9,675

Chatham, MA Homes

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  • /31

    $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
    • 34 Days On Market

    Current Estimated Value $1,739,548

    Last Listing Agent Kathleen Phelan Compass

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

      Est $1,533,730

      Not Listed For Sale

      33 Captains Walk, North Chatham, MA 02650

      • 4 Beds
      • 2.5 Baths
      • 2,279 Sq Ft
      • Built 1970
      33 Captains Walk, North Chatham, MA 02650

      Last Sold Summary

      • 12 Days On Market

  • /27

    $468,000

    • 2 Beds
    • 1.5 Baths
    • 576 Sq Ft

    19 Captain Richards Way, Chatham, MA 02633

    Beautifully remodeled in 2023, this charming 2 bedroom, 1.5 bath Seasonal Cottage is just 0.8 miles from Hardings Beach . Thoughtfully updated and move-in ready, it features a private deck, spacious patio and outdoor shower; perfect for enjoying the Cape lifestyle. Ideally located just minutes from Chatham's acclaimed restaurants, boutiques, and beaches, this turnkey property baosts strong rental

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    19 Captain Richards Way, Chatham, MA 02633
  • /10

    $510,000

    Sold Jan 20, 2026

    22 Pine Knoll Ave, Chatham, MA 02633

    • 3 Beds
    • 0.5 Baths
    • 532 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $959/SF
    • 0 Days On Market

    Current Estimated Value $549,142

    Last Listing Agent Brian Mullen Options 153, LLC

    22 Pine Knoll Ave, Chatham, MA 02633
    • /43

      Est $1,603,830

      Not Listed For Sale

      17 Menekish Ln, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 2,124 Sq Ft
      • Built 1984
      17 Menekish Ln, Chatham, MA 02633

      Last Sold Summary

      • 136 Days On Market

  • /2

    $5,900,000

    • 6 Beds
    • 8 Baths
    • 6,183 Sq Ft

    50 Sylvan Way, South Chatham, MA 02659

    The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    50 Sylvan Way, South Chatham, MA 02659
  • /28

    $461,260

    Sold Nov 10, 2025

    912 Main St Unit 304, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $375/SF
    • 4 Days On Market

    Current Estimated Value $483,896

    Last Listing Agent Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 304, Chatham, MA 02633
    • /42

      Est $2,557,553

      Not Listed For Sale

      25 Menekish Ln, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 3,865 Sq Ft
      • Built 2006
      25 Menekish Ln, Chatham, MA 02633

      Last Sold Summary

      • 28 Days On Market

  • /39

    $1,800,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,238 Sq Ft

    213 Main St, Chatham, MA 02633

    Perfectly positioned in the heart of Chatham's Old Village, this 4-bed, 2-bath home offers the rare combination of historic charm, water views of Chatham Harbor, and an exceptional in-town location. Just moments to Lighthouse Beach, Main Street shops, restaurants, and golf, this circa-1850 Greek Revival is filled with warmth and character. featuring a sunny eat-in family room with beamed ceiling

    The Bohman Hartung Group Gibson Sotheby's International Realty

    213 Main St, Chatham, MA 02633
  • /44

    $952,500

    Sold Mar 24, 2026

    24 Chickadee Ln, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $633/SF
    • 119 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    24 Chickadee Ln, Chatham, MA 02633
    • /30

      Est $1,288,822

      Not Listed For Sale

      6 Palmer Dr, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 1974
      6 Palmer Dr, Chatham, MA 02633

      Last Sold Summary

      • 41 Days On Market

  • /42

    $4,995,000

    $1M PRICE DROP
    • 4 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, beautifully blends elegance and comfort. The open floor plan features oversized windows and soaring ceilings, offering illuminating views of the swimming pool, spa, outdoor kitchen, patio, gas fire pit, and an irrigated, fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse

    The Bohman Hartung Group Gibson Sotheby's International Realty

    101 Morris Island Rd, Chatham, MA 02633
  • /15

    $615,000

    Sold Apr 15, 2026

    39 Meadow Brook Rd, Chatham, MA 02650

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft
    • Built 1957

    Last Sold Summary

    • 9% Below List Price
    • $800/SF
    • 129 Days On Market

    Current Estimated Value $658,278

    Last Listing Agent Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    39 Meadow Brook Rd, Chatham, MA 02650
    • /5

