9,682

Chatham, MA Homes

Section Image
    • 32 Little Beach Rd, Chatham, MA 02633
      32 Little Beach Rd, Chatham, MA 02633
      32 Little Beach Rd, 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
  • 0 Crows Pond Rd, Chatham, MA 02633
    0 Crows Pond Rd, Chatham, MA 02633
    0 Crows Pond Rd, 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

    Jen Pappalardo Christie's International Real Estate Atlantic Brokerage

    0 Crows Pond Rd, Chatham, MA 02633
  • 43 Chatham Heights Rd, Chatham, MA 02633
    43 Chatham Heights Rd, Chatham, MA 02633
    43 Chatham Heights Rd, Chatham, MA 02633
    /46

    $4,000,000 Sold Feb 21, 2025

    43 Chatham Heights Rd, Chatham, MA 02633

    • 5 Beds
    • 4.5 Baths
    • 4,195 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $954/SF
    • 2 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    43 Chatham Heights Rd, Chatham, MA 02633
    • 16 Windmill Ln, Chatham, MA 02633
      16 Windmill Ln, Chatham, MA 02633
      16 Windmill Ln, Chatham, MA 02633
      /53

      Est $2,711,121 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
  • 23 Shane Dr, Chatham, MA 02633
    23 Shane Dr, Chatham, MA 02633
    23 Shane Dr, Chatham, MA 02633
    /41

    $749,999

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    23 Shane Dr, Chatham, MA 02633

    Welcome to 23 Shane Dr, where coastal elegance meets everyday comfort. This charming single-level home offers 3 spacious bedrooms and 2 baths, perfectly blending modern convenience with classic character. Imagine relaxing by the cozy fireplace, or enjoying a good book from the built-in bookshelves that add a touch of sophistication to your living space. In addition to bright and airy bedrooms,

    Samantha Edwards Compass

    23 Shane Dr, Chatham, MA 02633
  • 1 Seastrand Way Unit 8, Chatham, MA 02633
    1 Seastrand Way Unit 8, Chatham, MA 02633
    1 Seastrand Way Unit 8, Chatham, MA 02633
    /48

    $582,500 Sold May 02, 2025

    1 Seastrand Way Unit 8, Chatham, MA 02633

    • 2 Beds
    • 1.5 Baths
    • 1,017 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $573/SF
    • 14 Days On Market

    Current Estimated Value $580,911

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    1 Seastrand Way Unit 8, Chatham, MA 02633
    • 43 Morris Island Rd, Chatham, MA 02633
      43 Morris Island Rd, Chatham, MA 02633
      43 Morris Island Rd, 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
  • 200 Hardings Beach Rd, Chatham, MA 02633
    200 Hardings Beach Rd, Chatham, MA 02633
    200 Hardings Beach Rd, Chatham, MA 02633
    /30

    $1,495,000 Pending

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

    200 Hardings Beach Rd, Chatham, MA 02633

    Located just a short stroll to Hardings Beach and close to many favorite local restaurants and conveniences, this classic Cape style two story cottage offers the option of summer or year-round living as well as a a rental investment opportunity. With 4 bedrooms and 2 full baths, the layout is designed for easy living, with bedrooms on both levels and full baths conveniently located adjacent to

    Chris Rhinesmith Compass Massachusetts, LLC

    200 Hardings Beach Rd, Chatham, MA 02633
  • 96 Island View Ln, South Chatham, MA 02659
    96 Island View Ln, South Chatham, MA 02659
    96 Island View Ln, South Chatham, MA 02659
    /28

    $795,000 Sold Jul 07, 2025

    96 Island View Ln, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 1975

    Last Sold Summary

    • 10% Below List Price
    • $475/SF
    • 20 Days On Market

    Current Estimated Value $835,531

    Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    96 Island View Ln, South Chatham, MA 02659
    • 32 Cranberry Ln, Chatham, MA 02633
      32 Cranberry Ln, Chatham, MA 02633
      32 Cranberry Ln, Chatham, MA 02633
      /20

      Est $2,241,065 Not Listed For Sale

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

      32 Cranberry Ln, Chatham, MA 02633

      32 Cranberry Ln, Chatham, MA 02633
  • 99 A Leonard Way, Chatham, MA 02633
    99 A Leonard Way, Chatham, MA 02633
    99 A Leonard Way, Chatham, MA 02633
    /6

