9,675

Chatham, MA Homes

Section Image
    • 41 Earles Way, Chatham, MA 02633
      41 Earles Way, Chatham, MA 02633
      41 Earles Way, Chatham, MA 02633
      /49

      Est $1,287,283 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,660 Sq Ft

      41 Earles Way, Chatham, MA 02633

      41 Earles Way, Chatham, MA 02633
  • 355 Training Field Rd, Chatham, MA 02633
    355 Training Field Rd, Chatham, MA 02633
    355 Training Field Rd, Chatham, MA 02633
    /40

    $1,475,000 Sold Nov 07, 2025

    355 Training Field Rd, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,225 Sq Ft
    • Built 2004

    Last Sold Summary

    • 10% Below List Price
    • $663/SF
    • 108 Days On Market

    Last Listing Agent Margaret McDonald Mathieu Newton Sotheby's International Realty

    355 Training Field Rd, Chatham, MA 02633
    • 88 Stepping Stones Rd, Chatham, MA 02633
      88 Stepping Stones Rd, Chatham, MA 02633
      88 Stepping Stones Rd, Chatham, MA 02633
      /47

      Est $905,907 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,501 Sq Ft

      88 Stepping Stones Rd, Chatham, MA 02633

      88 Stepping Stones Rd, Chatham, MA 02633
  • 86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    /49

    $2,830,000 Sold Jan 30, 2026

    86 Champlain Rd, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 4,361 Sq Ft
    • Built 1998

    Last Sold Summary

    • 28% Below List Price
    • $649/SF
    • 188 Days On Market

    Last Listing Agent Jack Bohman Gibson Sotheby's International Realty

    86 Champlain Rd, Chatham, MA 02633
    • 1010 Main St, Chatham, MA 02633
      1010 Main St, Chatham, MA 02633
      1010 Main St, Chatham, MA 02633
      /18

      Est $979,939 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,247 Sq Ft

      1010 Main St, Chatham, MA 02633

      1010 Main St, Chatham, MA 02633
  • 113 Seapine Rd, North Chatham, MA 02650
    113 Seapine Rd, North Chatham, MA 02650
    113 Seapine Rd, North Chatham, MA 02650
    /45

    $9,150,000 Sold Aug 28, 2025

    113 Seapine Rd, North Chatham, MA 02650

    • 4 Beds
    • 5.5 Baths
    • 5,850 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $1,564/SF
    • 155 Days On Market

    Current Estimated Value $9,210,633

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    113 Seapine Rd, North Chatham, MA 02650
    • 88 Perch Pond Dr, Chatham, MA 02633
      88 Perch Pond Dr, Chatham, MA 02633
      88 Perch Pond Dr, Chatham, MA 02633
      /34

      Est $973,212 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,129 Sq Ft

      88 Perch Pond Dr, Chatham, MA 02633

      88 Perch Pond Dr, Chatham, MA 02633
  • 80 Tisquantum Rd, Chatham, MA 02633
    80 Tisquantum Rd, Chatham, MA 02633
    80 Tisquantum Rd, Chatham, MA 02633
    /42

    $3,450,000 Sold Sep 12, 2025

    80 Tisquantum Rd, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,821 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $1,223/SF
    • 3 Days On Market

    Current Estimated Value $3,552,775

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

    80 Tisquantum Rd, Chatham, MA 02633
    • 52 Oyster Bluff, Chatham, MA 02633
      52 Oyster Bluff, Chatham, MA 02633
      52 Oyster Bluff, Chatham, MA 02633
      /76

      Est $7,652,610 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 5,219 Sq Ft

      52 Oyster Bluff, Chatham, MA 02633

      52 Oyster Bluff, Chatham, MA 02633
  • 25 Menekish Ln, Chatham, MA 02633
    25 Menekish Ln, Chatham, MA 02633
    25 Menekish Ln, Chatham, MA 02633
    /42

    $2,250,000 Sold Jun 04, 2025

    25 Menekish Ln, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 3,865 Sq Ft
    • Built 2006

    Last Sold Summary

    • 10% Below List Price
    • $582/SF
    • 28 Days On Market

    Current Estimated Value $2,373,500

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    25 Menekish Ln, Chatham, MA 02633
    • 127 Christopher Harding Ln, Chatham, MA 02633
      127 Christopher Harding Ln, Chatham, MA 02633
      127 Christopher Harding Ln, Chatham, MA 02633
      /43

