luxury waterfront house for sale Chilmark, United States

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

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.

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay, or taking a scenic shortcut to South Beach, this waterfront setting offers the very best of Vineyard living. Completing the property is a generous 2-car garage

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

On sheltered Eel Pond, with a large, licensed deepwater dock and direct access to Vineyard Sound and Buzzards Bay, this waterfront property presents a rare opportunity to create your own Woods Hole compound. Originally dating back to the 1820s, this classic New England home spans three separate dwellings - each with sweeping water views: a main 5-bedroom residence with a separate guest suite, plus two year-round cottages (one 2-bedroom and one 1-bedroom). Located on the village doorstep, with ample off-street parking and seclusion, you are moments from restaurants, shops, ferries, beaches, the vibrant harbor and renowned marine science institutions. Position, potential and provenance - and available for the first time in 70 years - this is a once-in-a-lifetime chance to establish your own Woods Hole legacy in a premium Cape Cod waterfront community.

Majestically sited atop a beautifully landscaped bluff overlooking Buzzards Bay, Stony Beach, and Penzance Point, this iconic Woods Hole residence is a rare expression of timeless coastal living. Beloved by the same family for more than 40 years, the home retains an unmistakable sense of authenticity, with hardwood floors throughout, rich wood paneling, and gracious rooms that reflect generations of summers by the sea. The main level offers a kitchen, den, dining room, living room, and a series of inviting porches and outdoor spaces, each designed to capture the extraordinary setting and sweeping water views. A charming waterfront cabana creates a private perch above the bay, while a separate walkway and deck wrap along the seawall, offering yet another remarkable vantage point from which to experience the coastline. Upstairs, five bedrooms and multiple baths provide generous accommodations for family and guests. Surrounded by established landscaping and set high above the water, this extraordinary property embodies the enduring character, beauty, and understated elegance that have long defined Woods Hole.

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.

Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft., providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand.

A rare opportunity to experience waterfront living at its finest, where exceptional craftsmanship, refined interiors, and effortless access to the water come together in a truly distinguished Cape Cod residence. Designed for those who appreciate the finer details, this extraordinary property offers a seamless balance of elegant living, sophisticated entertaining, and the unmistakable beauty of life on the water. A deepwater dock, complete with a boat lift, water, and electricity, places the pleasures of boating just steps from your door. Beautifully maintained, level grounds and expansive green lawns provide a picturesque setting along the waterfront, while a sun porch and all first floor rooms offers a front-row seat to the ever-changing maritime landscape. Spend afternoons watching the boats pass by and evenings dining outdoors beside the gas fire pit, overlooking the water. Inside, the thoughtfully conceived floor plan reflects a commitment to quality, comfort, and understated elegance. Four generously proportioned bedrooms, each with a private en-suite bathroom, provide exceptional accommodations for family and guests. Rich oak hardwood flooring, custom tile work, and carefully considered finishes distinguish the interiors throughout. Two separate office suites offer beautifully appointed spaces for working from home, while additional bonus rooms above the three-car garage provide flexibility for a variety of uses. Renowned builder Cataldo Homes was involved in every stage of construction, bringing an exacting level of craftsmanship and attention to detail to this exceptional residence. Just five years young and enjoyed only seasonally, the home has been meticulously maintained and presents in virtually new condition.