    $850,000

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

    99 A Leonard Way, Chatham, MA 02633

    Living the Cape Cod Dream: Relocating to ChathamHave you ever dreamed of waking up to salty sea air, scenic harbor views, and small-town charm? If so, relocating to Chatham, Massachusetts might just be the lifestyle upgrade you’ve been searching for. Nestled on the elbow of Cape Cod, Chatham blends coastal beauty with historic character, offering residents a unique mix of peace, recreation, and

    Terry Hayes The Paladin Group, LLC

    99 A Leonard Way, Chatham, MA 02633
  • 912 Main St Unit 305, Chatham, MA 02633
    912 Main St Unit 305, Chatham, MA 02633
    912 Main St Unit 305, Chatham, MA 02633
    /30

    $507,000 Sold Jul 25, 2025

    912 Main St Unit 305, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft
    • Built 1999

    Last Sold Summary

    • 15% Above List Price
    • $392/SF
    • 5 Days On Market

    Current Estimated Value $476,513

    Last Listing Agent Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 305, Chatham, MA 02633
    • 48 Salt Marsh Way, North Chatham, MA 02650
      48 Salt Marsh Way, North Chatham, MA 02650
      48 Salt Marsh Way, North Chatham, MA 02650
      /45

      Est $3,207,003 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
  • 2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    /4

    $315,000

    • Land
    • 1.07 Acres
    • $294,393 per Acre

    2386 Main St, South Chatham, MA 02659

    This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

    Judith Smith John C Ricotta & Assoc.

    2386 Main St, South Chatham, MA 02659
  • 38 Andover Dr, Chatham, MA 02633
    38 Andover Dr, Chatham, MA 02633
    38 Andover Dr, Chatham, MA 02633
    /34

    $674,000 Sold Oct 31, 2025

    38 Andover Dr, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 1,244 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $542/SF
    • 6 Days On Market

    Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    38 Andover Dr, Chatham, MA 02633
    • 39 Windward Passage, North Chatham, MA 02650
      39 Windward Passage, North Chatham, MA 02650
      39 Windward Passage, North Chatham, MA 02650
      /41

      Est $1,717,354 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
  • 404 Stage Harbor Rd, Chatham, MA 02633
    404 Stage Harbor Rd, Chatham, MA 02633
    404 Stage Harbor Rd, Chatham, MA 02633
    /94

    $2,995,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,905 Sq Ft

    404 Stage Harbor Rd, Chatham, MA 02633

    This stunning cedar-shingled, four-bedroom residence is just a short stroll from beautiful Chatham Village, Oyster Pond, and Stage Harbor. The home features many custom updates, numerous amenities, and fine details throughout. Custom tile work and high-end finishes create a luxurious atmosphere. The cozy interior exudes a beach cottage ambiance, highlighted by a great room equipped with a gas

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    404 Stage Harbor Rd, Chatham, MA 02633
  • 9 Bettys Path, Chatham, MA 02633
    9 Bettys Path, Chatham, MA 02633
    9 Bettys Path, Chatham, MA 02633
    /43

    $1,511,258 Sold Oct 01, 2025

    9 Bettys Path, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,008 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Below List Price
    • $753/SF
    • 175 Days On Market

    Last Listing Agent Shane Masaschi Compass

    9 Bettys Path, Chatham, MA 02633
    • 356 Stony Hill Rd, North Chatham, MA 02650
      356 Stony Hill Rd, North Chatham, MA 02650
      356 Stony Hill Rd, 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
  • 230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    /10

    $4,399,000 New Construction

    • 4 Beds
    • 6 Baths
    • 5,800 Sq Ft

    230 Barcliff Ave, Chatham, MA 02633

    Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The 5800 sf home will offer the best in new amenities with a

    Lori Fanning Smith Compass Massachusetts, LLC

    230 Barcliff Ave, Chatham, MA 02633
  • 372 Fox Hill Rd, Chatham, MA 02633
    372 Fox Hill Rd, Chatham, MA 02633
    372 Fox Hill Rd, Chatham, MA 02633
    /34

    $5,250,000 Sold May 09, 2025

    372 Fox Hill Rd, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 2,214 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $2,371/SF
    • 3 Days On Market

    Current Estimated Value $4,034,794

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    372 Fox Hill Rd, Chatham, MA 02633
    • 98 Orleans Rd, Chatham, MA 02633
      98 Orleans Rd, Chatham, MA 02633
      98 Orleans Rd, Chatham, MA 02633
      /40

