17

West Chatham, MA Houses for Sale

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  • /24

    $5,900,000

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    99 Uncle Alberts Drive Extension, Chatham, MA 2633

    Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

    Agent Photo

    Shane Masaschi

    Compass

    (508) 400-2035

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • /73

    $8,500,000

    • 7 Beds
    • 6.5 Baths
    • 6,521 Sq Ft

    44 Buena Vista Rd, Chatham, MA 02633

    Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

    Agent Photo

    Shane Masaschi

    Compass

    (508) 400-2035

    44 Buena Vista Rd, Chatham, MA 02633
  • /68

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 4,072 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

    Agent Photo

    Tara Schiffmann Brown

    Bayview Real Estate

    (508) 388-5284

    55 Winterset Dr, Chatham, MA 02633
  • /76

    $4,200,000

    • 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
  • /35

    $4,395,000

    • 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 masterpiece nestled in Hardings Beach Hills with panoramic views of the marsh and creek. Blending classic Cape vernacular with modern inspiration, the home is defined by extraordinary craftsmanship and architectural detail. The open main level features a curved fireplace wall with v-groove paneling that flows into

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Indian Trail, Chatham, MA 02633
  • /28

    $3,895,000

    • 4 Beds
    • 4 Baths
    • 3,000 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

    17 Bucks Ln, Chatham, MA 02633
  • /49

    $4,750,000

    • 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
  • /33

    $5,295,000 New Construction

    • 4 Beds
    • 6 Baths
    • 4,989 Sq Ft

    14 Pond View Ln, Chatham, MA 02633

    Sears Point Development presents another breathtaking home that could be your new year-round residence or the perfect summer escape for 2026. With panoramic water views of the Oyster Pond and Oyster River and deeded access to the Oyster Pond with mooring potential, this stunning Nantucket-style home boasts 4,989 sf of thoughtfully designed living space, featuring 4 BR and 4/2 Baths on town sewer.

    Jack Bohman Gibson Sotheby's International Realty

    14 Pond View Ln, Chatham, MA 02633
  • /43

    $800,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    29 Wilfred Rd, Chatham, MA 02633

    Don't miss this 3-bedroom, 2-bath, lovingly cared for home offering 1,536 sq. ft. of inviting living space including a large open great room and living room with fireplace. Beautiful hardwood floors run throughout. Ideally located in a quiet neighborhood, the house is situated on the bike path and a short distance to White Pond for kayaking and swimming . Relax on the welcoming front porch

    Jack Bohman Gibson Sotheby's International Realty

    29 Wilfred Rd, Chatham, MA 02633
  • /56

    $2,375,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 4 Baths
    • 3,226 Sq Ft

    94 Ocean Port Ln, Chatham, MA 02633

    Built in 2014, this beautifully designed home offers 3 bedrooms, 4 full baths, and over 3,400 sq. ft. of living space, including a finished basement and a bonus room above the detached garage. Hardwood floors flow throughout the open layout, where you'll find a chef ready kitchen, sun-filled living room with coffered ceilings and gas fireplace. The first floor is completed by a full bath, laundry

    Jack Bohman Gibson Sotheby's International Realty

    94 Ocean Port Ln, Chatham, MA 02633
  • /61

    $2,195,000

    • 4 Beds
    • 4.5 Baths
    • 3,069 Sq Ft

    6 Stephen Dr, Chatham, MA 02633

    Set in one of Chatham's most desirable neighborhoods, just minutes from Hardings and Ridgevale beaches, this residence stands out for its scale, flexibility, and refined design. Sunlight floods the interiors, where expansive windows frame backyard and cranberry bog views and create a bright, welcoming atmosphere.The layout offers four bedrooms plus a versatile office/bonus room and 4.5 baths,

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    6 Stephen Dr, Chatham, MA 02633
  • /30

    $1,495,000

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    200 Hardings Beach Rd, Chatham, MA 02633

    Located just a short stroll to Hardings Beach and close to many favorite local restaurants and conveniences, this classic Cape style two story cottage offers the option of summer or year-round living as well as a a rental investment opportunity. With 4 bedrooms and 2 full baths, the layout is designed for easy living, with bedrooms on both levels and full baths conveniently located adjacent to

    Chris Rhinesmith Compass Massachusetts, LLC

    200 Hardings Beach Rd, Chatham, MA 02633
  • /46

    $1,600,000

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

    114 Bucks Creek Rd, Chatham, MA 02633

    'Float to the ocean with the tide'' Fish, crab kayak, paddleboard and launch off the private association dock. This glorious landing is only two houses away. Offering four spacious bedrooms (including a new primary with ensuite and double showers) and three full baths, this home is sited on a deep lot affording privacy. Lovingly maintained, this custom built one owner home features beamed

    Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

    114 Bucks Creek Rd, Chatham, MA 02633
  • /43

    $2,200,000

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

    55 Christopher Harding Ln, Chatham, MA 02633

    Step into coastal elegance in this light-filled home, perfectly nestled in a peaceful neighborhood with deeded access to Oyster Pond. Savor your morning coffee in the sun-drenched four-season room, and take in sunset with your favorite beverage on the second-floor deck, where tranquil views set the scene. Inside, you'll find three spacious bedrooms and 2.5 beautifully designed bathrooms offering

    Diane Donahue Gibson Sotheby's International Realty

    55 Christopher Harding Ln, Chatham, MA 02633
  • /38

    $1,599,000

    • 4 Beds
    • 2 Baths
    • 2,392 Sq Ft

    56 Skyline Dr, Chatham, MA 02633

    Welcome to a quintessential Cape-Cod lifestyle, this updated home is steps away to one of the prettiest private lakes in Chatham. With deeded rights to Lovers Lake for kayaking, canoeing, swimming & fishing and set back on a gracious lot this 3BR plus home offers privacy and nature at every turn. First floor has granite/stainless kitchen w/ breakfast bar and dining area w/ fireplace, a great room

    Janet Stuart Coldwell Banker Realty - Concord

    56 Skyline Dr, Chatham, MA 02633
  • /47

    $1,650,000

    • 3 Beds
    • 2.5 Baths
    • 2,430 Sq Ft

    70 Lantern Ln, South Chatham, MA 02659

    Discover your dream home just a short stroll to Cockle Cove Beach! Incredible spot...Tucked away at the end of a private lane, this 3 bedroom 2 1/2 bath home with long leaf yellow pine floors throughout the first floor has plenty of living space for family and friends. Surrounded by an expansive wrap-around deck, the open concept first floor is highlighted by the living room with wood burning

    Judith Smith John C Ricotta & Assoc.

    70 Lantern Ln, South Chatham, MA 02659
  • /2

    $6,995,000

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft

    13 Captain Knowles Way, Chatham, MA 02633

    Experience luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship. Designed for both comfort and entertaining, it offers five spacious bedrooms, each

    Mina O'Keefe Gibson Sotheby's International Realty

    13 Captain Knowles Way, Chatham, MA 02633
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