2,561

West Chatham, MA Homes

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  • /6

    $250,000

    • Land
    • 0.72 Acre
    • $347,222 per Acre

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

    Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

    Agent Photo

    Shane Masaschi

    Compass

    (508) 691-8324

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
  • /73

    $2,685,000 Sold Jul 09, 2025

    • 3,056 Sq Ft
    • $879/SF
    • 13 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    7 Colonial Dr, Chatham, MA 02633

    A Chatham Beauty! Welcome to 7 Colonial Drive, a distinguished residence within one of Eastward Company's sought after residential communities. This expanded Cape home, being sold fully furnished, has been thoughtfully updated for today's lifestyle...offering 4 bedrooms, 2.5 baths and three levels of living. The main level features a bright living room with fireplace, open dining with direct

    Pam Roberts Gibson Sotheby's International Realty

    7 Colonial Dr, Chatham, MA 02633
    • /12

      Not Listed For Sale

      140 Happy Valley Rd, Chatham, MA 02633

      140 Happy Valley Rd, Chatham, MA 02633
  • /39

    $1,700,000

    • 3 Beds
    • 2 Baths
    • 2,008 Sq Ft

    9 Bettys Path, Chatham, MA 02633

    Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts. Step inside to find an inviting living room with a cozy fireplace, a dining room that opens onto a

    Agent Photo

    Shane Masaschi

    Compass

    (508) 682-4461

    9 Bettys Path, Chatham, MA 02633
  • /20

    $734,000 Sold Jun 27, 2025

    • 992 Sq Ft
    • $740/SF
    • 18 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    61 Pond View Ave, Chatham, MA 02633

    Welcome to your dream Cape Cod getaway! This delightful 2-bedroom, 1-bath home is nestled in one of West Chatham’s most desirable neighborhoods. This home is just minutes from Hardings Beach, local shopping, and great dining spots. Step inside to find a warm and inviting interior with natural tones that create a relaxed, coastal feel throughout. Whether you're enjoying a quiet weekend or

    Charles Quigley Keller Williams Realty

    61 Pond View Ave, Chatham, MA 02633
    • /4

      Est $3,265,162 Not Listed For Sale

      • 3 Beds
      • 5.5 Baths
      • 4,197 Sq Ft

      21 Hunter Rise, Chatham, MA 02633

      21 Hunter Rise, Chatham, MA 02633
  • /18

    $600,000

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

    19 Stoughton Ln, Chatham, MA 2633

    Here is your chance to own a slice of seaside Chatham! This prime location is only a short walk or .02 miles to stunning Ridgevale Beach on pristine Nantucket Sound. Included in the sale is a 3 bedroom Title V septic, ZBA approval to demolish the existing structure and to build a dwelling with a deck. Seller has building plans for a 3 bedroom, 2 bath, 1356 SF home. Imagine the possibilities of

    Agent Photo

    Shane Masaschi

    Compass

    (508) 400-2035

    19 Stoughton Ln, Chatham, MA 2633
  • /12

    $3,200,000 Sold Jun 20, 2025

    • 4,620 Sq Ft
    • $693/SF
    • 346 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 2024

    33 Jessies Landing, Chatham, MA 02633

    Get ready for summer and enjoy the saltwater pool, spa and firepit! A new residence is in progress by Eastward Companies, showcasing exquisite details and finishes. This beautifully designed home spans over 4,600 sq. ft. and checks off many items on everyone's wish list. It features a spacious open floor plan, a gourmet kitchen with a butler's pantry, and a first-floor master suite, making it

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    33 Jessies Landing, Chatham, MA 02633
    • /76

      Est $7,358,535 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 5,219 Sq Ft

      52 Oyster Bluff, Chatham, MA 02633

      52 Oyster Bluff, Chatham, MA 02633
  • /76

    $4,495,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 5.5 Baths
    • 4,908 Sq Ft

    45 Meadow View Rd S, Chatham, MA 02633

    New construction and a deeded boat slip in the Oyster River Hills private neighborhood marina. Another magnificent home by Sears Point Residential, move-in ready. 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape. The home's axis is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the