      Est $1,862,226 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
  • 319 Riverview Dr, Chatham, MA 02633
    319 Riverview Dr, Chatham, MA 02633
    319 Riverview Dr, Chatham, MA 02633
    /29

    $1,195,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,202 Sq Ft

    319 Riverview Dr, Chatham, MA 02633

    Sited on nearly an acre of land in Riverbay Estates, this spacious 3 bedroom, 3 bath home offers ample privacy and outdoor living space. Built in 1984 with an addition & updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite with gas fireplace, walk in closet, & outdoor access. The kitchen features abundant cabinet space, a

    Chris Rhinesmith Compass Massachusetts, LLC

    319 Riverview Dr, Chatham, MA 02633
  • 314 Cockle Cove Rd, Chatham, MA 02659
    314 Cockle Cove Rd, Chatham, MA 02659
    314 Cockle Cove Rd, Chatham, MA 02659
    /48

    $2,950,000 Sold Dec 02, 2025

    314 Cockle Cove Rd, Chatham, MA 02659

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $946/SF
    • 13 Days On Market

    Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    314 Cockle Cove Rd, Chatham, MA 02659
    • 6 Palmer Dr, Chatham, MA 02633
      6 Palmer Dr, Chatham, MA 02633
      6 Palmer Dr, Chatham, MA 02633
      /30

      Est $1,181,991 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,702 Sq Ft

      6 Palmer Dr, Chatham, MA 02633

      6 Palmer Dr, Chatham, MA 02633
  • 425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    /25

    $495,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula “It’s All About Me,” Unit D at 425 Main Street offers a rare blend of privacy, comfort, and true in-town living. One of only two residences on the second floor, it features a discreet private entrance and an open, light-filled layout with recent upgrades, including luxury vinyl flooring and refreshed finishes. The well-appointed kitchen flows into a spacious living and

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 54 Rowland Dr, North Chatham, MA 02650
    54 Rowland Dr, North Chatham, MA 02650
    54 Rowland Dr, North Chatham, MA 02650
    /50

    $1,200,000 Sold Apr 30, 2025

    54 Rowland Dr, North Chatham, MA 02650

    • 4 Beds
    • 3.5 Baths
    • 2,062 Sq Ft
    • Built 1970

    Last Sold Summary

    • 33% Below List Price
    • $582/SF
    • 282 Days On Market

    Current Estimated Value $1,306,431

    Last Listing Agent Barbara Garside eXp Realty, LLC

    54 Rowland Dr, North Chatham, MA 02650
    • 184 Barcliff Ave, Chatham, MA 02633
      184 Barcliff Ave, Chatham, MA 02633
      184 Barcliff Ave, Chatham, MA 02633
      /60

      Est $3,168,969 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,298 Sq Ft

      184 Barcliff Ave, Chatham, MA 02633

      184 Barcliff Ave, Chatham, MA 02633
  • 22 Pine Knoll Ave, Chatham, MA 02633
    22 Pine Knoll Ave, Chatham, MA 02633
    22 Pine Knoll Ave, Chatham, MA 02633
    /10

    $549,000

    • 3 Beds
    • 0.5 Baths
    • 1 Sq Ft

    22 Pine Knoll Ave, Chatham, MA 02633

    First time offered for sale in over 50 years! Welcome to this charming 3 bedroom 1 bath quintessential summer cottage located in the seaside town of Chatham just steps away from Ridgevale Beach. Inside you will find 2 comfortable bedrooms with a 3rd bedroom being used as a flex space as well as a cozy inviting living room. Outside the deck offers plenty of room to enjoy morning coffee and the

    Brian Mullen Options 153, LLC

    22 Pine Knoll Ave, Chatham, MA 02633
  • 290 Old Comers Rd, Chatham, MA 02633
    290 Old Comers Rd, Chatham, MA 02633
    290 Old Comers Rd, Chatham, MA 02633
    /40

    $2,400,000 Sold Oct 30, 2025

    290 Old Comers Rd, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 3,603 Sq Ft
    • Built 2005

    Last Sold Summary

    • 26% Below List Price
    • $666/SF
    • 246 Days On Market

    Last Listing Agent Catherine Baran Berkshire Hathaway HomeServices Robert Paul Properties

    290 Old Comers Rd, Chatham, MA 02633
    • 390 Old Harbor Rd, Chatham, MA 02633
      390 Old Harbor Rd, Chatham, MA 02633
      390 Old Harbor Rd, Chatham, MA 02633
      /53