      Est $3,152,628 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,416 Sq Ft

      127 Christopher Harding Ln, Chatham, MA 02633

      127 Christopher Harding Ln, Chatham, MA 02633
  • 101 Old Mail Rd, North Chatham, MA 02650
    101 Old Mail Rd, North Chatham, MA 02650
    101 Old Mail Rd, North Chatham, MA 02650
    /35

    $1,599,000 Sold Feb 24, 2025

    101 Old Mail Rd, North Chatham, MA 02650

    • 3 Beds
    • 1.5 Baths
    • 1,511 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,058/SF
    • 7 Days On Market

    Current Estimated Value $1,532,159

    Last Listing Agent Jessica King Compass Massachusetts, LLC

    101 Old Mail Rd, North Chatham, MA 02650
    • 371 Cedar St, Chatham, MA 02633
      371 Cedar St, Chatham, MA 02633
      371 Cedar St, Chatham, MA 02633
      /41

      Est $1,852,305 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,840 Sq Ft

      371 Cedar St, Chatham, MA 02633

      371 Cedar St, Chatham, MA 02633
  • 26 Sea Mist Ln, South Chatham, MA 02659
    26 Sea Mist Ln, South Chatham, MA 02659
    26 Sea Mist Ln, South Chatham, MA 02659
    /42

    $1,600,000 Sold Mar 13, 2025

    26 Sea Mist Ln, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft
    • Built 1950

    Last Sold Summary

    • $1,161/SF
    • 11 Days On Market

    Current Estimated Value $1,615,304

    Last Listing Agent Jan Nowak Craigville Realty Co

    26 Sea Mist Ln, South Chatham, MA 02659
    • 256 Woodland Way, North Chatham, MA 02650
      256 Woodland Way, North Chatham, MA 02650
      256 Woodland Way, North Chatham, MA 02650
      /81

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,995 Sq Ft

      256 Woodland Way, North Chatham, MA 02650

      256 Woodland Way, North Chatham, MA 02650
  • 552 Orleans Rd, North Chatham, MA 02650
    552 Orleans Rd, North Chatham, MA 02650
    552 Orleans Rd, North Chatham, MA 02650
    /31

    $1,315,000 Sold Oct 21, 2025

    552 Orleans Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 1,144 Sq Ft
    • Built 1978

    Last Sold Summary

    • 18% Below List Price
    • $1,149/SF
    • 177 Days On Market

    Current Estimated Value $1,345,492

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    552 Orleans Rd, North Chatham, MA 02650
    • 730 Orleans Rd, North Chatham, MA 02650
      730 Orleans Rd, North Chatham, MA 02650
      730 Orleans Rd, North Chatham, MA 02650
      /62

      Est $1,449,212 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      730 Orleans Rd, North Chatham, MA 02650

      730 Orleans Rd, North Chatham, MA 02650
  • 36 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    36 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    36 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    /34

    $425,000 Sold May 12, 2025

    36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

    • 2 Beds
    • 1.5 Baths
    • 930 Sq Ft
    • Built 1982

    Last Sold Summary

    • $457/SF
    • 5 Days On Market

    Current Estimated Value $435,085

    Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    36 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    • 875 Orleans Rd, North Chatham, MA 02650
      875 Orleans Rd, North Chatham, MA 02650
      875 Orleans Rd, North Chatham, MA 02650
      /45

      Est $1,860,459 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,300 Sq Ft

      875 Orleans Rd, North Chatham, MA 02650

      875 Orleans Rd, North Chatham, MA 02650
  • 27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    /36

    $1,230,000 Sold Jan 23, 2026

    27 Fairview Dr, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $536/SF
    • 17 Days On Market

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    27 Fairview Dr, South Chatham, MA 02659
    • 51 Northgate Rd, North Chatham, MA 02650
      51 Northgate Rd, North Chatham, MA 02650
      51 Northgate Rd, North Chatham, MA 02650
      /42

