9,675

Chatham, MA Homes

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  • /34

    $895,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,716 Sq Ft

    58 Tirrells Way, South Chatham, MA 02659

    A distinctive lifestyle begins its unfolding at 58 Tirrell's Way. This ranch style residence, constructed in 2001, offers a blend of comfort and easy maintenance all set on impressive .67 Acre level lot. The residence thoughtfully encompasses open plan living area, providing a relaxed concept of living/ dining and kitchen with cathedral ceiling, gas fireplace, gleaming hardwood floors and pretty

    Phyllis Power Compass

    58 Tirrells Way, South Chatham, MA 02659
  • /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 $6,397,905

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    150 Main St, Chatham, MA 02633
    • /27

      Est $1,056,781

      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

      • 55 Days On Market

  • /5

    $999,000

    • Land
    • 6,969 Sq Ft
    • $6,243,750 per Acre

    727 Main St, Chatham, MA 02633

    Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

    Noreen Kennedy Kennedy Real Estate

    727 Main St, Chatham, MA 02633
  • /46

    $1,385,000

    Sold Dec 16, 2025

    114 Bucks Creek Rd, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 2,289 Sq Ft
    • Built 1965

    Last Sold Summary

    • 21% Below List Price
    • $605/SF
    • 84 Days On Market

    Current Estimated Value $1,478,905

    Last Listing Agent Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

    114 Bucks Creek Rd, Chatham, MA 02633
    • /25

      Est $1,034,734

      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

      • 31 Days On Market

  • /52

    $1,275,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,062 Sq Ft

    58 Stepping Stones Rd, Chatham, MA 02633

    Nestled in the charming coastal town of Chatham, this beautifully updated TURN KEY Cape home offers a refined blend of privacy, comfort, and timeless appeal. Set more than 300 feet from Steppingstones Rd. This home is filled with natural light and offers a bright, airy feel throughout.Designed for effortless living and entertaining, the open-concept kitchen and dining area creates a graceful flow

    Sherrilynn Lombard New Homes Marketing, Inc.

    58 Stepping Stones Rd, Chatham, MA 02633
  • /2

    $1,000,000

    Sold Sep 29, 2025

    0 Woodland Way, Chatham, MA 02650

    • Land
    • 21,344 Sq Ft
    • $2,040,816 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Kimberly Howard Christie's International Real Estate Atlantic Brokerage

    0 Woodland Way, Chatham, MA 02650
    • /25

      Est $794,487

      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

      • 6 Days On Market

  • /44

    $2,390,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the

    Janet Stuart Coldwell Banker Realty

    55 Winterset Dr, Chatham, MA 02633
  • /41

    $898,000

    Sold Oct 30, 2025

    306 Old Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $535/SF
    • 14 Days On Market

    Current Estimated Value $941,551

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    306 Old Queen Anne Rd, Chatham, MA 02633
    • /38

      Est $1,950,971

      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

      • 152 Days On Market

  • /41

    $849,000

    $51K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    66 Snow Ln, Chatham, MA 02633

    Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenience, & natural beauty. This charming 2-bedroom, 1-bath ranch-style home is surrounded by conservation land, creating a peaceful setting where birds, wildlife, and wooded views can be enjoyed from every window. Thoughtfully designed for easy one-floor living, the home features a wood burning fireplace,

    Shane Masaschi Compass

    66 Snow Ln, Chatham, MA 02633
  • /36

    $775,000

    Sold Jun 05, 2026

    35 Bobbie's Ln, Chatham, MA 02659

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • 11% Above List Price
    • $673/SF
    • 6 Days On Market

    Last Listing Agent Richard Waystack Keller Williams Realty

    35 Bobbie's Ln, Chatham, MA 02659
    • /28

      Est $1,212,865

      Not Listed For Sale

      233 Barcliff Ave, Chatham, MA 02633

      • 2 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1957
      233 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 25 Days On Market

  • /28

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

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

    Tucked away on a quiet street in the heart of North Chatham, this charming second-floor condominium offers an exceptional opportunity to own in one of the Cape's most coveted locations. Whether you're seeking a seasonal retreat, an investment property, or a smart entry into the Chatham market, this residence delivers a perfect blend of convenience, charm, and value. Filled with natural light, the

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • /55

    $3,025,000

    Sold Dec 19, 2025

    93 Bucks Creek Rd, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 3,544 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $854/SF
    • 61 Days On Market

    Current Estimated Value $3,009,096

    Last Listing Agent Shane Masaschi Compass

    93 Bucks Creek Rd, Chatham, MA 02633
    • /65

      Est $2,943,025

      Not Listed For Sale

      25 Glover Square, Chatham, MA 02633

      • 3 Beds
      • 4.5 Baths
      • 4,105 Sq Ft
      • Built 2018
      25 Glover Square, Chatham, MA 02633

      Last Sold Summary

      • 165 Days On Market

  • /44

    $5,495,000

    $405K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    99 Uncle Alberts Drive Extension, Chatham, MA 2633

    Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

    Shane Masaschi Compass

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • /6

    $3,499,900

    Sold Dec 22, 2025

    29 Jessies Landing, Chatham, MA 2633

    • 3 Beds
    • 4.5 Baths
    • 4,565 Sq Ft
    • Built 2024

    Last Sold Summary

    • $767/SF
    • 3 Days On Market

    Current Estimated Value $3,681,252

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

    29 Jessies Landing, Chatham, MA 2633
    • /46

      Est $1,414,213

      Not Listed For Sale

      265 Barcliff Ave, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,491 Sq Ft
      • Built 1953
      265 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 2 Days On Market

  • /93

    $5,850,000

    $400K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,620 Sq Ft

    15 Windy Hill Way, Chatham, MA 02633

    This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

    Tim Bailey John C Ricotta & Assoc.