    Jack Bohman Gibson Sotheby's International Realty

    45 Meadow View Rd S, Chatham, MA 02633
  • /11

    $3,200,000 Sold Jun 20, 2025

    • 4,620 Sq Ft
    • $693/SF
    • 346 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 2024

    33 Jessie's Landing, Chatham, MA 02633

    Get ready for summer and enjoy the saltwater pool, spa and firepit! A new residence is in progress by Eastward Companies, showcasing exquisite details and finishes. This beautifully designed home spans over 4,600 sq. ft. and checks off many items on everyone's wish list. It features a spacious open floor plan, a gourmet kitchen with a butler's pantry, and a first-floor master suite, making it

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    33 Jessie's Landing, Chatham, MA 02633
    • /35

      Est $1,419,601 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 1,524 Sq Ft

      67 Lime Hill Rd, Chatham, MA 02633

      67 Lime Hill Rd, Chatham, MA 02633
  • /25

    $3,895,000

    • 4 Beds
    • 4 Baths
    • 3,030 Sq Ft

    17 Bucks Ln, Chatham, MA 02633

    This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style home with divine views over Nantucket Sound offers the idyllic Chatham beach lifestyle you have been dreaming of.....Steps to the private association beach of Harding's Shores for uncrowded enjoyment and warm water swimming. Classic 4BR 4 bath Cape home with two large decks for al fresco dining or morning

    Lori Fanning Smith Compass Massachusetts, LLC

    17 Bucks Ln, Chatham, MA 02633
  • /63

    $1,125,000 Sold Jun 18, 2025

    • 1,662 Sq Ft
    • $677/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1979

    155 Cranberry Ln, Chatham, MA 02633

    First time offered! Discover your Cape Cod retreat at 155 Cranberry Lane, South Chatham. This meticulously maintained 3-bedroom, 2-bath home offers serene living on a peaceful corner lot, bordered by conservation land. Enjoy easy access to Bucks Creek via a deeded right of way, and find yourself just moments from Ridgevale Beach. Inside, you'll appreciate hardwood floors, a renovated kitchen

    Kate Plummer Today Real Estate

    155 Cranberry Ln, Chatham, MA 02633
    • /72

      Est $1,322,367 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,073 Sq Ft

      335 Old Queen Anne Rd, Chatham, MA 02633

      335 Old Queen Anne Rd, Chatham, MA 02633
  • /76

    $3,295,000 Open Sun 12PM - 1:30PM

    • 3 Beds
    • 3.5 Baths
    • 3,014 Sq Ft

    7 Squanto Dr, Chatham, MA 02633

    This Nantucket-style home features extraordinary views across a tidal salt marsh, Oyster Pond, and the 3 church steeples in Town. Enjoy the fireworks display New Year's Eve, ever-changing beauty of the seasons, and a host of wildlife from this elevated .69 acre site. With just over 3,000 square feet this exceptionally-crafted home is the perfect size; with an open floor plan ideal for

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    7 Squanto Dr, Chatham, MA 02633
  • /40

    $1,320,000 Sold Jun 12, 2025

    • 2,238 Sq Ft
    • $590/SF
    • 78 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1980

    67 The Cornfield, Chatham, MA 02633

    Situated on a quiet cul-de-sac in a desirable neighborhood, this bright Cape enjoys a prime location just a mile from town with several shops & restaurants within walking distance. Encompassing 2,300 sq. ft of living space on three levels, an easy-flowing floor plan offers a granite & stainless kitchen with adjacent open dining & breakfast nook, sun-filled living room with walls of glass, and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    67 The Cornfield, Chatham, MA 02633
    • /21

      Est $1,029,400 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,593 Sq Ft

      66 Ethelma Dr, Chatham, MA 02633

      66 Ethelma Dr, Chatham, MA 02633
  • /44

    $4,950,000

    • 4 Beds
    • 3.5 Baths
    • 3,878 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

    Chris Rhinesmith Compass Massachusetts, LLC

    38 Indian Trail, Chatham, MA 02633
  • /38

    $6,895,000 Sold Jun 03, 2025

    • 7,111 Sq Ft
    • $970/SF
    • 196 Days On Market
    • 5 Beds
    • 8.5 Baths
    • Built 2016

