9,641

Chatham, MA Homes

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  • /2

    $619,000

    $40K PRICE DROP
    • Land
    • 1.01 Acres
    • $612,871 per Acre

    1761 Main St, Chatham, MA 02633

    Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

    Agent Photo

    Kimberly Clark

    Bayside Realty Consultants

    (508) 719-6244

    1761 Main St, Chatham, MA 02633
  • /42

    $20,000 Per Month

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

    101 Monomoyic Way, Chatham, MA 02633

    Furnished rental available June 1st to October 1st, 2026. 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

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

    101 Monomoyic Way, Chatham, MA 02633
  • /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 $5,926,167

    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

      • $917/SF
      • 3 Days On Market
      • Last Sold Price $708,115
      • Aug 15, 2024

      Last Listing Agent Shane Masaschi Compass

  • /71

    $5,995,000

    • 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
  • /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
  • /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 $1,282,500

    Last Listing Agent Cheryle Young Today Real Estate

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

      Est $3,277,819

      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

      • 17% Above List Price
      • $667/SF
      • 56 Days On Market
      • Last Sold Price $2,800,000
      • Apr 16, 2024

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /31

    $5,400,000

    • 5 Beds
    • 4.5 Baths
    • 5,587 Sq Ft

    169 Tisquantum Rd, Chatham, MA 02633

    Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this property is perfect for making lasting memories. Step into a the foyer with a stunning double curved staircase, leading to a vaulted living room with a fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the

    Sandra Tanco Kinlin Grover Compass

    169 Tisquantum Rd, Chatham, MA 02633
  • /5

    $2,600 Per Month

    • 1 Bed
    • 1 Bath
    • 250 Sq Ft
    • Apartment for Rent

    450 Main St Unit 1, Chatham, MA 02633

    Located in the heart of Historic Chatham charm is a one bedroom, one bath upper level apartment for lease. One year minimum lease with one parking space included, no pets, fully air conditioned. Offered for $2,600/Month plus utilities.

    Greg Hartel Hartel Realty

    450 Main St Unit 1, Chatham, MA 02633
  • /36

    $615,300

    Sold May 27, 2025

    369 Orleans Rd Unit A, Chatham, MA 2633

    • 2 Beds
    • 2.5 Baths
    • 1,283 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $480/SF
    • 18 Days On Market

    Current Estimated Value $633,136

    Last Listing Agent David Colville HomeSmart First Class Realty

    369 Orleans Rd Unit A, Chatham, MA 2633
    • /54

      Est $3,632,876

      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

      • 26% Below List Price
      • $1,781/SF
      • 10 Days On Market
      • Last Sold Price $4,900,000
      • May 22, 2024

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

  • /46

    $2,699,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,479 Sq Ft

    8 Captains Walk, North Chatham, MA 02650

    Nestled in highly sought after North Chatham neighborhood, this quintessential Cape Cod home offers the exceptional blend of elegance, comfort and modern amenities. Spanning an impressive 3479 sf , with 4BR's 2.5 baths , this pristine home is set on .50 acres of level yard with manicured grounds, large rear patio, outdoor shower, irrigation and fenced yard . Close proximity to the vibrant heart

    Lori Fanning Smith Compass Massachusetts, LLC

    8 Captains Walk, North Chatham, MA 02650
  • /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
  • /31

    $1,450,000

    Sold Jul 03, 2025

    450 Old Harbor Rd, Chatham, MA 02633

    • 2 Beds
    • 2.5 Baths
    • 1,510 Sq Ft
    • Built 1830

    Last Sold Summary

    • 24% Below List Price
    • $960/SF
    • 265 Days On Market

    Current Estimated Value $2,264,342

    Last Listing Agent Barbara Garside eXp Realty, LLC

    450 Old Harbor Rd, Chatham, MA 02633
    • /47

      Est $2,972,526

      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

      • 4% Above List Price
      • $1,188/SF
      • 91 Days On Market
      • Last Sold Price $2,850,000
      • Feb 03, 2025

      Last Listing Agent Kristin Muller John C Ricotta & Assoc.

  • /71

    $2,500,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    16 Old Salt Works Rd, Chatham, MA 02633

    This charming Cape-style home is located in Eastward Point, one of Chatham's most coveted coastal enclaves, near the eastern end of Fox Hill Road. Membership in the homeowners association grants access to private sandy beaches as well as use of a shared deep water dock on Crows Pond - leading to Pleasant Bay and the Atlantic.The thoughtful renovation, performed by Polhemus and Savory, seamlessly

    Chet Crabtree Christie's International Real Estate Atlantic Brokerage

    16 Old Salt Works 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 $781,658

    Last Listing Agent Samantha Edwards Compass

    23 Shane Dr, Chatham, MA 02633
    • /51

      Est $3,212,726

      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

      • 24% Above List Price
      • $582/SF
      • 589 Days On Market
      • Last Sold Price $2,590,000
      • Jul 31, 2023

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

  • /21

    $4,525,000

    New Construction $126K PRICE INCREASE Pending
    • 4 Beds
    • 6 Baths
    • 5,300 Sq Ft

    230 Barcliff Ave, Chatham, MA 02633

    Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway and anticipating delivery for late June 2026...Architecturally pleasing 4BR 6 bath shingled home with pool will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The

