9,682

Chatham, MA Homes

Section Image
  • 144 Countryside Dr, Chatham, MA 02633
    144 Countryside Dr, Chatham, MA 02633
    144 Countryside Dr, Chatham, MA 02633
    /58

    $1,309,000 Sold Jun 20, 2025

    144 Countryside Dr, Chatham, MA 02633

    • 2 Beds
    • 2.5 Baths
    • 2,590 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Above List Price
    • $505/SF
    • 1 Day On Market

    Current Estimated Value $1,308,906

    Last Listing Agent Maureen Green Kinlin Grover Compass

    144 Countryside Dr, Chatham, MA 02633
    • 32 Aire Ln, Chatham, MA 02633
      32 Aire Ln, Chatham, MA 02633
      32 Aire Ln, Chatham, MA 02633
      /28

      Est $1,115,831 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft

      32 Aire Ln, Chatham, MA 02633

      32 Aire Ln, Chatham, MA 02633
  • 58 Oyster Bluff, Chatham, MA 02633
    58 Oyster Bluff, Chatham, MA 02633
    58 Oyster Bluff, Chatham, MA 02633
    /86

    $5,750,000 Pending

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

    58 Oyster Bluff, Chatham, MA 02633

    Perched high above Oyster Pond, this generational estate--first known as ''The Beach Plum House'' and later as ''Adsamore''--is one of Chatham's rarest offerings. Set on a remarkable .93-acre parcel with expansive frontage, it offers sweeping views of town and Oyster Pond, a lifestyle at once connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, the home has been

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    58 Oyster Bluff, Chatham, MA 02633
  • 1996 Main St, Chatham, MA 02633
    1996 Main St, Chatham, MA 02633
    1996 Main St, Chatham, MA 02633
    /55

    $650,000 Sold Jul 31, 2025

    1996 Main St, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,813 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Below List Price
    • $359/SF
    • 93 Days On Market

    Current Estimated Value $694,143

    Last Listing Agent Shane Masaschi Compass

    1996 Main St, Chatham, MA 02633
    • 276 Orleans Rd, Chatham, MA 02633
      276 Orleans Rd, Chatham, MA 02633
      276 Orleans Rd, Chatham, MA 02633
      /13

      Est $703,152 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 955 Sq Ft

      276 Orleans Rd, Chatham, MA 02633

      276 Orleans Rd, Chatham, MA 02633
  • 12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    /60

    $7,299,000

    • 4 Beds
    • 5 Baths
    • 4,214 Sq Ft

    12 Pond St, Chatham, MA 02633

    Custom Home in Chatham Village. 4-bedroom, 5-bathroom residence located steps from Oyster Pond and its sandy beach. This thoughtful home offers open floor plan, high ceilings, hardwood floors and expansive water views. Deeded access to an association dock and mooring field for boating enthusiasts. The gourmet kitchen features stone countertops, large center island with seating, and premium

    Tim Bailey John C Ricotta & Assoc.

    12 Pond St, Chatham, MA 02633
  • 56 Monomoit Ln, Chatham, MA 02633
    56 Monomoit Ln, Chatham, MA 02633
    56 Monomoit Ln, Chatham, MA 02633
    /44

    $1,227,000 Sold Jul 25, 2025

    56 Monomoit Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,639 Sq Ft
    • Built 1998

    Last Sold Summary

    • 12% Below List Price
    • $749/SF
    • 28 Days On Market

    Current Estimated Value $1,231,352

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    56 Monomoit Ln, Chatham, MA 02633
    • 214 Barcliff Ave, Chatham, MA 02633
      214 Barcliff Ave, Chatham, MA 02633
      214 Barcliff Ave, Chatham, MA 02633
      /30

      Est $1,140,728 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,320 Sq Ft

      214 Barcliff Ave, Chatham, MA 02633

      214 Barcliff Ave, Chatham, MA 02633
  • 409 Main St, Chatham, MA 02633
    409 Main St, Chatham, MA 02633
    409 Main St, Chatham, MA 02633
    /42

    $1,995,000 Pending

    • 1 Bed
    • 1.5 Baths
    • 1,479 Sq Ft

    409 Main St, Chatham, MA 02633

    Location-Location-409 Main St. in Downtown Chatham offers you this very rare and desirable combination of a mixed use building with a 1st floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the 2nd floor in the heart of Chatham Village. The property offers 5 private in-town parking spaces

    Rick Smith Gibson Sotheby's International Realty

    409 Main St, Chatham, MA 02633
  • 23 Oyster Pond Ln, Chatham, MA 02633
    23 Oyster Pond Ln, Chatham, MA 02633
    23 Oyster Pond Ln, Chatham, MA 02633
    /42

