9,675

Chatham, MA Homes

Section Image
    • /35

      Est $1,183,397

      Not Listed For Sale

      8 Oyster Dr, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 748 Sq Ft
      • Built 1947
      8 Oyster Dr, Chatham, MA 02633

      Last Sold Summary

      • 10 Days On Market

  • /34

    $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
  • /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 $1,290,229

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    56 Monomoit Ln, Chatham, MA 02633
    • /22

      Est $737,200

      Not Listed For Sale

      16 Starfish Ln, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft
      • Built 1982
      16 Starfish Ln, Chatham, MA 02633

      Last Sold Summary

      • 38 Days On Market

  • /28

    $750,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,102 Sq Ft

    165 Tanglewood Dr, South Chatham, MA 02659

    Start enjoying your Cape Cod summer in this meticulously maintained 3-bedroom, 3-bathroom ranch being sold partially furnished. You'll love the cozy ambiance of two wood-burning fireplaces--one in the living room and another in the inviting den--perfect for chilly coastal nights. The updated kitchen features white cabinetry, a wine cooler, and a dual-fuel oven offering gas cooktop via propane and

    Kari Wagner Compass

    165 Tanglewood Dr, South Chatham, MA 02659
  • /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 $6,901,354

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    23 Oyster Pond Ln, Chatham, MA 02633
    • /55

      Est $2,605,363

      Not Listed For Sale

      15 Edgewater Dr, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1960
      15 Edgewater Dr, Chatham, MA 02633

      Last Sold Summary

      • 119 Days On Market

  • /60

    $3,390,000

    $210K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,978 Sq Ft

    60 Harbor Hill Rd, Chatham, MA 02633

    Tucked away in Chatham's most desirable residential enclaves, this property offers a blend of classic Cape Cod charm & refined living. Set on 40,500 sq. ft. of beautifully landscaped grounds, the home invites both quiet retreat and gracious living. Inside, rich pine floors flow throughout a lovely designed layout featuring 10 spacious rooms, including 4 bedrooms & 3.5 baths The gourmet kitchen is

    Jacquelyn Casey Shore Road Realty

    60 Harbor Hill 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
    • /54

      Est $3,989,828

      Not Listed For Sale

      173 Kendrick Rd, North Chatham, MA 02650

      • 6 Beds
      • 4.5 Baths
      • 4,106 Sq Ft
      • Built 2000
      173 Kendrick Rd, North Chatham, MA 02650

      Last Sold Summary

      • 174 Days On Market

  • /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
  • /25

    $440,000

    Sold Jun 24, 2026

    425 Main St Unit D, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Below List Price
    • $761/SF
    • 26 Days On Market

    Current Estimated Value $448,960

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
    • /30

      Est $2,600,566

      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

      • 1 Day On Market

  • /15

    $4,250,000

    New Construction Open Sat 1PM - 2:30PM $100K PRICE INCREASE
    • 4 Beds
    • 5.5 Baths
    • 3,980 Sq Ft

    222 Barcliff Ave, Chatham, MA 02633

    The location that has it all...walk to both town, fish pier, beach and baseball games....New Farmhouse with pool built by Morgan and Sons and expecting completion by August 1 st.. Enjoy Chatham from this 4BR 5.5 bath , 3980 sq foot home. All bedrooms offer spacious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings with

    Lori Fanning Smith Compass Massachusetts, LLC

    222 Barcliff Ave, Chatham, MA 02633
  • /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 $9,540,221

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    53 Gristmill Ln, Chatham, MA 02633
    • /54

      Est $1,895,136

      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

      • 3 Days On Market

  • /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
  • /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 $1,849,949

    Last Listing Agent Charles King Real Broker MA, LLC

    24 Shattuck Place, Chatham, MA 02633
    • /31

      Est $2,551,779

      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

      • 13 Days On Market

  • /35

    $6,800,000

    $400K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, North Chatham, MA 02650

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, North Chatham, MA 02650
  • /53

    $840,000

    Sold Jul 01, 2026

    61 Oak Hill Rd, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Below List Price
    • $498/SF
    • 34 Days On Market

