9,675

Chatham, MA Homes

Section Image
  • 28 Cranberry Ln, Chatham, MA 02633
    28 Cranberry Ln, Chatham, MA 02633
    28 Cranberry Ln, Chatham, MA 02633
    /41

    $3,295,000 Pending

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

    28 Cranberry Ln, Chatham, MA 02633

    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

    28 Cranberry Ln, Chatham, MA 02633
  • 552 Shore Rd, Chatham, MA 02633
    552 Shore Rd, Chatham, MA 02633
    552 Shore Rd, Chatham, MA 02633
    /42

    $11,250,000 Sold Jun 09, 2025

    552 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 6.5 Baths
    • 5,868 Sq Ft
    • Built 1930

    Last Sold Summary

    • 19% Below List Price
    • $1,917/SF
    • 326 Days On Market

    Current Estimated Value $7,690,627

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    552 Shore Rd, Chatham, MA 02633
    • 75 Whidah Rd, North Chatham, MA 02650
      75 Whidah Rd, North Chatham, MA 02650
      75 Whidah Rd, North Chatham, MA 02650
      /47

      Est $2,056,387 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,524 Sq Ft

      75 Whidah Rd, North Chatham, MA 02650

      75 Whidah Rd, North Chatham, MA 02650
  • 33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    /51

    $842,000

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

    33 Duck Marsh Ln, Chatham, MA 02633

    Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural

    Darci Sequin Gibson Sotheby's International Realty

    33 Duck Marsh Ln, Chatham, MA 02633
  • 35 Whistler Ln, Chatham, MA 02633
    35 Whistler Ln, Chatham, MA 02633
    35 Whistler Ln, Chatham, MA 02633
    /54

    $3,300,000 Sold Jul 22, 2025

    35 Whistler Ln, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,314 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $1,426/SF
    • 50 Days On Market

    Last Listing Agent MaryEllen Monahan Today Real Estate

    35 Whistler Ln, Chatham, MA 02633
    • 20 Spring Hill Rd, North Chatham, MA 02650
      20 Spring Hill Rd, North Chatham, MA 02650
      20 Spring Hill Rd, North Chatham, MA 02650
      /42

      Est $1,255,106 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft

      20 Spring Hill Rd, North Chatham, MA 02650

      20 Spring Hill Rd, North Chatham, MA 02650
  • 14 Pond View Ln, Chatham, MA 02633
    14 Pond View Ln, Chatham, MA 02633
    14 Pond View Ln, 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
  • 0 Reynolds Cir Unit 22501745, Chatham, MA 02633
    0 Reynolds Cir Unit 22501745, Chatham, MA 02633
    /2

    $540,000 Sold Sep 18, 2025

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633

    • Land
    • 1.2 Acres
    • $450,000 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 81 Days On Market

    Last Listing Agent Derek Greene The Greene Realty Group

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633
    • 197 Stony Hill Rd Unit C, Chatham, MA 02633
      197 Stony Hill Rd Unit C, Chatham, MA 02633
      197 Stony Hill Rd Unit C, Chatham, MA 02633
      /18

      Est $371,766 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft

      197 Stony Hill Rd Unit C, Chatham, MA 02633

      197 Stony Hill Rd Unit C, Chatham, MA 02633
  • 745 Main St, Chatham, MA 02633
    745 Main St, Chatham, MA 02633
    745 Main St, Chatham, MA 02633
    /52

    $1,399,900 Pending

    • 6 Beds
    • 3 Baths
    • 2,257 Sq Ft

    745 Main St, Chatham, MA 02633

    Attention Investors: Two homes on separate parcels are available in downtown Chatham. Enjoy walking distance to town, Veteran's Field, Oyster Pond, and a variety of restaurants. The first property, located at 747 Main Street, is a 4-bedroom, 2-bathroom bungalow featuring central A/C, natural gas heating, period details, hardwood floors, a spacious front porch perfect for lazy afternoons, and

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    745 Main St, Chatham, MA 02633
  • 51 Bucks Creek Rd, Chatham, MA 02633
    51 Bucks Creek Rd, Chatham, MA 02633
    51 Bucks Creek Rd, Chatham, MA 02633
    /56