    $11,500,000 Sold Jul 29, 2025

    23 Oyster Pond Ln, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 5,308 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $2,167/SF
    • 9 Days On Market

    Current Estimated Value $6,977,267

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    23 Oyster Pond Ln, Chatham, MA 02633
    • 161 Shane Dr, Chatham, MA 02633
      161 Shane Dr, Chatham, MA 02633
      161 Shane Dr, Chatham, MA 02633
      /25

      Est $806,597 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 966 Sq Ft

      161 Shane Dr, Chatham, MA 02633

      161 Shane Dr, Chatham, MA 02633
  • 2 Seapine Rd, North Chatham, MA 02650
    2 Seapine Rd, North Chatham, MA 02650
    2 Seapine Rd, North Chatham, MA 02650
    /38

    $2,499,000

    • 3 Beds
    • 4 Baths
    • 3,090 Sq Ft

    2 Seapine Rd, North Chatham, MA 02650

    Offered fully furnished, this light-filled contemporary Cape in North Chatham blends coastal elegance with casual sophistication. The main level features a welcoming den, an inviting living room with a fireplace, and a stylish kitchen and dining area that open to a sunny deck, ideal for seamless indoor-outdoor living. The serene first floor primary suite offers comfort and privacy. Upstairs, two

    Jack Bohman Gibson Sotheby's International Realty

    2 Seapine Rd, North Chatham, MA 02650
  • 718 Riverview Dr, Chatham, MA 02633
    718 Riverview Dr, Chatham, MA 02633
    718 Riverview Dr, Chatham, MA 02633
    /47

    $1,065,000 Sold May 09, 2025

    718 Riverview Dr, Chatham, MA 02633

    • 2 Beds
    • 2.5 Baths
    • 2,292 Sq Ft
    • Built 1971

    Last Sold Summary

    • 3% Below List Price
    • $465/SF
    • 16 Days On Market

    Current Estimated Value $1,074,162

    Last Listing Agent Tim Bailey John C Ricotta & Assoc.

    718 Riverview Dr, Chatham, MA 02633
    • 55 Eldredge Square S, Chatham, MA 02633
      55 Eldredge Square S, Chatham, MA 02633
      55 Eldredge Square S, Chatham, MA 02633
      /38

      Est $2,046,891 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,630 Sq Ft

      55 Eldredge Square S, Chatham, MA 02633

      55 Eldredge Square S, Chatham, MA 02633
  • 24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    /41

    $995,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft

    24 Chickadee Cir, Harwich, MA 02645

    Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

    Amy Harbeck Kinlin Grover Compass

    24 Chickadee Cir, Harwich, MA 02645
  • 30 Mill Hill Ln, Chatham, MA 02633
    30 Mill Hill Ln, Chatham, MA 02633
    30 Mill Hill Ln, Chatham, MA 02633
    /23

    $2,700,000 Sold Jul 24, 2025

    30 Mill Hill Ln, Chatham, MA 02633

    • 7 Beds
    • 3 Baths
    • 2,460 Sq Ft
    • Built 1840

    Last Sold Summary

    • 17% Below List Price
    • $1,098/SF
    • 238 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    30 Mill Hill Ln, Chatham, MA 02633
    • 233 Barcliff Ave, Chatham, MA 02633
      233 Barcliff Ave, Chatham, MA 02633
      233 Barcliff Ave, Chatham, MA 02633
      /28

      Est $1,268,831 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,196 Sq Ft

      233 Barcliff Ave, Chatham, MA 02633

      233 Barcliff Ave, Chatham, MA 02633
  • 72 Forest Beach Rd, South Chatham, MA 2659
    72 Forest Beach Rd, South Chatham, MA 2659
    72 Forest Beach Rd, South Chatham, MA 2659
    /41

    $1,499,000 Pending

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

    72 Forest Beach Rd, South Chatham, MA 2659

    South of 28! Renovated Beach Compound with 5 Income-Producing Suites. Just 4/10 of a mile from Nantucket Sound, this iconic South Chatham property blends classic Cape style with modern luxury. Formerly the historic Forest Beach Motel, now meticulously restored and transformed into a stylish coastal compound. Property is offered fully furnished and move-in ready. This unique 6-bedroom, 5-bath

    Michael Magner Berkshire Hathaway HomeServices Robert Paul Properties

    72 Forest Beach Rd, South Chatham, MA 2659
  • 53 Gristmill Ln, Chatham, MA 02633
    53 Gristmill Ln, Chatham, MA 02633
    53 Gristmill Ln, 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

