9,675

Chatham, MA Homes

Section Image
    • 6 Palmer Dr, Chatham, MA 02633
      6 Palmer Dr, Chatham, MA 02633
      6 Palmer Dr, Chatham, MA 02633
      /30

      Est $1,209,125 Not Listed For Sale

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

      6 Palmer Dr, Chatham, MA 02633

      6 Palmer Dr, Chatham, MA 02633
  • 24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    /41

    $995,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft

    24 Chickadee Cir, Harwich, MA 02645

    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 Cir, Harwich, MA 02645
  • 15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    /36

    $899,000 Sold Jan 02, 2026

    15 Sylvan Way, South Chatham, MA 02659

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft
    • Built 2002

    Last Sold Summary

    • 16% Below List Price
    • $511/SF
    • 70 Days On Market

    Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty

    15 Sylvan Way, South Chatham, MA 02659
    • 184 Barcliff Ave, Chatham, MA 02633
      184 Barcliff Ave, Chatham, MA 02633
      184 Barcliff Ave, Chatham, MA 02633
      /60

      Est $2,964,504 Not Listed For Sale

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

      184 Barcliff Ave, Chatham, MA 02633

      184 Barcliff Ave, 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 an exceptional blend of privacy, comfort, and in-town convenience. This updated 1-bedroom, 1-bath residence is one of only two homes on the second floor, accessed by a discreet private entrance that enhances its quiet, retreat-like feel. Inside, an open-concept layout is filled with natural light and features recent

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, 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
    • 390 Old Harbor Rd, Chatham, MA 02633
      390 Old Harbor Rd, Chatham, MA 02633
      390 Old Harbor Rd, Chatham, MA 02633
      /53

      Est $2,365,317 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
  • 2548 Main St, South Chatham, MA 2659
    2548 Main St, South Chatham, MA 2659
    /2

    $3,999,900 New Construction

    • 4 Beds
    • 5.5 Baths
    • 3,713 Sq Ft

    2548 Main St, South Chatham, MA 2659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers. Incorporating expansive open living space you will enjoy entertaining family

    Ward Brown William Raveis Real Estate & Home Services

    2548 Main St, South Chatham, MA 2659
  • 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
    • 581 Shore Rd, Chatham, MA 02633
      581 Shore Rd, Chatham, MA 02633
      581 Shore Rd, Chatham, MA 02633
      /74

      Est $5,307,216 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
  • 0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    /7

    $250,000 Pending

    • Land
    • 0.72 Acre
    • $347,222 per Acre

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

    Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

    Shane Masaschi Compass

    0 George Ryder Rd Unit 73104629, 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

    $510,000 Sold Jan 20, 2026

    22 Pine Knoll Ave, Chatham, MA 02633

    • 3 Beds
    • 0.5 Baths
    • 532 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $959/SF
    • 0 Days On Market

    Last Listing Agent Brian Mullen Options 153, LLC

    22 Pine Knoll Ave, Chatham, MA 02633
    • 30 Oceanview Terrace, Chatham, MA 02633
      30 Oceanview Terrace, Chatham, MA 02633
      30 Oceanview Terrace, Chatham, MA 02633
      /10

      Est $991,814 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 648 Sq Ft

      30 Oceanview Terrace, Chatham, MA 02633

      30 Oceanview Terrace, Chatham, MA 02633
  • 49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    /36

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    49 Duck Marsh Ln, Chatham, MA 02633

    Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

    Tim Bailey John C Ricotta & Assoc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • 169 Shore Rd, Chatham, MA 02633
    169 Shore Rd, Chatham, MA 02633
    169 Shore Rd, Chatham, MA 02633
    /35

    $5,000,000 Sold Mar 07, 2025

    169 Shore Rd, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 3,319 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $1,506/SF
    • 3 Days On Market

    Current Estimated Value $7,136,319

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    169 Shore Rd, 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
  • 99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    /33

    $5,495,000

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    99 Uncle Alberts Drive Extension, Chatham, MA 2633

    Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

    Shane Masaschi Compass

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • 912 Main St Unit 304, Chatham, MA 02633
    912 Main St Unit 304, Chatham, MA 02633
    912 Main St Unit 304, Chatham, MA 02633
    /28

    $461,260 Sold Nov 10, 2025

    912 Main St Unit 304, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $375/SF
    • 4 Days On Market

    Last Listing Agent Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 304, Chatham, MA 02633
    • 39 Seaview Terrace, Chatham, MA 02633
      39 Seaview Terrace, Chatham, MA 02633
      39 Seaview Terrace, Chatham, MA 02633
      /35

