9,676

Chatham, MA Homes

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  • /37

    $1,070,000

    Sold Jun 11, 2026

    27 Martha Kendrick Dr, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $518/SF
    • 64 Days On Market

    Current Estimated Value $1,220,623

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    27 Martha Kendrick Dr, Chatham, MA 02633
    • /38

      Est $3,329,356

      Not Listed For Sale

      137 Strong Island Rd, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 4,199 Sq Ft
      • Built 1982
      137 Strong Island Rd, Chatham, MA 02633

      Last Sold Summary

      • 5 Days On Market

  • /63

    $3,595,000

    $800K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,640 Sq Ft

    287 Cedar St, Chatham, MA 02633

    NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

    Shane Masaschi Compass

    287 Cedar St, 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 $3,141,569

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

    20 Jessies Landing, Chatham, MA 2633
    • /84

      Est $5,549,538

      Not Listed For Sale

      146 Strong Island Rd, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 4,142 Sq Ft
      • Built 2023
      146 Strong Island Rd, Chatham, MA 02633

      Last Sold Summary

      • 211 Days On Market

  • /37

    $799,000

    $26K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft

    7 Aunt Matties Rd, Chatham, MA 02633

    Move to Chatham just in time for summer! This 2 bedroom home (with a bonus room for guests or an office) feels like stepping into the best Cape Cod vacation, and it can be sold mostly furnished and equipped if desired. This easy living, one level home is made for your convenience with everything you need, including laundry, on the main floor. The primary suite includes its own full bathroom and

    Tiffany Callahan Greer Real Estate, LLC

    7 Aunt Matties Rd, Chatham, MA 02633
  • /77

    $1,622,500

    Sold Mar 09, 2026

    32 Sunset Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft
    • Built 1950

    Last Sold Summary

    • 19% Below List Price
    • $998/SF
    • 99 Days On Market

    Current Estimated Value $1,711,564

    Last Listing Agent Tom Riley Compass Massachusetts, LLC

    32 Sunset Ln, Chatham, MA 02633
    • /25

      Est $4,351,824

      Not Listed For Sale

      192 Eastward Rd, Chatham, MA 02633

      • 5 Beds
      • 3 Baths
      • 2,514 Sq Ft
      • Built 1957
      192 Eastward Rd, Chatham, MA 02633

      Last Sold Summary

      • 286 Days On Market

  • /70

    $1,495,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,384 Sq Ft

    333 Old Comers Rd, Chatham, MA 02633

    Tucked into one of Chatham's most coveted pockets - moments from Jackknife and Ryder's Cove - this fully renovated four-bedroom, three-bathroom expanded Cape is the rare offering that requires nothing but your arrival. The floorplan delivers effortless single-floor livability, anchored by a first-floor primary suite with skylights, walk-in closet, and en suite bath. Completed in its entirety by

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    333 Old Comers Rd, Chatham, MA 02633
  • /39

    $770,000

    Sold Apr 15, 2026

    37 Glendon Way, South Chatham, MA 02659

    • 2 Beds
    • 1 Bath
    • 817 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Below List Price
    • $942/SF
    • 20 Days On Market

    Current Estimated Value $800,609

    Last Listing Agent Dee Kerner Compass

    37 Glendon Way, South Chatham, MA 02659
    • /50

      Est $1,801,192

      Not Listed For Sale

      54 Rowland Dr, North Chatham, MA 02650

      • 4 Beds
      • 3.5 Baths
      • 2,062 Sq Ft
      • Built 1970
      54 Rowland Dr, North Chatham, MA 02650

      Last Sold Summary

      • 282 Days On Market

  • /50

    $1,495,000

    Open Sat 10AM - 11:30AM
    • 2 Beds
    • 3.5 Baths
    • 1,770 Sq Ft

    739 Main St Unit 1E, Chatham, MA 2633

    Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers ball games, concerts, Oyster Pond, and more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen, adjacent dining area, and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    739 Main St Unit 1E, Chatham, MA 2633
  • /42