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    53 Gristmill Ln, Chatham, MA 02633
    • 25 Glover Square, Chatham, MA 02633
      25 Glover Square, Chatham, MA 02633
      25 Glover Square, Chatham, MA 02633
      /65

      Est $3,110,128 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 4,105 Sq Ft

      25 Glover Square, Chatham, MA 02633

      25 Glover Square, Chatham, MA 02633
  • 213 Main St, Chatham, MA 02633
    213 Main St, Chatham, MA 02633
    213 Main St, Chatham, MA 02633
    /35

    $2,150,000

    • 4 Beds
    • 2 Baths
    • 1,238 Sq Ft

    213 Main St, Chatham, MA 02633

    Location! Location! Nestled In the heart of Chatham historic Old Village district, this 1850 Greek Revival has water views of Chatham harbor, with Lighthouse Beach, Main St shopping & dining, band concerts, golf, all nearby! This charming 4 BED/2 BA home has a sunny eat-in family room, beamed ceiling, with sliders to deck, cozy kitchen adjacent and front living room has gas fireplace & warm

    Phyllis Power Compass

    213 Main St, Chatham, MA 02633
  • 24 Shattuck Place, Chatham, MA 02633
    24 Shattuck Place, Chatham, MA 02633
    24 Shattuck Place, 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

    Last Listing Agent Charles King Real Broker MA, LLC

    24 Shattuck Place, Chatham, MA 02633
    • 265 Barcliff Ave, Chatham, MA 02633
      265 Barcliff Ave, Chatham, MA 02633
      265 Barcliff Ave, Chatham, MA 02633
      /46

      Est $1,411,747 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,491 Sq Ft

      265 Barcliff Ave, Chatham, MA 02633

      265 Barcliff Ave, 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
    /54

    $4,895,000 Pending

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

    785 Old Harbor Rd, North Chatham, MA 02650

    Welcome to '' Two Stars'' this meticulously crafted residence in coveted North Chatham. This beautiful sanctuary offers a harmonious blend of luxury & comfort. Nestled on a lush acre with water views of Chatham harbor, this custom built masterpiece by master/builder owner invites you to experience refined living with every detail. Spanning 4200 sq. ft of sophisticated space, this home boasts 9

    Phyllis Power Compass

    785 Old Harbor Rd, North Chatham, MA 02650
  • 33 Cross St Unit 4, Chatham, MA 02633
    33 Cross St Unit 4, Chatham, MA 02633
    33 Cross St Unit 4, Chatham, MA 02633
    /10

    $192,000 Sold Feb 13, 2025

    33 Cross St Unit 4, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Built 1991

    Last Sold Summary

    • 12% Below List Price
    • $427/SF
    • 37 Days On Market

    Last Listing Agent Brennan Finnegan William Raveis Real Estate & Home Services

    33 Cross St Unit 4, Chatham, MA 02633
    • 751 Main St, Chatham, MA 02633
      751 Main St, Chatham, MA 02633
      751 Main St, Chatham, MA 02633
      /30

      Est $1,246,767 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,552 Sq Ft

      751 Main St, Chatham, MA 02633

      751 Main St, Chatham, MA 02633
  • 127 Wapoos Trail, Chatham, MA 02633
    127 Wapoos Trail, Chatham, MA 02633
    127 Wapoos Trail, Chatham, MA 02633
    /35

    $8,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,307 Sq Ft

    127 Wapoos Trail, Chatham, MA 02633

    Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water view residence is a rare treasure offering architectural distinction and an intimate connection to Cape Cod's unspoiled coastal beauty. With panoramic views spanning Stage Harbor to the Atlantic shoreline, the home was thoughtfully designed to embrace its extraordinary setting—inviting nature's ever-changing

    Dee Sullivan Christie's International Real Estate Atlantic Brokerage

    127 Wapoos Trail, Chatham, MA 02633
  • 37 Bellamy Ln, North Chatham, MA 02650
    37 Bellamy Ln, North Chatham, MA 02650
    37 Bellamy Ln, North Chatham, MA 02650
    /31

    $1,600,000 Sold Mar 14, 2025

    37 Bellamy Ln, North Chatham, MA 02650

    • 5 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $2,396,320

    Last Listing Agent David Doherty Compass

    37 Bellamy Ln, North Chatham, MA 02650
    • 178 Queen Anne Rd, Chatham, MA 02633
      178 Queen Anne Rd, Chatham, MA 02633
      178 Queen Anne Rd, Chatham, MA 02633
      /30

