9,676

Chatham, MA Homes

Section Image
    • /48

      Est $1,118,934

      Not Listed For Sale

      31 Great Hill Rd, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,977 Sq Ft
      • Built 1965
      31 Great Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 234 Days On Market

  • /66

    $1,199,900

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,324 Sq Ft

    99 Shane Dr, Chatham, MA 02633

    This charming ranch-style home offers an exceptional opportunity to own in Chatham, with peaceful meadow views and a convenient location just about a mile from town and the beach. Thoughtfully updated and easy to enjoy, the home features 2 bedrooms, 1.5 baths, and comfortable single-level living. The spacious front-to-back primary bedroom includes a private half bath, while the additional bedroom

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    99 Shane Dr, Chatham, MA 02633
  • /95

    $2,025,000

    Sold Oct 10, 2025

    2016 Main St, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 3,902 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $519/SF
    • 64 Days On Market

    Current Estimated Value $2,259,742

    Last Listing Agent Daneen Law Gibson Sotheby's International Realty

    2016 Main St, Chatham, MA 02633
    • /27

      Est $711,848

      Not Listed For Sale

      79 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1968
      79 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 6 Days On Market

  • /72

    $4,750,000

    New Construction Open Sat 9:30AM - 11:30AM $500K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    Set within a private gated enclave in South Chatham's emerging luxury corridor, 48 Sylvan Way is a singular estate retreat discreetly positioned just moments from the Cape's most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational potential, the property offers rare privacy, scale, and versatility in one of Chatham's most compelling

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    48 Sylvan Way, South Chatham, MA 02659
  • /31

    $950,000

    Sold Jul 25, 2025

    68 Pleasant St, South Chatham, MA 02659

    • 5 Beds
    • 2.5 Baths
    • 2,016 Sq Ft
    • Built 1780

    Last Sold Summary

    • 3% Below List Price
    • $471/SF
    • 12 Days On Market

    Current Estimated Value $1,076,931

    Last Listing Agent Jen Graham Christie's International Real Estate Atlantic Brokerage

    68 Pleasant St, South Chatham, MA 02659
    • /24

      Est $1,109,328

      Not Listed For Sale

      59 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1966
      59 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 38 Days On Market

  • /42

    $2,100,000

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

    409 Main St, Chatham, MA 02633

    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 building and is

    Rick Smith Gibson Sotheby's International Realty

    409 Main St, Chatham, MA 02633
  • /37

    $2,232,500

    Sold Apr 28, 2026

    2 Seapine Rd, North Chatham, MA 02650

    • 3 Beds
    • 4 Baths
    • 3,090 Sq Ft
    • Built 1972

    Last Sold Summary

    • 14% Below List Price
    • $722/SF
    • 136 Days On Market

    Current Estimated Value $2,269,424

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

    2 Seapine Rd, North Chatham, MA 02650
    • /47

      Est $880,044

      Not Listed For Sale

      190 Heritage Ln, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 1973
      190 Heritage Ln, Chatham, MA 02633

      Last Sold Summary

      • 34 Days On Market

  • /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
  • /46

    $2,199,900

    Sold Apr 29, 2026

    8 Kingsbury Way, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 1,651 Sq Ft
    • Built 1943

    Last Sold Summary

    • $1,332/SF
    • 2 Days On Market

    Current Estimated Value $2,169,740

    Last Listing Agent Doug Grattan Christie's International Real Estate Atlantic Brokerage

    8 Kingsbury Way, Chatham, MA 02633
    • /28

      Est $673,612

      Not Listed For Sale

      46 Nob Hill Rd, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1965
      46 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 8 Days On Market

  • /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 recently retiled

    John Burke William Raveis Chatham

    95 Cotchpinicut, Chatham, MA 02633
  • /41

    $952,500

    Sold Mar 24, 2026

    24 Chickadee Cir, Harwich, MA 02645

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $815/SF
    • 119 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    24 Chickadee Cir, Harwich, MA 02645
    • /7

      Est $529,000

      Not Listed For Sale

      912 Main St Unit 310, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,177 Sq Ft
      • Built 1999
      912 Main St Unit 310, Chatham, MA 02633

      Last Sold Summary

      • 19 Days On Market

  • /39

    $699,900

    • 2 Beds
    • 1 Bath
    • 572 Sq Ft

    22 Country Ln, South Chatham, MA 02659

    Just 0.4 miles from the sandy shores of Pleasant Street Beach, this enchanting South Chatham Cape-style cottage captures the timeless charm of Cape Cod living. Set down a private lane on a tree-lined lot, this storybook home is filled with warmth and character. The sun-filled interior features an open living and dining area heated by a cozy natural gas stove, a cheerful kitchen with a butcher

    Laurie Miller Sotheby's International Realty, Inc.

