9,489

Chatham, MA Homes

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  • /59

    $1,950,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,198 Sq Ft

    4 Williams Way, Chatham, MA 02659

    Reaching into the ocean, the road to Chatham follows a path carved by memory, a line etched straight through the geography of the heart. At 4 Williams Way, that coastal journey finds its destination. Tucked away on a five-home cul-de-sac, this 1.5 acre Contemporary Cape Cod offers sanctuary in a prime location, just minutes to downtown Chatham and 1.7 miles to Cockle Cove Beach, all while being

    Erin Terkelsen LPT Realty

    4 Williams Way, Chatham, MA 02659
  • /40

    $1,381,000

    Sold Jul 17, 2026

    36 Pursel Dr, North Chatham, MA 02650

    • 4 Beds
    • 3 Baths
    • 2,268 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Above List Price
    • $609/SF
    • 16 Days On Market

    Current Estimated Value $1,376,250

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    36 Pursel Dr, North Chatham, MA 02650
    • /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

      • 251 Days On Market

      Last Listing Agent Kimberly Robbins Compass Massachusetts, LLC

  • /42

    $1,350,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    50 Pine Ridge Rd, Chatham, MA 02633

    Move right into this charming cottage-style ranch in the coveted beach neighborhood of Hardings Beach Hills. With close proximity to Hardings Beach, this gem is the ideal vacation home or rental investment. The open floor plan includes a cheerful sunroom with vaulted beamed ceilings, sliding door, and walls of windows. Eat-in-kitchen and adjacent living room with fireplace & bay window provide

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    50 Pine Ridge Rd, Chatham, MA 02633
  • /23

    $550,000

    Sold Apr 03, 2026

    28 Charles St, South Chatham, MA 02659

    • 4 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1967

    Last Sold Summary

    • $385/SF
    • 6 Days On Market

    Current Estimated Value $570,570

    Last Listing Agent Shane Masaschi Compass

    28 Charles St, South Chatham, MA 02659
    • /77

      Est $4,324,424

      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

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

  • /35

    $5,250,000

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft

    106 Barcliff Ave, Chatham, MA 02633

    Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings

    Jill Boudreau eXp Realty LLC - Corporate Office

    106 Barcliff Ave, Chatham, MA 02633
  • /62

    $889,000

    Sold May 18, 2026

    25 Wood Valley Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 2,004 Sq Ft
    • Built 1969

    Last Sold Summary

    • 1% Below List Price
    • $444/SF
    • 8 Days On Market

    Current Estimated Value $934,379

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

    25 Wood Valley Rd, Chatham, MA 02633
    • /2

      Est $4,073,484

      Not Listed For Sale

      39 Seaview Terrace, Chatham, MA 02633

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

  • /44

    $2,390,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property

    Janet Stuart Coldwell Banker Realty

    55 Winterset Dr, Chatham, MA 02633
  • /8

    $750,000

    Sold Jul 20, 2026

    165 Tanglewood Dr, South Chatham, MA 02659

    • 3 Beds
    • 3 Baths
    • 2,102 Sq Ft
    • Built 1976

    Last Sold Summary

    • $357/SF
    • 10 Days On Market

    Current Estimated Value $747,909

    Last Listing Agent Kari Wagner Compass

    165 Tanglewood Dr, South Chatham, MA 02659
    • /2

      Est $1,983,263

      Not Listed For Sale

      31 Mill Pond Rd, Chatham, MA 02633

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

  • /28

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

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

    Tucked away on a quiet street in the heart of North Chatham, this charming second-floor condominium offers an exceptional opportunity to own in one of the Cape's most coveted locations. Whether you're seeking a seasonal retreat, an investment property, or a smart entry into the Chatham market, this residence delivers a perfect blend of convenience, charm, and value. Filled with natural light, the

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • /24

    $775,000

    Sold Jun 05, 2026

    35 Bobbies Ln, Chatham, MA 2633

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • 11% Above List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $767,560

    Last Listing Agent Richard Waystack Keller Williams Realty

    35 Bobbies Ln, Chatham, MA 2633
    • /2

      Est $1,191,665

      Not Listed For Sale

      8 Oyster Dr, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 748 Sq Ft
      • Built 1947
      8 Oyster Dr, Chatham, MA 02633

  • /42

    $2,600,000

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10 Mill Hill Ln, Chatham, MA 02633

