9,489

Chatham, MA Homes

Section Image
  • /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 $2,659,912

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

    51 Shattuck Place, Chatham, MA 02633
    • /18

      Est $322,750

      Not Listed For Sale

      197 Stony Hill Rd Unit C, Chatham, MA 02633

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft
      • Built 1995
      197 Stony Hill Rd Unit C, Chatham, MA 02633

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent Caroline McAdams Covell Realty Inc

  • /39

    $1,899,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,514 Sq Ft

    70 Uncle Deane's Rd, Chatham, MA 02659

    Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully

    Patrick Davison Shining Sea Realty

    70 Uncle Deane's Rd, Chatham, MA 02659
  • /30

    $765,000

    Sold Dec 18, 2025

    47 Cranberry Way, South Chatham, MA 2659

    • 2 Beds
    • 2 Baths
    • 868 Sq Ft
    • Built 1941

    Last Sold Summary

    • 4% Below List Price
    • $881/SF
    • 11 Days On Market

    Current Estimated Value $807,422

    Last Listing Agent William Raye Gibson Sotheby's International Realty

    47 Cranberry Way, South Chatham, MA 2659
    • /53

      Est $1,231,267

      Not Listed For Sale

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

      • 2 Beds
      • 3.5 Baths
      • 2,546 Sq Ft
      • Built 2005
      43 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Kristen Savely Compass Massachusetts, LLC

  • /42

    $2,850,000

    $400K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    336 Stage Island Rd, Chatham, MA 02633

    Stage Island is among the most exclusive addresses on Cape Cod — a private enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    336 Stage Island Rd, Chatham, MA 02633
  • /35

    $1,100,000

    Sold Jun 26, 2026

    35 Pine Tree Rd, Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 2,257 Sq Ft
    • Built 1998

    Last Sold Summary

    • 12% Below List Price
    • $487/SF
    • 24 Days On Market

    Current Estimated Value $1,208,992

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    35 Pine Tree Rd, Chatham, MA 02659
    • /29

      Est $1,074,223

      Not Listed For Sale

      39 Misty Meadow Ln, North Chatham, MA 02650

      • 2 Beds
      • 2.5 Baths
      • 1,812 Sq Ft
      • Built 2005
      39 Misty Meadow Ln, North Chatham, MA 02650

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Team Guthrie - Mabile Berkshire Hathaway HomeServices Robert Paul Properties

  • /28

    $6,500,000

    • 10 Beds
    • 10 Baths
    • 7,658 Sq Ft

    150 Cross St, Chatham, MA 02633

    Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500

    Chris Rhinesmith Compass

    150 Cross St, Chatham, MA 02633
  • /15

    $3,699,900

    Sold Jun 30, 2026

    29 Jessies Landing, Chatham, MA 2633

    • 3 Beds
    • 4.5 Baths
    • 4,565 Sq Ft
    • Built 2026

    Last Sold Summary

    • $810/SF
    • 5 Days On Market

    Current Estimated Value $3,681,252

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

    29 Jessies Landing, Chatham, MA 2633
    • /2

      Est $1,071,154

      Not Listed For Sale

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

      • 2 Beds
      • 3 Baths
      • 1,906 Sq Ft
      • Built 2006
      37 Misty Meadow Ln Unit B, North Chatham, MA 02650

  • /50

    $1,450,000

    $45K PRICE DROP Pending
    • 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
  • /61

    $1,175,000

    Sold Jun 25, 2026

    40 Sam Ryder Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1995

    Last Sold Summary

    • $769/SF
    • 1 Day On Market

    Current Estimated Value $1,054,289

    Last Listing Agent Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    40 Sam Ryder Rd, Chatham, MA 02633
    • /25

      Est $1,163,419

      Not Listed For Sale

      61 Bishops Terrace, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft
      • Built 1966
      61 Bishops Terrace, Chatham, MA 02633

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /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
  • /42

    $3,675,000

    Sold Oct 31, 2025

    45 Meadow View Rd S, Chatham, MA 02633

    • 4 Beds
    • 5.5 Baths
    • 4,908 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $749/SF
    • 430 Days On Market

    Current Estimated Value $3,460,052

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

    45 Meadow View Rd S, Chatham, MA 02633
    • /27

      Est $1,201,786

      Not Listed For Sale

      32 Bishops Terrace, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,384 Sq Ft
      • Built 1965
      32 Bishops Terrace, Chatham, MA 02633

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Justin Blair Monomoy Properties Group LLC

  • /9

    $4,499,900

    New Construction
    • 3 Beds
    • 7 Baths
    • 5,820 Sq Ft

    33 Crowell Rd, Chatham, MA 02633

    A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    33 Crowell Rd, Chatham, MA 02633
  • /41

    $952,500

    Sold Mar 24, 2026

    24 Chickadee Cir, Harwich, MA 02645

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $815/SF
    • 119 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    24 Chickadee Cir, Harwich, MA 02645
    • /25

      Est $760,880

      Not Listed For Sale

      161 Shane Dr, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 966 Sq Ft
      • Built 1971
      161 Shane Dr, Chatham, MA 02633

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Darci Gervais Keller Williams Realty

  • /42

    $4,500,000

    $750K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    48 Sylvan Way, South Chatham, MA 02659
  • /7

    $4,525,000

    Sold Jun 26, 2026

    230 Barcliff Ave, Chatham, MA 02633

    • 4 Beds
    • 5.5 Baths
    • 5,300 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Above List Price
    • $854/SF
    • 52 Days On Market