      Est $2,377,056 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,670 Sq Ft

      390 Old Harbor Rd, Chatham, MA 02633

      390 Old Harbor Rd, Chatham, MA 02633
  • 24 Chickadee Ln, Chatham, MA 02633
    24 Chickadee Ln, Chatham, MA 02633
    24 Chickadee Ln, Chatham, MA 02633
    /44

    $995,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,504 Sq Ft

    24 Chickadee Ln, Chatham, MA 02633

    Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

    Amy Harbeck Kinlin Grover Compass

    24 Chickadee Ln, Chatham, MA 02633
  • 108 Shore Rd, Chatham, MA 02633
    108 Shore Rd, Chatham, MA 02633
    108 Shore Rd, Chatham, MA 02633
    /32

    $10,000,000 Sold Sep 24, 2025

    108 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 9 Baths
    • 6,276 Sq Ft
    • Built 1920

    Last Sold Summary

    • 16% Below List Price
    • $1,593/SF
    • 67 Days On Market

    Last Listing Agent Frank Denauw Frank G. Denauw, Esq.

    108 Shore Rd, Chatham, MA 02633
    • 581 Shore Rd, Chatham, MA 02633
      581 Shore Rd, Chatham, MA 02633
      581 Shore Rd, Chatham, MA 02633
      /74

      Est $5,492,011 Not Listed For Sale

      • 5 Beds
      • 6.5 Baths
      • 4,452 Sq Ft

      581 Shore Rd, Chatham, MA 02633

      581 Shore Rd, Chatham, MA 02633
  • 39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    /15

    $675,000

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft

    39 Meadow Brook Rd, Chatham, MA 02650

    Location! Location! Location! This Freshly painted charming North Chatham gem, remodeled in 2024, offers 768 sq/ft of living space and is located conveniently to the Cape Cod Rail trail, for recreational fun. Enjoy single story living in this 2 bedroom 1 bath home with hardwood floors and a fireplace. There is a 768 sq/ft walkout basement currently used as a single car garage which also has great

    Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    39 Meadow Brook Rd, Chatham, MA 02650
  • 44 Emery Ln, North Chatham, MA 02650
    44 Emery Ln, North Chatham, MA 02650
    44 Emery Ln, North Chatham, MA 02650
    /31

    $1,700,000 Sold Nov 17, 2025

    44 Emery Ln, North Chatham, MA 02650

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1983

    Last Sold Summary

    • $975/SF
    • 34 Days On Market

    Last Listing Agent Kathleen Phelan Compass

    44 Emery Ln, North Chatham, MA 02650
    • 30 Oceanview Terrace, Chatham, MA 02633
      30 Oceanview Terrace, Chatham, MA 02633
      30 Oceanview Terrace, Chatham, MA 02633
      /10

      Est $916,736 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 648 Sq Ft

      30 Oceanview Terrace, Chatham, MA 02633

      30 Oceanview Terrace, Chatham, MA 02633
  • 36 Moonbeam Ln, Chatham, MA 02633
    36 Moonbeam Ln, Chatham, MA 02633
    36 Moonbeam Ln, Chatham, MA 02633
    /42

    $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 area just 5 minutes to Town and includes deeded rights to the Oyster Pond River. You’ll enjoy 4,857 square feet of casual elegance in a thoughtfully-designed floor plan. This immaculate home offers 4 spacious BRs including a first-floor primary suite. Sunny granite & stainless kitchen opens to the family room w/fireplace.

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    36 Moonbeam Ln, Chatham, MA 02633
  • 22 Cahoons Hollow, Chatham, MA 02633
    22 Cahoons Hollow, Chatham, MA 02633
    22 Cahoons Hollow, Chatham, MA 02633
    /31

    $2,350,000 Sold Jan 25, 2025

    22 Cahoons Hollow, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 2% Below List Price
    • $904/SF
    • 78 Days On Market

    Last Listing Agent Chris Rhinesmith Compass

    22 Cahoons Hollow, Chatham, MA 02633
    • 111 Barcliff Ave, Chatham, MA 02633
      111 Barcliff Ave, Chatham, MA 02633
      111 Barcliff Ave, Chatham, MA 02633
      /64

      Not Listed For Sale

      • 8 Beds
      • 4.5 Baths
      • 4,413 Sq Ft

      111 Barcliff Ave, Chatham, MA 02633

      111 Barcliff Ave, Chatham, MA 02633

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Massachusetts Barnstable County Chatham

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