    Set on a tranquil dead-end lane in Chatham's Old Village, this 2006-built home pays homage to its 1720 predecessor, blending classic charm with modern living in one of the town's most appealing locations. Just steps from Lighthouse Beach and downtown Chatham, this remarkable property offers an exceptional opportunity for a full-time residence, summer getaway, or investment home. Designed for

    The Bohman Hartung Group Gibson Sotheby's International Realty

    10 Mill Hill Ln, Chatham, MA 02633
  • /39

    $1,800,000

    Sold Jul 31, 2026

    213 Main St, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • Built 1850

    Last Sold Summary

    • $1,454/SF
    • 52 Days On Market

    Current Estimated Value $2,270,132

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

    213 Main St, Chatham, MA 02633
    • /24

      Est $646,196

      Not Listed For Sale

      16 Starfish Ln, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 928 Sq Ft
      • Built 1982
      16 Starfish Ln, Chatham, MA 02633

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

  • /26

    $4,200,000

    • 3 Beds
    • 3 Baths
    • 2,418 Sq Ft

    30 Indian Trail, Chatham, MA 02633

    Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story

    Chris Rhinesmith Compass

    30 Indian Trail, Chatham, MA 02633
  • /67

    $2,550,000

    Sold May 22, 2026

    16 Old Salt Works Rd, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Above List Price
    • $1,051/SF
    • 6 Days On Market

    Current Estimated Value $2,510,007

    Last Listing Agent Chet Crabtree Christie's International Real Estate Atlantic Brokerage

    16 Old Salt Works Rd, Chatham, MA 02633
    • /55

      Est $2,659,295

      Not Listed For Sale

      15 Edgewater Dr, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1960
      15 Edgewater Dr, Chatham, MA 02633

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Shane Masaschi Compass

  • /43

    $810,000

    $11K PRICE INCREASE Pending
    • 1 Bed
    • 2 Baths
    • 1,468 Sq Ft

    24 Deep Water Ln, South Chatham, MA 02659

    This house was designed and built by Grattan Gill, a Taliesin Fellow and Frank Lloyd Wright apprentice (1952-57). This distinctive South Chatham home showcases timeless architecture, thoughtful design, and modern comfort. The main level offers the convenience of first-floor living, featuring a spacious primary bedroom, a full bath and direct access to a private balcony overlooking the expansive

    Karen St. Amand Today Real Estate

    24 Deep Water Ln, South Chatham, MA 02659
  • /41

    $3,619,000

    Sold Jul 01, 2026

    2548 Main St, South Chatham, MA 2659

    • 4 Beds
    • 5.5 Baths
    • 4,942 Sq Ft
    • Built 2026

    Last Sold Summary

    • 10% Below List Price
    • $732/SF
    • 264 Days On Market

    Current Estimated Value $4,168,000

    Last Listing Agent Ward Brown, III William Raveis Real Estate & Home Services

    2548 Main St, South Chatham, MA 2659
    • /2

      Est $4,161,370

      Not Listed For Sale

      173 Kendrick Rd, North Chatham, MA 02650

      • 6 Beds
      • 5 Baths
      • 4,106 Sq Ft
      • Built 2000
      173 Kendrick Rd, North Chatham, MA 02650

  • /20

    $675,000

    • 2 Beds
    • 2 Baths
    • 996 Sq Ft

    210 Orleans Rd Unit C, North Chatham, MA 02650

    Wonderful two bedroom, two bath end unit condominium close to Chatham village and beaches.. Recently renovated and three new split units for heat and air conditioning also added. Plenty of parking and storage and all the work is done for you. Insurance, landscaping, trash pickup, exterior maintenance, snow removal, and professional management are all covered in the reasonable monthly association

    John Burke William Raveis Real Estate & Home Services

    210 Orleans Rd Unit C, North Chatham, MA 02650
  • /30

    $895,000

    Sold Dec 10, 2025

    558 Riverview Dr, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 2,097 Sq Ft
    • Built 1966

    Last Sold Summary

    • $427/SF
    • 2 Days On Market

    Current Estimated Value $976,393

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    558 Riverview Dr, Chatham, MA 02633
    • /30

      Est $2,326,520

      Not Listed For Sale

      72 Old Field Bend, North Chatham, MA 02650

      • 4 Beds
      • 4.5 Baths
      • 3,776 Sq Ft
      • Built 2001
      72 Old Field Bend, North Chatham, MA 02650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  • /33