    22 Country Ln, South Chatham, MA 02659
  • /30

    $1,635,000

    Sold Sep 26, 2025

    24 Hillcrest Rd, North Chatham, MA 02650

    • 5 Beds
    • 3 Baths
    • 3,098 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Above List Price
    • $528/SF
    • 1 Day On Market

    Current Estimated Value $1,940,845

    Last Listing Agent Jessica King Compass Massachusetts, LLC

    24 Hillcrest Rd, North Chatham, MA 02650
    • /43

      Est $544,451

      Not Listed For Sale

      912 Main St Unit 306, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,508 Sq Ft
      • Built 1999
      912 Main St Unit 306, Chatham, MA 02633

      Last Sold Summary

      • 48 Days On Market

  • /58

    $750,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    260 Tanglewood Dr, South Chatham, MA 02659

    Designed for one-floor living, this home is ideal as a retreat or year-round residence! Inside, a cozy wood-burning fireplace anchors the inviting living room while a large bay window welcomes the sunlight! The primary bedroom offers an en suite bath and private outdoor access--ideal if you want to add a hot tub to the private outdoor space behind! A mudroom, laundry room, and flexible bonus

    Amy Harbeck Kinlin Grover Compass

    260 Tanglewood Dr, South Chatham, MA 02659
  • /39

    $1,500,000

    Sold Oct 03, 2025

    17 Bog Way Rd, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 1,633 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Above List Price
    • $919/SF
    • 3 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    17 Bog Way Rd, Chatham, MA 02633
    • /33

      Est $621,178

      Not Listed For Sale

      912 Main St Unit 303, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,649 Sq Ft
      • Built 1999
      912 Main St Unit 303, Chatham, MA 02633

      Last Sold Summary

      • 1 Day On Market

  • /43

    $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
  • /37

    $1,385,000

    Sold Jun 04, 2026

    1114 Orleans Rd Unit 2, North Chatham, MA 02650

    • 2 Beds
    • 3 Baths
    • 2,212 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $626/SF
    • 25 Days On Market

    Current Estimated Value $1,354,180

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    1114 Orleans Rd Unit 2, North Chatham, MA 02650
    • /28

      Est $510,710

      Not Listed For Sale

      912 Main St Unit 301, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1999
      912 Main St Unit 301, Chatham, MA 02633

      Last Sold Summary

      • 4 Days On Market

  • /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
  • /40

    $5,400,000

    Sold Mar 31, 2026

    121 Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 7 Baths
    • 3,702 Sq Ft
    • Built 2015

    Last Sold Summary

    • $1,459/SF
    • 1 Day On Market

    Current Estimated Value $5,093,003

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    121 Queen Anne Rd, Chatham, MA 02633
    • /24

      Est $439,004

      Not Listed For Sale

      912 Main St Unit 216, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,087 Sq Ft
      • Built 1999
      912 Main St Unit 216, Chatham, MA 02633

      Last Sold Summary

      • 1 Day On Market

  • /40

    $2,795,000

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

    44 Baileys Path, Chatham, MA 2633

    Built by Eastward Companies in 2013, this thoughtfully designed, turnkey home is located in one of Chatham's highly desirable neighborhoods. Offering over 3,500 sq. ft. of beautifully appointed living space, this Cape features 3 bedrooms and 3.5 baths with an open-concept floor plan that seamlessly blends timeless Cape Cod style with modern conveniences. Filled with natural light, the spacious

    Chris Rhinesmith Compass Massachusetts, LLC

    44 Baileys Path, Chatham, MA 2633
  • /41

    $1,300,000

    Sold Dec 31, 2025

    72 Forest Beach Rd, South Chatham, MA 2659

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft
    • Built 1953

    Last Sold Summary

    • 13% Below List Price
    • $541/SF
    • 125 Days On Market

    Current Estimated Value $1,300,336

    Last Listing Agent Michael Magner Berkshire Hathaway HomeServices Robert Paul Properties