    $1,675,000 Sold Apr 01, 2025

    51 Bucks Creek Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1959

    Last Sold Summary

    • $1,047/SF
    • 26 Days On Market

    Current Estimated Value $1,627,761

    Last Listing Agent Dawn Lee Gibson Sotheby's International Realty

    51 Bucks Creek Rd, Chatham, MA 02633
    • 43 Misty Meadow Ln Unit B, North Chatham, MA 02650
      43 Misty Meadow Ln Unit B, North Chatham, MA 02650
      43 Misty Meadow Ln Unit B, North Chatham, MA 02650
      /53

      Est $1,342,396 Not Listed For Sale

      • 2 Beds
      • 3.5 Baths
      • 2,546 Sq Ft

      43 Misty Meadow Ln Unit B, North Chatham, MA 02650

      43 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • 0 George Ryder Rd Unit 22301591, Chatham, MA 02633
    0 George Ryder Rd Unit 22301591, Chatham, MA 02633
    0 George Ryder Rd Unit 22301591, Chatham, MA 02633
    /8

    $250,000 Pending

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

    0 George Ryder Rd Unit 22301591, 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, with approvals a 4-bedroom may be possible. Buyer's & buyer brokers verify sewer regulations with Board of Health as rules continue to change. The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to

    Shane Masaschi Kinlin Grover Compass

    0 George Ryder Rd Unit 22301591, Chatham, MA 02633
  • 291 Ridgevale Rd, Chatham, MA 02633
    291 Ridgevale Rd, Chatham, MA 02633
    291 Ridgevale Rd, Chatham, MA 02633
    /53

    $1,495,000 Sold Dec 15, 2025

    291 Ridgevale Rd, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,424 Sq Ft
    • Built 1950

    Last Sold Summary

    • $1,050/SF
    • 8 Days On Market

    Last Listing Agent Jan Nowak Craigville Realty Co

    291 Ridgevale Rd, Chatham, MA 02633
    • 39 Misty Meadow Ln, North Chatham, MA 02650
      39 Misty Meadow Ln, North Chatham, MA 02650
      39 Misty Meadow Ln, North Chatham, MA 02650
      /29

      Est $1,086,816 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,812 Sq Ft

      39 Misty Meadow Ln, North Chatham, MA 02650

      39 Misty Meadow Ln, North Chatham, MA 02650
  • 207 Horizon Dr, Chatham, MA 02633
    207 Horizon Dr, Chatham, MA 02633
    207 Horizon Dr, Chatham, MA 02633
    /35

    $1,450,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,843 Sq Ft

    207 Horizon Dr, Chatham, MA 02633

    Tucked in a well-loved Chatham neighborhood, with deeded rights to Lover's Lake, this gracious 4-bedroom Cape seamlessly blends coastal living and Cape Cod charm. 207 Horizon Drive possess charm throughout with its spacious and traditional floor plan. Featuring two fireplaces, two full and two half baths, and a sunlit family room off the kitchen. This home is designed for easy living. Enoy

    Jacquelyn Casey Shore Road Realty

    207 Horizon Dr, Chatham, MA 02633
  • 20 Hardings Beach Rd, Chatham, MA 02633
    20 Hardings Beach Rd, Chatham, MA 02633
    20 Hardings Beach Rd, Chatham, MA 02633
    /20

    $1,975,000 Sold Oct 08, 2025

    20 Hardings Beach Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 2,770 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $713/SF
    • 31 Days On Market

    Current Estimated Value $1,961,715

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633
    • 37 Misty Meadow Ln Unit B, North Chatham, MA 02650
      37 Misty Meadow Ln Unit B, North Chatham, MA 02650
      37 Misty Meadow Ln Unit B, North Chatham, MA 02650
      /27

      Est $1,152,140 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,906 Sq Ft

      37 Misty Meadow Ln Unit B, North Chatham, MA 02650

      37 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • 47 Cranberry Way, South Chatham, MA 2659
    47 Cranberry Way, South Chatham, MA 2659
    47 Cranberry Way, South Chatham, MA 2659
    /32

    $765,000 Sold Dec 18, 2025

    47 Cranberry Way, South Chatham, MA 2659

    • 2 Beds
    • 2 Baths
    • 868 Sq Ft
    • Built 1941

    Last Sold Summary

    • 4% Below List Price
    • $881/SF
    • 11 Days On Market

    Last Listing Agent William Raye Gibson Sotheby's International Realty

    47 Cranberry Way, South Chatham, MA 2659
    • 61 Bishops Terrace, Chatham, MA 02633
      61 Bishops Terrace, Chatham, MA 02633
      61 Bishops Terrace, Chatham, MA 02633
      /25

