9,636

Chatham, MA Homes

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  • /48

    $6,950,000 Sold Jul 24, 2025

    16 Seapine Rd, North Chatham, MA 02650

    • 5 Beds
    • 6.5 Baths
    • 6,508 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,068/SF
    • 307 Days On Market

    Current Estimated Value $5,053,566

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    16 Seapine Rd, North Chatham, MA 02650
    • /28

      Est $1,097,579 Not Listed For Sale

      32 Aire Ln, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1965
      32 Aire Ln, Chatham, MA 02633

      Last Sold Summary

      • 29% Above List Price
      • $526/SF
      • 1 Day On Market

      Last Sold Price $852,500

      Last Listing Agent Shane Masaschi Kinlin Grover Compass

  • /93

    $6,250,000

    • 5 Beds
    • 5.5 Baths
    • 5,620 Sq Ft

    15 Windy Hill Way, Chatham, MA 02633

    This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

    Tim Bailey John C Ricotta & Assoc.

    15 Windy Hill Way, Chatham, MA 02633
  • /50

    $955,000 Sold Oct 14, 2025

    67 A Leonard Way, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $713/SF
    • 17 Days On Market

    Current Estimated Value $949,991

    Last Listing Agent Shane Masaschi Compass

    67 A Leonard Way, Chatham, MA 02633
    • /13

      Est $648,537 Not Listed For Sale

      276 Orleans Rd, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 955 Sq Ft
      • Built 1920
      276 Orleans Rd, Chatham, MA 02633

      Last Sold Summary

      • 1% Above List Price
      • $670/SF
      • 35 Days On Market

      Last Sold Price $640,000

      Last Listing Agent Siobhan Costello Weber Castinetti Realty Group

  • /34

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,802 Sq Ft

    32 Tip Cart Dr, Chatham, MA 02633

    Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision. Additional features include wood

    Shane Masaschi Compass

    32 Tip Cart Dr, Chatham, MA 02633
  • /46

    $4,000,000 Sold Oct 03, 2025

    85 Main St, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,998 Sq Ft
    • Built 1820

    Last Sold Summary

    • 27% Below List Price
    • $1,334/SF
    • 150 Days On Market

    Current Estimated Value $4,068,697

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633
    • /25

      Est $771,259 Not Listed For Sale

      161 Shane Dr, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 966 Sq Ft
      • Built 1971
      161 Shane Dr, Chatham, MA 02633

      Last Sold Summary

      • 13% Above List Price
      • $708/SF
      • 6 Days On Market

      Last Sold Price $684,374

      Last Listing Agent Darci Gervais Keller Williams Realty

  • /36

    $6,800,000

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

    238 Cranberry Ln, Chatham, MA 02633

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, Chatham, MA 02633
  • /38

    $2,000,000 Sold Sep 16, 2025

    595 Main St Unit 37, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $931/SF
    • 18 Days On Market

    Current Estimated Value $1,951,163

    Last Listing Agent Sandra Tanco Kinlin Grover Compass

    595 Main St Unit 37, Chatham, MA 02633
    • /38

      Est $1,987,677 Not Listed For Sale

      55 Eldredge Square S, Chatham, MA 02633

      • 3 Beds
      • 4 Baths
      • 2,630 Sq Ft
      • Built 2003
      55 Eldredge Square S, Chatham, MA 02633

      Last Sold Summary

      • 7% Above List Price
      • $703/SF
      • 152 Days On Market

      Last Sold Price $1,850,000

      Last Listing Agent Jessica Metzler Compass

  • /2

    $3,999,900 New Construction

    • 3 Beds
    • 4.5 Baths
    • 4,393 Sq Ft

    2550 Main St, South Chatham, MA 02659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer. Incorporating expansive open living space you will

    Ward Brown William Raveis Real Estate & Home Services

    2550 Main St, South Chatham, MA 02659
  • /46

    $1,385,000 Sold Dec 16, 2025

    114 Bucks Creek Rd, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 2,289 Sq Ft
    • Built 1965

    Last Sold Summary

    • 21% Below List Price
    • $605/SF
    • 84 Days On Market

    Current Estimated Value $1,396,964

    Last Listing Agent Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

    114 Bucks Creek Rd, Chatham, MA 02633
    • /28

      Est $1,203,139 Not Listed For Sale

      233 Barcliff Ave, Chatham, MA 02633

      • 2 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1957
      233 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 9% Above List Price
      • $920/SF
      • 25 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Jack Tobin Corcoran Property Advisors

  • /7

    $315,000 Pending

    • Land
    • 0.47 Acre
    • $670,213 per Acre

    0 Tirrells Way, Chatham, MA 02659

    Building lot available! Privately located at the end of a cul-de-sac and abutting the Town Forest. Water Department has an easement for a road over the property at the edge of the lot boundary. All due diligence required for building allowances and restrictions are responsibility of the buyer. See the document section for engineering information and a rendering for the type of home that can be

