9,489

Chatham, MA Homes

Section Image
  • /40

    $2,795,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 3,514 Sq Ft

    44 Baileys Path, Chatham, MA 2633

    Built by Eastward Companies in 2013, this thoughtfully designed, turnkey home is located in one of Chatham's highly desirable neighborhoods. Offering over 3,500 sq. ft. of beautifully appointed living space, this Cape features 3 bedrooms and 3.5 baths with an open-concept floor plan that seamlessly blends timeless Cape Cod style with modern conveniences. Filled with natural light, the spacious

    Chris Rhinesmith Compass Massachusetts, LLC

    44 Baileys Path, Chatham, MA 2633
  • /54

    $2,520,000

    Sold Jul 02, 2026

    320 Old Harbor Rd, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,212 Sq Ft
    • Built 1976

    Last Sold Summary

    • 7% Above List Price
    • $1,139/SF
    • 5 Days On Market

    Current Estimated Value $2,422,381

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

    320 Old Harbor Rd, Chatham, MA 02633
    • /48

      Est $1,138,296

      Not Listed For Sale

      31 Great Hill Rd, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,977 Sq Ft
      • Built 1965
      31 Great Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 236 Days On Market

      Last Listing Agent Judith Smith John C Ricotta & Assoc.

  • /21

    $675,000

    • 2 Beds
    • 2 Baths
    • 996 Sq Ft

    210 Orleans Rd Unit C, North Chatham, MA 02650

    Wonderful two-bedroom, two bath end unit condominium close to Chatham village and beaches.. Recently renovated and three split units for heat and air conditioning also added. Plenty of parking and storage and all the work is done for you. Insurance, landscaping, trash pickup, exterior maintenance, professional management, snow removal, are all covered in the reasonable monthly association fee.

    John Burke William Raveis Chatham

    210 Orleans Rd Unit C, North Chatham, MA 02650
  • /29

    $1,695,000

    Sold Jun 02, 2026

    68 Levis Path, South Chatham, MA 2659

    • 2 Beds
    • 3.5 Baths
    • 2,016 Sq Ft
    • Built 2015

    Last Sold Summary

    • $841/SF
    • 16 Days On Market

    Current Estimated Value $1,631,047

    Last Listing Agent Betsy Hargreaves Gibson Sotheby's International Realty

    68 Levis Path, South Chatham, MA 2659
    • /30

      Est $667,926

      Not Listed For Sale

      79 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1968
      79 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Kathleen Phelan Compass Massachusetts, LLC

  • /46

    $1,275,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,070 Sq Ft

    240 Riverview Dr, Chatham, MA 02633

    Sought after neighborhood of Riverbay. Light and bright home with incredible gardens and fabulous outdoor space. Three bedrooms 2 newly redone baths with livingroom, dinng room and primary suite all with sliders onto the deck with spiral stairway to back yard for super summer fun. Room for a pool! Lower level could be finished off-high ceilings and windows overlooking the back yard. Deeded rights

    Judith Smith John C Ricotta & Assoc.

    240 Riverview Dr, Chatham, MA 02633
  • /34

    $895,000

    Sold Aug 31, 2026

    58 Tirrells Way, South Chatham, MA 02659

    • 2 Beds
    • 2 Baths
    • 1,716 Sq Ft
    • Built 2001

    Last Sold Summary

    • $522/SF
    • 23 Days On Market

    Current Estimated Value $895,552

    Last Listing Agent Phyllis Power Compass

    58 Tirrells Way, South Chatham, MA 02659
    • /24

      Est $1,051,755

      Not Listed For Sale

      59 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1966
      59 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /5

    $999,000

    • Land
    • 6,969 Sq Ft
    • $6,243,750 per Acre

    727 Main St, Chatham, MA 02633

    Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

    Noreen Kennedy Kennedy Real Estate

    727 Main St, Chatham, MA 02633
  • /32

    $1,300,000

    Sold Dec 23, 2025

    72 Forest Beach Rd, South Chatham, MA 2659

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft
    • Built 1953

    Last Sold Summary

    • 13% Below List Price
    • $541/SF
    • 16 Days On Market

    Current Estimated Value $1,332,847

    Last Listing Agent Michael Magner The Mega Group

    72 Forest Beach Rd, South Chatham, MA 2659
    • /28

      Est $648,353

      Not Listed For Sale

      46 Nob Hill Rd, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1965
      46 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 8 Days On Market

