9,675

Chatham, MA Homes

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  • /41

    $5,250,000

    $245K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,932 Sq Ft

    56 Stage Island Rd, Chatham, MA 02633

    Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed

    Agent Photo

    Jim Lowenstern

    eXp Realty LLC

    56 Stage Island Rd, Chatham, MA 02633
  • /19

    $4,950 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    101 Monomoyic Way, Chatham, MA 02633

    Available furnished rental September 15 - April 30! Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate

    Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

    101 Monomoyic Way, Chatham, MA 02633
  • /81

    $1,350,000

    Sold Jun 05, 2026

    134 Northgate Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,329 Sq Ft
    • Built 1982

    Last Sold Summary

    • 3% Below List Price
    • $580/SF
    • 21 Days On Market

    Last Listing Agent Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    134 Northgate Rd, Chatham, MA 02633
    • /35

      Not Listed For Sale

      20 Judys Ln, Chatham, MA 02633

      • 3 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1960
      20 Judys Ln, Chatham, MA 02633

      Last Sold Summary

      • 12 Days On Market

  • /40

    $1,069,000

    $126K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft

    65 Captain Kendrick Dr, Chatham, MA 02633

    Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in

    Agent Photo

    Barbara Garside

    eXp Realty LLC

    65 Captain Kendrick Dr, Chatham, MA 02633
  • /29

    $14,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,941 Sq Ft
    • House for Rent

    351 Whidah Rd, North Chatham, MA 02650

    **Summer Weekly or Monthly rental, please inquire about availability** Incredible views and exclusive location! Located in North Chatham, with expansive, commanding and sweeping saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to Pleasant Bay and Orleans from this classic Cape Cod home located at end of a quiet road located in Cannon Hill. High on a

    Anthony Escobedo Coldwell Banker Realty - Newton

    351 Whidah Rd, North Chatham, MA 02650
  • /30

    $5,300,000

    Sold Jan 14, 2026

    4 Ministers Ln, North Chatham, MA 02650

    • 5 Beds
    • 6.5 Baths
    • 5,143 Sq Ft
    • Built 2003

    Last Sold Summary

    • 12% Below List Price
    • $1,031/SF
    • 256 Days On Market

    Current Estimated Value $5,967,130

    Last Listing Agent Chris Rhinesmith Compass

    4 Ministers Ln, North Chatham, MA 02650
    • /30

      Not Listed For Sale

      25 Bobbie's Ln, Chatham, MA 02659

      • 2 Beds
      • 1 Bath
      • 772 Sq Ft
      • Built 1950
      25 Bobbie's Ln, Chatham, MA 02659

      Last Sold Summary

      • 3 Days On Market

  • /48

    $1,069,000

    $126K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,384 Sq Ft

    65 Captain Kendrick Dr, Chatham, MA 02633

    Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility. Offering 1,754 sqft of main-level living, the home many features include an updated eat-in

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    65 Captain Kendrick Dr, Chatham, MA 02633
  • /12

    $6,500 Per Month

    • 4 Beds
    • 2 Baths
    • 864 Sq Ft
    • House for Rent

    15 Myrtle Dr, South Chatham, MA 02659

    SEASONAL RENTAL JUNE -AUGUSTClassic cedar shingled Cape Cod-style 4-bedroom, 2-bath home on a quiet street in South Chatham. This lovely home sets the scene for slow mornings with coffee and a good book. Inside, sunny rooms and gleaming hardwood floors flow from a cozy living room to a well-equipped kitchen--perfect for baking warm bread or prepping fresh-caught seafood. Four comfortable bedrooms

    Eleanor Bright BHHS Commonwealth Real Estate

    15 Myrtle Dr, South Chatham, MA 02659
  • /59

    $1,282,500

    Sold Oct 08, 2025

    591 Crowell Rd, North Chatham, MA 02650

    • 4 Beds
    • 3 Baths
    • 1,661 Sq Ft
    • Built 1850

    Last Sold Summary

    • 3% Below List Price
    • $772/SF
    • 15 Days On Market

    Current Estimated Value $1,325,360

    Last Listing Agent Cheryle Young Today Real Estate

    591 Crowell Rd, North Chatham, MA 02650
    • /4

      Est $3,117,613

      Not Listed For Sale

      21 Hunter Rise, Chatham, MA 02633

      • 3 Beds
      • 5.5 Baths
      • 4,197 Sq Ft
      • Built 2018
      21 Hunter Rise, Chatham, MA 02633

      Last Sold Summary

      • 56 Days On Market

  • /47

    $1,650,000

    Pending
    • 3 Beds
    • 3 Baths
    • 3,190 Sq Ft

    700 Riverview Dr, Chatham, MA 02633

    Nestled in one of Chatham's sought-after neighborhoods, this home is designed for both everyday living and entertaining. The heart of the home is an open kitchen flowing into a family room with vaulted ceilings and a cozy fireplace. From there, step into the sunroom--a favorite spot with views of the landscaped backyard. The oversized deck, accessible from the sunroom and dining room, is ideal