    Kathy Doyle Gibson Sotheby's International Realty

    0 Tirrells Way, Chatham, MA 02659
  • /2

    $1,000,000 Sold Sep 29, 2025

    0 Woodland Way, Chatham, MA 02650

    • Land
    • 0.49 Acre
    • $2,040,816 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Kimberly Howard Christie's International Real Estate Atlantic Brokerage

    0 Woodland Way, Chatham, MA 02650
    • /65

      Est $3,047,373 Not Listed For Sale

      25 Glover Square, Chatham, MA 02633

      • 3 Beds
      • 4.5 Baths
      • 4,105 Sq Ft
      • Built 2018
      25 Glover Square, Chatham, MA 02633

      Last Sold Summary

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

      Last Sold Price $2,995,000

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

  • /41

    $1,750,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,039 Sq Ft

    146 Old Field Bend, North Chatham, MA 02650

    Elevated on a .57 acre lot in a serene North Chatham setting within Ryder's Cove Landing Association, this privately situated 3 bedroom, 3.5 bath home offers three levels of living. The main level features an inviting eat-in kitchen with island, a welcoming living room with fireplace, and a three-season sunroom with TV overlooking peaceful surroundings. The primary suite includes a private bath

    Chris Rhinesmith Compass Massachusetts, LLC

    146 Old Field Bend, North Chatham, MA 02650
  • /41

    $898,000 Sold Oct 30, 2025

    306 Old Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $535/SF
    • 14 Days On Market

    Current Estimated Value $904,390

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    306 Old Queen Anne Rd, Chatham, MA 02633
    • /46

      Est $1,414,249 Not Listed For Sale

      265 Barcliff Ave, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,491 Sq Ft
      • Built 1953
      265 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 9% Above List Price
      • $872/SF
      • 2 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Barbara Garside Compass Massachusetts, LLC

  • /24

    $599,000 Pending

    • 4 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    100 Heritage Ln, Chatham, MA 02633

    Located in desirable Chatham, this 4-bedroom, 1.5-bath home presents a rare opportunity to create your own Cape Cod retreat. The property abuts scenic cranberry bogs, offering a unique natural backdrop with no neighbors behind - an increasingly hard-to-find setting.With 1,144 square feet of living space, the home features a flexible layout ready for your vision. Whether you're an investor,

    Geoffrey MacKenzie William Raveis Real Estate & Home Services

    100 Heritage Ln, Chatham, MA 02633
  • /55

    $3,025,000 Sold Dec 19, 2025

    93 Bucks Creek Rd, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 3,544 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $854/SF
    • 61 Days On Market

    Current Estimated Value $3,072,583

    Last Listing Agent Shane Masaschi Compass

    93 Bucks Creek Rd, Chatham, MA 02633
    • /30

      Est $1,288,822 Not Listed For Sale

      751 Main St, Chatham, MA 02633

      • 2 Beds
      • 2.5 Baths
      • 1,552 Sq Ft
      • Built 1910
      751 Main St, Chatham, MA 02633

      Last Sold Summary

      • 12% Above List Price
      • $741/SF
      • 102 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Michael Masci North Atlantic Realty Group

  • /38

    $1,425,000

    • 2 Beds
    • 3 Baths
    • 2,212 Sq Ft

    1114 Orleans Rd Unit 2, Chatham, MA 2633

    This two-bedroom, three bath condominium, part of the historic Christopher Ryder House, blends timeless architecture with elegant design. The residence features high ceilings, wood floors, large windows, and generously scaled rooms. The foyer opens to a grand living room with gas fireplace flowing into the dining area and adjoining pantry, with views into the chef’s kitchen featuring a Thermador

    Chris Rhinesmith Compass

    1114 Orleans Rd Unit 2, Chatham, MA 2633
  • /6

    $3,499,900 Sold Dec 22, 2025

    29 Jessies Landing, Chatham, MA 2633

    • 3 Beds
    • 4.5 Baths
    • 4,565 Sq Ft
    • Built 2024

    Last Sold Summary

    • $767/SF
    • 3 Days On Market

    Current Estimated Value $3,036,000

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

    29 Jessies Landing, Chatham, MA 2633
    • /30

      Not Listed For Sale

      178 Queen Anne Rd, Chatham, MA 02633

      • 6 Beds
      • 8 Baths
      • 7,700 Sq Ft
      • Built 1820
      178 Queen Anne Rd, Chatham, MA 02633

      Last Sold Summary

      • $1,237/SF
      • 21 Days On Market

      Last Sold Price $9,525,000

      Last Listing Agent Brian Dougherty Corcoran Property Advisors

  • /65

    $459,000

    • 1 Bed
    • 2 Baths
    • 1,284 Sq Ft

    912 Main St Unit 308, Chatham, MA 02633

    Park Place is the Premiere Chatham address for an easy-care, maintenance-free lifestyle! These apartment-style condos cater to age 62+ residents seeking to enjoy a walkable location in Town, numerous opportunities for social engagement (including daily continental breakfast and Friday night cocktails), an exercise room, library, guest suite, garage parking, elevator and more. Unit 308 is located