      Est $1,979,133 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,116 Sq Ft

      51 Northgate Rd, North Chatham, MA 02650

      51 Northgate Rd, North Chatham, MA 02650
  • 79 Forest Beach Rd, South Chatham, MA 02659
    79 Forest Beach Rd, South Chatham, MA 02659
    79 Forest Beach Rd, South Chatham, MA 02659
    /60

    $1,295,000 Sold Jan 13, 2026

    79 Forest Beach Rd, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,634 Sq Ft
    • Built 1940

    Last Sold Summary

    • $793/SF
    • 24 Days On Market

    Last Listing Agent Shane Masaschi Compass

    79 Forest Beach Rd, South Chatham, MA 02659
    • 79 Lakeshore Dr, Chatham, MA 02633
      79 Lakeshore Dr, Chatham, MA 02633
      79 Lakeshore Dr, Chatham, MA 02633
      /50

      Est $2,491,271 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,719 Sq Ft

      79 Lakeshore Dr, Chatham, MA 02633

      79 Lakeshore Dr, Chatham, MA 02633
  • 2519 Main St, South Chatham, MA 02659
    2519 Main St, South Chatham, MA 02659
    2519 Main St, South Chatham, MA 02659
    /5

    $2,350,000 Sold Apr 30, 2025

    2519 Main St, South Chatham, MA 02659

    • 3 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • Built 1977

    Last Sold Summary

    • 2% Below List Price
    • $1,043/SF
    • 12 Days On Market

    Current Estimated Value $2,273,407

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    2519 Main St, South Chatham, MA 02659
    • 34 Horizon Dr, Chatham, MA 02633
      34 Horizon Dr, Chatham, MA 02633
      34 Horizon Dr, Chatham, MA 02633
      /40

      Est $1,090,587 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,400 Sq Ft

      34 Horizon Dr, Chatham, MA 02633

      34 Horizon Dr, Chatham, MA 02633
  • 93 Orleans Rd, Chatham, MA 02633
    93 Orleans Rd, Chatham, MA 02633
    93 Orleans Rd, Chatham, MA 02633
    /42

    $1,288,000 Sold Jan 20, 2026

    93 Orleans Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 1958

    Last Sold Summary

    • 8% Below List Price
    • $757/SF
    • 120 Days On Market

    Last Listing Agent Derek Greene The Greene Realty Group

    93 Orleans Rd, Chatham, MA 02633
    • 55 Winterset Dr, Chatham, MA 02633
      55 Winterset Dr, Chatham, MA 02633
      55 Winterset Dr, Chatham, MA 02633
      /45

      Est $2,222,104 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,072 Sq Ft

      55 Winterset Dr, Chatham, MA 02633

      55 Winterset Dr, Chatham, MA 02633
  • 558 Riverview Dr, Chatham, MA 02633
    558 Riverview Dr, Chatham, MA 02633
    558 Riverview Dr, Chatham, MA 02633
    /31

    $895,000 Sold Dec 10, 2025

    558 Riverview Dr, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 2,097 Sq Ft
    • Built 1966

    Last Sold Summary

    • $427/SF
    • 2 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    558 Riverview Dr, Chatham, MA 02633
    • 66 Ethelma Dr, Chatham, MA 02633
      66 Ethelma Dr, Chatham, MA 02633
      66 Ethelma Dr, Chatham, MA 02633
      /21

      Est $915,124 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,593 Sq Ft

      66 Ethelma Dr, Chatham, MA 02633

      66 Ethelma Dr, Chatham, MA 02633
  • 369 Orleans Rd Unit A, North Chatham, MA 02650
    369 Orleans Rd Unit A, North Chatham, MA 02650
    369 Orleans Rd Unit A, North Chatham, MA 02650
    /36

    $615,300 Sold May 27, 2025

    369 Orleans Rd Unit A, North Chatham, MA 02650

    • 2 Beds
    • 2.5 Baths
    • 1,283 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $480/SF
    • 18 Days On Market

    Current Estimated Value $629,465

    Last Listing Agent David Colville HomeSmart First Class Realty

    369 Orleans Rd Unit A, North Chatham, MA 02650
    • 47 Barbara Dr, Chatham, MA 02633
      47 Barbara Dr, Chatham, MA 02633
      47 Barbara Dr, Chatham, MA 02633
      /3

