Chatham, MA Homes

• 

  

  

  /41

  $1,795,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,514 Sq Ft

  24 Shattuck Place, Chatham, MA 02633

  Nestled on a quiet street in the heart of downtown Chatham, 24 Shattuck Place is a beautifully maintained 4-bedroom, 2.5-bath home offered fully furnished and turnkey. The thoughtful floor plan includes a first-floor primary suite, an updated kitchen, central air, and a new hot water heater and gas furnace. 3 additional bedrooms and full bath on the second level offer flexibility and privacy from

  Charles King Real Broker MA, LLC

  24 Shattuck Place, Chatham, MA 02633
• 

  

  

  /35

  $1,095,000 Sold Jul 18, 2025

  • 1,064 Sq Ft
  • $1,029/SF
  • 12 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  20 Judys Ln, Chatham, MA 02633

  Welcome Summer from this charming beach home, beautifully renovated in 2020 with coastal accents and modern updates. Vaulted ceilings in an open floor plan create an airy feel; where original knotty pine blends nicely with shiplap and bleached wood floors throughout. A bright living room with fireplace is adjacent to a like-new quartz & stainless kitchen with nearby casual dining. There are 3

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  20 Judys Ln, Chatham, MA 02633
• 

  

  

  /32

  Est $336,664 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 975 Sq Ft

  912 Main St Unit 204, Chatham, MA 02633

  912 Main St Unit 204, Chatham, MA 02633
• 

  

  

  /42

  $1,995,000 Pending

  • 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
• 

  

  

  /3

  $1,370,000 Sold Jul 17, 2025

  • 2,877 Sq Ft
  • $476/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  30 Monomessat Way, Chatham, MA 02633

  A truly exceptional residence, nestled in the picturesque town of Chatham. This impeccably maintained home offers a harmonious blend of elegance and comfort, surrounded by lovely landscaped grounds. The heart of the home is the family room, with cathedral ceiling and a magnificent stone fireplace. A cook's kitchen includes a sub zero refrigerator and breakfast bar. Adjacent to the kitchen is a

  Jan Pulit Kinlin Grover Compass

  30 Monomessat Way, Chatham, MA 02633
• 

  

  /30

  Est $421,259 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  912 Main St Unit 203, Chatham, MA 02633

  912 Main St Unit 203, Chatham, MA 02633
• 

  

  /31

  $1,699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  44 Emery Ln, North Chatham, MA 02650

  Welcome to 44 Emery Lane is North Chatham! This welcoming sunny 3 bedroom cape on .7 level acres is sure to please, especially given its excellent location. Walk to historic Old Harbor road and stop by Cow Yard beach to get your feet wet, or saunter over to Scatteree point and take a few casts....This is what living in Chatham is about. Hardwood floors greet you along with a wood burning

  Kathleen Phelan Compass

  44 Emery Ln, North Chatham, MA 02650
• 

  

  /40

  $900,000 Sold Jul 11, 2025

  • 1,344 Sq Ft
  • $670/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  100 Potonumecot Rd, Chatham, MA 02633

  Now is your opportunity to own in the Riverbay community. Situated on a lovely corner lot with a park-like yard, this 3-bedroom, 2 bath home is ideal for one floor living.The layout consists of a kitchen with a vaulted ceiling and skylights, an adjoining dining area and a living room with a gas fireplace. There are three spacious bedrooms and two baths. The primary bedroom is bright and airy

  Andy Falconio Kinlin Grover Compass

  100 Potonumecot Rd, Chatham, MA 02633
• 

  

  /10

  Est $387,945 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft

  912 Main St Unit 202, Chatham, MA 02633

  912 Main St Unit 202, Chatham, MA 02633
• 

  

  /31

  $895,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,097 Sq Ft

  558 Riverview Dr, Chatham, MA 02633

  Located in Chatham's desirable Riverbay, this two bedroom, two bath, 2,097 sq. ft. residence rests on a private, irrigated .91-acre lot with mature plantings. The kitchen with laundry opens to a welcoming fireplace family room, while the adjoining dining room flows to a bright living room featuring wood floors, a second fireplace, bay window, and window seat overlooking the tranquil back yard. A