    114 Cranberry Ln, North Chatham, MA 02650

    Sited on a picturesque lane in a coveted North Chatham location, this custom estate home with deeded access to a private sandy beach on Pleasant Bay is being offered fully furnished and turn key!! Featuring the absolute best of coastal Cape Cod living, the 5+ bedroom Main House and 2 bedroom Guest House are like new, having been further improved and maintained to exacting standards. Thoughtfully

    Brian Dougherty Corcoran Property Advisors

    114 Cranberry Ln, North Chatham, MA 02650
    • /3

      Est $883,294 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 945 Sq Ft

      47 Barbara Dr, Chatham, MA 02633

      47 Barbara Dr, Chatham, MA 02633
  • /41

    $3,995,000

    • 5 Beds
    • 8 Baths
    • 5,578 Sq Ft

    67 Uncle Alberts Dr, Chatham, MA 02633

    This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan. The main level flows seamlessly between the

    Chris Rhinesmith Compass

    67 Uncle Alberts Dr, Chatham, MA 02633
  • /34

    $1,150,000 Sold Jun 02, 2025

    • 1,456 Sq Ft
    • $790/SF
    • 26 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1970

    56 Barn Hill Ln, Chatham, MA 02633

    Classic coastal charm embodies this 4BR 2 bath Cape . Renovated in 2020, every inch of this home is a reflection of the Chatham lifestyle. From the light filled rooms, living room with wood burning fireplace, ship lapped accent walls, renovated kitchen and baths ,this home feels like a vacation. The two second floor bedrooms are very spacious with sitting areas. Located just around the corner

    Lori Fanning Smith Compass Massachusetts, LLC

    56 Barn Hill Ln, Chatham, MA 02633
    • /58

      Est $1,489,835 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,251 Sq Ft

      25 Ethelma Dr, Chatham, MA 02633

      25 Ethelma Dr, Chatham, MA 02633
  • /50

    $3,995,000

    • 5 Beds
    • 8 Baths
    • 5,578 Sq Ft

    67 Uncle Alberts Dr, Chatham, MA 02633

    GRACIOUS LIVING ON OVER TWO ACRES NEAR CHATHAM BEACHES AND BELOVED DINING DESTINATIONS // Space, Luxury, Convenience! This impressive home, situated on 2.07 acres in a quiet cul-de-sac, is just minutes away from restaurants, the Chatham bike path, and nearby Chatham beaches. Built by Eastward Companies in 2014, this home offers a tremendous sense of living space, spanning 5,578 square feet, and

    Chris Rhinesmith Compass Massachusetts, LLC

    67 Uncle Alberts Dr, Chatham, MA 02633
  • /12

    $750,000 Sold May 30, 2025

    • 2,625 Sq Ft
    • $286/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1947

    86 Vineyard Ave, Chatham, MA 02633

    Looking for a project? Great location for investors/builders to bring your imagination to this nostalgic 1947 era Cape Cod style home, enlarged to 2625 Sq Ft with a 1988 addition. This 3 Bed/2 bath Cape is located on.51 Acre sunny lot in a popular neighborhood with town landing at Oyster Pond at end of street. Property sold AS IS... Bring you vision for a fresh renovation worth the effort

    Phyllis Power Compass

    86 Vineyard Ave, Chatham, MA 02633
    • /47

      Est $936,251 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      105 Perch Pond Dr, Chatham, MA 02633

      105 Perch Pond Dr, Chatham, MA 02633
  • /14

    $1,000,000

    • Land
    • 0.16 Acre
    • $6,250,000 per Acre

    723 Main St, Chatham, MA 02633

    Town of Chatham officially assigned new street address 723 MAIN STREET! Take advantage of this last opportunity to build on a vacant lot on Main Street in downtown Chatham! This lot is 7,010 square feet (0.16 acres) located across from Chatham Veterans Field, home of the Chatham Anglers baseball team. This truly is the last opportunity to build on a vacant lot in downtown Chatham. For those who

    Matthew Burger Kinlin Grover Compass

    723 Main St, Chatham, MA 02633
  • /62

    $2,100,000 Sold May 15, 2025

    • 3,199 Sq Ft
    • $656/SF
    • 319 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1984

