9,641

Chatham, MA Homes

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  • /34

    $1,150,000

    Sold Jun 02, 2025

    56 Barn Hill Ln, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $790/SF
    • 26 Days On Market

    Current Estimated Value $1,195,673

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    56 Barn Hill Ln, Chatham, MA 02633
    • /43

      Est $2,779,639

      Not Listed For Sale

      30 Pine Ln, North Chatham, MA 02650

      • 4 Beds
      • 3.5 Baths
      • 4,406 Sq Ft
      • Built 1982
      30 Pine Ln, North Chatham, MA 02650

      Last Sold Summary

      • 39% Above List Price
      • $454/SF
      • 109 Days On Market
      • Last Sold Price $2,000,000
      • Oct 25, 2023

      Last Listing Agent Tracey Oringer Kinlin Grover Compass

  • /31

    $769,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    26 Pine Tree Rd, Chatham, MA 2633

    Rare opportunity to own a classic 2-bed Cape Cod cottage in highly desirable South Chatham. This family-owned home for many years features 6 rooms, a cozy fireplaced living room, and a sunny bonus room with cathedral ceilings and skylights. Modern amenities include gas heat, central air and new septic system. Features an oversized detached garage and parking for 4-5 cars. Minutes to several

    John Raso Apex Realty Group, LLC

    26 Pine Tree Rd, Chatham, MA 2633
  • /77

    $1,622,500

    Sold Mar 09, 2026

    32 Sunset Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft
    • Built 1950

    Last Sold Summary

    • 19% Below List Price
    • $998/SF
    • 99 Days On Market

    Current Estimated Value $1,804,663

    Last Listing Agent Tom Riley Compass Massachusetts, LLC

    32 Sunset Ln, Chatham, MA 02633
    • /47

      Est $2,733,190

      Not Listed For Sale

      74 Frost Fish Rd, North Chatham, MA 02650

      • 5 Beds
      • 4.5 Baths
      • 4,996 Sq Ft
      • Built 2002
      74 Frost Fish Rd, North Chatham, MA 02650

      Last Sold Summary

      • 20% Above List Price
      • $456/SF
      • 160 Days On Market
      • Last Sold Price $2,275,895
      • May 31, 2023

      Last Listing Agent David Carter Compass Massachusetts, LLC

  • /2

    $3,999,900

    New Construction Open Sat 10AM - 12PM
    • 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
  • /39

    $770,000

    Sold Apr 15, 2026

    37 Glendon Way, South Chatham, MA 02659

    • 2 Beds
    • 1 Bath
    • 817 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Below List Price
    • $942/SF
    • 20 Days On Market

    Current Estimated Value $796,905

    Last Listing Agent Dee Kerner Compass

    37 Glendon Way, South Chatham, MA 02659
    • /22

      Est $429,143

      Not Listed For Sale

      409 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 1 Bath
      • 1,013 Sq Ft
      • Built 1987
      409 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 1% Below List Price
      • $429/SF
      • 6 Days On Market
      • Last Sold Price $435,000
      • Mar 14, 2025

      Last Listing Agent Debra Bassett Cape Cod Associates R E

  • /7

    $315,000

    $35K PRICE DROP Pending
    • Land
    • 20,473 Sq Ft
    • $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
  • /42

    $2,150,000

    Sold Apr 28, 2026

    55 Christopher Harding Ln, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,510 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $857/SF
    • 207 Days On Market

    Current Estimated Value $2,103,614

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    55 Christopher Harding Ln, Chatham, MA 02633
    • /25

      Est $451,157

      Not Listed For Sale

      409 Orleans Rd Unit A, North Chatham, MA 02650

      • 2 Beds
      • 1.5 Baths
      • 1,038 Sq Ft
      • Built 1987
      409 Orleans Rd Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 10% Above List Price
      • $395/SF
      • 61 Days On Market
      • Last Sold Price $410,000
      • Sep 12, 2023

      Last Listing Agent Marie Kelly Berkshire Hathaway HomeServices Robert Paul Properties

  • /50

    $1,615,000

    Pending
    • 3 Beds
    • 4 Baths
    • 3,645 Sq Ft

    393 Training Field Rd, Chatham, MA 02633

    Welcome to 393 Training Field Road, a beautifully renovated three-bedroom, two full and two half-bath ranch in Chatham's desirable Riverbay Estates. Designed for easy one-floor living, the home features a primary ensuite, new sunroom addition, expanded side entry w/mudroom, new front door and entryway, new bay window w/built-in cabinet, new flooring, fresh interior paint, 2 full & 2 half new