  Chris Rhinesmith Compass Massachusetts, LLC

  558 Riverview Dr, Chatham, MA 02633
• 

  

  /73

  $2,685,000 Sold Jul 09, 2025

  • 3,056 Sq Ft
  • $879/SF
  • 13 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  7 Colonial Dr, Chatham, MA 02633

  A Chatham Beauty! Welcome to 7 Colonial Drive, a distinguished residence within one of Eastward Company's sought after residential communities. This expanded Cape home, being sold fully furnished, has been thoughtfully updated for today's lifestyle...offering 4 bedrooms, 2.5 baths and three levels of living. The main level features a bright living room with fireplace, open dining with direct

  Pam Roberts Gibson Sotheby's International Realty

  7 Colonial Dr, Chatham, MA 02633
• 

  

  /38

  Est $593,436 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  912 Main St Unit 101, Chatham, MA 02633

  912 Main St Unit 101, Chatham, MA 02633
• 

  

  /30

  $5,295,000 Pending

  • 4 Beds
  • 6 Baths
  • 4,989 Sq Ft

  14 Pond View Ln, Chatham, MA 02633

  Sears Point Development presents another breathtaking home that could be your new year-round residence or the perfect summer escape for 2026. With panoramic water views of the Oyster Pond and Oyster River and deeded access to the Oyster Pond with mooring potential, this stunning Nantucket-style home boasts 4,989 sf of thoughtfully designed living space, featuring 4 BR and 4/2 Baths on town sewer.

  Jack Bohman Gibson Sotheby's International Realty

  14 Pond View Ln, Chatham, MA 02633
• 

  

  /28

  $795,000 Sold Jul 07, 2025

  • 1,672 Sq Ft
  • $475/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  96 Island View Ln, South Chatham, MA 02659

  Attention Builders! This 3 BR, 2 Bath Cape offers curb appeal and a desirable cul-de-sac neighborhood location just 8/10 mile to Cockle Cove Beach. Huge potential awaits to create your Chatham dream home; bring your ideas! Great floor plan to work with includes open living and dining, good-sized kitchen, BRs and a bath on each level, plus a 12 x 19 attic perfect for finishing. Full walk-out

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  96 Island View Ln, South Chatham, MA 02659
• 

  

  /40

  Est $1,256,291 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  920 Main St, Chatham, MA 02633

  920 Main St, Chatham, MA 02633
• 

  

  /28

  $465,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,231 Sq Ft

  912 Main St Unit 304, Chatham, MA 02633

  Welcome home to easy living at Park Place, a 62+ active senior independent living community centrally located in the quaint seaside village of Chatham! Privacy abounds in this third floor, condo offering a great floor plan, easy access to elevator, with upgrades to kitchen, two full baths and 2 bedrooms. Outdoor space includes a private balcony, community garden beds and a courtyard with mature

  Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

  912 Main St Unit 304, Chatham, MA 02633
• 

  

  /31

  $1,450,000 Sold Jul 03, 2025

  • 1,510 Sq Ft
  • $960/SF
  • 265 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1830

  450 Old Harbor Rd, Chatham, MA 02633

  Once in a lifetime are you fortunate enough to be presented with an opportunity to own beachfront property! Waterfront Haven with Seawall Bulkhead & Stunning Views of Chatham Harbor. Experience the potential of this unique waterfront property nestled along Chatham Harbor. This two-bedroom, two and a half bath home features a private sandy beach with panoramic views out to the Atlantic Ocean. The

  Barbara Garside eXp Realty, LLC

  450 Old Harbor Rd, Chatham, MA 02633
• 

  

  /25

  Est $883,791 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,644 Sq Ft

  89 Heritage Ln, Chatham, MA 02633

  89 Heritage Ln, Chatham, MA 02633
• 

  

  /42

  $9,750,000 Pending

  • 5 Beds
  • 8 Baths
  • 4,970 Sq Ft

  53 Gristmill Ln, Chatham, MA 02633

  Wake up to captivating and shimmering water views from nearly every room in this stunning Little Mill Pond home. Completely rebuilt just a few years ago with exceptional craftsmanship, it blends custom trim, cabinetry & timeless design. This residence blends coastal elegance with modern convenience, all within walking distance to the charming shops and dining of downtown Chatham. Inside, you'll

  Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

  53 Gristmill Ln, Chatham, MA 02633
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  /38

  $2,200,000 Sold Jul 03, 2025

  • 1,863 Sq Ft
  • $1,181/SF
  • 356 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  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
• 

  

  /40

  Est $821,928 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,368 Sq Ft

  199 Crowell Rd, Chatham, MA 02633

  199 Crowell Rd, Chatham, MA 02633
• 

  

  /86

  $5,750,000 Pending

  • 7 Beds
  • 3.5 Baths
  • 3,734 Sq Ft

  58 Oyster Bluff, Chatham, MA 02633

  Perched high above Oyster Pond, this generational estate--first known as ''The Beach Plum House'' and later as ''Adsamore''--is one of Chatham's rarest offerings. Set on a remarkable .93-acre parcel with expansive frontage, it offers sweeping views of town and Oyster Pond, a lifestyle at once connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, the home has been

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  58 Oyster Bluff, Chatham, MA 02633
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  /6

  $635,000 Sold Jul 01, 2025

  • 912 Sq Ft
  • $696/SF
  • 135 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1972

  127 Oak Hill Rd, Chatham, MA 02633

  Almost 1 acre in a desirable quiet neighborhood. The land provides space to remodel or update the exiting house and make it your own. House needs work and is being sold As Is. Septic Inspection completed early December- passed Title V for 3 bedroom - report attached to listing.

  Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

  127 Oak Hill Rd, Chatham, MA 02633
• 

  

  /11

  Est $908,935 Not Listed For Sale

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

  135 Crowell Rd, Chatham, MA 02633

  135 Crowell Rd, Chatham, MA 02633
• 

  

  /33

  $1,475,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,225 Sq Ft

  355 Training Field Rd, Chatham, MA 02633

  MOTIVATED SELLERS!Just 8/10 of a mile to Jackknife Point Beach, this beautifully appointed Chatham retreat offers the perfect blend of comfort, style, and solar efficiency. A charming farmer's porch welcomes you into a light-filled home with high ceilings, an open layout, and a skylit kitchen with granite counters, stainless steel appliances, and a large island. The living room features a cozy

  Margaret McDonald Mathieu Newton Sotheby's Int'l Realty

  355 Training Field Rd, Chatham, MA 02633
• 

  

  /20

  $734,000 Sold Jun 27, 2025

  • 992 Sq Ft
  • $740/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  61 Pond View Ave, Chatham, MA 02633

  Welcome to your dream Cape Cod getaway! This delightful 2-bedroom, 1-bath home is nestled in one of West Chatham’s most desirable neighborhoods. This home is just minutes from Hardings Beach, local shopping, and great dining spots. Step inside to find a warm and inviting interior with natural tones that create a relaxed, coastal feel throughout. Whether you're enjoying a quiet weekend or

  Charles Quigley Keller Williams Realty

  61 Pond View Ave, Chatham, MA 02633
• 

  

  /22

  Est $1,756,481 Not Listed For Sale

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

  14 Windsong Landing, Chatham, MA 02633

  14 Windsong Landing, Chatham, MA 02633
• 

  

  /40

  $4,895,000 Pending

  • 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
• 

  

  /58

  $1,309,000 Sold Jun 20, 2025

  • 2,590 Sq Ft
  • $505/SF
  • 1 Day On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  144 Countryside Dr, Chatham, MA 02633

  Welcome to this meticulously maintained Cape Cod gem in highly sought-after Chatham, lovingly cared for by a single family and used only seasonally until recently. Perched on a gentle slope for added privacy, this home offers a serene retreat surrounded by nature, and lush, manicured gardens with classic Cape plantings. Inside, a spacious family room with vaulted ceilings, a cozy fireplace, and

  Maureen Green Kinlin Grover Compass

  144 Countryside Dr, Chatham, MA 02633
• 

  

  /29

  Est $3,500,257 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  67 Capri Ln, Chatham, MA 02633

  67 Capri Ln, Chatham, MA 02633
• 

  