    $1,350,000

    $100K PRICE DROP Pending
    • 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
  • /38

    $2,232,500

    Sold Apr 28, 2026

    2 Seapine Rd, North Chatham, MA 02650

    • 3 Beds
    • 4 Baths
    • 3,090 Sq Ft
    • Built 1972

    Last Sold Summary

    • 14% Below List Price
    • $722/SF
    • 136 Days On Market

    Current Estimated Value $2,261,731

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

    2 Seapine Rd, North Chatham, MA 02650
    • /54

      Est $1,859,346

      Not Listed For Sale

      52 Wentworth Ln, North Chatham, MA 02650

      • 5 Beds
      • 2.5 Baths
      • 2,352 Sq Ft
      • Built 1972
      52 Wentworth Ln, North Chatham, MA 02650

      Last Sold Summary

      • 4 Days On Market

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

  • /17

    $950,000

    $300K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,637,931 per Acre

    1134 &1142 Main St, Chatham, MA 02633

    Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.Properties located at 1134 Main Street and 1142 Main

    Timothy Bailey John C Ricotta & Assoc.

    1134 &1142 Main St, Chatham, MA 02633
  • /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 $772,034

    Last Listing Agent Dee Kerner Compass

    37 Glendon Way, South Chatham, MA 02659
    • /31

      Est $2,306,586

      Not Listed For Sale

      37 Bellamy Ln, North Chatham, MA 02650

      • 5 Beds
      • 3 Baths
      • 3,401 Sq Ft
      • Built 1988
      37 Bellamy Ln, North Chatham, MA 02650

      Last Sold Summary

      • 362 Days On Market

      Last Listing Agent David Doherty Compass

  • /62

    $2,995,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,405 Sq Ft

    5 Kingsbury Way, Chatham, MA 02633

    Set along the shores of Oyster Pond, this beautifully renovated residence embodies the timeless character of a Chatham colonial while offering the ease and comfort today's most discerning buyers expect. Wood floors, a wood-burning fireplace, and a chef's eat-in kitchen anchored by a quartz island and sunlit breakfast nook define interiors that balance heritage with refinement. A first-floor

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    5 Kingsbury Way, Chatham, MA 02633
  • /69

    $3,450,000

    Sold Sep 12, 2025

    80 Tisquantum Rd, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,821 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $1,223/SF
    • 3 Days On Market

    Current Estimated Value $3,518,008

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

    80 Tisquantum Rd, Chatham, MA 02633
    • /34

      Est $1,418,988

      Not Listed For Sale

      20 Spring Hill Rd, North Chatham, MA 02650

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1994
      20 Spring Hill Rd, North Chatham, MA 02650

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Julie Chapin William Raveis Real Estate & Home Services

  • /60

    $1,375,000

    • 2 Beds
    • 2.5 Baths
    • 2,306 Sq Ft

    1114 Orleans Rd Unit 8, North Chatham, MA 02650

    One of the iconic Christopher Ryder House condominiums can be yours in time for the Fall season. This elegant two-bedroom, three-bath home blends timeless architectural character with refined two-level living. Gracious rooms, high ceilings, oversized windows, skylights, original beams, and warm wood floors create an inviting atmosphere throughout. The open floor plan features a spacious living

    Betsy Hargreaves Gibson Sotheby's International Realty

    1114 Orleans Rd Unit 8, North Chatham, MA 02650
  • /39

    $1,975,000

    Sold Dec 18, 2025

    98 Horizon Dr, Chatham, MA 02633

    • 3 Beds
    • 4.5 Baths
    • 3,310 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Below List Price
    • $597/SF
    • 252 Days On Market

    Current Estimated Value $1,974,673

    Last Listing Agent Lori Fanning Smith Compass Massachusetts, LLC

    98 Horizon Dr, Chatham, MA 02633
    • /35

      Est $1,497,123

      Not Listed For Sale

      101 Old Mail Rd, North Chatham, MA 02650

      • 3 Beds
      • 1.5 Baths
      • 1,511 Sq Ft
      • Built 1940
      101 Old Mail Rd, North Chatham, MA 02650

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jessica King Compass Massachusetts, LLC

  • /33

    $4,500,000

    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    346 Morris Island Rd, Chatham, MA 02633

    Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water

    Chris Rhinesmith Compass

    346 Morris Island Rd, Chatham, MA 02633

Showing Results 161 - 200, Page 5 of 18

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