      Est $4,421,112 Not Listed For Sale

      • 4 Beds
      • 6.5 Baths
      • 3,533 Sq Ft

      39 Seaview Terrace, Chatham, MA 02633

      39 Seaview Terrace, Chatham, MA 02633
  • 28 Cranberry Ln, North Chatham, MA 02650
    28 Cranberry Ln, North Chatham, MA 02650
    28 Cranberry Ln, North Chatham, MA 02650
    /58

    $3,295,000 Pending

    • 3 Beds
    • 4.5 Baths
    • 3,759 Sq Ft

    28 Cranberry Ln, North Chatham, MA 02650

    Perfectly sited in sought-after North Chatham, this new construction home is a masterwork of coastal design. The entryway sets a refined tone, opening to a great room with shiplapped and coffered ceilings that create balance and elegance. At one end, a clean-lined kitchen boasts custom cabinetry, a striking quartz island, and premium Thermador and Fisher & Paykel appliances. A dining area flows

    Chris Rhinesmith Compass Massachusetts, LLC

    28 Cranberry Ln, North Chatham, MA 02650
  • 86 Vineyard Ave, Chatham, MA 02633
    86 Vineyard Ave, Chatham, MA 02633
    86 Vineyard Ave, Chatham, MA 02633
    /12

    $750,000 Sold May 30, 2025

    86 Vineyard Ave, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,625 Sq Ft
    • Built 1947

    Last Sold Summary

    • 12% Below List Price
    • $286/SF
    • 24 Days On Market

    Current Estimated Value $874,150

    Last Listing Agent Phyllis Power Compass

    86 Vineyard Ave, Chatham, MA 02633
    • 84 Doane Rd, Chatham, MA 02633
      84 Doane Rd, Chatham, MA 02633
      84 Doane Rd, Chatham, MA 02633
      /11

      Est $5,193,930 Not Listed For Sale

      • 5 Beds
      • 9 Baths
      • 5,750 Sq Ft

      84 Doane Rd, Chatham, MA 02633

      84 Doane Rd, Chatham, MA 02633
  • 238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    /36

    $7,200,000

    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, Chatham, MA 02633

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, Chatham, MA 02633
  • 20 Judys Ln, South Chatham, MA 2659
    20 Judys Ln, South Chatham, MA 2659
    20 Judys Ln, South Chatham, MA 2659
    /47

    $1,095,000 Sold Jul 18, 2025

    20 Judys Ln, South Chatham, MA 2659

    • 3 Beds
    • 1.5 Baths
    • 1,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $1,029/SF
    • 12 Days On Market

    Current Estimated Value $1,078,210

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

    20 Judys Ln, South Chatham, MA 2659
    • 22 Cahoons Hollow Rd, Chatham, MA 02633
      22 Cahoons Hollow Rd, Chatham, MA 02633
      22 Cahoons Hollow Rd, Chatham, MA 02633
      /31

      Est $2,462,060 Not Listed For Sale

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

      22 Cahoons Hollow Rd, Chatham, MA 02633

      22 Cahoons Hollow Rd, Chatham, MA 02633
  • 2550 Main St, South Chatham, MA 02659
    2550 Main St, South Chatham, MA 02659
    /2

    $3,999,900 New Construction

    • 3 Beds
    • 4.5 Baths
    • 4,393 Sq Ft

    2550 Main St, South Chatham, MA 02659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer. Incorporating expansive open living space you will

    Ward Brown William Raveis Real Estate & Home Services

    2550 Main St, South Chatham, MA 02659
  • 30 Monomessat Way, Chatham, MA 02633
    30 Monomessat Way, Chatham, MA 02633
    30 Monomessat Way, Chatham, MA 02633
    /3

    $1,370,000 Sold Jul 17, 2025

    30 Monomessat Way, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $476/SF
    • 18 Days On Market

    Current Estimated Value $1,412,170

    Last Listing Agent Jan Pulit Kinlin Grover Compass

    30 Monomessat Way, Chatham, MA 02633
    • 31 Mill Pond Rd, Chatham, MA 02633
      31 Mill Pond Rd, Chatham, MA 02633
      31 Mill Pond Rd, Chatham, MA 02633
      /37

      Est $2,039,286 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,896 Sq Ft

      31 Mill Pond Rd, Chatham, MA 02633

      31 Mill Pond Rd, Chatham, MA 02633
  • 56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    /32

    $1,599,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,392 Sq Ft

    56 Skyline Dr, Chatham, MA 02633

    Enjoy breezy summer days and lots of lake time from this updated 4 Bedroom home located on Great Hill. With deeded rights to Lovers Lake and lake access less than 100 yards outside your door, this classic cape style home invites family fun & enjoying nature all year long. Updates include granite/stainless kitchen w/ breakfast bar, a great room / rec room w/ vaulted beamed ceiling, french doors,