      Est $2,587,976

      Not Listed For Sale

      172 Barcliff Ave, Chatham, MA 02633

      • 5 Beds
      • 3 Baths
      • 1,724 Sq Ft
      • Built 1900
      172 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 2 Days On Market

  • /37

    $985,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    33 Jeanette Rd, Chatham, MA 02633

    Lovingly updated and meticulously maintained, this turnkey 3-bedroom, 2-bath ranch offers the perfect blend of comfort, convenience, and Cape Cod charm. Gently used and move-in ready, this furnished home features gorgeous wood floors, a wood-burning fireplace, an updated kitchen, and two renovated full bathrooms. The mini-split heated and cooled sunroom provides additional year-round living space

    Kari Wagner Compass

    33 Jeanette Rd, Chatham, MA 02633
  • /27

    $349,999

    Sold Feb 02, 2026

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $503/SF
    • 76 Days On Market

    Current Estimated Value $381,580

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    • /60

      Est $2,767,913

      Not Listed For Sale

      184 Barcliff Ave, Chatham, MA 02633

      • 4 Beds
      • 5 Baths
      • 3,298 Sq Ft
      • Built 2024
      184 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 210 Days On Market

  • /56

    $2,150,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,481 Sq Ft

    234 Round Cove Rd, Chatham, MA 02633

    Tucked within Chatham's coveted Riverbay community, 234 Round Cove Road offers a rare blend of walkability and private, resort-style living. Moments to Jackknife Beach and Pleasant Bay, the setting delivers coastal access while feeling entirely private and your own.Designed for effortless living, the single-level layout features three oversized bedrooms and 2.5 baths, including a secluded primary

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    234 Round Cove Rd, Chatham, MA 02633
  • /32

    $5,750,000

    Sold Sep 30, 2025

    25 Wikis Way, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 4,654 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $1,235/SF
    • 107 Days On Market

    Current Estimated Value $6,124,944

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
    • /53

      Est $2,291,868

      Not Listed For Sale

      390 Old Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 2,670 Sq Ft
      • Built 1988
      390 Old Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 2 Days On Market

  • /39

    $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

    83 Old Mail Rd, North Chatham, MA 02650
  • /29

    $3,400,000

    Sold Dec 30, 2025

    450 Main St, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 7,396 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $460/SF
    • 55 Days On Market

    Current Estimated Value $3,440,617

    Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, Chatham, MA 02633
    • /74

      Est $4,928,828

      Not Listed For Sale

      581 Shore Rd, Chatham, MA 02633

      • 5 Beds
      • 6.5 Baths
      • 4,452 Sq Ft
      • Built 2018
      581 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 49 Days On Market

  • /58

    $1,374,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    88 Indian Hill Rd N, Chatham, MA 02633

    Welcome to 88 Indian Hill Road, where stunning curb appeal and timeless Cape Cod charm welcomes you home. Perfectly situated on a prominent, beautifully landscaped large lot, this sprawling Cape has been meticulously maintained and thoughtfully designed for both everyday living and entertainment. The private, tranquil grounds are a true highlight, featuring flowering ornamental trees, lush

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    88 Indian Hill Rd N, Chatham, MA 02633
  • /2

    $540,000

    Sold Sep 18, 2025

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633

    • Land
    • 1.2 Acres
    • $450,000 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 81 Days On Market

    Last Listing Agent Derek Greene The Greene Realty Group

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633
    • /64

      Not Listed For Sale

      111 Barcliff Ave, Chatham, MA 02633

      • 8 Beds
      • 4.5 Baths
      • 4,413 Sq Ft
      • Built 1910
      111 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 250 Days On Market

  • /69

    $4,495,000

    $255K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,967 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living. A chef's kitchen, dual living areas, and an

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    38 Indian Trail, Chatham, MA 02633
  • /53

