• Home
  • About
    1. About Chris
    2. Our Team
  • Listings
    1. Signature Collection
    2. Urban Luxury
    3. New Developments
    4. Neighborhoods
  • Waypoint Group
  • Buy & Sell
    1. Buyer's Roadmap
    2. Sell With Confidence
    3. Free Valuation
  • Connect
    1. Client Stories
    2. Contact
    • Register
    • Sign In
    Price
    • Any
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • $ 800,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 1,000,000
      Beds Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
      Baths Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
    • List
    • Mixed
    • Map
    City: Chatham, MA
    Listing Status: Active
    Map
    52 Properties Available In Chatham

    52 Properties Available In Chatham

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    MA >Chatham >
    Market Insights
    7 Aunt Matties Rd, Chatham, MA 02633
    1/38
    Open Fri 10AM-12PM

    $825,000

    2 Beds2 Baths1,563 SqFt

    7 Aunt Matties Rd, Chatham, MA 02633

    Listed by Tiffany Callahan of Greer Real Estate, LLC

    335 Stage Island, Chatham, MA 02633
    1/42
    Open Sat 11AM-1PM

    $4,495,000

    4 Beds5.5 Baths5,372 SqFt

    335 Stage Island, Chatham, MA 02633

    Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

    70 Uncle Deane's Rd, Chatham, MA 02659
    1/42
    Open Sat 12PM-1:30PM

    $1,999,000

    3 Beds3 Baths3,514 SqFt

    70 Uncle Deane's Rd, Chatham, MA 02659

    Listed by Patrick Davison of Shining Sea Realty

    260 Tanglewood Dr, Chatham, MA 02659
    1/41
    Open Sun 12PM-2PM

    $750,000

    3 Beds2 Baths1,442 SqFt

    260 Tanglewood Dr, Chatham, MA 02659

    Listed by Amy Harbeck of Kinlin Grover Compass

    1114 Orleans Rd #1, Chatham, MA 02650
    1/42
    New

    $1,595,000

    3 Beds3 Baths2,961 SqFt

    1114 Orleans Rd #1, Chatham, MA 02650

    Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties

    36 Pursel Dr, Chatham, MA 02650
    1/40
    New

    $1,349,000

    4 Beds3 Baths2,268 SqFt

    36 Pursel Dr, Chatham, MA 02650

    Listed by Diane Donahue of Gibson Sotheby's International Realty

    66 Snow Ln, Chatham, MA 02633
    1/41
    New

    $900,000

    2 Beds1 Bath864 SqFt

    66 Snow Ln, Chatham, MA 02633

    Listed by Shane Masaschi of Compass

    213 Main St, Chatham, MA 02633
    1/39
    New

    $1,800,000

    4 Beds2 Baths1,238 SqFt

    213 Main St, Chatham, MA 02633

    Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

    1068 Main St #1068, Chatham, MA 02633
    1/33
    Active

    $899,000

    2 Beds2 Baths2,127 SqFt

    1068 Main St #1068, Chatham, MA 02633

    Listed by Kristin Coletti of William Raveis R.E. & Home Services

    15 Bay Lane, Chatham, MA 02633
    1/40
    Active

    $4,950,000

    4 Beds4.5 Baths5,110 SqFt

    15 Bay Lane, Chatham, MA 02633

    Listed by Chris Rhinesmith of Compass

    2653 Main St, Chatham, MA 02659
    1/28
    Active

    $950,000

    3 Beds2.5 Baths2,252 SqFt

    2653 Main St, Chatham, MA 02659

    Listed by Sharon Dixon of William Raveis Real Estate & Homes Services

    30 Indian Trail, Chatham, MA 02633
    1/26
    Active

    $4,200,000

    3 Beds3 Baths2,418 SqFt

    30 Indian Trail, Chatham, MA 02633

    Listed by Chris Rhinesmith of Compass

    336 Stage Island Rd, Chatham, MA 02633
    1/42
    Active

    $3,250,000

    3 Beds2.5 Baths2,205 SqFt

    336 Stage Island Rd, Chatham, MA 02633

    Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties

    38 Indian Trail, Chatham, MA 02633
    1/37
    Active
    3D

    $4,750,000

    4 Beds3.5 Baths4,967 SqFt

    38 Indian Trail, Chatham, MA 02633

    Listed by Lori Jurkowski of Christie's International Real Estate Atlantic Brokerage

