sold Summary

      • 194 Days On Market

      Last Listing Agent Phyllis Power Compass

  • /20

    $12,999,900

    New Construction
    • 4 Beds
    • 7 Baths
    • 6,234 Sq Ft

    157 Bridge St, Chatham, MA 02633

    In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    157 Bridge St, Chatham, MA 02633
  • /42

    $9,650,000

    Sold Nov 06, 2025

    53 Gristmill Ln, Chatham, MA 02633

    • 5 Beds
    • 8 Baths
    • 4,970 Sq Ft
    • Built 1989

    Last Sold Summary

    • 1% Below List Price
    • $1,942/SF
    • 30 Days On Market

    Current Estimated Value $9,627,416

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    53 Gristmill Ln, Chatham, MA 02633
    • /42

      Est $1,454,234

      Not Listed For Sale

      33 Captains Walk, North Chatham, MA 02650

      • 4 Beds
      • 2.5 Baths
      • 2,279 Sq Ft
      • Built 1970
      33 Captains Walk, North Chatham, MA 02650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

  • /42

    $5,850,000

    $400K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,620 Sq Ft

    15 Windy Hill Way, Chatham, MA 02633

    This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

    Tim Bailey John C. Ricotta & Associates, Inc.

    15 Windy Hill Way, Chatham, MA 02633
  • /41

    $1,785,000

    Sold Nov 24, 2025

    24 Shattuck Place, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 1,514 Sq Ft
    • Built 1920

    Last Sold Summary

    • 1% Below List Price
    • $1,179/SF
    • 7 Days On Market

    Current Estimated Value $1,760,242

    Last Listing Agent Charles King Real Broker MA, LLC

    24 Shattuck Place, Chatham, MA 02633
    • /43

      Est $1,618,514

      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

      • 136 Days On Market

      Last Listing Agent Daren Marvin Sotheby's International Realty

  • /54

    $2,950,000

    $650K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,978 Sq Ft

    60 Harbor Hill Rd, Chatham, MA 02633

    TURNKEY!! Chatham Living — Ready to Enjoy from Day One Privately sited on nearly an acre, this beautifully maintained 4-bedroom Chatham home offers nearly 4,000 square feet of comfortable, gracious living—turnkey and ready to enjoy from the moment you arrive. Spacious and welcoming, the home features a well-appointed kitchen, generous gathering spaces, three fireplaces, central air, a first-floor

    Jacquelyn Casey Shore Road Realty

    60 Harbor Hill Rd, Chatham, MA 02633
  • /27

    $5,000,000

    Sold May 15, 2026

    14 Pond View Ln, Chatham, MA 02633

    • 4 Beds
    • 6 Baths
    • 4,989 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $1,002/SF
    • 59 Days On Market

    Current Estimated Value $4,817,102

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

    14 Pond View Ln, Chatham, MA 02633
    • /42

      Est $2,764,704

      Not Listed For Sale

      25 Menekish Ln, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 3,865 Sq Ft
      • Built 2006
      25 Menekish Ln, Chatham, MA 02633

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  • /61

    $5,900,000

    • 4 Beds
    • 5.5 Baths
    • 5,254 Sq Ft

    48 Hillcrest Rd, North Chatham, MA 02650

    An Ed Acton/Harbor Builders home built in 2019, located in the highly desired section of North Chatham. Offering 4 bedrooms, 6 baths, this home has expansive views of Chatham's inner harbor and beyond. Over 5,000 sq ft of refined entertainment space meeting town requirements for a pool, necessary piping already installed, on a level plot of land. This property has beautiful mature flowering