    Shane Masaschi Compass

    393 Training Field Rd, Chatham, MA 02633
  • /35

    $695,000

    Sold Apr 21, 2026

    1 Seastrand Way Unit 1, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1983

    Last Sold Summary

    • $536/SF
    • 11 Days On Market

    Current Estimated Value $673,888

    Last Listing Agent Phyllis Power Compass

    1 Seastrand Way Unit 1, Chatham, MA 02633
    • /18

      Est $499,683

      Not Listed For Sale

      407 Orleans Rd Unit B, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,013 Sq Ft
      • Built 1987
      407 Orleans Rd Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 6% Above List Price
      • $464/SF
      • 70 Days On Market
      • Last Sold Price $470,000
      • Dec 11, 2023

      Last Listing Agent Ryan Mann Sotheby's International Realty

  • /42

    $3,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    336 Stage Island Rd, Chatham, MA 02633

    Stage Island is among the most exclusive addresses on Cape Cod — a private enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    336 Stage Island Rd, Chatham, MA 02633
  • /18

    $575,000

    Sold Sep 25, 2025

    19 Stoughton Ln, Chatham, MA 2633

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1951

    Last Sold Summary

    • 26% Below List Price
    • $424/SF
    • 354 Days On Market

    Current Estimated Value $603,099

    Last Listing Agent Shane Masaschi Compass

    19 Stoughton Ln, Chatham, MA 2633
    • /27

      Est $655,305

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,551 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit B, North Chatham, MA 02650

      Last Sold Summary

      • 4% Below List Price
      • $442/SF
      • 14 Days On Market
      • Last Sold Price $685,000
      • Aug 09, 2024

      Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

  • /49

    $575,000

    Pending
    • 1 Bed
    • 1 Bath
    • 399 Sq Ft

    73 Main St Unit 6, Chatham, MA 02633

    Looking for a Chatham getaway near Town and the beach with amazing views? Welcome to 73 Main Street! This charming 1-bedroom condo sits adjacent to Chatham Lighthouse and directly across from Lighthouse Beach, offering picturesque water and lighthouse views. A bright open layout includes living area with dining area, small kitchen, one bedroom, and full bath. You'll also enjoy an exclusive-use

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    73 Main St Unit 6, Chatham, MA 02633
  • /11

    $345,000

    Sold Aug 15, 2025

    281 Orleans Rd Unit 5, Chatham, MA 02633

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $571/SF
    • 1 Day On Market

    Current Estimated Value $339,113

    Last Listing Agent Isaac Sargent Compass Massachusetts, LLC

    281 Orleans Rd Unit 5, Chatham, MA 02633
    • /27

      Est $572,103

      Not Listed For Sale

      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      • 2 Beds
      • 2 Baths
      • 1,489 Sq Ft
      • Built 1985
      108 Misty Meadow Ln Unit A, North Chatham, MA 02650

      Last Sold Summary

      • 3% Below List Price
      • $396/SF
      • 3 Days On Market
      • Last Sold Price $590,000
      • Mar 12, 2025

      Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

  • /41

    $5,995,000

    $255K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,060 Sq Ft

    70 Judges Way, Chatham, MA 02633

    Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence w/multiple living spaces blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    70 Judges Way, Chatham, MA 02633
  • /37

    $2,610,000

    Sold Oct 02, 2025

    51 Shattuck Place, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,133 Sq Ft
    • Built 1810

    Last Sold Summary

    • 9% Above List Price
    • $1,224/SF
    • 4 Days On Market

    Current Estimated Value $2,716,515

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

    51 Shattuck Place, Chatham, MA 02633
    • /34

      Est $450,312

      Not Listed For Sale

      36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

      • 2 Beds
      • 1.5 Baths
      • 930 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 4, North Chatham, MA 02650

      Last Sold Summary

      • 6% Above List Price
      • $457/SF
      • 5 Days On Market
      • Last Sold Price $425,000
      • May 12, 2025

      Last Listing Agent Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

  • /65

    $459,000

    Pending
    • 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
  • /52

    $7,000,000

    Sold Dec 18, 2025

    30 Tisquantum Rd, Chatham, MA 02633

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft
    • Built 1973

    Last Sold Summary

    • 18% Below List Price
    • $1,626/SF
    • 129 Days On Market

    Current Estimated Value $7,156,581

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum Rd, Chatham, MA 02633
    • /26

      Est $412,994

      Not Listed For Sale

      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      • 1 Bed
      • 1.5 Baths
      • 836 Sq Ft
      • Built 1982
      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      Last Sold Summary

      • 9% Above List Price
      • $452/SF
      • 60 Days On Market
      • Last Sold Price $378,000
      • Mar 14, 2024

      Last Listing Agent Margaret Fallon Keller Williams Realty

  • /47

    $4,950,000

    • 4 Beds
    • 4.5 Baths
    • 5,371 Sq Ft

    15 Bay Ln, Chatham, MA 02633

    Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance. Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even

