Chatham, MA Homes for Sale with Garage

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  $1,450,000

  • 3 Beds
  • 2.5 Baths
  • 1,144 Sq Ft

  552 Orleans Rd, Chatham, MA 2633

  Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

  Chris Rhinesmith Compass

  552 Orleans Rd, Chatham, MA 2633
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  /32

  $1,450,000

  • 3 Beds
  • 2.5 Baths
  • 1,144 Sq Ft

  552 Orleans Rd, North Chatham, MA 02650

  Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

  Chris Rhinesmith Compass Massachusetts, LLC

  552 Orleans Rd, North Chatham, MA 02650
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  /30

  $899,900

  • 3 Beds
  • 3 Baths
  • 1,492 Sq Ft

  25 Crosby Ln, Chatham, MA 02633

  TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

  Amanda Bender Christie's International Real Estate Atlantic Brokerage

  25 Crosby Ln, Chatham, MA 02633
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  /30

  $899,900

  • 3 Beds
  • 3 Baths
  • 1,492 Sq Ft

  25 Crosby Ln, Chatham, MA 02633

  TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

  Amanda Bender Christie's International Real Estate Atlantic Brokerage

  25 Crosby Ln, Chatham, MA 02633
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  $975,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 3 Baths
  • 2,399 Sq Ft

  1082 Main St Unit 1082, Chatham, MA 02633

  Motivated sellers! Come take a look at this turn key, end unit townhome in beautiful Chatham! This serene setting overlooks Perch Pond where nature abounds.This 3 level townhome has an attached garage and private driveway, an extra "flex space" room on the 2nd level (could be an office, art studio, gym, 3rd bedroom, etc) and a finished lower level w/ large great room & full bath. This complex is

  Kristin Coletti William Raveis R.E. & Home Services

  1082 Main St Unit 1082, Chatham, MA 02633
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  /64

  $3,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,857 Sq Ft

  36 Moonbeam Ln, Chatham, MA 02633

  This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborhood, and includes deeded rights to the Oyster Pond River. Immaculate and lightly used, you'll find 4,857 square feet of comfortable, casual elegance in a thoughtfully-designed floor plan. There are 4 spacious bedrooms including a lovely first-floor primary En-suite. Bright granite & stainless kitchen opens

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  36 Moonbeam Ln, Chatham, MA 02633
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  /40

  $1,675,000

  • 3 Beds
  • 2.5 Baths
  • 2,238 Sq Ft

  315 Pleasant St, South Chatham, MA 02659

  Chatham - Nantucket Sound with water views greets you instantly here at 315 Pleasant Street! This is a rare opportunity to live high and dry and a mere 350 yards from one of the finest and best stretches of sandy beach on Nantucket Sound. 315 Pleasant Street has been lovingly maintained and recently improved and upgraded by the current owners. Enjoy water views from the primary bedroom's solid

  Ritu Chawla Gibson Sotheby's International Realty

  315 Pleasant St, South Chatham, MA 02659
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  /32

  $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 turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and

  John DePreaux Corcoran Property Advisors

  558 Fox Hill Rd, Chatham, MA 02633
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  $1,699,000

  • 4 Beds
  • 2.5 Baths
  • 2,844 Sq Ft

  4 Nickerson's Cir, Chatham, MA 02659

  New construction! This Retreat Lot is conveniently located mid-way between Chatham Village and Harwich Port with their charming shops, galleries, fabulous restaurants AND less than one mile to several Nantucket Sound beaches! This custom designed home was completed, 2025. The expansive open First Level has an oversized Great Room, Custom Cook's Kitchen with Thermador appliances, a Large Dining

  Pat Butler Coldwell Banker Realty - Hingham

  4 Nickerson's Cir, Chatham, MA 02659
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  $4,400,000

  • 5 Beds
  • 8 Baths
  • 5,578 Sq Ft

  67 Uncle Alberts Dr, Chatham, MA 02633

  This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan. The main level flows seamlessly between the

  Chris Rhinesmith Compass

  67 Uncle Alberts Dr, Chatham, MA 02633
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  /50

  $4,400,000

  • 5 Beds
  • 8 Baths
  • 5,578 Sq Ft

  67 Uncle Alberts Dr, Chatham, MA 02633

  GRACIOUS LIVING ON OVER TWO ACRES NEAR CHATHAM BEACHES AND BELOVED DINING DESTINATIONS // Space, Luxury, Convenience! This impressive home, situated on 2.07 acres in a quiet cul-de-sac, is just minutes away from restaurants, the Chatham bike path, and nearby Chatham beaches. Built by Eastward Companies in 2014, this home offers a tremendous sense of living space, spanning 5,578 square feet, and

  Chris Rhinesmith Compass Massachusetts, LLC

  67 Uncle Alberts Dr, Chatham, MA 02633
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  $2,295,000

  • 3 Beds
  • 3.5 Baths
  • 1,863 Sq Ft

  16 Little Beach Rd, Chatham, MA 02633

  OFFERED FULLY FURNISHED AND READY FOR SUMMER OCCUPANCY. Immerse yourself in the ultimate beach lifestyle. Superbly located in a highly desirable Lighthouse Beach neighborhood, this luxurious beach house built in 2018 was extensively refreshed in 2023 with all new bathrooms, appliances, light and plumbing fixtures, smart technology and exterior curb appeal. The interiors are both elegant and

  Chris Rhinesmith Compass Massachusetts, LLC

  16 Little Beach Rd, Chatham, MA 02633
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  $1,750,000

  • 1 Bath
  • 2,586 Sq Ft

  231 Crowell Rd, Chatham, MA 2633

  Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

  Judith Smith John C. Ricotta & Associates, Inc.

  231 Crowell Rd, Chatham, MA 2633
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  $13,950,000

  • 5 Beds
  • 6.5 Baths
  • 7,259 Sq Ft

  301 Whidah Rd, Chatham, MA 02650

  Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  301 Whidah Rd, Chatham, MA 02650
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  /90

  $13,950,000

  • 5 Beds
  • 6.5 Baths
  • 7,259 Sq Ft

  301 Whidah Rd, North Chatham, MA 2650

  Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  301 Whidah Rd, North Chatham, MA 2650
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  /23

  $399,000

  • 1 Bed
  • 1 Bath
  • 696 Sq Ft

  109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
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  $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
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  /2

  $6,995,000 New Construction

  • 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

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