    72 Forest Beach Rd, South Chatham, MA 2659
    • /25

      Est $420,223

      Not Listed For Sale

      912 Main St Unit 213, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,011 Sq Ft
      • Built 1999
      912 Main St Unit 213, Chatham, MA 02633

      Last Sold Summary

      • 125 Days On Market

  • /53

    $1,275,000

    Open Sat 10AM - 12PM $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,070 Sq Ft

    240 Riverview Dr, Chatham, MA 02633

    Sought after neighborhood of Riverbay. Light and bright home with incredible gardens and fabulous outdoor space. Three bedrooms 2 newly redone baths with livingroom, dinng room and primary suite all with sliders onto the deck with spiral stairway to back yard for super summer fun. Room for a pool! Lower level could be finished off-high ceilings and windows overlooking the back yard. Deeded rights

    Judith Smith John C Ricotta & Assoc.

    240 Riverview Dr, Chatham, MA 02633
  • /2

    $3,550,000

    Sold Oct 30, 2025

    17 Bucks Ln, Chatham, MA 02633

    • 4 Beds
    • 4 Baths
    • 3,030 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Below List Price
    • $1,172/SF
    • 51 Days On Market

    Current Estimated Value $3,447,192

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    17 Bucks Ln, Chatham, MA 02633
    • /32

      Est $439,610

      Not Listed For Sale

      912 Main St Unit 209, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,167 Sq Ft
      • Built 1999
      912 Main St Unit 209, Chatham, MA 02633

      Last Sold Summary

      • 101 Days On Market

  • /60

    $1,049,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,673 Sq Ft

    149 Island View Ln, South Chatham, MA 02659

    Tucked away at the end of a quiet cul-de-sac on desirable Island View Lane, this 3-bedroom, 2-bath South Chatham home offers the perfect blend of comfort and space. The first floor features both a convenient primary bedroom and a second bedroom with a shared full bath. An eat-in kitchen leads to a sunroom overlooking a large, flat backyard that's perfect for gardening, playing, or simply enjoying

    Martha Knapp Christie's International Real Estate Atlantic Brokerage

    149 Island View Ln, South Chatham, MA 02659
  • /34

    $700,000

    Sold Aug 04, 2025

    89 Ocean Port Ln, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Built 1948

    Last Sold Summary

    • 8% Above List Price
    • $1,167/SF
    • 3 Days On Market

    Current Estimated Value $766,597

    Last Listing Agent Kathleen Phelan Compass Massachusetts, LLC

    89 Ocean Port Ln, Chatham, MA 02633
    • /22

      Est $448,955

      Not Listed For Sale

      912 Main St Unit 207, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1999
      912 Main St Unit 207, Chatham, MA 02633

      Last Sold Summary

      • 71 Days On Market

  • /42

    $2,199,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,520 Sq Ft

    330 Champlain Rd, Chatham, MA 02633

    Location! Location! On " The Loop" at 330 Champlain Rd you have an exceptional 42,518 Sq Ft lot near Stage Harbor & 2 town landings! This charming Colonial offers 2520 square feet of space in a coveted locale, great for summer or year round. The living room has an oversized wood burning fireplace hearth & is open plan to formal dining room, cathedral ceiling & slider to a private patio and

    Phyllis Power Compass

    330 Champlain Rd, Chatham, MA 02633
  • /45

    $6,995,000

    Sold Nov 21, 2025

    13 Captain Knowles Way, Chatham, MA 02633

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft
    • Built 2025

    Last Sold Summary

    • $1,227/SF
    • 147 Days On Market

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

    13 Captain Knowles Way, Chatham, MA 02633
    • /32

      Est $361,182

      Not Listed For Sale

      912 Main St Unit 204, Chatham, MA 02633

      • 1 Bed
      • 2 Baths
      • 975 Sq Ft
      • Built 1999
      912 Main St Unit 204, Chatham, MA 02633

      Last Sold Summary

      • 141 Days On Market

Showing Results 241 - 280, Page 7 of 18

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