  /26

  $3,500,000 Pending

  • Land
  • 1.61 Acres
  • $2,173,913 per Acre

  111 Enterprise Dr, Chatham, MA 02633

  1.61 plus acres of Industrial Land at the Enterprise Road in Chatham, Cape Cod, MA, USA now available for sale. The land has many potential uses including light industrial, warehouse and much more. There are multiple structures on the site currently. Located within close proximity to all of Chatham and easy access to US Route 6. Encompassing a mere 16 square miles of high ground and surrounded on

  John Ciluzzi Premier Commercial

  111 Enterprise Dr, Chatham, MA 02633
• 

  

  /12

  $3,200,000 Sold Jun 20, 2025

  • 4,620 Sq Ft
  • $693/SF
  • 346 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2024

  33 Jessies Landing, Chatham, MA 02633

  Get ready for summer and enjoy the saltwater pool, spa and firepit! A new residence is in progress by Eastward Companies, showcasing exquisite details and finishes. This beautifully designed home spans over 4,600 sq. ft. and checks off many items on everyone's wish list. It features a spacious open floor plan, a gourmet kitchen with a butler's pantry, and a first-floor master suite, making it

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  33 Jessies Landing, Chatham, MA 02633
• 

  /2

  Est $2,360,269 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,037 Sq Ft

  51 Oyster Bay Ln, Chatham, MA 02633

  51 Oyster Bay Ln, Chatham, MA 02633
• 

  

  /16

  $2,499,000 Pending

  • Land
  • 2.46 Acres
  • $1,015,854 per Acre

  0 Crows Pond Rd, Chatham, MA 02633

  2.46 acre waterfront lot in Chatham with 220 feet of frontage directly on salt water Crow's Pond. Land is set on a bluff and has direct water access to Ryders Cove, Pleasant Bay, Chatham Harbor and the Atlantic Ocean. Near Eastward Ho! Country Club. Paved driveway has been installed and there is town water already on the property. Custom build the home of your dreams. Site plan and covenants are

  Jennifer Pappalardo Christie's International Real Estate Atlantic Brokerage

  0 Crows Pond Rd, Chatham, MA 02633
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  /36

  $2,100,000 Sold Jun 18, 2025

  • 2,270 Sq Ft
  • $925/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  84 Emery Ln, North Chatham, MA 02650

  Location! Location! North Chatham! Sought after Emery Lane at the top of Look Out Hill, offers privacy & the convenience of town center nearby & Cow Yard landing. The best of both worlds! This custom designed Cape built by Ted Spencer offers gracious living in the spacious 2270 Sq. ft.. The sweeping staircase foyer with skylight sets the tone for elegance and charm as you enter the open plan

  Phyllis Power Compass

  84 Emery Ln, North Chatham, MA 02650
• 

  

  /65

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,000 Sq Ft

  356 Stage Harbor Rd, Chatham, MA 02633

  356 Stage Harbor Rd, Chatham, MA 02633
• 

  

  /40

  $1,195,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  3 Oyster Dr, Chatham, MA 02633

  Welcome home to 3 Oyster Drive, a perfectly idyllic Chatham getaway! This enchanting cottage enjoys dazzling water views and a prime location near Outermost Harbor Marina, beaches, & Town. This 3 BR, 2 BA home is a blend of classic Cape Cod and some newer features and is the ideal backdrop to begin your own Chatham story. Many will find the home comfortable just the way it is, or choose to take

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  3 Oyster Dr, Chatham, MA 02633
• 

  

  /63

  $1,125,000 Sold Jun 18, 2025

  • 1,662 Sq Ft
  • $677/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  155 Cranberry Ln, Chatham, MA 02633

  First time offered! Discover your Cape Cod retreat at 155 Cranberry Lane, South Chatham. This meticulously maintained 3-bedroom, 2-bath home offers serene living on a peaceful corner lot, bordered by conservation land. Enjoy easy access to Bucks Creek via a deeded right of way, and find yourself just moments from Ridgevale Beach. Inside, you'll appreciate hardwood floors, a renovated kitchen

  Kate Plummer Today Real Estate

  155 Cranberry Ln, Chatham, MA 02633
• 

  

  /82

  Est $3,849,058 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,929 Sq Ft

  48 Strong Island Rd, Chatham, MA 02633

  48 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

Showing Results 241 - 280, Page 7 of 18