      Est $773,191 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 945 Sq Ft

      47 Barbara Dr, Chatham, MA 02633

      47 Barbara Dr, Chatham, MA 02633
  • 44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
    /12

    $415,000 Sold Aug 14, 2025

    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650

    • 1 Bed
    • 1.5 Baths
    • 836 Sq Ft
    • Built 1982

    Last Sold Summary

    • $496/SF
    • 3 Days On Market

    Current Estimated Value $414,004

    Last Listing Agent Jack Farrell Compass

    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
    • 25 Ethelma Dr, Chatham, MA 02633
      25 Ethelma Dr, Chatham, MA 02633
      25 Ethelma Dr, Chatham, MA 02633
      /58

      Est $1,418,588 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,251 Sq Ft

      25 Ethelma Dr, Chatham, MA 02633

      25 Ethelma Dr, Chatham, MA 02633
  • 98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    /39

    $1,975,000 Sold Dec 18, 2025

    98 Horizon Dr, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 3,310 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Below List Price
    • $597/SF
    • 252 Days On Market

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    98 Horizon Dr, Chatham, MA 02633
    • 105 Perch Pond Dr, Chatham, MA 02633
      105 Perch Pond Dr, Chatham, MA 02633
      105 Perch Pond Dr, Chatham, MA 02633
      /47

      Est $872,778 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      105 Perch Pond Dr, Chatham, MA 02633

      105 Perch Pond Dr, Chatham, MA 02633
  • 2 Crowell Rd, Chatham, MA 2633
    2 Crowell Rd, Chatham, MA 2633
    2 Crowell Rd, Chatham, MA 2633
    /10

    $460,000 Sold Sep 18, 2025

    2 Crowell Rd, Chatham, MA 2633

    • Land
    • 0.44 Acre
    • $1,045,455 per Acre

    Last Sold Summary

    • 16% Above List Price
    • 13 Days On Market

    Current Estimated Value $384,757

    Last Listing Agent G Howard Hayes Gibson Sotheby's International Realty

    2 Crowell Rd, Chatham, MA 2633
    • 1235 Main St Unit 7, Chatham, MA 02633
      1235 Main St Unit 7, Chatham, MA 02633
      1235 Main St Unit 7, Chatham, MA 02633
      /29

      Est $958,468 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,681 Sq Ft

      1235 Main St Unit 7, Chatham, MA 02633

      1235 Main St Unit 7, Chatham, MA 02633
  • 107 School St, Chatham, MA 02633
    107 School St, Chatham, MA 02633
    107 School St, Chatham, MA 02633
    /42

    $3,800,000 Sold Feb 28, 2025

    107 School St, Chatham, MA 02633

    • 4 Beds
    • 5.5 Baths
    • 4,372 Sq Ft
    • Built 2014

    Last Sold Summary

    • 10% Below List Price
    • $869/SF
    • 39 Days On Market

    Current Estimated Value $4,161,436

    Last Listing Agent John Burke William Raveis Chatham

    107 School St, Chatham, MA 02633
    • 88 Fox Hill Rd, Chatham, MA 02633
      88 Fox Hill Rd, Chatham, MA 02633
      88 Fox Hill Rd, Chatham, MA 02633
      /47

      Est $1,562,368 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,716 Sq Ft

      88 Fox Hill Rd, Chatham, MA 02633

      88 Fox Hill Rd, Chatham, MA 02633
  • 31 Joshua Jethro Rd, Chatham, MA 02633
    31 Joshua Jethro Rd, Chatham, MA 02633
    31 Joshua Jethro Rd, Chatham, MA 02633
    /42

    $1,050,000 Sold Aug 21, 2025

    31 Joshua Jethro Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $642/SF
    • 30 Days On Market

    Current Estimated Value $1,061,286

    Last Listing Agent Julie Chapin William Raveis Real Estate & Home Services

    31 Joshua Jethro Rd, Chatham, MA 02633

Showing Results 281 - 320, Page 8 of 18

Massachusetts Barnstable County Chatham

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group