9,641

Chatham, MA Homes

Section Image
    • /30

      Est $2,372,624

      Not Listed For Sale

      72 Old Field Bend, North Chatham, MA 02650

      • 4 Beds
      • 4.5 Baths
      • 3,776 Sq Ft
      • Built 2001
      72 Old Field Bend, North Chatham, MA 02650

      Last Sold Summary

      • 8% Above List Price
      • $582/SF
      • 1 Day On Market
      • Last Sold Price $2,195,800
      • Jan 31, 2025

      Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  • /55

    $2,150,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,481 Sq Ft

    234 Round Cove Rd, Chatham, MA 02633

    Tucked within Chatham's coveted Riverbay community, 234 Round Cove Road offers a rare blend of walkability and private, resort-style living. Moments to Jackknife Beach and Pleasant Bay, the setting delivers coastal access while feeling entirely private and your own.Designed for effortless living, the single-level layout features three oversized bedrooms and 2.5 baths, including a secluded primary

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    234 Round Cove Rd, Chatham, MA 02633
  • /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

    Current Estimated Value $793,327

    Last Listing Agent William Raye Gibson Sotheby's International Realty

    47 Cranberry Way, South Chatham, MA 2659
    • /54

      Est $1,786,699

      Not Listed For Sale

      52 Wentworth Ln, North Chatham, MA 02650

      • 5 Beds
      • 2.5 Baths
      • 2,352 Sq Ft
      • Built 1972
      52 Wentworth Ln, North Chatham, MA 02650

      Last Sold Summary

      • 2% Above List Price
      • $746/SF
      • 3 Days On Market
      • Last Sold Price $1,754,000
      • Sep 15, 2023

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

  • /10

    $4,499,900

    New Construction
    • 3 Beds
    • 7 Baths
    • 5,820 Sq Ft

    33 Crowell Rd, Chatham, MA 02633

    A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    33 Crowell Rd, 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 $1,413,712

    Last Listing Agent Maureen Green Kinlin Grover Compass

    144 Countryside Dr, Chatham, MA 02633
    • /31

      Est $2,417,084

      Not Listed For Sale

      37 Bellamy Ln, North Chatham, MA 02650

      • 5 Beds
      • 3 Baths
      • 3,401 Sq Ft
      • Built 1988
      37 Bellamy Ln, North Chatham, MA 02650

      Last Sold Summary

      • 51% Above List Price
      • $470/SF
      • 13 Days On Market
      • Last Sold Price $1,600,000
      • Mar 14, 2025

      Last Listing Agent David Doherty Compass

  • /27

    $1,650,000

    $345K PRICE DROP
    • 1 Bath
    • 2,586 Sq Ft

    231 Crowell Rd, Chatham, MA 2633

    Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

    Judith Smith John C. Ricotta & Associates, Inc.

    231 Crowell Rd, Chatham, MA 2633
  • /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 $752,199

    Last Listing Agent Shane Masaschi Compass

    1996 Main St, Chatham, MA 02633
    • /47

      Est $2,202,719

      Not Listed For Sale

      75 Whidah Rd, North Chatham, MA 02650

      • 4 Beds
      • 2.5 Baths
      • 2,524 Sq Ft
      • Built 1969
      75 Whidah Rd, North Chatham, MA 02650

      Last Sold Summary

      • 7% Above List Price
      • $812/SF
      • 4 Days On Market
      • Last Sold Price $2,050,000
      • Aug 23, 2024

      Last Listing Agent Tim Bailey John C Ricotta & Assoc.

  • /41

    $699,000

    $196K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,773 Sq Ft

    6 Munson Meeting Way Unit 894, Chatham, MA 02633

    894 Main Street presents a rare mixed-use investment in one of Cape Cod's most visible and enduring locations. This iconic Main Street address benefits from exceptional foot traffic, strong frontage, and effortless walkability to the town's most desirable destinations. Comprising 1,773 square feet, the property offers a fully leased commercial space at street level paired with a two-bedroom

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    6 Munson Meeting Way Unit 894, 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 $1,293,336

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    56 Monomoit Ln, Chatham, MA 02633
    • /42

      Est $1,216,759

      Not Listed For Sale

      20 Spring Hill Rd, North Chatham, MA 02650

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1994
      20 Spring Hill Rd, North Chatham, MA 02650

      Last Sold Summary

      • 1% Below List Price
      • $766/SF
      • 26 Days On Market
      • Last Sold Price $1,225,000
      • Jan 08, 2025

      Last Listing Agent Julie Chapin William Raveis Chatham

  • /23

    $1,995,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    50 Eldredge Square S, Chatham, MA 02633

    Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings. Thoughtfully designed for effortless single-level living, the main floor

    Chris Rhinesmith Compass Massachusetts, LLC

    50 Eldredge Square S, 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 $7,090,062

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    23 Oyster Pond Ln, Chatham, MA 02633
    • /35

      Est $1,385,872

      Not Listed For Sale

      101 Old Mail Rd, North Chatham, MA 02650

      • 3 Beds
      • 1.5 Baths
      • 1,511 Sq Ft
      • Built 1940
      101 Old Mail Rd, North Chatham, MA 02650

      Last Sold Summary

      • 13% Below List Price
      • $1,058/SF
      • 7 Days On Market
      • Last Sold Price $1,599,000
      • Feb 24, 2025

      Last Listing Agent Jessica King Compass Massachusetts, LLC

  • /33

    $4,500,000

    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    346 Morris Island Rd, Chatham, MA 02633

    Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water

    Chris Rhinesmith Compass Massachusetts, LLC

    346 Morris Island Rd, 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
    • /18

      Est $347,433

      Not Listed For Sale

      197 Stony Hill Rd Unit C, Chatham, MA 02633

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft
      • Built 1995
      197 Stony Hill Rd Unit C, Chatham, MA 02633

      Last Sold Summary

      • 16% Above List Price
      • $500/SF
      • 185 Days On Market
      • Last Sold Price $300,000
      • Sep 22, 2023

      Last Listing Agent Caroline McAdams Covell Realty Inc

  • /37

    $1,425,000

    Pending
    • 2 Beds
    • 3 Baths
    • 2,212 Sq Ft

    1114 Orleans Rd Unit 2, North Chatham, MA 02650

    Part of the historic Christopher Ryder House, this elegant two-bedroom, three bath condominium blends one floor living with timeless architectural charm. The residence offers beautifully proportioned rooms, high ceilings, large sun-filled windows, and warm wood floors throughout. A gracious foyer opens to a grand living room with gas fireplace that flows seamlessly into the dining room and

    Chris Rhinesmith Compass Massachusetts, LLC

    1114 Orleans Rd Unit 2, North Chatham, MA 02650
  • /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

    Current Estimated Value $9,521,132

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    53 Gristmill Ln, Chatham, MA 02633
    • /53

      Est $1,262,003

      Not Listed For Sale

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

      • 2 Beds
      • 3.5 Baths
      • 2,546 Sq Ft
      • Built 2005
      43 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 7% Above List Price
      • $463/SF
      • 10 Days On Market
      • Last Sold Price $1,180,000
      • Dec 13, 2023

      Last Listing Agent Kristen Savely Compass Massachusetts, LLC

  • /72

    $4,750,000

    • 4 Beds
    • 3.5 Baths
    • 4,967 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living. A chef's kitchen, dual living areas, and an

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    38 Indian Trail, 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

    Current Estimated Value $1,842,938

    Last Listing Agent Charles King Real Broker MA, LLC

    24 Shattuck Place, Chatham, MA 02633
    • /29

      Est $1,044,530

      Not Listed For Sale

      39 Misty Meadow Ln, North Chatham, MA 02650

      • 2 Beds
      • 2.5 Baths
      • 1,812 Sq Ft
      • Built 2005
      39 Misty Meadow Ln, North Chatham, MA 02650

      Last Sold Summary

      • 4% Above List Price
      • $555/SF
      • 10 Days On Market
      • Last Sold Price $1,005,000
      • Nov 29, 2023

      Last Listing Agent Team Guthrie - Mabile Berkshire Hathaway HomeServices Robert Paul Properties

  • /20

    $12,999,900

    New Construction
    • 4 Beds
    • 7 Baths
    • 6,234 Sq Ft

    157 Bridge St, Chatham, MA 02633

    In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    157 Bridge St, Chatham, MA 02633
  • /48

    $6,950,000

    Sold Jul 24, 2025

    16 Seapine Rd, North Chatham, MA 02650

    • 5 Beds
    • 6.5 Baths
    • 6,508 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,068/SF
    • 307 Days On Market

    Current Estimated Value $5,053,566

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    16 Seapine Rd, North Chatham, MA 02650
    • /27

      Est $1,046,497

      Not Listed For Sale

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

      • 2 Beds
      • 2.5 Baths
      • 1,906 Sq Ft
      • Built 2005
      37 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 7% Above List Price
      • $512/SF
      • 55 Days On Market
      • Last Sold Price $975,000
      • Dec 29, 2023