      Est $1,178,297 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft

      61 Bishops Terrace, Chatham, MA 02633

      61 Bishops Terrace, Chatham, MA 02633
  • 144 Countryside Dr, Chatham, MA 02633
    144 Countryside Dr, Chatham, MA 02633
    144 Countryside Dr, Chatham, MA 02633
    /58

    $1,309,000 Sold Jun 20, 2025

    144 Countryside Dr, Chatham, MA 02633

    • 2 Beds
    • 2.5 Baths
    • 2,590 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Above List Price
    • $505/SF
    • 1 Day On Market

    Current Estimated Value $1,319,770

    Last Listing Agent Maureen Green Kinlin Grover Compass

    144 Countryside Dr, Chatham, MA 02633
    • 32 Aire Ln, Chatham, MA 02633
      32 Aire Ln, Chatham, MA 02633
      32 Aire Ln, Chatham, MA 02633
      /28

      Est $1,120,677 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft

      32 Aire Ln, Chatham, MA 02633

      32 Aire Ln, Chatham, MA 02633
  • 1996 Main St, Chatham, MA 02633
    1996 Main St, Chatham, MA 02633
    1996 Main St, Chatham, MA 02633
    /55

    $650,000 Sold Jul 31, 2025

    1996 Main St, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,813 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Below List Price
    • $359/SF
    • 93 Days On Market

    Current Estimated Value $748,305

    Last Listing Agent Shane Masaschi Compass

    1996 Main St, Chatham, MA 02633
    • 276 Orleans Rd, Chatham, MA 02633
      276 Orleans Rd, Chatham, MA 02633
      276 Orleans Rd, Chatham, MA 02633
      /13

      Est $799,688 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 955 Sq Ft

      276 Orleans Rd, Chatham, MA 02633

      276 Orleans Rd, Chatham, MA 02633
  • 56 Monomoit Ln, Chatham, MA 02633
    56 Monomoit Ln, Chatham, MA 02633
    56 Monomoit Ln, Chatham, MA 02633
    /44

    $1,227,000 Sold Jul 25, 2025

    56 Monomoit Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,639 Sq Ft
    • Built 1998

    Last Sold Summary

    • 12% Below List Price
    • $749/SF
    • 28 Days On Market

    Current Estimated Value $1,239,986

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    56 Monomoit Ln, Chatham, MA 02633
    • 214 Barcliff Ave, Chatham, MA 02633
      214 Barcliff Ave, Chatham, MA 02633
      214 Barcliff Ave, Chatham, MA 02633
      /30

      Est $1,154,427 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,320 Sq Ft

      214 Barcliff Ave, Chatham, MA 02633

      214 Barcliff Ave, Chatham, MA 02633
  • 23 Oyster Pond Ln, Chatham, MA 02633
    23 Oyster Pond Ln, Chatham, MA 02633
    23 Oyster Pond Ln, Chatham, MA 02633
    /42

    $11,500,000 Sold Jul 29, 2025

    23 Oyster Pond Ln, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 5,308 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $2,167/SF
    • 9 Days On Market

    Current Estimated Value $9,178,735

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    23 Oyster Pond Ln, Chatham, MA 02633
    • 161 Shane Dr, Chatham, MA 02633
      161 Shane Dr, Chatham, MA 02633
      161 Shane Dr, Chatham, MA 02633
      /25

      Est $820,533 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 966 Sq Ft

      161 Shane Dr, Chatham, MA 02633

      161 Shane Dr, Chatham, MA 02633
  • 718 Riverview Dr, Chatham, MA 02633
    718 Riverview Dr, Chatham, MA 02633
    718 Riverview Dr, Chatham, MA 02633
    /47

    $1,065,000 Sold May 09, 2025

    718 Riverview Dr, Chatham, MA 02633

    • 2 Beds
    • 2.5 Baths
    • 2,292 Sq Ft
    • Built 1971

    Last Sold Summary

    • 3% Below List Price
    • $465/SF
    • 16 Days On Market

    Current Estimated Value $1,066,925

    Last Listing Agent Tim Bailey John C Ricotta & Assoc.