    $2,150,000

    Sold Apr 28, 2026

    55 Christopher Harding Ln, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,510 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $857/SF
    • 207 Days On Market

    Current Estimated Value $2,179,468

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    55 Christopher Harding Ln, Chatham, MA 02633
    • /43

      Est $2,841,563

      Not Listed For Sale

      30 Pine Ln, North Chatham, MA 02650

      • 4 Beds
      • 3.5 Baths
      • 4,406 Sq Ft
      • Built 1982
      30 Pine Ln, North Chatham, MA 02650

      Last Sold Summary

      • 109 Days On Market

  • /30

    $2,250,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,220 Sq Ft

    148 Seapine Rd, North Chatham, MA 02650

    Nestled in the sought-after Harbor Coves Association of North Chatham and offering access to a private association beach, this well maintained 3 bedroom, 2 bath home offers the perfect blend of privacy, coastal charm and comfortable one-floor living. Set on over half an acre, this 2,220 sq. ft. residence is surrounded by impressive grounds with mature landscaping, peaceful outdoor spaces, and a

    Chris Rhinesmith Compass Massachusetts, LLC

    148 Seapine Rd, North Chatham, MA 02650
  • /35

    $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 $699,850

    Last Listing Agent Phyllis Power Compass

    1 Seastrand Way Unit 1, Chatham, MA 02633
    • /22

      Est $446,908

      Not Listed For Sale

      409 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 1 Bath
      • 1,013 Sq Ft
      • Built 1987
      409 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 6 Days On Market

  • /58

    $9,995,000

    • 3 Beds
    • 2.5 Baths
    • 3,079 Sq Ft

    153 Shore Rd, Chatham, MA 02633

    Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and

    Sarah Keith eXp Realty, LLC

    153 Shore Rd, Chatham, MA 02633
  • /18

    $575,000

    Sold Sep 25, 2025

    19 Stoughton Ln, Chatham, MA 2633

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1951

    Last Sold Summary

    • 26% Below List Price
    • $424/SF
    • 354 Days On Market

    Current Estimated Value $613,502

    Last Listing Agent Shane Masaschi Compass

    19 Stoughton Ln, Chatham, MA 2633
    • /25

      Est $462,344

      Not Listed For Sale

      409 Orleans Rd Unit A, North Chatham, MA 02650

      • 2 Beds
      • 1.5 Baths
      • 1,038 Sq Ft
      • Built 1987
      409 Orleans Rd Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 61 Days On Market

  • /24

    $4,250,000

    • 3 Beds
    • 3.5 Baths
    • 3,071 Sq Ft

    600 Fox Hill Rd, Chatham, MA 2633

    Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and

    Chris Rhinesmith Compass Massachusetts, LLC

    600 Fox Hill Rd, Chatham, MA 2633
  • /11

    $345,000

    Sold Aug 15, 2025

    281 Orleans Rd Unit 5, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $571/SF
    • 1 Day On Market

    Current Estimated Value $346,771

    Last Listing Agent Isaac Sargent Compass Massachusetts, LLC

    281 Orleans Rd Unit 5, Chatham, MA 02633
    • /18

      Est $501,039

      Not Listed For Sale

      407 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,013 Sq Ft
      • Built 1987
      407 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 70 Days On Market

  • /42

    $5,750,000

    $500K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,060 Sq Ft

    70 Judges Way, Chatham, MA 02633

    Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    70 Judges Way, Chatham, MA 02633
  • /37

    $2,610,000

    Sold Oct 02, 2025

    51 Shattuck Place, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,133 Sq Ft
    • Built 1810

    Last Sold Summary

    • 9% Above List Price
    • $1,224/SF
    • 4 Days On Market

    Current Estimated Value $2,746,069

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

    51 Shattuck Place, Chatham, MA 02633
    • /27

      Est $673,456

      Not Listed For Sale

      108 Misty Meadow Ln Unit B, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,551 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 14 Days On Market

  • /48

    $2,700,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    78 Indian Trail, Chatham, MA 02633

    Discover the charm of coastal living just moments from Hardings Beach. This inviting 3-bedroom, 2-bath home enjoys beautiful water views over Bucks Creek and spectacular west-facing sunsets. Private stairs lead directly to the water's edge, making it easy to launch a kayak, explore the creek, or simply relax by the shore. The light-filled sunroom provides the perfect place to unwind while taking

    Judith Smith John C Ricotta & Assoc.