    Current Estimated Value $4,298,763

    Last Listing Agent Lori Fanning Smith Compass

    230 Barcliff Ave, Chatham, MA 02633
    • /40

      Est $2,019,487

      Not Listed For Sale

      55 Eldredge Square S, Chatham, MA 02633

      • 3 Beds
      • 4 Baths
      • 2,630 Sq Ft
      • Built 2003
      55 Eldredge Square S, Chatham, MA 02633

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Jessica Metzler Compass Massachusetts, LLC

  • /80

    $1,795,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,719 Sq Ft

    23 Taylors Pond Rd, South Chatham, MA 02659

    Steps from Cockle Cove Beach! This gorgeous, pristine 3-bedroom, 3-bathroom home offers the perfect blend of modern updates and beachside living. Located just steps from Cockle Cove Beach and right across the street from the Taylors Pond dock, this spotless property is completely move-in ready. Kitchen & Baths have been beautifully remodeled within the past few years. Walls were opened up to

    Kathleen Phelan Compass Massachusetts, LLC

    23 Taylors Pond Rd, South Chatham, MA 02659
  • /46

    $7,312,500

    Sold May 21, 2026

    246 Stage Island Rd, Chatham, MA 02633

    • 4 Beds
    • 6 Baths
    • 4,717 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $1,550/SF
    • 65 Days On Market

    Current Estimated Value $7,510,763

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    246 Stage Island Rd, Chatham, MA 02633
    • /28

      Est $1,156,943

      Not Listed For Sale

      233 Barcliff Ave, Chatham, MA 02633

      • 2 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1957
      233 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Jack Tobin Corcoran Property Advisors

  • /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
  • /38

    $1,650,000

    Sold Apr 16, 2026

    146 Old Field Bend, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,039 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $809/SF
    • 15 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    146 Old Field Bend, Chatham, MA 02633
    • /65

      Est $3,117,482

      Not Listed For Sale

      25 Glover Square, Chatham, MA 02633

      • 3 Beds
      • 4.5 Baths
      • 4,105 Sq Ft
      • Built 2018
      25 Glover Square, Chatham, MA 02633

      Last Sold Summary

      • 166 Days On Market

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

  • /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
  • /15

    $635,000

    Sold Jan 13, 2026

    Lot 6 Bobbie's Ln, Chatham, MA 02659

    • Land
    • 30,056 Sq Ft
    • $920,290 per Acre

    Last Sold Summary

    • 5% Above List Price
    • 22 Days On Market

    Last Listing Agent Shane Masaschi Compass

    Lot 6 Bobbie's Ln, Chatham, MA 02659
    • /46

      Est $1,332,977

      Not Listed For Sale

      265 Barcliff Ave, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,491 Sq Ft
      • Built 1953
      265 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Barbara Garside Compass Massachusetts, LLC

  • /76

    $6,990,000

    $1M PRICE DROP
    • 5 Beds
    • 6 Baths
    • 4,248 Sq Ft

    108 Queen Anne Rd, Chatham, MA 02633

    Experience the very best of Chatham living. Few properties offer this extraordinary combination of premium waterfront living and the ability to stroll to everything the historic village center has to offer. Set behind privacy fencing and mature plantings on Oyster Pond, this distinctive home sits steps from your private boat dock and steps from vibrant downtown Chatham. Walk to your morning

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    108 Queen Anne Rd, Chatham, MA 02633
  • /40

    $5,400,000

    Sold Mar 31, 2026

    121 Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 7 Baths
    • 3,702 Sq Ft
    • Built 2015

    Last Sold Summary

    • $1,459/SF
    • 1 Day On Market

    Current Estimated Value $5,093,003

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    121 Queen Anne Rd, Chatham, MA 02633
    • /2

      Not Listed For Sale

      178 Queen Anne Rd, Chatham, MA 02633

      • 6 Beds
      • 8 Baths
      • 7,700 Sq Ft
      • Built 1820
      178 Queen Anne Rd, Chatham, MA 02633

  • /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
  • /38

    $729,000

    Sold Aug 03, 2026

    7 Aunt Matties Rd, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Below List Price
    • $466/SF
    • 27 Days On Market

    Current Estimated Value $806,870

    Last Listing Agent Tiffany Callahan Greer Real Estate, LLC

    7 Aunt Matties Rd, Chatham, MA 02633
    • /2

      Est $3,839,886

      Not Listed For Sale

      125 Stage Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 6 Baths
      • 3,624 Sq Ft
      • Built 1946
      125 Stage Harbor Rd, Chatham, MA 02633

  • /48

    $1,280,000

    $70K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,278 Sq Ft

    243 Crowell Rd, Chatham, MA 02633

    Comfortable, Cape style 3 bedroom home with free standing 2 car garage, set way back from the road on a level .6+ acre lot; room for a swimming pool. Large fireplaced living room, Updated chef's kitchen, newer A/C splits, fenced, sunny back yard with deck, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Unfinished second floor offers expansion potential. Potential

    Michael Hall William Raveis Real Estate & Home Services

    243 Crowell Rd, Chatham, MA 02633
  • /30

    $1,635,000

    Sold Sep 26, 2025

    24 Hillcrest Rd, Chatham, MA 02633

    • 5 Beds
    • 3 Baths
    • 3,098 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Above List Price
    • $528/SF
    • 1 Day On Market

    Last Listing Agent Jessica King Compass Massachusetts, LLC

    24 Hillcrest Rd, Chatham, MA 02633

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home