    Sandra Tanco Kinlin Grover Compass

    700 Riverview Dr, Chatham, MA 02633
  • /21

    $3,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 836 Sq Ft
    • Condo for Rent

    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650

    This fully furnished one-bedroom, one-and-a-half-bath condominium in sought-after Chatham is available for year-round occupancy beginning August 15th.The interior features a bright, open living and dining area and a modern kitchen with granite countertops, updated cabinetry, a dishwasher, and pantry storage. The spacious bedroom includes a private en-suite bathroom with a walk-in shower. An

    Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties

    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
  • /2

    $4,050,000

    Sold Jul 13, 2026

    85 Cedar St, Chatham, MA 02633

    • 5 Beds
    • 3.5 Baths
    • 3,080 Sq Ft
    • Built 1850

    Last Sold Summary

    • 19% Below List Price
    • $1,315/SF
    • 202 Days On Market

    Last Listing Agent Tim Bailey John C. Ricotta & Associates, Inc.

    85 Cedar St, Chatham, MA 02633
    • /12

      Est $3,515,561

      Not Listed For Sale

      33 Jessies Landing, Chatham, MA 02633

      • 3 Beds
      • 4.5 Baths
      • 4,620 Sq Ft
      • Built 2024
      33 Jessies Landing, Chatham, MA 02633

      Last Sold Summary

      • 346 Days On Market

  • /78

    $2,995,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 3,014 Sq Ft

    7 Squanto Dr, Chatham, MA 02633

    This Nantucket-style home features extraordinary views across a tidal salt marsh and Oyster Pond to the 3 church steeples in Town. Enjoy the ever-changing beauty of the seasons, and a host of wildlife from this elevated .69 acre site. With just over 3,000 square feet this exceptionally-crafted home is the perfect size with an open floor plan ideal for entertaining but not too much house to

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    7 Squanto Dr, Chatham, MA 02633
  • /41

    $765,000

    Sold Mar 12, 2026

    23 Shane Dr, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Above List Price
    • $724/SF
    • 41 Days On Market

    Current Estimated Value $806,403

    Last Listing Agent Samantha Edwards Compass

    23 Shane Dr, Chatham, MA 02633
    • /54

      Est $3,780,020

      Not Listed For Sale

      110 Sea Shells Dr, South Chatham, MA 02659

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft
      • Built 1982
      110 Sea Shells Dr, South Chatham, MA 02659

      Last Sold Summary

      • 10 Days On Market

  • /17

    $1,250,000

    • Land
    • 25,264 Sq Ft
    • $2,155,172 per Acre

    1134 &1142 Main St, Chatham, MA 02633

    Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.Properties located at 1134 Main Street and 1142 Main Street

    Tim Bailey John C Ricotta & Assoc.

    1134 &1142 Main St, Chatham, MA 02633
  • /44

    $1,520,000

    Sold Aug 15, 2025

    457 Training Field Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 3,027 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $502/SF
    • 8 Days On Market

    Current Estimated Value $1,632,684

    Last Listing Agent Shane Masaschi Compass

    457 Training Field Rd, Chatham, MA 02633
    • /47

      Est $3,040,462

      Not Listed For Sale

      47 Quasson Rd, Chatham, MA 02633

      • 4 Beds
      • 4 Baths
      • 2,399 Sq Ft
      • Built 1956
      47 Quasson Rd, Chatham, MA 02633

      Last Sold Summary

      • 91 Days On Market

  • /42

    $4,395,000

    Open Sat 10AM - 12PM $100K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 5,372 Sq Ft

    335 Stage Island Rd, Chatham, MA 02633

    Located on Chatham’s exclusive Stage Island, this 4 BR, 5.5 bath shingle-style residence is built for entertaining. The airy first floor features 10’ ceilings, a great room with a Rumford fireplace, and a professional kitchen with a wet bar and large island. Luxurious primary suites are found on both floors, while the second story adds an inviting family room and a deck overlooking the Atlantic

    The Bohman Hartung Group Gibson Sotheby's International Realty

    335 Stage Island Rd, Chatham, MA 02633
  • /30

    $1,415,000

    Sold Jan 12, 2026

    200 Hardings Beach Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Below List Price
    • $777/SF
    • 75 Days On Market

    Current Estimated Value $1,532,574

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    200 Hardings Beach Rd, Chatham, MA 02633
    • /51

      Est $3,114,824

      Not Listed For Sale

      114 Main St, Chatham, MA 02633

      • 6 Beds
      • 4 Baths
      • 4,449 Sq Ft
      • Built 1809
      114 Main St, Chatham, MA 02633

      Last Sold Summary

      • 589 Days On Market

  • /40

    $3,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    92 Indian Trail, Chatham, MA 02633