    718 Riverview Dr, Chatham, MA 02633
    • 55 Eldredge Square S, Chatham, MA 02633
      55 Eldredge Square S, Chatham, MA 02633
      55 Eldredge Square S, Chatham, MA 02633
      /38

      Est $2,066,122 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,630 Sq Ft

      55 Eldredge Square S, Chatham, MA 02633

      55 Eldredge Square S, Chatham, MA 02633
  • 30 Mill Hill Ln, Chatham, MA 02633
    30 Mill Hill Ln, Chatham, MA 02633
    30 Mill Hill Ln, Chatham, MA 02633
    /23

    $2,700,000 Sold Jul 24, 2025

    30 Mill Hill Ln, Chatham, MA 02633

    • 7 Beds
    • 3 Baths
    • 2,460 Sq Ft
    • Built 1840

    Last Sold Summary

    • 17% Below List Price
    • $1,098/SF
    • 238 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    30 Mill Hill Ln, Chatham, MA 02633
    • 233 Barcliff Ave, Chatham, MA 02633
      233 Barcliff Ave, Chatham, MA 02633
      233 Barcliff Ave, Chatham, MA 02633
      /28

      Est $1,294,811 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,196 Sq Ft

      233 Barcliff Ave, Chatham, MA 02633

      233 Barcliff Ave, Chatham, MA 02633
  • 53 Gristmill Ln, Chatham, MA 02633
    53 Gristmill Ln, Chatham, MA 02633
    53 Gristmill Ln, Chatham, MA 02633
    /42

    $9,650,000 Sold Nov 06, 2025

    53 Gristmill Ln, Chatham, MA 02633

    • 5 Beds
    • 8 Baths
    • 4,970 Sq Ft
    • Built 1989

    Last Sold Summary

    • 1% Below List Price
    • $1,942/SF
    • 30 Days On Market

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    53 Gristmill Ln, Chatham, MA 02633
    • 25 Glover Square, Chatham, MA 02633
      25 Glover Square, Chatham, MA 02633
      25 Glover Square, Chatham, MA 02633
      /65

      Est $3,222,137 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 4,105 Sq Ft

      25 Glover Square, Chatham, MA 02633

      25 Glover Square, Chatham, MA 02633
  • 24 Shattuck Place, Chatham, MA 02633
    24 Shattuck Place, Chatham, MA 02633
    24 Shattuck Place, Chatham, MA 02633
    /41

    $1,785,000 Sold Nov 24, 2025

    24 Shattuck Place, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 1,514 Sq Ft
    • Built 1920

    Last Sold Summary

    • 1% Below List Price
    • $1,179/SF
    • 7 Days On Market

    Last Listing Agent Charles King Real Broker MA, LLC

    24 Shattuck Place, Chatham, MA 02633
    • 265 Barcliff Ave, Chatham, MA 02633
      265 Barcliff Ave, Chatham, MA 02633
      265 Barcliff Ave, Chatham, MA 02633
      /46

      Est $1,426,268 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,491 Sq Ft

      265 Barcliff Ave, Chatham, MA 02633

      265 Barcliff Ave, Chatham, MA 02633
  • 33 Cross St Unit 4, Chatham, MA 02633
    33 Cross St Unit 4, Chatham, MA 02633
    33 Cross St Unit 4, Chatham, MA 02633
    /10

    $192,000 Sold Feb 13, 2025

    33 Cross St Unit 4, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Built 1991

    Last Sold Summary

    • 12% Below List Price
    • $427/SF
    • 37 Days On Market

    Last Listing Agent Brennan Finnegan William Raveis Real Estate & Home Services

    33 Cross St Unit 4, Chatham, MA 02633
    • 751 Main St, Chatham, MA 02633
      751 Main St, Chatham, MA 02633
      751 Main St, Chatham, MA 02633
      /30

      Est $1,280,206 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,552 Sq Ft

      751 Main St, Chatham, MA 02633

      751 Main St, Chatham, MA 02633
  • 37 Bellamy Ln, North Chatham, MA 02650
    37 Bellamy Ln, North Chatham, MA 02650
    37 Bellamy Ln, North Chatham, MA 02650
    /31

    $1,600,000 Sold Mar 14, 2025

    37 Bellamy Ln, North Chatham, MA 02650

    • 5 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $2,297,152

    Last Listing Agent David Doherty Compass

    37 Bellamy Ln, North Chatham, MA 02650
    • 178 Queen Anne Rd, Chatham, MA 02633
      178 Queen Anne Rd, Chatham, MA 02633
      178 Queen Anne Rd, Chatham, MA 02633
      /30

      Not Listed For Sale

      • 6 Beds
      • 8 Baths
      • 7,700 Sq Ft

      178 Queen Anne Rd, Chatham, MA 02633

      178 Queen Anne Rd, Chatham, MA 02633

Showing Results 121 - 160, Page 4 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