9,682

Chatham, MA Homes

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  • /29

    $3,500,000 Pending

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

    450 Main St, Chatham, MA 02633

    Welcome to 450 Main Street! A premier mixed-use investment opportunity in the heart of Chatham, MA, Where Cape Cod charm meets Main Street style. Located in the highly desirable GB2 zoning district, this 7,396 sq ft property offers a compelling blend of residential and retail potential. Featuring five well-appointed apartments with solid rental appeal, along with prime street level retail

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, Chatham, MA 02633
  • /35

    $5,000,000 Sold Mar 07, 2025

    169 Shore Rd, Chatham, MA 02633

    • 4 Beds
    • 2.5 Baths
    • 3,319 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $1,506/SF
    • 3 Days On Market

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    169 Shore Rd, Chatham, MA 02633
    • /35

      Est $4,223,188 Not Listed For Sale

      • 4 Beds
      • 6.5 Baths
      • 3,533 Sq Ft

      39 Seaview Terrace, Chatham, MA 02633

      39 Seaview Terrace, Chatham, MA 02633
  • /40

    $1,195,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,026 Sq Ft

    3 Oyster Dr, Chatham, MA 02633

    Welcome home to 3 Oyster Drive, a perfectly idyllic Chatham getaway! This enchanting cottage enjoys dazzling water views and a prime location near Outermost Harbor Marina, beaches, & Town. This 3 BR, 2 BA home is a blend of classic Cape Cod and some newer features and is the ideal backdrop to begin your own Chatham story. Many will find the home comfortable just the way it is, or choose to take

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    3 Oyster Dr, Chatham, MA 02633
  • /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

    Last Listing Agent Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 304, Chatham, MA 02633
    • /11

      Est $5,022,215 Not Listed For Sale

      • 5 Beds
      • 9 Baths
      • 5,750 Sq Ft

      84 Doane Rd, Chatham, MA 02633

      84 Doane Rd, Chatham, MA 02633
  • /39

    $1,469,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a

    Brian Dougherty Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • /12

    $750,000 Sold May 30, 2025

    86 Vineyard Ave, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,625 Sq Ft
    • Built 1947

    Last Sold Summary

    • 12% Below List Price
    • $286/SF
    • 24 Days On Market

    Current Estimated Value $803,806

    Last Listing Agent Phyllis Power Compass

    86 Vineyard Ave, Chatham, MA 02633
    • /37

      Est $2,003,966 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,896 Sq Ft

      31 Mill Pond Rd, Chatham, MA 02633

      31 Mill Pond Rd, Chatham, MA 02633
  • /6

    $3,499,900 Pending

    • 3 Beds
    • 4.5 Baths
    • 4,565 Sq Ft

    29 Jessies Landing, Chatham, MA 2633

    A new luxury residence is currently under construction by Eastward Companies in Chatham. Located in a desirable neighborhood with other remarkable homes, this beautifully designed 4,500 square foot home features amenities often seen on a discerning buyer's wish list. Outside entertaining is centered around a saltwater pool, spa, and fire pit while inside you'll discover easy living with a

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    29 Jessies Landing, Chatham, MA 2633
  • /47

    $1,095,000 Sold Jul 18, 2025

    20 Judys Ln, South Chatham, MA 2659

    • 3 Beds
    • 1.5 Baths
    • 1,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $1,029/SF
    • 12 Days On Market

    Current Estimated Value $1,071,050

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

    20 Judys Ln, South Chatham, MA 2659
    • /59

      Est $3,093,939 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,097 Sq Ft

      81 Mill Pond Rd, Chatham, MA 02633

      81 Mill Pond Rd, Chatham, MA 02633
  • /63

    $1,525,000

    • 3 Beds
    • 2.5 Baths
    • 2,441 Sq Ft

    28 Lakeview Ave, Chatham, MA 02633

    Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated with hardwood throughout, this 3 bedroom, 2.5 bath home offers a comfortable floor plan including a first floor primary ensuite bedroom and 2 large guest bedooms and bath on the second level. In addition to the inviting living room and dining room, adjacent to well apppointed eat-in kitchen, the den with

    Ella Leavitt Compass

    28 Lakeview Ave, Chatham, MA 02633
  • /3

    $1,370,000 Sold Jul 17, 2025

    30 Monomessat Way, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $476/SF
    • 18 Days On Market

    Current Estimated Value $1,395,941

    Last Listing Agent Jan Pulit Kinlin Grover Compass

    30 Monomessat Way, Chatham, MA 02633
    • /35

      Est $1,056,121 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 748 Sq Ft

      8 Oyster Dr, Chatham, MA 02633

      8 Oyster Dr, Chatham, MA 02633
  • /36

    $650,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft

    407 Orleans Rd Unit D, North Chatham, MA 02650

    Beautifully renovated 1,500+ sq ft two-level condo in the desirable Quail Run Association. The main level was renovated in 2023, and the lower level was just completed in 2025. The open living and dining area is filled with natural light and features a stylish wet bar and slider to a large deck overlooking lush, quiet conservation land. The kitchen boasts white stone countertops, tile backsplash,

    Tom Riley Compass Massachusetts, LLC

    407 Orleans Rd Unit D, North Chatham, MA 02650
  • /52

    $970,000 Sold Feb 07, 2025

    58 Diane Dr, Chatham, MA 02633

    • 2 Beds
    • 1 Bath
    • 1,331 Sq Ft
    • Built 1947

    Last Sold Summary

    • 10% Below List Price
    • $729/SF
    • 51 Days On Market

    Current Estimated Value $1,018,461

    Last Listing Agent A Cape Life Today Real Estate

    58 Diane Dr, Chatham, MA 02633
    • /22

      Est $672,823 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft

      16 Starfish Ln, Chatham, MA 02633

      16 Starfish Ln, Chatham, MA 02633
  • /35

    $979,000

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft

    46 Chippingstone Rd, Chatham, MA 02633

    Riverbay, Chatham... True One Level living with Garage/parking on home level. 8 room custom built ranch with side loading garages, high profile roofline, integrated front porch. Inside, abundant common areas and living space. entrance hallway opens to the living and dining rooms, and two hallways leading to the 3 bedrooms. At the back of the home- 3 additional rooms: a fireplaced family room, an