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    912 Main St Unit 308, Chatham, MA 02633
  • /35

    $1,095,000 Sold Jul 18, 2025

    20 Judys Ln, Chatham, MA 02633

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

    Last Sold Summary

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

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

    20 Judys Ln, Chatham, MA 02633
    • /24

      Est $3,718,838 Not Listed For Sale

      125 Stage Harbor Rd, Chatham, MA 02633

      • 3 Beds
      • 2.5 Baths
      • 2,421 Sq Ft
      • Built 1946
      125 Stage Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 20% Above List Price
      • $1,280/SF
      • 506 Days On Market

      Last Sold Price $3,100,000

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /5

    $399,000

    • Land
    • 0.84 Acre
    • $475,000 per Acre

    0 Evergreen Ln, Chatham, MA 02633

    .8 Acres- In the Heart of it All- Chatham- where you want your Family Memories to be made- Ridgevale Beach- Hardings Beach- Landings and Marinas close by- Private and Wooded Lot- Imagine building your dream Summer Home or Fulltime Residence and waking up to privacy and just minutes to Nantucket Sound- Oyster River- Goose Pond- School House Pond and more... South of Route 28-Building Information

    Noreen Kennedy Kennedy Real Estate

    0 Evergreen Ln, Chatham, MA 02633
  • /50

    $995,000 Sold Oct 10, 2025

    56 Chatham Crest Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Above List Price
    • $575/SF
    • 5 Days On Market

    Current Estimated Value $1,030,891

    Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

    56 Chatham Crest Dr, Chatham, MA 02633
    • /62

      Est $2,619,750 Not Listed For Sale

      276 Stage Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 3.5 Baths
      • 2,732 Sq Ft
      • Built 1988
      276 Stage Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 31% Above List Price
      • $732/SF
      • 33 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent David Carter Compass Massachusetts, LLC

  • /80

    $4,999,000 New Construction

    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    Set within a private gated enclave in South Chatham's emerging luxury corridor, 48 Sylvan Way is a singular estate retreat discreetly positioned just moments from the Cape's most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational potential, the property offers rare privacy, scale, and versatility in one of Chatham's most compelling

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    48 Sylvan Way, South Chatham, MA 02659
  • /36

    $645,000 Sold Jan 06, 2026

    407 Orleans Rd Unit D, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $422/SF
    • 4 Days On Market

    Current Estimated Value $639,946

    Last Listing Agent Tom Riley Compass Massachusetts, LLC

    407 Orleans Rd Unit D, North Chatham, MA 02650
    • /78

      Est $3,730,590 Not Listed For Sale

      155 Inlet Rd, Chatham, MA 02633

      • 5 Beds
      • 5.5 Baths
      • 4,048 Sq Ft
      • Built 2010
      155 Inlet Rd, Chatham, MA 02633

      Last Sold Summary

      • 10% Above List Price
      • $840/SF
      • 205 Days On Market

      Last Sold Price $3,400,000

      Last Listing Agent Janice Alex Christie's International Real Estate Atlantic Brokerage

  • /51

    $842,000

    • 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
  • /24

    $780,000 Sold Jun 06, 2025

    15 Stephen Dr, Chatham, MA 02633

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Above List Price
    • $682/SF
    • 5 Days On Market

    Current Estimated Value $802,425

    Last Listing Agent Stephen Laska RE/MAX Vision

    15 Stephen Dr, Chatham, MA 02633
    • /40

      Est $3,872,037 Not Listed For Sale

      98 Attucks Trail, Chatham, MA 02633

      • 4 Beds
      • 4.5 Baths
      • 3,915 Sq Ft
      • Built 1971
      98 Attucks Trail, Chatham, MA 02633

      Last Sold Summary

      • 5% Above List Price
      • $939/SF
      • 111 Days On Market

      Last Sold Price $3,675,000

      Last Listing Agent Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties

  • /62

    $899,900 Open Sat 11AM - 2PM

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

    25 Wood Valley Rd, Chatham, MA 02633

    Nestled on a quiet cul-de-sac with deeded access to Lovers Lake, this 4-bedroom, 2-bath Cape-style home offers the perfect blend of comfort, convenience, and Chatham charm. Ideally located near the bike path, tennis and pickleball courts, and just minutes from downtown Chatham, the property is well suited for both year-round living and seasonal enjoyment. The first floor features a spacious

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    25 Wood Valley Rd, Chatham, MA 02633
  • /41

    $1,599,000 Sold Aug 15, 2025

    751 Crowell Rd, North Chatham, MA 02650

    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Above List Price
    • $682/SF
    • 2 Days On Market

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

    751 Crowell Rd, North Chatham, MA 02650

Showing Results 161 - 200, Page 5 of 18

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