    Current Estimated Value $866,488

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

    61 Oak Hill Rd, Chatham, MA 02633
    • /47

      Est $2,158,542

      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

      • 4 Days On Market

  • /32

    $1,585,000

    $65K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,531 Sq Ft

    48 Glover Square, Chatham, MA 02633

    Chatham By The Sea. Rare 50-year offering where LOCATION presents a premier opportunity in Chatham. Coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, Cow Yard Landing, shopping, groceries, tennis, golf, 1/2 mile away. Spacious one-floor living with room to expand! Ranch home is 1531 square feet and includes 3 bedrooms, large formal living room

    Laurie McCann Gibson Sotheby's International Realty

    48 Glover Square, 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 $3,842,654

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    16 Seapine Rd, North Chatham, MA 02650
    • /36

      Est $645,960

      Not Listed For Sale

      369 Orleans Rd Unit A, North Chatham, MA 02650

      • 2 Beds
      • 2.5 Baths
      • 1,283 Sq Ft
      • Built 1988
      369 Orleans Rd Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 18 Days On Market

  • /40

    $1,349,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,268 Sq Ft

    36 Pursel Dr, North Chatham, MA 02650

    Nestled on a quiet dead-end street in desirable North Chatham, this beautifully maintained 3-bedroom, 3-bath Cape offers the perfect blend of privacy, coastal lifestyle, and energy-efficient living. Set on a generous 20,435 sq ft lot, this 2,268 sq ft home combines classic Cape charm with features designed for comfort and enjoyment.Enjoy deeded access to Ryders Cove and embrace the boating and

    Diane Donahue Gibson Sotheby's International Realty

    36 Pursel Dr, North Chatham, MA 02650
  • /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 $967,787

    Last Listing Agent Shane Masaschi Compass

    67 A Leonard Way, Chatham, MA 02633
    • /42

      Est $1,357,619

      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

      • 26 Days On Market

  • /78

    $2,995,000

    $255K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    336 Stage Island Rd, Chatham, MA 02633

    Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, this property delivers a generational setting defined by sweeping marsh and water views,

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    336 Stage Island Rd, Chatham, MA 02633
  • /36

    $670,000

    Sold Jun 30, 2026

    216 Orleans Rd Unit E, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 996 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $597,621

    Last Listing Agent Ella Leavitt Compass

    216 Orleans Rd Unit E, North Chatham, MA 02650
    • /35

      Est $1,400,393

      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

      • 7 Days On Market

  • /42

    $1,350,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    50 Pine Ridge Rd, Chatham, MA 02633

    Move right into this charming cottage-style ranch in the coveted beach neighborhood of Hardings Beach Hills. With close proximity to Hardings Beach, this gem is the ideal vacation home or rental investment. The open floor plan includes a cheerful sunroom with vaulted beamed ceilings, sliding door, and walls of windows. Eat-in-kitchen and adjacent living room with fireplace & bay window provide

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    50 Pine Ridge Rd, Chatham, MA 02633
  • /30

    $1,695,000

    Sold Jun 02, 2026

    68 Levis Path, South Chatham, MA 2659

    • 2 Beds
    • 3.5 Baths
    • 2,016 Sq Ft
    • Built 2015

    Last Sold Summary

    • $841/SF
    • 16 Days On Market

    Current Estimated Value $1,660,288

    Last Listing Agent Betsy Hargreaves Gibson Sotheby's International Realty

    68 Levis Path, South Chatham, MA 2659
    • /18

      Est $355,465

      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

      • 185 Days On Market

  • /39

    $789,000

    $106K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    49 Duck Marsh Ln, Chatham, MA 02633

    Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

    Tim Bailey John C Ricotta & Assoc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • /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 $3,997,930

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633
    • /53

      Est $1,282,532

      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

      • 10 Days On Market

  • /31

    $1,350,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,802 Sq Ft

    32 Tip Cart Dr, Chatham, MA 02633

    Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision. Additional features include wood

    Shane Masaschi Compass

    32 Tip Cart Dr, Chatham, MA 02633
  • /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 $1,987,154

    Last Listing Agent Sandra Tanco Kinlin Grover Compass

    595 Main St Unit 37, Chatham, MA 02633
    • /29

      Est $1,112,170

      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

      • 10 Days On Market

Showing Results 121 - 160, Page 4 of 18

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