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West Chatham, MA Homes for Sale with Acreage

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  • /52

    $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
  • /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
  • /33

    $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
  • /43

    $2,299,999

    • 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
  • /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
  • /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
  • /68

    $2,445,000 Open Sat 11AM - 2PM

    • 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

    Tara Schiffmann Brown Bayview Real Estate

    55 Winterset Dr, Chatham, MA 02633
  • /2

    $6,995,000 New Construction

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

    13 Captain Knowles Way, Chatham, MA 02633

    Experience the perfect blend of 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 throughout.Designed for both comfort and entertaining, the home

    Mina O'Keefe Gibson Sotheby's International Realty

    13 Captain Knowles Way, Chatham, MA 02633
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