9,756

Chatham, MA Homes

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    • /44

      Est $3,609,668 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,422 Sq Ft

      50 Chase St, Chatham, MA 02633

      50 Chase St, Chatham, MA 02633
  • /76

    $3,295,000 Open House 7/20

    • 3 Beds
    • 3.5 Baths
    • 3,014 Sq Ft

    7 Squanto Dr, Chatham, MA 02633

    This Nantucket-style home features extraordinary views across a tidal salt marsh, Oyster Pond, and the 3 church steeples in Town. Enjoy the fireworks display New Year's Eve, ever-changing beauty of the seasons, and a host of wildlife from this elevated .69 acre site. With just over 3,000 square feet this exceptionally-crafted home is the perfect size; with an open floor plan ideal for

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    7 Squanto Dr, Chatham, MA 02633
  • /33

    $1,737,000 Sold Jun 11, 2025

    • 2,532 Sq Ft
    • $686/SF
    • 210 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2005

    36 Ocean View Terrace, Chatham, MA 02633

    NEW PRICE ~ This Pristine Custom Built, 3 bedroom/ 3 full bath Cape spares no details!! Located down a secluded dead-end, surrounded by conservation and Chatham Links. Just a stones throw from Veterans Field for evenings watching the Chatham Anglers, people watching in Downtown Chatham, and Oyster Pond are all around the corner. Relax on your quiet three season porch or enjoy a rousing game night

    Kim Arestad eXp Realty

    36 Ocean View Terrace, Chatham, MA 02633
    • /59

      Est $4,341,501 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,440 Sq Ft

      62 Chase St, Chatham, MA 02633

      62 Chase St, Chatham, MA 02633
  • /41

    $4,895,000

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

    785 Old Harbor Rd, North Chatham, MA 02650

    Welcome to " Two Stars" this meticulously crafted residence located in coveted North Chatham. This beautiful sanctuary offers an 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 thoughtful detail. Spanning 4200sq. ft of sophisticated space, this

    Phyllis Power Compass

    785 Old Harbor Rd, North Chatham, MA 02650
  • /42

    $11,250,000 Sold Jun 09, 2025

    • 5,868 Sq Ft
    • $1917/SF
    • 326 Days On Market
    • 7 Beds
    • 6.5 Baths
    • Built 1930

    552 Shore Rd, Chatham, MA 02633

    Situated on a bluff with commanding views over Chatham Harbor, North Beach, and the Atlantic beyond, this extraordinary offering stands as one of the most significant estate properties on exclusive Shore Road. A short stroll from everything Chatham Village has to offer, the property boasts an unprecedented 2.86 acres with rolling lawns, mature landscaping, and a private sandy beach. Mesmerizing

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    552 Shore Rd, Chatham, MA 02633
    • /31

      Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,209 Sq Ft

      90 Silver Leaf Ave, Chatham, MA 02633

      90 Silver Leaf Ave, Chatham, MA 02633
  • /49

    $3,950,000

    • 3 Beds
    • 4.5 Baths
    • 4,361 Sq Ft

    86 Champlain Rd, Chatham, MA 02633

    Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lighthouse and Nantucket Sound. Savor the warm summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to the sandy shores of Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an

    Jack Bohman Gibson Sotheby's International Realty

    86 Champlain Rd, Chatham, MA 02633
  • /42

    $2,250,000 Sold Jun 04, 2025

    • 3,865 Sq Ft
    • $582/SF
    • 28 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2006

    25 Menekish Ln, Chatham, MA 02633

    Tucked away on a private lane in North Chatham, 25 Menekish Lane offers a rare blend of privacy and proximity—just steps from Cow Yard Beach, Chatham Bars Inn, the Fish Pier, and Main Street. Built in 2006, the nearly 4,000 sq ft home blends timeless Cape charm with modern ease: soaring ceilings, abundant natural light, and a flowing floor plan ideal for entertaining. A chef’s kitchen with island

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    25 Menekish Ln, Chatham, MA 02633
    • /35

      Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 1,713 Sq Ft

      32 Little Beach Rd, Chatham, MA 02633

      32 Little Beach Rd, Chatham, MA 02633
  • /95

    $2,150,000

    • 3 Beds
    • 4.5 Baths
    • 3,902 Sq Ft

    2016 Main St, Chatham, MA 02633

    Stunning Magazine-Quality Home with Resort-Style Living on Main StreetTucked privately off Main Street, this breathtaking home offers the perfect balance of privacy and prime location. Designed for both relaxed living and stylish entertaining, the interior boasts an open floor plan with beautiful shiplap walls, a dedicated dining room with built-in wet bar, and a thoughtfully placed half bath

    Daneen Law Gibson Sotheby's International Realty

    2016 Main St, Chatham, MA 02633
  • /33

    $3,388,000 Sold Jun 03, 2025

    • 3,436 Sq Ft
    • $986/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1996

    525 Shore Rd, Chatham, MA 02633

    This Quintessential Chatham retreat on picturesque Shore Road exudes timeless charm and sits in close proximity to beautiful beaches and the village. The well maintained home provides a welcoming floor plan with comfortable spaces for gathering, and private rooms for peaceful reflection. The entertaining sized living room has a cozy gas fireplace, and leads to the open concept kitchen and dining

    Peggy Rowland Sotheby's International Realty

    525 Shore Rd, Chatham, MA 02633
    • /31

      Est $1,491,211 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 793 Sq Ft

      27 Clam Shell Dr, Chatham, MA 02633

      27 Clam Shell Dr, Chatham, MA 02633
  • /44

    $4,950,000

    • 4 Beds
    • 3.5 Baths
    • 3,878 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

    Chris Rhinesmith Compass Massachusetts, LLC

    38 Indian Trail, Chatham, MA 02633
  • /38

    $6,895,000 Sold Jun 03, 2025

    • 7,111 Sq Ft
    • $970/SF
    • 196 Days On Market
    • 5 Beds
    • 8.5 Baths
    • Built 2016

    114 Cranberry Ln, North Chatham, MA 02650

    Sited on a picturesque lane in a coveted North Chatham location, this custom estate home with deeded access to a private sandy beach on Pleasant Bay is being offered fully furnished and turn key!! Featuring the absolute best of coastal Cape Cod living, the 5+ bedroom Main House and 2 bedroom Guest House are like new, having been further improved and maintained to exacting standards. Thoughtfully

    Brian Dougherty Corcoran Property Advisors

    114 Cranberry Ln, North Chatham, MA 02650
    • /53

      Est $2,495,329 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,669 Sq Ft

      16 Windmill Ln, Chatham, MA 02633

      16 Windmill Ln, Chatham, MA 02633
  • /46

    $2,750,000

    • 3 Beds
    • 3 Baths
    • 2,969 Sq Ft

    104 Seapine Rd, North Chatham, MA 02650

    Set within the coveted Harbor Coves Association of North Chatham, 104 Seapine Road is a rare opportunity to own in one of Cape Cod's most exclusive enclaves. With sweeping views over Crow's Pond and direct access to a private association beach just steps away, the setting is exceptional. Built in 1999 by noted local firm von Thaden Builders, the 3-bedroom, 2.5-bath home offers nearly 3,000 sq ft

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    104 Seapine Rd, North Chatham, MA 02650
  • /34

    $1,150,000 Sold Jun 02, 2025

    • 1,456 Sq Ft
    • $790/SF
    • 26 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1970

    56 Barn Hill Ln, Chatham, MA 02633

    Classic coastal charm embodies this 4BR 2 bath Cape . Renovated in 2020, every inch of this home is a reflection of the Chatham lifestyle. From the light filled rooms, living room with wood burning fireplace, ship lapped accent walls, renovated kitchen and baths ,this home feels like a vacation. The two second floor bedrooms are very spacious with sitting areas. Located just around the corner

    Lori Fanning Smith Compass Massachusetts, LLC

    56 Barn Hill Ln, Chatham, MA 02633
    • /53

      Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 5,861 Sq Ft

      43 Morris Island Rd, Chatham, MA 02633

      43 Morris Island Rd, Chatham, MA 02633
  • /68

    $2,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,072 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

    Tara Schiffmann Brown Bayview Real Estate

    55 Winterset Dr, Chatham, MA 02633
  • /12

    $750,000 Sold May 30, 2025

    • 2,625 Sq Ft
    • $286/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1947

    86 Vineyard Ave, Chatham, MA 02633

    Looking for a project? Great location for investors/builders to bring your imagination to this nostalgic 1947 era Cape Cod style home, enlarged to 2625 Sq Ft with a 1988 addition. This 3 Bed/2 bath Cape is located on.51 Acre sunny lot in a popular neighborhood with town landing at Oyster Pond at end of street. Property sold AS IS... Bring you vision for a fresh renovation worth the effort

    Phyllis Power Compass

    86 Vineyard Ave, Chatham, MA 02633
    • /4

      Est $977,512 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 650 Sq Ft

      28 Cranberry Ln, Chatham, MA 02633

      28 Cranberry Ln, Chatham, MA 02633
  • /29

    $2,300,000

    • 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
  • /36

    $615,300 Sold May 27, 2025

    • 1,283 Sq Ft
    • $480/SF
    • 18 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1988

    369 Orleans Rd Unit A, Chatham, MA 2633

    Well-cared-for end-unit townhouse in sought-after Chatham, proudly owned by the same owner for 31 years. This bright and spacious 2-bedroom, 2.5-bath home offers a finished basement, cozy gas-burning stove, gas heat, and an attached 1-car garage beneath the unit. The private back deck is perfect for relaxing or entertaining. With added privacy, natural light, and a convenient location, it’s ideal

    David Colville HomeSmart First Class Realty

    369 Orleans Rd Unit A, Chatham, MA 2633
    • /20

      Est $2,101,213 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft

      32 Cranberry Ln, Chatham, MA 02633

      32 Cranberry Ln, Chatham, MA 02633
  • /30

    $2,300,000

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

    213 Main St, Chatham, MA 02633

    Location! Location in the heart of Chatham! Historic Greek Revival circa 1850's in the Old Village, with water views of Chatham Harbor, Andrew Harding's landing and Lighthouse beach & Main St shopping/dining, Band Concerts, nearby! This charming 4 bed/2 bath home has a sunny eat-in beamed family room with sliders to deck, cozy kitchen adjacent and a front Living room with gas fireplace, warm