    Bill Storff Compass Massachusetts, LLC

    48 Hillcrest Rd, North Chatham, MA 02650
  • /46

    $1,385,000

    Sold Dec 16, 2025

    114 Bucks Creek Rd, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 2,289 Sq Ft
    • Built 1965

    Last Sold Summary

    • 21% Below List Price
    • $605/SF
    • 84 Days On Market

    Current Estimated Value $1,439,720

    Last Listing Agent Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

    114 Bucks Creek Rd, Chatham, MA 02633
    • /30

      Est $1,236,720

      Not Listed For Sale

      6 Palmer Dr, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 1974
      6 Palmer Dr, Chatham, MA 02633

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /29

    $4,250,000

    New Construction $100K PRICE INCREASE
    • 4 Beds
    • 5.5 Baths
    • 3,980 Sq Ft

    222 Barcliff Ave, Chatham, MA 02633

    The location that has it all...walk to both town, fish pier, beach and baseball games....New Farmhouse with pool built by Morgan and Sons is completed. Enjoy Chatham from this 4BR 5.5 bath , 3980 sq foot home. All bedrooms offer spacious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings with large slider with views

    Lori Fanning Smith Compass Massachusetts, LLC

    222 Barcliff Ave, Chatham, MA 02633
  • /46

    $4,000,000

    Sold Oct 03, 2025

    85 Main St, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,998 Sq Ft
    • Built 1820

    Last Sold Summary

    • 27% Below List Price
    • $1,334/SF
    • 150 Days On Market

    Current Estimated Value $4,049,510

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633
    • /5

      Est $2,542,249

      Not Listed For Sale

      172 Barcliff Ave, Chatham, MA 02633

      • 5 Beds
      • 3 Baths
      • 1,724 Sq Ft
      • Built 1900
      172 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Louise Coakley Shanahan Real Estate Group, LLC

  • /35

    $6,800,000

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

    238 Cranberry Ln, North Chatham, MA 02650

    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, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, North Chatham, MA 02650
  • /32

    $650,000

    Sold Jul 17, 2026

    18 Quail Trail, South Chatham, MA 02659

    • 2 Beds
    • 1 Bath
    • 1,094 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Above List Price
    • $594/SF
    • 3 Days On Market

    Current Estimated Value $630,553

    Last Listing Agent David Carter Compass Massachusetts, LLC

    18 Quail Trail, South Chatham, MA 02659
    • /60

      Est $2,841,696

      Not Listed For Sale

      184 Barcliff Ave, Chatham, MA 02633

      • 4 Beds
      • 5 Baths
      • 3,298 Sq Ft
      • Built 2024
      184 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 211 Days On Market

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

  • /32

    $1,585,000

    $65K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,531 Sq Ft

    48 Glover Square, Chatham, MA 02633

    Chatham By The Sea. Rare 50-year offering where LOCATION presents a premier opportunity in Chatham. Coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, Cow Yard Landing, shopping, groceries, tennis, golf, 1/2 mile away. Spacious one-floor living with room to expand! Ranch home is 1531 square feet and includes 3 bedrooms, large formal living room

    Laurie McCann Gibson Sotheby's International Realty

    48 Glover Square, Chatham, MA 02633
  • /66

    $3,200,000

    Sold Apr 30, 2026

    20 Jessies Landing, Chatham, MA 2633

    • 3 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $1,088/SF
    • 28 Days On Market

    Current Estimated Value $3,103,985

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

    20 Jessies Landing, Chatham, MA 2633
    • /53

      Est $2,447,395

      Not Listed For Sale

      390 Old Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 2,670 Sq Ft
      • Built 1988
      390 Old Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent David Doherty Compass

  • /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
  • /35

    $850,000

    Sold May 05, 2026

    46 Chippingstone Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft
    • Built 1973

    Last Sold Summary

    • 13% Below List Price
    • $496/SF
    • 125 Days On Market

    Current Estimated Value $882,030

    Last Listing Agent Derek Greene The Greene Realty Group

    46 Chippingstone Rd, Chatham, MA 02633
    • /74

      Est $5,179,509

      Not Listed For Sale

      581 Shore Rd, Chatham, MA 02633

      • 5 Beds
      • 6.5 Baths
      • 4,452 Sq Ft
      • Built 2018
      581 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

Showing Results 121 - 160, Page 4 of 18

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