    83 Old Mail Rd, Chatham, MA 02650
    1/39
    Active

    $3,695,000

    3 Beds4.5 Baths5,154 SqFt

    83 Old Mail Rd, Chatham, MA 02650

    Listed by Lori Fanning Smith of Compass

    60 Harbor Hill Rd, Chatham, MA 02633
    1/24
    Active

    $3,600,000

    4 Beds3.5 Baths3,978 SqFt

    60 Harbor Hill Rd, Chatham, MA 02633

    Listed by Jacqueline Casey of Shore Road Realty, LLC

    70 Judges Way, Chatham, MA 02633
    1/41
    Price Dropped by $255K
    3D

    $5,995,000

    5 Beds4.5 Baths4,060 SqFt

    70 Judges Way, Chatham, MA 02633

    Listed by Lori Jurkowski of Christie's International Real Estate Atlantic Brokerage

    48 Glover Sq, Chatham, MA 02633
    1/33
    Active

    $1,650,000

    3 Beds2 Baths1,531 SqFt

    48 Glover Sq, Chatham, MA 02633

    Listed by Laurie McCann of Gibson Sotheby's International Realty

    109 Misty Meadow Ln #4, Chatham, MA 02650
    1/28
    Active

    $475,000

    2 Beds1 Bath869 SqFt

    109 Misty Meadow Ln #4, Chatham, MA 02650

    Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties

    101 Morris Island Rd, Chatham, MA 02633
    1/42
    Active

    $5,995,000

    4 Beds4.5 Baths3,225 SqFt

    101 Morris Island Rd, Chatham, MA 02633

    Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

    15 Windy Hill Way, Chatham, MA 02633
    1/42
    Active

    $6,250,000

    5 Beds5.5 Baths5,620 SqFt

    15 Windy Hill Way, Chatham, MA 02633

    Listed by Timothy Bailey of John C. Ricotta & Associates, Inc.

    222 Barcliff, Chatham, MA 02633
    1/2
    Active

    $4,250,000

    4 Beds5.5 Baths3,980 SqFt

    222 Barcliff, Chatham, MA 02633

    Listed by Lori Fanning Smith of Compass

    351 Whidah Rd, Chatham, MA 02650
    1/29
    Active

    $14,000

    6 Beds4.5 Baths3,941 SqFt

    351 Whidah Rd, Chatham, MA 02650

    Listed by Anthony Escobedo of Coldwell Banker Realty - Newton

    118 Wilfred Rd, Chatham, MA 02633
    1/41
    Active

    $1,200,000

    3 Beds3 Baths1,804 SqFt

    118 Wilfred Rd, Chatham, MA 02633

    Listed by Shane Masaschi of Compass

    • 1
    • 2
    • 3

    explore listings in Chatham

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
    image (2)
    Waypoint Group
    Chris Sanner
    +1(216) 394-9821
    chriswaypointgroup@gmail.com
    91 Main St, Charlestown, MA, 02129, USA

    Get My App

      • Home
        Buy & Sell
        1. Buyer's Roadmap
        2. Sell With Confidence
        3. Free Valuation
      • About
        1. About Chris
        2. Our Team
        Connect
        1. Client Stories
        2. Contact
      • Listings
        1. Signature Collection
        2. Urban Luxury
        3. New Developments
        4. Neighborhoods

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    QUICK SEARCH
    • Boston, MA For Sale
    • Melrose, MA For Sale
    • Cambridge, MA For Sale
    • Newton, MA For Sale
    • Burlington, MA For Sale
    • Charlestown, Charlestown, MA For Sale
    • Lumen Charlestown, Charlestown, MA For Sale
    • Monument Square, Charlestown, MA For Sale
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
    image (2)
    Waypoint Group
    Chris Sanner
    +1(216) 394-9821
    chriswaypointgroup@gmail.com
    91 Main St, Charlestown, MA, 02129, USA

    Get My App

      • Home
        Buy & Sell
        1. Buyer's Roadmap
        2. Sell With Confidence
        3. Free Valuation
      • About
        1. About Chris
        2. Our Team
        Connect
        1. Client Stories
        2. Contact
      • Listings
        1. Signature Collection
        2. Urban Luxury
        3. New Developments
        4. Neighborhoods

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility