luxury waterfront house for sale Chilmark, United States

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

The best architecture doesn't compete with nature... It embraces it. At 78 Gardiner Road, walls of glass, expansive decks, and clean modern lines place the ever-changing waters of Buzzards Bay at center stage. Presiding over a rugged shoreline in one of Cape Cod's most intellectually and culturally rich communities, this restored waterfront residence captures the spirit of a remarkable era in architecture while providing an extraordinary setting for life today. Walls of glass frame endless water views. Clean lines and soaring ceilings dissolve the boundaries between indoors and out. Sunlight dances across the bay from morning until evening when sunsets astound. The rhythms of tide, wind, and sea become part of everyday life. This is not a home that competes with its surroundings... It is at one with them. A broad sweep of lawn gives way to a seating area overlooking a dramatic natural shoreline where weathered boulders, native vegetation, and the waters of Buzzards Bay create a landscape that changes by the hour and by the season. Morning coffee on the deck. Afternoon swims. Sailboats crossing the horizon. Winter storms rolling in from the west. Every day offers a different perspective. Inside, this four bedroom 3,700+ square foot home has been carefully restored to its original coolness. There are huge ocean front family rooms on each level, multiple other gathering areas for both larger and intimate. Please verify all information contained herein.

Some properties offer water views. This one invites you to live on the water. Tucked away at the end of a quiet cul-de-sac in Lower Davisville, this is a rare opportunity to purchase a single-owner property that enjoys spectacular views of Israels Cove and Bournes Pond from nearly every room. Across the water, protected conservation land preserves the natural setting and safeguards the view. Designed for easy first-floor living, the home features 4 bedrooms, 2½ baths, hardwood floors, and a newer deck overlooking the pond. The backyard becomes your gateway to summer, with direct water access for swimming, kayaking, canoeing, paddleboarding, and small sailboat adventures. For additional boating, the Green Pond Marina is nearby. Additional highlights include a passing Title V septic system installed in 2022, whole-house generator, outdoor shower, and two storage sheds. Just one mile from Menauhant Beach and available for the first time, this special waterfront property offers a setting that is increasingly rare to find and impossible to replicate.