    Janet Stuart Coldwell Banker Realty - Concord

    56 Skyline Dr, Chatham, MA 02633
  • 58 Diane Dr, Chatham, MA 02633
    58 Diane Dr, Chatham, MA 02633
    58 Diane Dr, Chatham, MA 02633
    /52

    $970,000 Sold Feb 07, 2025

    58 Diane Dr, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 1,331 Sq Ft
    • Built 1947

    Last Sold Summary

    • 10% Below List Price
    • $729/SF
    • 51 Days On Market

    Current Estimated Value $1,032,923

    Last Listing Agent A Cape Life Today Real Estate

    58 Diane Dr, Chatham, MA 02633
    • 81 Mill Pond Rd, Chatham, MA 02633
      81 Mill Pond Rd, Chatham, MA 02633
      81 Mill Pond Rd, Chatham, MA 02633
      /59

      Est $3,131,127 Not Listed For Sale

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

      81 Mill Pond Rd, Chatham, MA 02633

      81 Mill Pond Rd, Chatham, MA 02633
  • 0 Tirrells Way, Chatham, MA 02659
    0 Tirrells Way, Chatham, MA 02659
    0 Tirrells Way, Chatham, MA 02659
    /7

    $315,000 Pending

    • Land
    • 0.47 Acre
    • $670,213 per Acre

    0 Tirrells Way, Chatham, MA 02659

    Building lot available! Privately located at the end of a cul-de-sac and abutting the Town Forest. Water Department has an easement for a road over the property at the edge of the lot boundary. All due diligence required for building allowances and restrictions are responsibility of the buyer. See the document section for engineering information and a rendering for the type of home that can be

    Kathy Doyle Gibson Sotheby's International Realty

    0 Tirrells Way, Chatham, MA 02659
  • 109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    /27

    $349,999 Sold Feb 02, 2026

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

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $503/SF
    • 76 Days On Market

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    • 8 Oyster Dr, Chatham, MA 02633
      8 Oyster Dr, Chatham, MA 02633
      8 Oyster Dr, Chatham, MA 02633
      /35

      Est $1,197,350 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 748 Sq Ft

      8 Oyster Dr, Chatham, MA 02633

      8 Oyster Dr, Chatham, MA 02633
  • 78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    /35

    $2,800,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    78 Indian Trail, Chatham, MA 02633

    Professional photos coming soon!Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in beautiful water views and unforgettable sunsets, with private stairs leading down to the water's edge of Bucks Creek

    Judith Smith John C Ricotta & Assoc.

    78 Indian Trail, Chatham, MA 02633
  • 25 Wikis Way, Chatham, MA 02633
    25 Wikis Way, Chatham, MA 02633
    25 Wikis Way, Chatham, MA 02633
    /32

    $5,750,000 Sold Sep 30, 2025

    25 Wikis Way, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 4,654 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $1,235/SF
    • 107 Days On Market

    Current Estimated Value $5,894,179

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
    • 16 Starfish Ln, Chatham, MA 02633
      16 Starfish Ln, Chatham, MA 02633
      16 Starfish Ln, Chatham, MA 02633
      /22

      Est $706,649 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft

      16 Starfish Ln, Chatham, MA 02633

      16 Starfish Ln, Chatham, MA 02633
  • 0 Evergreen Ln, Chatham, MA 02633
    0 Evergreen Ln, Chatham, MA 02633
    0 Evergreen Ln, Chatham, MA 02633
    /5

    $399,000

    • Land
    • 0.84 Acre
    • $475,000 per Acre

    0 Evergreen Ln, Chatham, MA 02633

    .8 Acres- In the Heart of it All- Chatham- where you want your Family Memories to be made- Ridgevale Beach- Hardings Beach- Landings and Marinas close by- Private and Wooded Lot- Imagine building your dream Summer Home or Fulltime Residence and waking up to privacy and just minutes to Nantucket Sound- Oyster River- Goose Pond- School House Pond and more... South of Route 28-Building Information

    Noreen Kennedy Kennedy Real Estate

    0 Evergreen Ln, Chatham, MA 02633
  • 450 Main St, Chatham, MA 02633
    450 Main St, Chatham, MA 02633
    450 Main St, Chatham, MA 02633
    /29

    $3,400,000 Sold Dec 30, 2025

    450 Main St, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 7,396 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $460/SF
    • 55 Days On Market

    Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, Chatham, MA 02633
    • 52 Wentworth Ln, North Chatham, MA 02650
      52 Wentworth Ln, North Chatham, MA 02650
      52 Wentworth Ln, North Chatham, MA 02650
      /54

      Est $1,835,462 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,352 Sq Ft

      52 Wentworth Ln, North Chatham, MA 02650

      52 Wentworth Ln, North Chatham, MA 02650

Showing Results 81 - 120, Page 3 of 18

Massachusetts Barnstable County Chatham

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