    Lori Fanning Smith Compass Massachusetts, LLC

    230 Barcliff Ave, 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 $1,661,903

    Last Listing Agent Shane Masaschi Compass

    457 Training Field Rd, Chatham, MA 02633
    • /42

      Est $7,156,374

      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

      • 16% Below List Price
      • $1,749/SF
      • 156 Days On Market
      • Last Sold Price $8,500,000
      • Oct 21, 2024

      Last Listing Agent Phyllis Power Compass

  • /75

    $2,975,000

    Pending
    • 5 Beds
    • 6 Baths
    • 4,822 Sq Ft

    35 Northgate Rd, North Chatham, MA 02650

    Set on 2.04 acres, this exceptionally-crafted residence offers 4,800 square feet of refined living space and understated luxury throughout. Multiple beautifully-appointed living spaces include a great room, living room, and sunroom, each with elegant architectural details. The gourmet Chef's kitchen is the heart of the home; perfect for grand entertaining or everyday living. A luxurious primary

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    35 Northgate Rd, North Chatham, MA 02650
  • /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 $1,476,301

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    200 Hardings Beach Rd, Chatham, MA 02633
    • /37

      Est $2,515,203

      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

      • 7% Above List Price
      • $734/SF
      • 13 Days On Market
      • Last Sold Price $2,350,000
      • Jun 27, 2024

      Last Listing Agent John Hopkins Frank A Sullivan Real Estate

  • /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
  • /40

    $900,000

    Sold Jul 11, 2025

    100 Potonumecot Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $670/SF
    • 16 Days On Market

    Current Estimated Value $986,551

    Last Listing Agent Andy Falconio Kinlin Grover Compass

    100 Potonumecot Rd, Chatham, MA 02633
    • /42

      Est $4,133,173

      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

      • 9% Above List Price
      • $1,186/SF
      • 6 Days On Market
      • Last Sold Price $3,800,000
      • Aug 27, 2024

      Last Listing Agent Team Real Market Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /51

    $3,600,000

    • 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
  • /40

    $1,320,000

    Sold Jun 12, 2025

    67 The Cornfield, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 2,238 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $590/SF
    • 78 Days On Market

    Current Estimated Value $1,492,518

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

    67 The Cornfield, Chatham, MA 02633
    • /26

      Est $1,951,724

      Not Listed For Sale

      393 Main St, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 1,650 Sq Ft
      • Built 1910
      393 Main St, Chatham, MA 02633

      Last Sold Summary

      • 2% Below List Price
      • $1,209/SF
      • 98 Days On Market
      • Last Sold Price $1,995,000
      • Jun 28, 2023

      Last Listing Agent Chris Rhinesmith Compass

  • /49

    $3,695,000

    • 3 Beds
    • 4.5 Baths
    • 5,154 Sq Ft

    83 Old Mail Rd, North Chatham, MA 02650

    Brand new shingled style Coastal retreat offers resort style living in sought after North Chatham location. Sited on .5 of an acre( with pool potential) near beaches and close proximity to town, Chatham Bars Inn and Chatham Seaside Links Golf , this home was curated with luxury and comfort in mind. Exceptional scale, volume and open feel, delivering high end finishes and compelling value at $717

    Lori Fanning Smith Compass Massachusetts, LLC

    83 Old Mail Rd, North Chatham, MA 02650
  • /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
    • /26

      Est $2,535,631

      Not Listed For Sale

      10 Mill Hill Ln, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 2,174 Sq Ft
      • Built 1720
      10 Mill Hill Ln, Chatham, MA 02633

      Last Sold Summary

      • 10% Above List Price
      • $1,061/SF
      • 44 Days On Market
      • Last Sold Price $2,307,500
      • Apr 12, 2024

      Last Listing Agent Jessica King Compass Massachusetts, LLC

  • /34

    $3,200,000

    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    92 Indian Trail, Chatham, MA 02633

    Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living. This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted setting within a friendly

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, Chatham, MA 02633
  • /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 $3,363,117

    Last Listing Agent Jill Boudreau eXp Realty, LLC

    174 Seapine Rd, North Chatham, MA 02650
    • /42

      Not Listed For Sale

      67 School St, Chatham, MA 02633

      • 4 Beds
      • 2 Baths
      • 1,595 Sq Ft
      • Built 1910
      67 School St, Chatham, MA 02633

      Last Sold Summary

      • $1,113/SF
      • 26 Days On Market
      • Last Sold Price $1,775,000
      • Jan 24, 2025

      Last Listing Agent Phyllis Power Compass

  • /36

    $2,650,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,969 Sq Ft

    104 Seapine Rd, North Chatham, MA 02650

    Optimally sited on the lot to maximize views of Crows Pond from every room, this 3-bedroom 2.5-bath home is just steps away from the private Harbor Coves Association beach & ready to make your Chatham dreams come true. The first floor of this custom-built home features multiple living areas perfect for entertaining company or enjoying the peace of all four seasons in Chatham. With hardwood floors

    Kristin Muller John C Ricotta & Assoc.

    104 Seapine Rd, North Chatham, MA 02650
  • /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 $2,711,090

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

    106 Stage Neck Rd, Chatham, MA 02633
    • /4

      Est $3,012,081

      Not Listed For Sale

      35 Mill Hill Ln, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 2,016 Sq Ft
      • Built 1987
      35 Mill Hill Ln, Chatham, MA 02633

      Last Sold Summary

      • 6% Below List Price
      • $1,585/SF
      • 3 Days On Market
      • Last Sold Price $3,195,000
      • Oct 25, 2024

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

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