    15 Windy Hill Way, Chatham, MA 02633
  • /24

    $775,000

    Sold Jun 05, 2026

    35 Bobbies Ln, Chatham, MA 2633

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • 11% Above List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $717,682

    Last Listing Agent Richard Waystack William Raveis Harwich Port

    35 Bobbies Ln, Chatham, MA 2633
    • /30

      Est $1,420,020

      Not Listed For Sale

      751 Main St, Chatham, MA 02633

      • 2 Beds
      • 2.5 Baths
      • 1,552 Sq Ft
      • Built 1910
      751 Main St, Chatham, MA 02633

      Last Sold Summary

      • 102 Days On Market

  • /36

    $1,199,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,391 Sq Ft

    68 Chippingstone Rd, Chatham, MA 02633

    Coffee on the deck while overlooking the water. Enjoy peaceful mornings and beautiful water views from nearly every room in this spacious home. Welcome to Riverbay Estates, where Cape Cod charm meets endless potential. This, well-built 4-bedroom, 3-bath home offers direct access to Pickerel Pond for kayaking and enjoying nature. A true "diamond in the rough" project with great bones ready for

    Marcie Smith Christie's International Real Estate Atlantic Brokerage

    68 Chippingstone Rd, Chatham, MA 02633
  • /50

    $995,000

    Sold Oct 10, 2025

    56 Chatham Crest Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Above List Price
    • $575/SF
    • 5 Days On Market

    Current Estimated Value $1,098,054

    Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

    56 Chatham Crest Dr, Chatham, MA 02633
    • /30

      Not Listed For Sale

      178 Queen Anne Rd, Chatham, MA 02633

      • 6 Beds
      • 8 Baths
      • 7,700 Sq Ft
      • Built 1820
      178 Queen Anne Rd, Chatham, MA 02633

      Last Sold Summary

      • 21 Days On Market

  • /26

    $4,200,000

    • 3 Beds
    • 3 Baths
    • 2,418 Sq Ft

    30 Indian Trail, Chatham, MA 02633

    Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story

    Chris Rhinesmith Compass

    30 Indian Trail, Chatham, MA 02633
  • /63

    $1,435,000

    Sold May 14, 2026

    28 Lakeview Ave, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,441 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $588/SF
    • 133 Days On Market

    Current Estimated Value $1,401,122

    Last Listing Agent Ella Leavitt Compass

    28 Lakeview Ave, Chatham, MA 02633
    • /24

      Est $3,878,438

      Not Listed For Sale

      125 Stage Harbor Rd, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 2,421 Sq Ft
      • Built 1946
      125 Stage Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 506 Days On Market

  • /47

    $1,475,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft

    367 Deer Meadow Ln, Chatham, MA 02633

    Nestled in Chatham's highly sought-after RiverBay neighborhood, this beautifully updated Cape-style home offers the perfect blend of classic charm and modern comfort. Featuring 3 bedrooms and 2.5 baths, the home is thoughtfully designed for both everyday living and effortless entertaining.A first-floor primary suite provides a private retreat, complete with a generous walk-in closet and a cozy

    Kathy Doyle Gibson Sotheby's International Realty

    367 Deer Meadow Ln, Chatham, MA 02633
  • /36

    $645,000

    Sold Jan 06, 2026

    407 Orleans Rd Unit D, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $422/SF
    • 4 Days On Market

    Current Estimated Value $678,704

    Last Listing Agent Tom Riley Compass Massachusetts, LLC

    407 Orleans Rd Unit D, North Chatham, MA 02650
    • /62

      Est $2,990,339

      Not Listed For Sale

      276 Stage Harbor Rd, Chatham, MA 02633

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

      Last Sold Summary

      • 33 Days On Market

  • /52

    $889,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,618 Sq Ft

    96 Stage Coach Dr, South Chatham, MA 02659

    Back on the market! Lovingly maintained and thoughtfully enjoyed over the years, this classic Chatham ranch reflects true pride of ownership. A traditional layout offers three bedrooms, including a primary with en suite bath, and easy, comfortable living throughout. Recently refreshed with a full interior paint update and beautifully staged, the home feels bright, welcoming, and ready for its

    Dawn Lee Gibson Sotheby's International Realty

    96 Stage Coach Dr, South Chatham, MA 02659
  • /35

    $850,000

    Sold May 05, 2026

    46 Chippingstone Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft
    • Built 1973

    Last Sold Summary

    • 13% Below List Price
    • $496/SF
    • 125 Days On Market

    Current Estimated Value $865,421

    Last Listing Agent Derek Greene The Greene Realty Group

    46 Chippingstone Rd, Chatham, MA 02633
    • /78

      Est $3,723,674

      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

      • 205 Days On Market

  • /12

    $4,499,900

    New Construction Pending
    • 3 Beds
    • 7 Baths
    • 4,450 Sq Ft

    1 Peirce Path, South Chatham, MA 02659

    South of Route 28 and moments from the shimmering shores of Nantucket Sound, this new residence by Eastward Companies captures the essence of refined coastal living. Gracefully sited on over two-thirds of an acre, the home's striking Dutch Gambrel architecture evokes timeless Cape heritage while delivering over 4,450 square feet of sophisticated, modern design across three impeccably finished

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    1 Peirce Path, South Chatham, MA 02659
  • /41

    $1,599,000

    Sold Aug 15, 2025

    751 Crowell Rd, North Chatham, MA 02650

    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Above List Price
    • $682/SF
    • 2 Days On Market

    Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    751 Crowell Rd, North Chatham, MA 02650
    • /40

      Est $3,976,915

      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

      • 111 Days On Market

  • /64

    $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

Showing Results 161 - 200, Page 5 of 18

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