Chatham, MA Homes for Sale

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  /60

  $1,175,000

  $175K 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
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  $2,100,000

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

  409 Main St, Chatham, MA 02633

  Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the

  Rick Smith Gibson Sotheby's International Realty

  409 Main St, Chatham, MA 02633
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  /63

  $5,950,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  5 Hillcrest Ln, Chatham, MA 02633

  This spectacular custom built " Rick Roy" home has undergone another massive renovation in 2025-2026. The home is now " free flowing" connecting the antique portion of the home built in 1952 to the gorgeous massive " great room addition" to the home in 2008. All of the rooms flow into each other with the addition of a large ensuite master bedroom and bathroom on the first floor. The current owner

  Emily Boynton BMTF Partnership

  5 Hillcrest Ln, Chatham, MA 02633
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  $1,695,000

  $100K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 2,331 Sq Ft

  43 Tobey Turtle Rd, Chatham, MA 02633

  Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3½ baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the

  Timothy Bailey John C Ricotta & Assoc.

  43 Tobey Turtle Rd, Chatham, MA 02633
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  $975,000

  Open Sat 10AM - 12PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  800 Riverview Dr, Chatham, MA 02633

  Welcome to 800 Riverview Drive, a charming three-bedroom, two-bath ranch offering relaxed coastal living in desirable Riverbay Estates. Set on a beautifully situated half-acre lot, this home provides easy one-level living with an en-suite primary bedroom, comfortable sunroom, one-car garage, fireplace, natural gas heat and central AC. Just over a half-mile from Jackknife Beach and Pleasant Bay,

  Shane Masaschi Compass

  800 Riverview Dr, Chatham, MA 02633
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  /73

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 4,763 Sq Ft

  65 Harbor View Rd, Chatham, MA 02633

  The ultimate Chatham compound! Set high on a bluff with views of Hardings Beach and Nantucket Sound, this impressive property features a 4,100+ sqft main house, oversized two-car garage with private guest suite above, and a resort-style backyard with an expansive patio and pool. Inside, ten-foot ceilings, custom built-ins, abundant natural light, and generous living spaces set the tone. The grand

  Chris Rhinesmith Compass Massachusetts, LLC

  65 Harbor View Rd, Chatham, MA 02633
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  $2,199,900

  • 3 Beds
  • 3 Baths
  • 2,576 Sq Ft

  20 Lords Pond Rd, Chatham, MA 02633

  This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers

  The Grattan Group Christie's International Real Estate Atlantic Brokerage

  20 Lords Pond Rd, Chatham, MA 02633
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  $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
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  /25

  $659,000

  • 2 Beds
  • 2 Baths
  • 999 Sq Ft

  216 Orleans Rd Unit D, North Chatham, MA 02650

  Spacious and sunny condo in North Chatham set on the corner of Stoney Hill Rd. Walk to Cow yard beach and admire the historic homes along the way. Or walk in the opposite direction towards down town Chatham. The location and size of this condo will win your heart. Offered completely furnished with many recent upgrades including new AC, new deck, new windows and roof. This condo is graced with

  Kathleen Phelan Compass Massachusetts, LLC

  216 Orleans Rd Unit D, North Chatham, MA 02650
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  /17

  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,622 Sq Ft

  23 Wentworth Ln, North Chatham, MA 02650

  Wonderful ranch house on 7/10's of an acre lot in Ryder's Cove Landing in North Chatham. All living on one floor just a quick walk away from the large inground pool, tennis court, beach, and a DOCK that all compliment this area and are reserved for the homeowners in the association. Partially finished lower level serves as a bonus room and second living area. Town field card has 3 bedrooms and

  John Burke William Raveis Chatham

  23 Wentworth Ln, North Chatham, MA 02650
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  $1,469,000

  • 5 Beds
  • 10 Baths
  • 11,000 Sq Ft

  558 Fox Hill Rd, Chatham, MA 02633

  New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho and Pleasant Bay from nearly every angle. The shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  558 Fox Hill Rd, Chatham, MA 02633
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  /42

  $2,199,900

  • 3 Beds
  • 3.5 Baths
  • 2,576 Sq Ft

  20 Lords Pond Ln, Chatham, MA 02633

  This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers

  Andrew Grattan Christie's International Real Estate Atlantic Brokerage

  20 Lords Pond Ln, Chatham, MA 02633
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  /22

  $675,000

  • 2 Beds
  • 2 Baths
  • 996 Sq Ft

  210 Orleans Rd Unit C, North Chatham, MA 02650

  Wonderful two-bedroom, two bath end unit condominium close to Chatham village and beaches.. Recently renovated and three split units for heat and air conditioning also added. Plenty of parking and storage and all the work is done for you. Insurance, landscaping, trash pickup, exterior maintenance, professional management, snow removal, are all covered in the reasonable monthly association fee.

  John Burke William Raveis Chatham

  210 Orleans Rd Unit C, North Chatham, MA 02650
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  $4,250,000

  • 4 Beds
  • 4.5 Baths
  • 4,298 Sq Ft

  22 Moonpenny Ln, Chatham, MA 02633

  This exceptional Chatham residence blends coastal luxury with country farmhouse charm in the exclusive Stage Neck neighborhood. Sited on nearly an acre lot with a separate barn/out-building, this property allows for privacy, with easy access to the Chatham Loop and vibrant downtown life. Abundant curb appeal starts with the circular driveway, mature plantings, and covered mahogany farmer's porch.

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  22 Moonpenny Ln, Chatham, MA 02633
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  /5

  $899,000

  $100K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $5,618,750 per Acre

  727 Main St, Chatham, MA 02633

  Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

  Noreen Kennedy Kennedy Real Estate

  727 Main St, Chatham, MA 02633

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