    Wake each morning to sparkling water views and end your day with spectacular sunsets over Bucks Creek. Located in Chatham's coveted Hardings Beach Hills neighborhood, this thoughtfully updated and meticulously maintained 3-bedroom, 3-bath home captures sweeping westerly water views. The primary suite features a private balcony overlooking the water, while a dedicated office offers flexibility for

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, Chatham, MA 02633
  • /48

    $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
    • 9 Days On Market

    Last Listing Agent INSPIRE Team Keller Williams Realty

    55 Meadowview Rd S, Chatham, MA 02633
    • /42

      Est $6,749,235

      Not Listed For Sale

      504 Old Harbor Rd, North Chatham, MA 02650

      • 8 Beds
      • 5.5 Baths
      • 4,859 Sq Ft
      • Built 1940
      504 Old Harbor Rd, North Chatham, MA 02650

      Last Sold Summary

      • 156 Days On Market

  • /38

    $2,295,000

    Open Sun 11AM - 1PM $655K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,504 Sq Ft

    41 Court St, North Chatham, MA 02650

    Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments

    Phyllis Power Compass

    41 Court St, North Chatham, MA 02650
  • /47

    $3,350,000

    Sold Dec 11, 2025

    174 Seapine Rd, North Chatham, MA 02650

    • 4 Beds
    • 3.5 Baths
    • 3,899 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Below List Price
    • $859/SF
    • 88 Days On Market

    Current Estimated Value $3,373,001

    Last Listing Agent Jill Boudreau eXp Realty, LLC

    174 Seapine Rd, North Chatham, MA 02650
    • /33

      Est $3,616,173

      Not Listed For Sale

      525 Shore Rd, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 3,436 Sq Ft
      • Built 1996
      525 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 8 Days On Market

  • /46

    $2,800,000

    Pending
    • 3 Beds
    • 2.5 Baths

    266 Seapine Rd, North Chatham, MA 02650

    Nestled on over an acre of private land, this charming Cape-style home offers 3 bedrooms and 2.5 baths, filled with timeless character throughout. Sunlight fills the spacious interior, creating a warm and welcoming atmosphere with plenty of room to gather and entertain. A separate rustic garden cottage provides a peaceful retreat--ideal for a home office, studio, or quiet escape. An additional

    Jessica Metzler Compass Massachusetts, LLC

    266 Seapine Rd, North Chatham, MA 02650
  • /58

    $730,000

    Sold Jul 22, 2026

    260 Tanglewood Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Below List Price
    • $506/SF
    • 35 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    260 Tanglewood Dr, Chatham, MA 02633
    • /42

      Est $7,360,438

      Not Listed For Sale

      552 Shore Rd, Chatham, MA 02633

      • 7 Beds
      • 6.5 Baths
      • 5,868 Sq Ft
      • Built 1930
      552 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 326 Days On Market

  • /48

    $1,350,000

    • 3 Beds
    • 1.5 Baths
    • 2,278 Sq Ft

    243 Crowell Rd, Chatham, MA 02633

    Comfortable Cape style 3 bedroom home, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Set back from the road on a level, grassy front lawn, Updated chef's kitchen, newer A/C splits, fenced, sunny back yard with deck. Free standing 2 car garage on over .6 acre lot. Unfinished second floor offers expansion potential with previously permitted plan. Large unfinished

    Michael Hall William Raveis Real Estate & Home Services

    243 Crowell Rd, Chatham, MA 02633
  • /41

    $2,500,000

    Sold Oct 24, 2025

    106 Stage Neck Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 3,834 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Below List Price
    • $652/SF
    • 152 Days On Market

    Current Estimated Value $2,839,082

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

    106 Stage Neck Rd, Chatham, MA 02633
    • /37

      Est $2,728,447

      Not Listed For Sale

      47 Gladen Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 3,203 Sq Ft
      • Built 1987
      47 Gladen Ln, Chatham, MA 02633

      Last Sold Summary

      • 13 Days On Market

  • /41

    $1,495,000

    • 2 Beds
    • 3.5 Baths
    • 1,770 Sq Ft

    739 Main St Unit 739, Chatham, MA 2633

    Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers baseball games, band concerts, a sandy beach at Oyster Pond, and much more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen,

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    739 Main St Unit 739, Chatham, MA 2633
  • /23

    $949,000

    Sold Jun 10, 2026

    66 Ethelma Dr, Chatham, MA 02633

    • 4 Beds
    • 1 Bath
    • 1,547 Sq Ft
    • Built 1956

    Last Sold Summary

    • $613/SF
    • 9 Days On Market

    Current Estimated Value $919,183

    Last Listing Agent Shane Masaschi Compass

    66 Ethelma Dr, Chatham, MA 02633
    • /42

      Est $3,892,176

      Not Listed For Sale

      38 Sandy Shoes Ln, Chatham, MA 02633

      • 7 Beds
      • 5 Baths
      • 3,203 Sq Ft
      • Built 1930
      38 Sandy Shoes Ln, Chatham, MA 02633

      Last Sold Summary

      • 6 Days On Market

Showing Results 1 - 40, Page 1 of 18

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