    Derek Greene The Greene Realty Group

    46 Chippingstone 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

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
    • /54

      Est $1,791,810 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,352 Sq Ft

      52 Wentworth Ln, North Chatham, MA 02650

      52 Wentworth Ln, North Chatham, MA 02650
  • /37

    $1,200,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    27 Martha Kendrick Dr, Chatham, MA 02633

    Welcome to this delightful 3-bedroom, 2.5-bath Cape-style home nestled just moments from the heart of downtown Chatham. With its classic architecture and thoughtful layout, this property offers the perfect blend of coastal charm and modern convenience.Step inside to discover sun-drenched living spaces with abundant natural light and a cozy fireplace that anchors the main living area. The

    Kathy Doyle Gibson Sotheby's International Realty

    27 Martha Kendrick Dr, Chatham, MA 02633
  • /42

    $11,250,000 Sold Jun 09, 2025

    552 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 6.5 Baths
    • 5,868 Sq Ft
    • Built 1930

    Last Sold Summary

    • 19% Below List Price
    • $1,917/SF
    • 326 Days On Market

    Current Estimated Value $7,565,116

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    552 Shore Rd, Chatham, MA 02633
    • /47

      Est $2,020,026 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,524 Sq Ft

      75 Whidah Rd, North Chatham, MA 02650

      75 Whidah Rd, North Chatham, MA 02650
  • /77

    $1,850,000

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    32 Sunset Ln, Chatham, MA 02633

    Extremely rare opportunity! Available for the first time in 60+ years, this property is tucked away on a quiet lane in Chatham's coveted Old Village. The location offers the best of both worlds -- peaceful surroundings with easy access to Chatham's most beloved spots. Take the neighborhood path around Little Mill Pond for your morning coffee downtown, spend the day at Lighthouse Beach, launch a

    Tom Riley Compass Massachusetts, LLC

    32 Sunset Ln, Chatham, MA 02633
  • /54

    $3,300,000 Sold Jul 22, 2025

    35 Whistler Ln, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,314 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $1,426/SF
    • 50 Days On Market

    Last Listing Agent MaryEllen Monahan Today Real Estate

    35 Whistler Ln, Chatham, MA 02633
    • /18

      Est $367,588 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft

      197 Stony Hill Rd Unit C, Chatham, MA 02633

      197 Stony Hill Rd Unit C, Chatham, MA 02633
  • /34

    $3,200,000

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

    92 Indian Trail, Chatham, MA 02633

    Professional photos coming soon! 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

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, 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
    • /53

      Est $1,323,521 Not Listed For Sale

      • 2 Beds
      • 3.5 Baths
      • 2,546 Sq Ft

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

      43 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • /26

    $399,000

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft

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

    Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This second-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front. Inside, the unit is

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
  • /56

    $1,675,000 Sold Apr 01, 2025

    51 Bucks Creek Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1959

    Last Sold Summary

    • $1,047/SF
    • 26 Days On Market

    Current Estimated Value $1,621,199

    Last Listing Agent Dawn Lee Gibson Sotheby's International Realty

    51 Bucks Creek Rd, Chatham, MA 02633
    • /29

      Est $1,131,355 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,812 Sq Ft

      39 Misty Meadow Ln, North Chatham, MA 02650

      39 Misty Meadow Ln, North Chatham, MA 02650
  • /67

    $3,495,000 Pending

    • 4 Beds
    • 4 Baths
    • 4,797 Sq Ft

    40 Youngs Farm Ln, Chatham, MA 02633

    Tucked away next to a coastal inlet that ebbs and flows with the tide, this remarkable home delivers WOW FACTOR with unobstructed water views to enjoy captivating sunsets! The private location at the end of a cul-de-sac abuts acres of town-owned Conservation and is a peaceful haven of ever-changing natural vistas. This residence was designed by Royal Barry Wills for both ease of living and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    40 Youngs Farm Ln, 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

    Last Listing Agent Jan Nowak Craigville Realty Co

    291 Ridgevale Rd, Chatham, MA 02633
    • /27

      Est $1,137,743 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,906 Sq Ft

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

      37 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • /52

    $7,999,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    30 Tisquantum Rd, Chatham, MA 02633

    What. A. View! 180 degree panoramic water vistas over The Atlantic Ocean, Chatham Harbor, and picturesque Stage Harbor set the tone for this shingled style home located high on a hill on private Morris Island. Sweeping ocean views and a private association beach combine with 2.33 acres to create a luxurious yet comfortable coastal retreat located in the Quitnesset Association. Tastefully and

    Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum 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

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633
    • /25

      Est $1,193,447 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft

      61 Bishops Terrace, Chatham, MA 02633

      61 Bishops Terrace, Chatham, MA 02633
  • /76

    $1,225,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft

    597 Orleans Rd, North Chatham, MA 02650

    Nestled on a sprawling 1.55-acre parcel set back from Route 28, this exquisite North Chatham residence captures the essence of tranquil coastal living. This beautifully renovated home spans 1,942 square feet (including the beautiful finished walkout lower level) and boasts three spacious bedrooms and two pristine bathrooms, offering an exceptional blend of comfort and sophistication.
As you

    Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650

Showing Results 81 - 120, Page 3 of 18

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