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Modern Homes for Sale in Vineyard Haven, MA

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  • /36

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelia's Crossing, Tisbury, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass

    54 Amelia's Crossing, Tisbury, MA 02568
  • /40

    $3,675,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first

    Agent Photo

    Wendy Harman

    Compass

    28 Beach Rd, Oak Bluffs, MA 02557
  • /12

    $3,400,000

    New Construction
    • 3 Beds
    • 4.5 Baths
    • 3,260 Sq Ft

    27 Double Ox Rd, Oak Bluffs, MA 02557

    Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

    Lesley Heidt Sandpiper Realty, Inc.

    27 Double Ox Rd, Oak Bluffs, MA 02557
  • /41

    $1,975,000

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • /42

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    64 Christiantown Rd, Vineyard Haven, MA 02568

    This stunning 3,000 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
  • /26

    $1,850,000

    • 4 Beds
    • 2 Baths
    • 1,833 Sq Ft

    22 Old Harbor Ln, Oak Bluffs, MA 02557

    Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

    Lisa Stewart Sandpiper Realty, Inc.

    22 Old Harbor Ln, Oak Bluffs, MA 02557
  • /40

    $1,750,000

    • 3 Beds
    • 3.5 Baths
    • 2,376 Sq Ft

    28 Grovedale Rd, Oak Bluffs, MA 02557

    GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

    David White OwnerEntry.com

    28 Grovedale Rd, Oak Bluffs, MA 02557
  • /16

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Karen Overtoom Karen M. Overtoom R.E.

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
  • /28

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557

    Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

    Rose Ryley Wallace & Co. Sotheby's International Realty

    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
  • /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
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