9,489

Chatham, MA Homes

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    • /2

      Est $3,018,938

      Not Listed For Sale

      276 Stage Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 4 Baths
      • 2,732 Sq Ft
      • Built 1988
      276 Stage Harbor Rd, Chatham, MA 02633

  • /32

    $899,000

    Pending
    • 2 Beds
    • 2 Baths
    • 2,127 Sq Ft

    1068 Main St, Chatham, MA 02633

    Welcome to ''the Perch''! This 3 level townhome is located in beautiful Chatham! This serene setting overlooks Perch Pond- where nature abounds.This 3 level townhome has a finished lower level w/ great room and sleeping area (w/ 2 queen beds). This complex is located close to downtown shops & restaurants, local beaches & the Old Colony Rail Trail. There are 2 bedroom suites incl a first floor

    William Raveis Non-Member William Raveis Non-Member Office

    1068 Main St, Chatham, MA 02633
  • /42

    $2,000,000

    Sold Sep 08, 2025

    55 Meadowview Rd S, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 1,897 Sq Ft
    • Built 1965

    Last Sold Summary

    • 5% Above List Price
    • $1,054/SF
    • 6 Days On Market

    Last Listing Agent Serena LoPiccolo Smith Keller Williams Realty

    55 Meadowview Rd S, Chatham, MA 02633
    • /78

      Est $3,644,610

      Not Listed For Sale

      155 Inlet Rd, Chatham, MA 02633

      • 5 Beds
      • 5.5 Baths
      • 4,048 Sq Ft
      • Built 2010
      155 Inlet Rd, Chatham, MA 02633

      Last Sold Summary

      • 207 Days On Market

      Last Listing Agent Janice Alex Christie's International Real Estate Atlantic Brokerage

  • /31

    $1,230,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,294 Sq Ft

    72 Smith St, Chatham, MA 02633

    NEW to Chatham! Tucked along a quiet lane, just minutes from Harding's Beach, village shops and beloved local dining, this light-filled home offers the chance to step into the Chatham's lifestyle so many only dream about. Freshly painted, high ceilings, hardwood flooring and abundant windows that offer both light and privacy. Outdoors is framed by beautiful blue hydrangeas, colorful perennials

    Laura Johnson Gibson Sotheby's International Realty

    72 Smith St, Chatham, MA 02633
  • /45

    $1,350,000

    Sold Oct 23, 2025

    116 Happy Valley Rd, Chatham, MA 02633

    • 2 Beds
    • 3 Baths
    • 1,861 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Below List Price
    • $725/SF
    • 106 Days On Market

    Current Estimated Value $1,328,552

    Last Listing Agent Ward Brown, III William Raveis Real Estate & Home Services

    116 Happy Valley Rd, Chatham, MA 02633
    • /40

      Est $3,868,071

      Not Listed For Sale

      98 Attucks Trail, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 3,915 Sq Ft
      • Built 1971
      98 Attucks Trail, Chatham, MA 02633

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties

  • /49

    $2,100,000

    • 1 Bed
    • 1.5 Baths
    • 1,479 Sq Ft

    409 Main St, Chatham, MA 02633

    Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the

    Rick Smith Gibson Sotheby's International Realty

    409 Main St, Chatham, MA 02633
  • /2

    $1,800,000

    Sold Dec 05, 2025

    68 Capri Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft
    • Built 1957

    Last Sold Summary

    • $1,038/SF
    • 0 Days On Market

    Current Estimated Value $1,972,347

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

    68 Capri Ln, Chatham, MA 02633
    • /38

      Est $3,163,038

      Not Listed For Sale

      137 Strong Island Rd, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 4,199 Sq Ft
      • Built 1982
      137 Strong Island Rd, Chatham, MA 02633

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Phyllis Power 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 & Assoc.

    231 Crowell Rd, Chatham, MA 2633
  • /45

    $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
    • 140 Days On Market

    Current Estimated Value $1,310,889

    Last Listing Agent Derek Greene The Greene Realty Group

    93 Orleans Rd, Chatham, MA 02633
    • /25

      Est $4,201,138

      Not Listed For Sale

      192 Eastward Rd, Chatham, MA 02633

      • 5 Beds
      • 3 Baths
      • 2,514 Sq Ft
      • Built 1957
      192 Eastward Rd, Chatham, MA 02633

      Last Sold Summary

      • 286 Days On Market

      Last Listing Agent Judith Smith John C. Ricotta & Associates, Inc.

  • /44

    $1,695,000

    $100K PRICE DROP
    • 2 Beds
    • 3.5 Baths
    • 2,331 Sq Ft

    43 Tobey Turtle Rd, Chatham, MA 02633

    Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3½ baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the

    Timothy Bailey John C Ricotta & Assoc.

    43 Tobey Turtle Rd, Chatham, MA 02633
  • /41

    $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
    • 22 Days On Market

    Current Estimated Value $1,217,284

    Last Listing Agent Shane Masaschi Compass

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

      Est $1,647,173

      Not Listed For Sale

      54 Rowland Dr, North Chatham, MA 02650

      • 4 Beds
      • 3.5 Baths
      • 2,062 Sq Ft
      • Built 1970
      54 Rowland Dr, North Chatham, MA 02650

      Last Sold Summary

      • 283 Days On Market

      Last Listing Agent Barbara Garside eXp Realty, LLC

  • /40

    $1,399,000

    $96K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    137 Shane Dr, Chatham, MA 02633

    Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530

    Tom Riley Compass Massachusetts, LLC

    137 Shane Dr, Chatham, MA 02633
  • /31

    $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

    Current Estimated Value $942,188

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

    15 Sylvan Way, South Chatham, MA 02659
    • /43

      Est $2,869,558

      Not Listed For Sale

      30 Pine Ln, North Chatham, MA 02650

      • 4 Beds
      • 3.5 Baths
      • 4,406 Sq Ft
      • Built 1982
      30 Pine Ln, North Chatham, MA 02650

