9,709

Chatham, MA Homes

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  • /44

    $1,350,000 Sold Jun 17, 2025

    • 2,279 Sq Ft
    • $592/SF
    • 12 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    33 Captains Walk, North Chatham, MA 02650

    This inviting 4-bedroom Colonial-style home with an attached garage is nestled in one of North Chatham's most sought-after neighborhoods. Just a short stroll to downtown Chatham and beautiful beaches, this well-loved and meticulously maintained home has been cherished by the same family for many years.Situated on a level lot with mature perennials, the property offers plenty of space to enjoy the

    Natalia Weiner Gibson Sotheby's International Realty

    33 Captains Walk, North Chatham, MA 02650
    • /43

      Est $2,780,209 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,764 Sq Ft

      27 Strong Island Rd, Chatham, MA 02633

      27 Strong Island Rd, Chatham, MA 02633
  • /2

    $6,995,000 Pending

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft

    13 Captain Knowles Way, Chatham, MA 02633

    Experience the perfect blend of luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship throughout.Designed for both comfort and entertaining, the home

    Mina O'Keefe Gibson Sotheby's International Realty

    13 Captain Knowles Way, Chatham, MA 02633
  • /40

    $1,320,000 Sold Jun 12, 2025

    • 2,238 Sq Ft
    • $590/SF
    • 78 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1980

    67 The Cornfield, Chatham, MA 02633

    Situated on a quiet cul-de-sac in a desirable neighborhood, this bright Cape enjoys a prime location just a mile from town with several shops & restaurants within walking distance. Encompassing 2,300 sq. ft of living space on three levels, an easy-flowing floor plan offers a granite & stainless kitchen with adjacent open dining & breakfast nook, sun-filled living room with walls of glass, and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    67 The Cornfield, Chatham, MA 02633
    • /41

      Est $2,568,515 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,275 Sq Ft

      789 Fox Hill Rd, Chatham, MA 02633

      789 Fox Hill Rd, 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
    • /41

      Est $6,791,325 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,439 Sq Ft

      771 Fox Hill Rd, Chatham, MA 02633

      771 Fox Hill Rd, Chatham, MA 02633
  • /42

    $11,250,000 Sold Jun 09, 2025

    • 5,868 Sq Ft
    • $1,917/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
    • /62

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,947 Sq Ft

      266 Seapine Rd, North Chatham, MA 02650

      266 Seapine Rd, North Chatham, MA 02650
  • /24

    $780,000 Sold Jun 06, 2025

    • 1,144 Sq Ft
    • $682/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    15 Stephen Dr, Chatham, MA 02633

    RE/MAX Vision proudly presents 15 Stephen Drive – a beautifully renovated 3 bedroom ranch style home in a highly sought after, adorable neighborhood. Since 2008, nearly everything has been updated. Roof, siding, windows, doors, kitchen, bath, hardwood flooring, tile, and a new septic system in 2024. Move right in – this home needs absolutely nothing. This is truly one level living at its best

