9,489

Chatham, MA Homes

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  • /41

    $4,995,000

    $500K 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
  • /17

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 872 Sq Ft
    • House for Rent

    175 Sam Ryder Rd, Chatham, MA 02633

    Off Season Rental! Available 9/15 to 5/15 only! Welcome to this charming furnished 2 Bed 1 Bath Ranch, a true Chatham gem that has undergone a complete renovation, offering modern comforts and stylish finishes throughout. The open-concept layout features a fully equipped kitchen with stainless steel appliances and inviting island providing ample space for preparation and entertaining. The kitchen

    Alison Shanley Keller Williams Realty Signature Properties

    175 Sam Ryder Rd, Chatham, MA 02633
  • /37

    $1,700,000

    Sold Nov 17, 2025

    44 Emery Ln, North Chatham, MA 02650

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1983

    Last Sold Summary

    • $975/SF
    • 33 Days On Market

    Current Estimated Value $1,750,536

    Last Listing Agent Kathleen Phelan Compass Massachusetts, LLC

    44 Emery Ln, North Chatham, MA 02650
    • /42

      Not Listed For Sale

      113 Seapine, Chatham, MA 02635

      • 4 Beds
      • 5.5 Baths
      • 3,504 Sq Ft
      • Built 2016
      113 Seapine, Chatham, MA 02635

      Last Sold Summary

      • 155 Days On Market

      Last Listing Agent Chris Rhinesmith Compass

  • /39

    $995,000

    $200K 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
  • /56

    $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 $1,301,856

    Last Listing Agent Cheryle Young Today Real Estate

    591 Crowell Rd, North Chatham, MA 02650
    • /3

      Est $3,073,676

      Not Listed For Sale

      21 Hunter Rise, Chatham, MA 02633

      • 3 Beds
      • 5 Baths
      • 3,160 Sq Ft
      • Built 2018
      21 Hunter Rise, Chatham, MA 02633

      Last Sold Summary

      • 88 Days On Market

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

  • /56

    $699,000

    Pending
    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    57 Whitman Ave Unit A, Chatham, MA 02633

    This fabulous, move-in-ready condominium is one of only two units and enjoys a private, desirable location at the end of the street overlooking the marsh. Extensive renovations completed in 2018 include the kitchen, bathrooms, roof, siding, windows, natural-gas heating and central air conditioning, plumbing, electrical systems, and IA septic system. In 2026, the private patio and fire pit were

    Agent Photo

    Kimberly Clark

    Bayside Realty Consultants

    57 Whitman Ave Unit A, Chatham, MA 02633
  • /22

    $2,450 Per Month

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

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

    This one-bedroom, one-and-a-half-bath condominium in sought-after Chatham is available for year-round occupancy right away. 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 additional half bathroom,

    Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties

    44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
  • /34

    $2,480,000

    Sold Jul 07, 2026

    104 Seapine Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 2,969 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $835/SF
    • 43 Days On Market

    Current Estimated Value $2,716,208

    Last Listing Agent Kristin Muller John C Ricotta & Assoc.

    104 Seapine Rd, North Chatham, MA 02650
    • /54

      Est $3,954,502

      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

      • 11 Days On Market

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

  • /48

    $995,000

    $200K 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

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    65 Captain Kendrick Dr, Chatham, MA 02633
  • /32

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    60 Snow Ln, Chatham, MA 02633

    Available September 1, 2026 through May 31, 2027, this furnished two bedroom Cape-style home offers a wonderful opportunity to enjoy Chatham during the quieter months. Whether you're renovating your home, relocating to Cape Cod, between home purchases, working remotely, or simply looking for quality off-season housing, 60 Snow Lane provides a comfortable and convenient place to call home for the

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    60 Snow Ln, Chatham, MA 02633
  • /38

    $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

    • 18% Below List Price
    • $1,031/SF
    • 256 Days On Market

    Current Estimated Value $6,265,847

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    4 Ministers Ln, North Chatham, MA 02650
    • /3

      Not Listed For Sale

      559 Meetinghouse Rd, South Chatham, MA 2659

      • 3 Beds
      • 1 Bath
      • 878 Sq Ft
      • Built 1910
      559 Meetinghouse Rd, South Chatham, MA 2659

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Rebecca Ryan Today Real Estate

  • /82

    $2,995,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 1,969 Sq Ft

    156 Chatham Bars Ave, Chatham, MA 02633

    SOLITUDE | A Sophisticated Chatham Antique Tucked away in one of Chatham's most coveted locations, "Solitude" offers a blend of a private tranquil setting while just moments from town, Seaside Links Golf Course, and Claflin Landing Beach. This exquisite 5-bedroom, 3.5-bath antique has been masterfully restored, with an emphasis preserving its timeless character with refined aesthetics. original

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    156 Chatham Bars Ave, Chatham, MA 02633
  • /41

    $730,000

    Sold Jul 22, 2026

    260 Tanglewood Dr, South Chatham, MA 02659

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

    Last Sold Summary

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

    Current Estimated Value $746,676

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    260 Tanglewood Dr, South Chatham, MA 02659
    • /48

      Not Listed For Sale

      751 Crowell Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 2,344 Sq Ft
      • Built 1930
      751 Crowell Rd, Chatham, MA 02633

      Last Sold Summary

      • 10 Days On Market

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

  • /42

    $4,395,000

    $100K PRICE DROP Pending
    • 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
  • /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
    • /32

      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

      Last Listing Agent David Colville HomeSmart First Class Realty

  • /76

    $4,995,000

    $1M PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    101 Morris Island Rd, Chatham, MA 02633

    LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated

    The Bohman Hartung Group Gibson Sotheby's International Realty

    101 Morris Island Rd, 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 $773,930

    Last Listing Agent Samantha Edwards Compass

    23 Shane Dr, Chatham, MA 02633
    • /27

      Not Listed For Sale

      108 Misty Meadow Ln Unit A, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,489 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit A, Chatham, MA 02633

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

  • /2

    $4,500,000

    • 4 Beds
    • 4.5 Baths
    • 4,689 Sq Ft

    66 Ethelma Dr, Chatham, MA 02633

    Waterfront new construction in one of Chatham's most preeminent locations, minutes from town. This rare half-acre offering on Emery Pond is to be built by R.A. Martin, one of the Cape's premier builders, with select interior finishes and customizations still available to the right buyer. New construction of this scale is exceptionally rare on Cape Cod, offering the perfect mix of estate-level

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    66 Ethelma Dr, Chatham, MA 02633
  • /46

    $2,950,000

    Sold Dec 02, 2025

    314 Cockle Cove Rd, Chatham, MA 02659

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $946/SF
    • 13 Days On Market

    Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    314 Cockle Cove Rd, Chatham, MA 02659
    • /16

      Not Listed For Sale

      407 Orleans Rd Unit B, Chatham, MA 2633

      • 2 Beds
      • 2 Baths
      • 1,013 Sq Ft
      • Built 1987
      407 Orleans Rd Unit B, Chatham, MA 2633

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent John Burke William Raveis Real Estate & Home Services

  • /30

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln Unit 4, Chatham, MA 02633

    Tucked away on a quiet street in the heart of North Chatham, this second-floor condominium offers a rare opportunity to own in one of Cape Cod's most coveted locations. Perfect as a seasonal retreat, investment property, or smart entry into the Chatham market, it blends convenience and charm. Sunlight fills the welcoming interior, highlighting hardwood floors, a cozy wood-burning fireplace, and

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, Chatham, MA 02633
  • /42

    $1,615,000

    Sold Jun 01, 2026

    393 Training Field Rd, Chatham, MA 02633

    • 3 Beds
    • 4 Baths
    • 3,645 Sq Ft
    • Built 1972

    Last Sold Summary

    • $443/SF
    • 2 Days On Market

    Current Estimated Value $1,561,358

    Last Listing Agent Shane Masaschi Compass

    393 Training Field Rd, Chatham, MA 02633
    • /31

      Not Listed For Sale

      450 Old Harbor Rd, North Chatham, MA 02650

      • 2 Beds
      • 2.5 Baths
      • 1,510 Sq Ft
      • Built 1830
      450 Old Harbor Rd, North Chatham, MA 02650

      Last Sold Summary

      • 268 Days On Market

      Last Listing Agent Barbara Garside eXp Realty, LLC

  • /16

    $4,000,000

    • 5 Beds
    • 3 Baths
    • 2,303 Sq Ft

    64 Harbor View Rd, Chatham, MA 02633

    A rare opportunity awaits high above the dunes of Hardings Beach to build the bluff house of your dreams. Nestled within the private enclave of Hall's Bluff, this five-bedroom home boasts majestic, sweeping views of Nantucket Sound, Monomoy Island, and beyond. The sunsets are spectacular. Ownership includes deeded access to a neighborhood footpath leading directly to Harding's Beach and the

    The Bohman Hartung Group Gibson Sotheby's International Realty

    64 Harbor View Rd, Chatham, MA 02633
  • /20

    $1,975,000

    Sold Oct 08, 2025

    20 Hardings Beach Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 2,770 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $713/SF
    • 31 Days On Market

    Current Estimated Value $1,788,993

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633
    • /47

      Not Listed For Sale

      75 Whidah Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 2,524 Sq Ft
      • Built 1969
      75 Whidah Rd, Chatham, MA 02633

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Timothy Bailey John C Ricotta & Assoc.

  • /49

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 1,415 Sq Ft

    87 Cranberry Ln, Chatham, MA 02633

    Location, location, location! Exceptional opportunity to own this charming year-round home and vacation retreat just steps from coveted Ridgevale Beach. This warm, inviting ranch has 3 bedrooms and 2 full baths, offering easy one floor living as well as additional living space with a separate entrance on the lower level for home office, guests, recreation or extended stays. Savor the saltwater

    David Carter Compass Massachusetts, LLC

    87 Cranberry Ln, Chatham, MA 02633
  • /35

    $835,000

    Sold Oct 17, 2025

    93 Stephen Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 1983

    Last Sold Summary

    • 5% Above List Price
    • $730/SF
    • 2 Days On Market

    Current Estimated Value $849,326

    Last Listing Agent Richard Robbins Chatham Shores Realty

    93 Stephen Dr, Chatham, MA 02633
    • /30

      Not Listed For Sale

      25 Bobbies Ln, South Chatham, MA 02659

      • 2 Beds
      • 1 Bath
      • 772 Sq Ft
      • Built 1950
      25 Bobbies Ln, South Chatham, MA 02659

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /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
  • /62

    $1,500,000

    Sold Nov 03, 2025

    216 Forest Beach Rd, South Chatham, MA 02659

    • 4 Beds
    • 4 Baths
    • 2,427 Sq Ft
    • Built 1971

    Last Sold Summary

    • $618/SF
    • 3 Days On Market

    Current Estimated Value $1,550,884

    Last Listing Agent Maureen Green Kinlin Grover Compass

    216 Forest Beach Rd, South Chatham, MA 02659
    • /62

      Not Listed For Sale

      174 Seapine Rd, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 3,899 Sq Ft
      • Built 1961
      174 Seapine Rd, Chatham, MA 02633

      Last Sold Summary

      • 218 Days On Market

      Last Listing Agent Judith Smith John C Ricotta & Assoc.

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