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Tracey Oringer Kinlin Grover Compass

  • /63

    $3,595,000

    $800K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,640 Sq Ft

    287 Cedar St, Chatham, MA 02633

    NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

    Shane Masaschi Compass

    287 Cedar St, Chatham, MA 02633
  • /33

    $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

    Current Estimated Value $1,299,522

    Last Listing Agent Kathy Doyle Gibson Sotheby's International Realty

    27 Fairview Dr, South Chatham, MA 02659
    • /22

      Est $439,068

      Not Listed For Sale

      409 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 1 Bath
      • 1,013 Sq Ft
      • Built 1987
      409 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Debra Bassett Cape Cod Associates R E

  • /7

    $315,000

    $35K PRICE DROP Pending
    • Land
    • 20,473 Sq Ft
    • $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
  • /54

    $3,100,000

    Sold Mar 27, 2026

    28 Cranberry Ln, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 3,759 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $825/SF
    • 17 Days On Market

    Current Estimated Value $3,033,511

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    28 Cranberry Ln, Chatham, MA 02633
    • /16

      Est $503,027

      Not Listed For Sale

      407 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,013 Sq Ft
      • Built 1987
      407 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 134 Days On Market

      Last Listing Agent John Burke William Raveis Chatham

  • /41

    $5,900,000

    • 4 Beds
    • 5 Baths
    • 4,394 Sq Ft

    95 Cotchpinicut, Chatham, MA 02633

    Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and rooms and additions in several directions in this very private location of North Chatham....Choice of three primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the heated Gunite

    John Burke William Raveis Chatham

    95 Cotchpinicut, Chatham, MA 02633
  • /41

    $2,150,000

    Sold Apr 28, 2026

    55 Christopher Harding Ln, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,510 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $857/SF
    • 207 Days On Market

    Current Estimated Value $2,137,315

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    55 Christopher Harding Ln, Chatham, MA 02633
    • /27

      Est $672,782

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,551 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

  • /25

    $659,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 999 Sq Ft

    216 Orleans Rd Unit D, North Chatham, MA 02650

    Spacious and sunny condo in North Chatham set on the corner of Stoney Hill Rd. Walk to Cow yard beach and admire the historic homes along the way. Or walk in the opposite direction towards down town Chatham. The location and size of this condo will win your heart. Offered completely furnished with many recent upgrades including new AC, new deck, new windows and roof. This condo is graced with

    Kathleen Phelan Compass Massachusetts, LLC

    216 Orleans Rd Unit D, North Chatham, MA 02650
  • /73

    $1,175,000

    Sold Jan 22, 2026

    597 Orleans Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $605/SF
    • 181 Days On Market

    Current Estimated Value $1,286,766

    Last Listing Agent Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
    • /25

      Est $586,932

      Not Listed For Sale

      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,489 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 126 Days On Market

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /33

    $1,469,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho and Pleasant Bay from nearly every angle. The shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    558 Fox Hill Rd, Chatham, MA 02633
  • /42

    $4,700,000

    Sold Jun 22, 2026

    92 Barcliff Ave, Chatham, MA 02633

    • 5 Beds
    • 3.5 Baths
    • 2,659 Sq Ft
    • Built 1870

    Last Sold Summary

    • 2% Above List Price
    • $1,768/SF
    • 6 Days On Market

    Current Estimated Value $4,283,720

    Last Listing Agent Mina O'Keefe Gibson Sotheby's International Realty

    92 Barcliff Ave, Chatham, MA 02633
    • /34

      Est $436,731

      Not Listed For Sale

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

      • 2 Beds
      • 1.5 Baths
      • 930 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

  • /40

    $949,000

    Pending
    • 2 Beds
    • 1 Bath
    • 750 Sq Ft

    79 Cranberry Ln, Chatham, MA 02633

    Rare opportunity to own a move in ready beach home in Chatham's coveted Ridgevale Beach neighborhood, where homes rarely become available. Just 0.3 miles from Ridgevale Beach, this thoughtfully designed 750± sq. ft. home blends coastal charm with modern style. The home features 2 bedrooms, 1 bath, plus a versatile loft area offering additional sleeping space for children or guests. Bright, open

    Katie Norton William Raveis R.E. & Home Services

    79 Cranberry Ln, Chatham, MA 02633
  • /22

    $860,000

    Sold Dec 30, 2025

    41 Woodland Rd, South Chatham, MA 02659

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • Built 1960

    Last Sold Summary

    • 8% Above List Price
    • $517/SF
    • 4 Days On Market

    Current Estimated Value $930,867

    Last Listing Agent Phyllis Power Compass

    41 Woodland Rd, South Chatham, MA 02659
    • /26

      Est $405,298

      Not Listed For Sale

      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      • 1 Bed
      • 1.5 Baths
      • 836 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Margaret Fallon LPT Realty

  • /42

    $2,150,000

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

    234 Round Cove Rd, Chatham, MA 02633

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

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    234 Round Cove Rd, Chatham, MA 02633
  • /7

    $250,000

    Sold May 19, 2026

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

    • Land
    • 31,363 Sq Ft
    • $347,222 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 991 Days On Market

    Last Listing Agent Shane Masaschi Compass

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    • /29

      Est $1,188,599

      Not Listed For Sale

      56 Meadowbrook Rd, North Chatham, MA 02650

      • 4 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 1961
      56 Meadowbrook Rd, North Chatham, MA 02650

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Shane Masaschi Compass

Showing Results 241 - 280, Page 7 of 18

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