    92 Absegami Run, Chatham, MA 02633

    Don't miss out on living in one of Chatham's most desired neighborhoods. Located in an exclusive enclave near Oyster Pond, this 4 bedroom, 3.5 bath home offers the discriminating buyer the opportunity for an exceptional residence in an area of remarkable homes. With over 3,200 s.f. of living space, this Post and Beam constructed home has the open and airy space people love for entertaining and

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    92 Absegami Run, Chatham, MA 02633
    • /51

      Est $1,194,084 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft

      1239 Main St Unit 22, Chatham, MA 02633

      1239 Main St Unit 22, Chatham, MA 02633
  • /2

    $659,000

    • Land
    • 1.01 Acres
    • $652,475 per Acre

    1761 Main St, Chatham, MA 02633

    Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

    Kimberly Clark Bayside Realty Consultants

    1761 Main St, Chatham, MA 02633
  • /48

    $582,500 Sold May 02, 2025

    • 1,017 Sq Ft
    • $573/SF
    • 14 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1983

    1 Seastrand Way Unit 8, Chatham, MA 02633

    Welcome to this inviting townhouse-style condo nestled in the tranquil enclave of West Chatham. Featuring a thoughtfully designed layout, this residence offers two spacious bedrooms on the second level and one and a half modern bathrooms, providing both comfort and convenience.The heart of the home boasts an open-concept living and dining area, complete with gleaming hardwood floors that flow

    Kathy Doyle Gibson Sotheby's International Realty

    1 Seastrand Way Unit 8, Chatham, MA 02633
    • /29

      Est $959,944 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,681 Sq Ft

      1235 Main St Unit 7, Chatham, MA 02633

      1235 Main St Unit 7, Chatham, MA 02633
  • /45

    $1,399,500 Open Sun 10AM - 12PM

    • 2 Beds
    • 3 Baths
    • 1,861 Sq Ft

    116 Happy Valley Rd, Chatham, MA 02633

    Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless

    Ward Brown William Raveis Real Estate & Home Services

    116 Happy Valley Rd, Chatham, MA 02633
  • /40

    $1,117,000 Sold May 01, 2025

    • 1,508 Sq Ft
    • $741/SF
    • 51 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    3 Whiteleys Way, Chatham, MA 02633

    Completely renovated home with quality finish work, already on town sewer with the lowest tax rate on the Cape, this Chatham beauty features one level living, a cathedral ceiling in the open concept living area, central air, a garage, and the ability to add a pool. The living area has a gas connection for the fireplace, white oak floors, and plenty of space to make this work for your year round

    Tiffany Callahan Greer Real Estate, LLC

    3 Whiteleys Way, Chatham, MA 02633
    • /36

      Est $1,082,609 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,312 Sq Ft

      20 Chatham Heights Rd, Chatham, MA 02633

      20 Chatham Heights Rd, Chatham, MA 02633
  • /30

    $899,900

    • 3 Beds
    • 3 Baths
    • 1,492 Sq Ft

    25 Crosby Ln, Chatham, MA 02633

    TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

    Amanda Bender Christie's International Real Estate Atlantic Brokerage

    25 Crosby Ln, Chatham, MA 02633
  • /41

    $840,000 Sold Apr 16, 2025

    • 2,212 Sq Ft
    • $380/SF
    • 66 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1964

    23 Malabar Rd, Chatham, MA 02633

    This is a wonderful opportunity in Chatham to purchase a four-bedroom, two-bath home with a beautiful backyard. The 8-room house totals 2,212 sq ft of finished living space, 1,547 sq ft on the first two floors, and an additional 665 sq ft of finished basement. Highlights include an open living room/kitchen floor plan, two bedrooms and a full bath on the first floor, and two large bedrooms and a

    The Bohman Hartung Group Gibson Sotheby's International Realty

    23 Malabar Rd, Chatham, MA 02633
    • /34

      Est $1,170,777 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,608 Sq Ft

      455 Old Queen Anne Rd, Chatham, MA 02633

      455 Old Queen Anne Rd, Chatham, MA 02633
  • /30

    $899,900

    • 3 Beds
    • 3 Baths
    • 1,492 Sq Ft

    25 Crosby Ln, Chatham, MA 02633

    TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

    Amanda Bender Christie's International Real Estate Atlantic Brokerage

    25 Crosby Ln, Chatham, MA 02633

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