    78 Indian Trail, Chatham, MA 02633
  • /52

    $7,000,000

    Sold Dec 18, 2025

    30 Tisquantum Rd, Chatham, MA 02633

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft
    • Built 1973

    Last Sold Summary

    • 18% Below List Price
    • $1,626/SF
    • 129 Days On Market

    Current Estimated Value $7,228,993

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum Rd, Chatham, MA 02633
    • /27

      Est $558,885

      Not Listed For Sale

      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,489 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 3 Days On Market

  • /65

    $459,000

    Pending
    • 1 Bed
    • 2 Baths
    • 1,284 Sq Ft

    912 Main St Unit 308, Chatham, MA 02633

    Park Place is the Premiere Chatham address for an easy-care, maintenance-free lifestyle! These apartment-style condos cater to age 62+ residents seeking to enjoy a walkable location in Town, numerous opportunities for social engagement (including daily continental breakfast and Friday night cocktails), an exercise room, library, guest suite, garage parking, elevator and more. Unit 308 is located

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    912 Main St Unit 308, Chatham, MA 02633
  • /53

    $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 $1,583,052

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

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

      Est $448,465

      Not Listed For Sale

      36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

      • 2 Beds
      • 1.5 Baths
      • 930 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

      Last Sold Summary

      • 5 Days On Market

  • /21

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    2653 Main St, South Chatham, MA 02659

    Discover a unique opportunity to own a versatile property in one of Cape Cod's most desirable towns, offering potential as a private residence, multi-family retreat, or investment property. Located less than three-quarters of a mile from the beach, this property has multiple possibilities.The property currently includes a two-bedroom apartment and a separate studio apartment, providing immediate

    Sharon Kingman Dixon William Raveis Real Estate & Home Services

    2653 Main St, South Chatham, MA 02659
  • /53

    $900,000

    Sold Oct 01, 2025

    61 Cod Ln, Chatham, MA 02633

    • 2 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Above List Price
    • $758/SF
    • 6 Days On Market

    Current Estimated Value $950,151

    Last Listing Agent Sarah Keith eXp Realty, LLC

    61 Cod Ln, Chatham, MA 02633
    • /26

      Est $416,106

      Not Listed For Sale

      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      • 1 Bed
      • 1.5 Baths
      • 836 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      Last Sold Summary

      • 60 Days On Market

  • /42

    $3,250,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 3,902 Sq Ft

    87 Squanto Dr, Chatham, MA 02633

    Distinctive Home-Exceptional Location-Unmatched Location. Discover refined coastal living in this custom-built Gambrel home perfectly situated next to conservation land and less than a mile from idyllic Hardings Beach on Nantucket Sound. Enjoy sweeping views overlooking Oyster River stretching out to Oyster Pond and the quaint village of Chatham and direct waterway access— ideal for boating

    Julie Chapin William Raveis Chatham

    87 Squanto Dr, Chatham, MA 02633
  • /76

    $1,175,000

    Sold Jan 22, 2026

    597 Orleans Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $605/SF
    • 181 Days On Market

    Current Estimated Value $1,330,282

    Last Listing Agent Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
    • /29

      Est $1,180,082

      Not Listed For Sale

      56 Meadowbrook Rd, North Chatham, MA 02650

      • 4 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 1961
      56 Meadowbrook Rd, North Chatham, MA 02650

      Last Sold Summary

      • 14 Days On Market

  • /47

    $4,950,000

    • 4 Beds
    • 4.5 Baths
    • 5,371 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 Massachusetts, LLC

    15 Bay Ln, Chatham, MA 02633
  • /86

    $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 $6,090,630

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

    58 Oyster Bluff, Chatham, MA 02633

Showing Results 201 - 240, Page 6 of 18

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