      Not Listed For Sale

      • 6 Beds
      • 8 Baths
      • 7,700 Sq Ft

      178 Queen Anne Rd, Chatham, MA 02633

      178 Queen Anne Rd, Chatham, MA 02633
  • 292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    /29

    $1,970,000

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

    292 Stage Harbor Rd, Chatham, MA 02633

    Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower

    Ward Brown William Raveis Real Estate & Home Services

    292 Stage Harbor Rd, Chatham, MA 02633
  • 15 Wood Valley Rd, Chatham, MA 02633
    15 Wood Valley Rd, Chatham, MA 02633
    15 Wood Valley Rd, Chatham, MA 02633
    /44

    $1,150,000 Sold Apr 18, 2025

    15 Wood Valley Rd, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 2,881 Sq Ft
    • Built 1969

    Last Sold Summary

    • $399/SF
    • 2 Days On Market

    Current Estimated Value $1,316,285

    Last Listing Agent Jack Bohman Gibson Sotheby's International Realty

    15 Wood Valley Rd, Chatham, MA 02633
    • 125 Stage Harbor Rd, Chatham, MA 02633
      125 Stage Harbor Rd, Chatham, MA 02633
      125 Stage Harbor Rd, Chatham, MA 02633
      /24

      Est $4,079,375 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,421 Sq Ft

      125 Stage Harbor Rd, Chatham, MA 02633

      125 Stage Harbor Rd, Chatham, MA 02633
  • 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

    $495,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula ''It's All About Me,'' Unit D at 425 Main Street offers an exceptional blend of privacy, comfort, and in-town convenience. This updated 1-bedroom, 1-bath residence is one of only two homes on the second floor, accessed by a discreet private entrance that enhances its quiet, retreat-like feel. Inside, an open-concept layout is filled with natural light and features recent

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 16 Seapine Rd, North Chatham, MA 02650
    16 Seapine Rd, North Chatham, MA 02650
    16 Seapine Rd, North Chatham, MA 02650
    /48

    $6,950,000 Sold Jul 24, 2025

    16 Seapine Rd, North Chatham, MA 02650

    • 5 Beds
    • 6.5 Baths
    • 6,508 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,068/SF
    • 307 Days On Market

    Current Estimated Value $5,301,281

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    16 Seapine Rd, North Chatham, MA 02650
    • 276 Stage Harbor Rd, Chatham, MA 02633
      276 Stage Harbor Rd, Chatham, MA 02633
      276 Stage Harbor Rd, Chatham, MA 02633
      /62

      Est $2,727,871 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,732 Sq Ft

      276 Stage Harbor Rd, Chatham, MA 02633

      276 Stage Harbor Rd, Chatham, MA 02633
  • 2548 Main St, South Chatham, MA 2659
    2548 Main St, South Chatham, MA 2659
    /2

    $3,999,900 New Construction

    • 4 Beds
    • 5.5 Baths
    • 3,713 Sq Ft

    2548 Main St, South Chatham, MA 2659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers. Incorporating expansive open living space you will enjoy entertaining family

    Ward Brown William Raveis Real Estate & Home Services

    2548 Main St, South Chatham, MA 2659
  • 67 A Leonard Way, Chatham, MA 02633
    67 A Leonard Way, Chatham, MA 02633
    67 A Leonard Way, Chatham, MA 02633
    /50

    $955,000 Sold Oct 14, 2025

    67 A Leonard Way, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $713/SF
    • 17 Days On Market

    Last Listing Agent Shane Masaschi Compass

    67 A Leonard Way, Chatham, MA 02633
    • 155 Inlet Rd, Chatham, MA 02633
      155 Inlet Rd, Chatham, MA 02633
      155 Inlet Rd, Chatham, MA 02633
      /78

      Est $3,800,629 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 4,048 Sq Ft

      155 Inlet Rd, Chatham, MA 02633

      155 Inlet Rd, Chatham, MA 02633
  • 92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    /53

    $3,500,000

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

    92 Barcliff Ave, Chatham, MA 02633

    Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical residence was meticulously restored to perfection in 2002, seamlessly blending its storied heritage with the finest modern luxuries. Nestled in a prime yet private locale, the home's enchanting exterior teases with a glimpse of the lush, secluded garden, a serene oasis framed by a stately pergola. The

    Chris Rhinesmith Compass Massachusetts, LLC

    92 Barcliff Ave, Chatham, MA 02633
  • 85 Main St, Chatham, MA 02633
    85 Main St, Chatham, MA 02633
    85 Main St, 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

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633

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Massachusetts Barnstable County Chatham

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