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

  • /37

    $725,000

    $70K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 1,687 Sq Ft

    19 Joshuas Way, Chatham, MA 02633

    Motivated Seller price reduced $70,000...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

    Phyllis Power Compass

    19 Joshuas Way, Chatham, MA 02633
  • /42

    $1,400,000

    Sold Apr 29, 2026

    1239 Main St Unit 18, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,029/SF
    • 2 Days On Market

    Current Estimated Value $1,257,260

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    1239 Main St Unit 18, Chatham, MA 02633
    • /33

      Est $593,647

      Not Listed For Sale

      912 Main St Unit 303, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,649 Sq Ft
      • Built 1999
      912 Main St Unit 303, Chatham, MA 02633

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Jane Burleson Concierge Real Estate, LLC

  • /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
  • /4

    $621,850

    Sold Jun 25, 2026

    99 Depot Rd Unit 23, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,045 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $595/SF
    • 1 Day On Market

    Current Estimated Value $616,133

    Last Listing Agent Judith Smith John C Ricotta & Assoc.

    99 Depot Rd Unit 23, Chatham, MA 02633
    • /2

      Est $391,150

      Not Listed For Sale

      912 Main St Unit 213, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,011 Sq Ft
      • Built 1999
      912 Main St Unit 213, Chatham, MA 02633

  • /46

    $975,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    1455 Old Queen Anne Rd, Chatham, MA 02633

    This special home circa 1865 was completely restored down to the studs with a long list of improvements inside and out. Everything has been done here so you can move in and enjoy the wonderful Fall months ahead! A stunning new kitchen is the heart of the home, and features a Bertazonni professional range and hood, white custom cabinets, quartz countertops and center island. Relax in the adjacent

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    1455 Old Queen Anne Rd, Chatham, MA 02633
  • /15

    $510,000

    Sold Jan 22, 2026

    22 Pine Knoll Ave, Chatham, MA 02633

    • 3 Beds
    • 0.5 Baths
    • 532 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $959/SF
    • 13 Days On Market

    Current Estimated Value $526,161

    Last Listing Agent Evon Loranger Options 153, Mullen & Partners

    22 Pine Knoll Ave, Chatham, MA 02633
    • /2

      Est $417,024

      Not Listed For Sale

      912 Main St Unit 209, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,167 Sq Ft
      • Built 1999
      912 Main St Unit 209, Chatham, MA 02633

  • /51

    $2,499,000

    Open Sat 10AM - 12PM Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,547 Sq Ft

    72 Ridgevale Rd, Chatham, MA 02633

    Perched in one of Chatham's most sought-after coastal neighborhoods, 72 Ridgevale Road South is a rare Cape Cod offering with sweeping views of Bucks Creek, Nantucket Sound, and Ridgevale Beach. Rebuilt in 2002 and beautifully maintained, this move-in ready Chatham home captures sparkling water views from nearly every angle and offers the coastal lifestyle buyers come to Cape Cod to find. A

    Shane Masaschi Compass

    72 Ridgevale Rd, Chatham, MA 02633
  • /33

    $1,335,000

    Sold Jul 15, 2026

    92 Hitching Post Rd, Chatham, MA 02633

    • 4 Beds
    • 1.5 Baths
    • 1,951 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Below List Price
    • $684/SF
    • 5 Days On Market

    Last Listing Agent Betsy & Gerry Ciarcia Home*Land Realty

    92 Hitching Post Rd, Chatham, MA 02633
    • /22

      Est $416,679

      Not Listed For Sale

      912 Main St Unit 207, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1999
      912 Main St Unit 207, Chatham, MA 02633

      Last Sold Summary

      • 71 Days On Market

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

  • /49

    $1,520,000

    Sold Dec 11, 2025

    73 Joshua Jethro Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,307 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $659/SF
    • 79 Days On Market