    Chris Rhinesmith Compass Massachusetts, LLC

    15 Bay Ln, Chatham, MA 02633
  • /53

    $1,520,000

    Sold Dec 11, 2025

    73 Joshua Jethro Rd, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,307 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $659/SF
    • 79 Days On Market

    Current Estimated Value $1,552,494

    Last Listing Agent Paul Borde Christie's International Real Estate Atlantic Brokerage

    73 Joshua Jethro Rd, Chatham, MA 02633
    • /29

      Est $1,120,522

      Not Listed For Sale

      56 Meadowbrook Rd, North Chatham, MA 02650

      • 4 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 1961
      56 Meadowbrook Rd, North Chatham, MA 02650

      Last Sold Summary

      • 60% Above List Price
      • $413/SF
      • 14 Days On Market
      • Last Sold Price $699,000
      • Dec 15, 2023

      Last Listing Agent Shane Masaschi Compass

  • /80

    $4,999,000

    New Construction $251K PRICE DROP
    • 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
  • /53

    $900,000

    Sold Oct 01, 2025

    61 Cod Ln, Chatham, MA 02633

    • 2 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Above List Price
    • $758/SF
    • 6 Days On Market

    Current Estimated Value $930,635

    Last Listing Agent Sarah Keith eXp Realty, LLC

    61 Cod Ln, Chatham, MA 02633
    • /48

      Est $1,110,468

      Not Listed For Sale

      31 Great Hill Rd, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,977 Sq Ft
      • Built 1965
      31 Great Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 19% Above List Price
      • $470/SF
      • 234 Days On Market
      • Last Sold Price $930,000
      • May 30, 2024

      Last Listing Agent Judith Smith John C Ricotta & Assoc.

  • /25

    $760,000

    • 2 Beds
    • 2 Baths
    • 950 Sq Ft

    22 Starfish Ln Unit 22, Chatham, MA 02633

    Beautifully renovated inside and out oceanfront townhome nestled in the heart of Chatham. Fully furnished 2 bedroom, 2 bathroom home offers the epitome of Cape Cod living with breathtaking ocean views and private association beach access just steps from your door. Wake up to stunning sunrises over the water. The vaulted ceilings allow natural light to fill the bedrooms. Located just a short walk

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    22 Starfish Ln Unit 22, Chatham, MA 02633
  • /76

    $1,175,000

    Sold Jan 22, 2026

    597 Orleans Rd, North Chatham, MA 02650

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $605/SF
    • 181 Days On Market

    Current Estimated Value $1,313,836

    Last Listing Agent Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
    • /27

      Est $707,136

      Not Listed For Sale

      79 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1968
      79 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 7% Above List Price
      • $688/SF
      • 6 Days On Market
      • Last Sold Price $660,000
      • Sep 30, 2024

      Last Listing Agent Kathleen Phelan Compass

  • /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
  • /86

    $5,805,000

    Sold Dec 18, 2025

    58 Oyster Bluff, Chatham, MA 02633

    • 7 Beds
    • 3.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • 1% Above List Price
    • $1,555/SF
    • 25 Days On Market

    Current Estimated Value $5,851,503

    Last Listing Agent Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    58 Oyster Bluff, Chatham, MA 02633
    • /24

      Est $1,099,937

      Not Listed For Sale

      59 Nob Hill Rd, Chatham, MA 02633

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1966
      59 Nob Hill Rd, Chatham, MA 02633

      Last Sold Summary

      • 42% Above List Price
      • $577/SF
      • 38 Days On Market
      • Last Sold Price $775,000
      • Dec 20, 2023

      Last Listing Agent Shane Masaschi Kinlin Grover Compass

  • /39

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 2,257 Sq Ft

    35 Pine Tree Rd, Chatham, MA 02659

    Perfect for kayak and canoe enthusiasts, this inviting South Chatham home, south of Rt 28, sits just one tenth of a mile from the town landing on Mill Creek, offering effortless access to serene paddling, birdwatching, and peaceful mornings on the water.Inside, the open concept first floor features hardwood floors throughout, creating a warm, cohesive flow from the living area to the dining space

    Kathy Doyle Gibson Sotheby's International Realty

    35 Pine Tree Rd, Chatham, MA 02659
  • /95

    $2,025,000

    Sold Oct 10, 2025

    2016 Main St, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 3,902 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $519/SF
    • 64 Days On Market

    Current Estimated Value $2,238,835

    Last Listing Agent Daneen Law Gibson Sotheby's International Realty

    2016 Main St, Chatham, MA 02633

Showing Results 201 - 240, Page 6 of 18

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