      Last Listing Agent Tia Lilly Property Cape Cod

  • /42

    $1,999,000

    • 3 Beds
    • 3 Baths
    • 3,514 Sq Ft

    70 Uncle Deane's Rd, Chatham, MA 02659

    Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully

    Patrick Davison Shining Sea Realty

    70 Uncle Deane's Rd, Chatham, MA 02659
  • /50

    $955,000

    Sold Oct 14, 2025

    67 A Leonard Way, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $713/SF
    • 17 Days On Market

    Current Estimated Value $989,513

    Last Listing Agent Shane Masaschi Compass

    67 A Leonard Way, Chatham, MA 02633
    • /25

      Est $1,077,383

      Not Listed For Sale

      61 Bishops Terrace, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft
      • Built 1966
      61 Bishops Terrace, Chatham, MA 02633

      Last Sold Summary

      • 46% Above List Price
      • $460/SF
      • 31 Days On Market
      • Last Sold Price $740,000
      • Sep 08, 2023

      Last Listing Agent Shane Masaschi Kinlin Grover Compass

  • /41

    $3,999,900

    New Construction Open Sat 10AM - 12PM
    • 4 Beds
    • 5.5 Baths
    • 4,942 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
  • /46

    $4,000,000

    Sold Oct 03, 2025

    85 Main St, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,998 Sq Ft
    • Built 1820

    Last Sold Summary

    • 27% Below List Price
    • $1,334/SF
    • 150 Days On Market

    Current Estimated Value $3,994,530

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633
    • /13

      Est $641,643

      Not Listed For Sale

      276 Orleans Rd, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 955 Sq Ft
      • Built 1920
      276 Orleans Rd, Chatham, MA 02633

      Last Sold Summary

      • $670/SF
      • 35 Days On Market
      • Last Sold Price $640,000
      • Jun 20, 2023

      Last Listing Agent Siobhan Costello Weber Castinetti Realty Group

  • /15

    $699,999

    • 0.5 Baths
    • 600 Sq Ft

    1772 Main St, Chatham, MA 2633

    Residential Potential in Chatham'sR20 Zone!This unique property offers a rare chance to create a standalone single-family home just moments from downtown Chatham. Note that the building is currently a commercial barber shop under a 1969 variance; however, it is situated in the R20 residential zone. This provides a clear path for conversion: by petitioning the Zoning Board of Appeals (ZBA) to lift

    Erin Terkelsen LPT Realty, LLC

    1772 Main St, Chatham, MA 2633
  • /38

    $2,000,000

    Sold Sep 16, 2025

    595 Main St Unit 37, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $931/SF
    • 18 Days On Market

    Current Estimated Value $1,949,915

    Last Listing Agent Sandra Tanco Kinlin Grover Compass

    595 Main St Unit 37, Chatham, MA 02633
    • /25

      Est $782,419

      Not Listed For Sale

      161 Shane Dr, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 966 Sq Ft
      • Built 1971
      161 Shane Dr, Chatham, MA 02633

      Last Sold Summary

      • 14% Above List Price
      • $708/SF
      • 6 Days On Market
      • Last Sold Price $684,374
      • May 22, 2024

      Last Listing Agent Darci Gervais Keller Williams Realty

  • /54

    $3,699,900

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,199 Sq Ft

    92 Absegami Run, Chatham, MA 02633

    Newly renovated and beautifully refreshed, this exceptional 4-bedroom, 3.5-bath home is set in one of Chatham's most sought-after neighborhoods, within an exclusive enclave near Oyster Pond and surrounded by remarkable properties. Offering over 3,200 square feet of living space, this post-and-beam residence combines classic Cape charm with the open, airy design today's buyers seek for

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    92 Absegami Run, Chatham, MA 02633
  • /17

    $6,000,000

    Sold Apr 14, 2026

    150 Main St, Chatham, MA 02633

    • 7 Beds
    • 2.5 Baths
    • 2,552 Sq Ft
    • Built 1840

    Last Sold Summary

    • 14% Below List Price
    • $2,351/SF
    • 31 Days On Market

    Current Estimated Value $6,722,515

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    150 Main St, Chatham, MA 02633
    • /38

      Est $1,883,033

      Not Listed For Sale

      55 Eldredge Square S, Chatham, MA 02633

      • 3 Beds
      • 4 Baths
      • 2,630 Sq Ft
      • Built 2003
      55 Eldredge Square S, Chatham, MA 02633

      Last Sold Summary

      • 2% Above List Price
      • $703/SF
      • 152 Days On Market
      • Last Sold Price $1,850,000
      • Oct 29, 2024

      Last Listing Agent Jessica Metzler Compass

Showing Results 121 - 160, Page 4 of 18

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