    Phyllis Power Compass

    213 Main St, Chatham, MA 02633
  • /36

    $615,300 Sold May 27, 2025

    • 1,283 Sq Ft
    • $480/SF
    • 18 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1988

    369 Orleans Rd Unit A, North Chatham, MA 02650

    Well-cared-for end-unit condo in sought-after Chatham, proudly owned by the same owner for 31 years. This bright and spacious 2-bedroom, 2.5-bath home offers a finished basement, cozy gas-burning stove, gas heat, and an attached 1-car garage beneath the unit. The private back deck is perfect for relaxing or entertaining. With added privacy, natural light, and a convenient location, it's ideal for

    David Colville HomeSmart First Class Realty

    369 Orleans Rd Unit A, North Chatham, MA 02650
    • /45

      Est $3,838,936 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,448 Sq Ft

      48 Salt Marsh Way, North Chatham, MA 02650

      48 Salt Marsh Way, North Chatham, MA 02650
  • /41

    $2,699,000

    • 4 Beds
    • 3.5 Baths
    • 3,834 Sq Ft

    106 Stage Neck Rd, Chatham, MA 02633

    Nestled on just over an acre of meticulously landscaped grounds with a private well for irrigation near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a small, shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and lovingly cared for by its original owner, the home retains its classic charm

    Jen Graham Christie's International Real Estate Atlantic Brokerage

    106 Stage Neck Rd, Chatham, MA 02633
  • /62

    $2,100,000 Sold May 15, 2025

    • 3,199 Sq Ft
    • $656/SF
    • 319 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1984

    92 Absegami Run, Chatham, MA 02633

    Don't miss out on living in one of Chatham's most desired neighborhoods. Located in an exclusive enclave near Oyster Pond, this 4 bedroom, 3.5 bath home offers the discriminating buyer the opportunity for an exceptional residence in an area of remarkable homes. With over 3,200 s.f. of living space, this Post and Beam constructed home has the open and airy space people love for entertaining and

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    92 Absegami Run, Chatham, MA 02633
    • /41

      Est $1,701,333 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,205 Sq Ft

      39 Windward Passage, North Chatham, MA 02650

      39 Windward Passage, North Chatham, MA 02650
  • /27

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln, North Chatham, MA 02650

    Tucked away on a quiet street in the heart of North Chatham, this charming second-floor condominium offers an exceptional opportunity to own in one of the Cape's most coveted locations. Whether you're seeking a seasonal retreat, an investment property, or a smart entry into the Chatham market, this residence delivers a perfect blend of convenience, charm, and value.Filled with natural light, the

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln, North Chatham, MA 02650
  • /34

    $425,000 Sold May 12, 2025

    • 930 Sq Ft
    • $457/SF
    • 5 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1982

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

    If you've been searching for the perfect pied-a-terre in the coveted town of Chatham, look no further. This newly painted and well-maintained corner unit is the ideal place to unpack, unwind and savor everything this vibrant area has to offer. Enjoy perfect flow for indoor/outdoor entertaining from the kitchen to your second-story deck with peaceful, scenic views. Relax in your spacious living

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    36 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    • /16

      Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 4,581 Sq Ft

      356 Stony Hill Rd, North Chatham, MA 02650

      356 Stony Hill Rd, North Chatham, MA 02650
  • /42

    $1,995,000

    • 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
  • /47

    $1,065,000 Sold May 09, 2025

    • 2,292 Sq Ft
    • $465/SF
    • 16 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1971

    718 Riverview Dr, Chatham, MA 02633

    Well appointed one-story living in Riverbay Estates on .47 acre lot. Beautifully updated 2-bed, 2.5-bath cape ranch features an open-concept living, dining, and kitchen area filled with natural light. The modern kitchen boasts a spacious island, engineered quartz countertops and stainless steel appliances. The large primary suite offers a walk-in closet and an updated ensuite with a deep Kohler

    Tim Bailey John C Ricotta & Assoc.

    718 Riverview Dr, Chatham, MA 02633
    • /40

      Est $1,874,092 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,428 Sq Ft

      98 Orleans Rd, Chatham, MA 02633

      98 Orleans Rd, Chatham, MA 02633
  • /26

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

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

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • /34

    $5,250,000 Sold May 09, 2025

    • 2,214 Sq Ft
    • $2371/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1963

    372 Fox Hill Rd, Chatham, MA 02633

    Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club. The

    Chris Rhinesmith Compass Massachusetts, LLC

    372 Fox Hill Rd, Chatham, MA 02633
    • /20

      Est $2,091,696 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 1,945 Sq Ft

      303 Old Harbor Rd, Chatham, MA 02633

      303 Old Harbor Rd, Chatham, MA 02633

Showing Results 41 - 80, Page 2 of 18

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