    $1,495,000

    Sold Dec 15, 2025

    291 Ridgevale Rd, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,424 Sq Ft
    • Built 1950

    Last Sold Summary

    • $1,050/SF
    • 8 Days On Market

    Current Estimated Value $1,550,428

    Last Listing Agent Jan Nowak Craigville Realty Co

    291 Ridgevale Rd, Chatham, MA 02633
    • /77

      Est $4,669,788

      Not Listed For Sale

      79 Barcliff Ave, Chatham, MA 02633

      • 3 Beds
      • 5 Baths
      • 3,724 Sq Ft
      • Built 2007
      79 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 3 Days On Market

  • /11

    $4,499,900

    New Construction
    • 3 Beds
    • 7 Baths
    • 5,820 Sq Ft

    33 Crowell Rd, Chatham, MA 02633

    A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    33 Crowell 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 $1,826,046

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633
    • /35

      Est $3,650,524

      Not Listed For Sale

      39 Seaview Terrace, Chatham, MA 02633

      • 4 Beds
      • 6.5 Baths
      • 3,533 Sq Ft
      • Built 2007
      39 Seaview Terrace, Chatham, MA 02633

      Last Sold Summary

      • 64 Days On Market

  • /36

    $829,000

    $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    33 Duck Marsh Ln, Chatham, MA 02633

    Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural

    Darci Sequin Gibson Sotheby's International Realty

    33 Duck Marsh Ln, Chatham, MA 02633
  • /32

    $765,000

    Sold Dec 18, 2025

    47 Cranberry Way, South Chatham, MA 2659

    • 2 Beds
    • 2 Baths
    • 868 Sq Ft
    • Built 1941

    Last Sold Summary

    • 4% Below List Price
    • $881/SF
    • 11 Days On Market

    Current Estimated Value $802,480

    Last Listing Agent William Raye Gibson Sotheby's International Realty

    47 Cranberry Way, South Chatham, MA 2659
    • /31

      Est $2,655,683

      Not Listed For Sale

      22 Cahoons Hollow Rd, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft
      • Built 2009
      22 Cahoons Hollow Rd, Chatham, MA 02633

      Last Sold Summary

      • 78 Days On Market

  • /13

    $689,000

    • 2 Beds
    • 2 Baths
    • 1,083 Sq Ft

    212 Orleans Rd Unit D, North Chatham, MA 02650

    Beautifully appointed, fully furnished, and turnkey, this exceptional end-unit 2-bedroom, 2-bath second-floor condominium is located in the desirable Nickerson Corners community in North Chatham, offering effortless Cape Cod living in a quiet, well-maintained association. Ideally situated just moments from Chatham Harbor and downtown Chatham, this exceptional location provides easy access to

    Jim Peterson Peterson Realty Inc.

    212 Orleans Rd Unit D, North Chatham, MA 02650
  • /53

    $1,289,900

    Sold Jun 24, 2026

    41 Misty Meadow Ln Unit B, North Chatham, MA 02650

    • 2 Beds
    • 2.5 Baths
    • 3,094 Sq Ft
    • Built 2005

    Last Sold Summary

    • $417/SF
    • 38 Days On Market

    Current Estimated Value $1,218,977

    Last Listing Agent amy maloney Tom Hester Real Estate

    41 Misty Meadow Ln Unit B, North Chatham, MA 02650
    • /37

      Est $2,009,522

      Not Listed For Sale

      31 Mill Pond Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 1,896 Sq Ft
      • Built 1950
      31 Mill Pond Rd, Chatham, MA 02633

      Last Sold Summary

      • 14 Days On Market

  • /27

    $1,650,000

    $345K PRICE DROP
    • 1 Bath
    • 2,586 Sq Ft

    231 Crowell Rd, Chatham, MA 2633

    Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

    Judith Smith John C. Ricotta & Associates, Inc.

    231 Crowell Rd, Chatham, MA 2633
  • /55

    $650,000

    Sold Jul 31, 2025

    1996 Main St, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,813 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Below List Price
    • $359/SF
    • 93 Days On Market

    Current Estimated Value $771,019

    Last Listing Agent Shane Masaschi Compass

    1996 Main St, Chatham, MA 02633

Showing Results 81 - 120, Page 3 of 18

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