    Current Estimated Value $1,531,656

    Last Listing Agent Paul Borde Christie's International Real Estate Atlantic Brokerage

    73 Joshua Jethro Rd, Chatham, MA 02633
    • /34

      Est $356,156

      Not Listed For Sale

      912 Main St Unit 204, Chatham, MA 02633

      • 1 Bed
      • 2 Baths
      • 975 Sq Ft
      • Built 1999
      912 Main St Unit 204, Chatham, MA 02633

      Last Sold Summary

      • 142 Days On Market

      Last Listing Agent Margaret Fallon LPT Realty

  • /51

    $1,250,000

    Sold Jul 31, 2026

    58 Stepping Stones Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,062 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Below List Price
    • $606/SF
    • 12 Days On Market

    Current Estimated Value $1,184,645

    Last Listing Agent Sherrilynn Lombard New Homes Marketing, Inc.

    58 Stepping Stones Rd, Chatham, MA 02633
    • /2

      Est $617,176

      Not Listed For Sale

      912 Main St Unit 101, Chatham, MA 02633

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

  • /84

    $5,805,000

    Sold Dec 18, 2025

    58 Oyster Bluff, Chatham, MA 02633

    • 7 Beds
    • 3.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • 1% Above List Price
    • $1,555/SF
    • 25 Days On Market

    Current Estimated Value $5,772,623

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

    58 Oyster Bluff, Chatham, MA 02633
    • /40

      Est $1,428,738

      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

      • 56 Days On Market

      Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

  • /33

    $1,315,000

    Sold Oct 21, 2025

    552 Orleans Rd, Chatham, MA 2633

    • 3 Beds
    • 2.5 Baths
    • 1,144 Sq Ft
    • Built 1978

    Last Sold Summary

    • 18% Below List Price
    • $1,149/SF
    • 177 Days On Market

    Current Estimated Value $1,419,890

    Last Listing Agent Chris Rhinesmith Compass

    552 Orleans Rd, Chatham, MA 2633
    • /2

      Est $7,165,498

      Not Listed For Sale

      23 Oyster Pond Ln, Chatham, MA 02633

      • 5 Beds
      • 6 Baths
      • 5,308 Sq Ft
      • Built 1963
      23 Oyster Pond Ln, Chatham, MA 02633

  • /42

    $2,650,000

    Sold Mar 17, 2026

    101 Oyster Pond Furlong St, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 2,057 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $1,288/SF
    • 4 Days On Market

    Current Estimated Value $2,566,260

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    101 Oyster Pond Furlong St, Chatham, MA 02633
    • /22

      Est $1,840,284

      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

      • 13 Days On Market

      Last Listing Agent Judith Smith John C Ricotta & Assoc.

  • /34

    $851,000

    Sold Apr 30, 2026

    152 Emery Ln, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft
    • Built 1960

    Last Sold Summary

    • 22% Above List Price
    • $619/SF
    • 3 Days On Market

    Current Estimated Value $817,785

    Last Listing Agent Phyllis Power Compass

    152 Emery Ln, North Chatham, MA 02650
    • /13

      Est $3,618,844

      Not Listed For Sale

      67 Capri Ln, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 1,082 Sq Ft
      • Built 1957
      67 Capri Ln, Chatham, MA 02633

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lori Fanning Smith Compass

  • /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 $2,861,110

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

    92 Absegami Run, Chatham, MA 02633
    • /40

      Est $2,488,535

      Not Listed For Sale

      51 Oyster Bay Ln, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 2,310 Sq Ft
      • Built 1986
      51 Oyster Bay Ln, Chatham, MA 02633

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Coldwell Banker Real Non-Member Coldwell Banker Non-Member

  • /42

    $2,925,000

    Sold Jul 08, 2026

    35 Northgate Rd, North Chatham, MA 02650

    • 5 Beds
    • 6 Baths
    • 4,822 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $607/SF
    • 24 Days On Market

    Current Estimated Value $2,967,791

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

    35 Northgate Rd, North Chatham, MA 02650
    • /2

      Not Listed For Sale

      356 Stage Harbor Rd, Chatham, MA 02633

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

Showing Results 281 - 320, Page 8 of 18

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