    Stephen Laska RE/MAX Vision

    15 Stephen Dr, Chatham, MA 02633
    • /30

      Est $3,722,279 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 2,971 Sq Ft

      66 Woodland Way, North Chatham, MA 02650

      66 Woodland Way, North Chatham, MA 02650
  • /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
    • /38

      Est $1,660,470 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft

      121 Middle Rd, North Chatham, MA 02650

      121 Middle Rd, North Chatham, MA 02650
  • /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
    • /35

      Est $831,879 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,166 Sq Ft

      689 Orleans Rd, North Chatham, MA 02650

      689 Orleans Rd, North Chatham, MA 02650
  • /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
    • /42

      Est $1,284,002 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,150 Sq Ft

      52 Court St, North Chatham, MA 02650

      52 Court St, 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
    • /21

      Est $1,588,418 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,393 Sq Ft

      32 Wells Hollow Rd, North Chatham, MA 02650

      32 Wells Hollow Rd, North Chatham, MA 02650
  • /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
    • /40

      Est $1,006,386 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,472 Sq Ft

      714 Crowell Rd, North Chatham, MA 02650

      714 Crowell Rd, North Chatham, MA 02650
  • /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
    • /41

      Est $864,208 Not Listed For Sale

      • 2 Beds

      693 Orleans Rd, North Chatham, MA 02650

      693 Orleans Rd, North Chatham, MA 02650
  • /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
    • /21

      Est $775,545 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,319 Sq Ft

      739 Crowell Rd, North Chatham, MA 02650

      739 Crowell Rd, North Chatham, MA 02650
  • /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
    • /25

      Est $943,728 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft

      486 Crowell Rd, Chatham, MA 02633

      486 Crowell Rd, Chatham, MA 02633
  • /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
    • /29

      Est $1,050,538 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,877 Sq Ft

      148 Old Queen Anne Rd, Chatham, MA 02633

      148 Old Queen Anne Rd, 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
    • /26

      Est $1,100,070 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,228 Sq Ft

      58 Stepping Stones Rd, Chatham, MA 02633

      58 Stepping Stones Rd, Chatham, MA 02633
  • /34

    $5,250,000 Sold May 09, 2025

    • 2,214 Sq Ft
    • $2,371/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
    • /68

      Est $1,192,442 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,858 Sq Ft

      52 Earles Way, Chatham, MA 02633

      52 Earles Way, Chatham, MA 02633
  • /32

    $385,000 Sold May 07, 2025

    • 1,167 Sq Ft
    • $330/SF
    • 101 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1999

    912 Main St Unit 209, Chatham, MA 02633

    Ready to downsize for easy living? Come home to Chatham's finest over 62 independent living community in the heart of Chatham. This 2 BED/2BAth condo has been freshly painted & offers maintenance free living, ie peace living/dining area, a '' split plan'' with Primary bedroom en-suite on one end of unit, and guest suite with en-suite bathroom on either side. With full size stack W/D, AC and lots

    Phyllis Power Compass

    912 Main St Unit 209, Chatham, MA 02633
    • /43

      Est $894,472 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,578 Sq Ft

      16 Janes Way, Chatham, MA 02633

      16 Janes Way, Chatham, MA 02633
  • /41

    $1,565,000 Sold May 02, 2025

    • 2,760 Sq Ft
    • $567/SF
    • 30 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1988

    55 Twine Field Dr, Chatham, MA 02659

    2 Acres in Chatham! Invite the outdoors in with this sun-filled home in a serene setting. Large sliding doors from the dining room and owner's suite let you step out onto an expansive deck and patio overlooking a tranquil inground pool, established gardens, and the Twine Field Conservation Land. This backyard oasis is perfect for hosting and relaxing. Continue enjoying Cape Cod nature on the Old

    Jen Whitaker Gibson Sotheby's International Realty

    55 Twine Field Dr, Chatham, MA 02659
    • /49

      Est $1,252,130 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,660 Sq Ft

      41 Earles Way, Chatham, MA 02633

      41 Earles Way, Chatham, MA 02633
  • /48

    $582,500 Sold May 02, 2025

    • 1,017 Sq Ft
    • $573/SF
    • 14 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1983

    1 Seastrand Way Unit 8, Chatham, MA 02633

    Welcome to this inviting townhouse-style condo nestled in the tranquil enclave of West Chatham. Featuring a thoughtfully designed layout, this residence offers two spacious bedrooms on the second level and one and a half modern bathrooms, providing both comfort and convenience.The heart of the home boasts an open-concept living and dining area, complete with gleaming hardwood floors that flow

    Kathy Doyle Gibson Sotheby's International Realty

    1 Seastrand Way Unit 8, Chatham, MA 02633
    • /47

      Est $891,178 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,501 Sq Ft

      88 Stepping Stones Rd, Chatham, MA 02633

      88 Stepping Stones Rd, Chatham, MA 02633
  • /62

    $7,275,000 Sold May 02, 2025

    • 6,128 Sq Ft
    • $1,187/SF
    • 207 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 2014

    30 Fairway Dr, Chatham, MA 2633

    This architectural masterpiece perched above Chatham Seaside Links in a highly coveted Village enclave offers an incredible array of breathtaking vistas with easterly views of Chatham Harbor. The five bedroom home embodies elegant coastal style with showpiece finishes, custom detailing and countless amenities. The foyer with soaring ceilings discloses a great room with grand windows, fireplace,

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Fairway Dr, Chatham, MA 2633

Showing Results 281 - 320, Page 8 of 18

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