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Oak Bluffs, MA Homes for Sale with Pool

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  • /33

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,701 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • /42

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    64 Christiantown Rd, Vineyard Haven, MA 02568

    This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

    Karen Overtoom Karen M. Overtoom R.E.

    64 Christiantown Rd, Vineyard Haven, MA 02568
  • /67

    $3,790,000

    $335K PRICE DROP
    • 7 Beds
    • 4.5 Baths
    • 3,313 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    THE COMPOUND AT INDIAN HILL Some properties are a house. This one is a world. Set on more than 3 private acres, this true multi-dwelling compound was built for the way people live now: together, apart, & on their own terms. 4,464 SF across the 3 dwellings. The main house anchors it all, with glass doors & big windows framing meadow views, a stone fireplace, & a kitchen built for gathering. The

    Peyton Wallace Studio Realty LLC

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • /31

    $15,400,000

    • 6 Beds
    • 9 Baths
    • 6,967 Sq Ft

    8 Snail Rd, Chilmark, MA 02535

    Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

    Brian Dougherty Corcoran Property Advisors

    8 Snail Rd, Chilmark, MA 02535
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