Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a private mooring, an extraordinary opportunity to enjoy one of Martha’s Vineyard’s most coveted waterfront locations.

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This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

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This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

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Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

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Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room features soaring cathedral ceilings, rich paneling, and exquisite millwork. Bathed in natural light from dormers and oversized windows, the space is both grand and inviting. Three sets of French doors open to a bluestone terrace with multiple seating areas and a heated saltwater pool—creating a stunning backdrop for al fresco dining, entertaining, and quiet relaxation. The chef’s kitchen is thoughtfully positioned to overlook both the dining area and great room, allowing for effortless everyday living and gracious hosting. The home’s layout is equally intentional: one wing offers a secondary living room or study, along with a luxurious primary suite complete with a spa-like bath and dressing room. The opposite wing features three spacious guest bedrooms, each with cathedral ceilings, walk-in closets, and ensuite baths, ensuring comfort and privacy for family and guests alike. Additional amenities include a well-appointed mudroom with side entrance, a dedicated laundry room, and a finished lower level with a media room, full bath, and abundant storage. Custom built-ins, refined finishes, and thoughtful architectural details enhance the home’s timeless appeal throughout. Surrounded by beautifully curated grounds, the property offers a true sense of seclusion. Residents of The Preserve enjoy access to scenic walking trails connecting to conservation land, as well as convenient proximity to the bike path, Farm Neck Golf Club, and all down-island towns.

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With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the rear of the property, a private guest house—affectionately known as The Nest—has undergone a similar transformation and offers a private escape. Adjacent to the main home, the charming bunk house completes the ensemble, perfectly complementing this unique and inviting expansive compound. Though the wraparound porch invites you to linger with its endless ocean views, the nearby beaches, boutique shops, acclaimed restaurants, and the contagious energy of Circuit Avenue and the Harbor are all steps away, offering something for everyone to enjoy. For those seeking flexibility, the home’s established rental history further highlights the desirability of both the property and its coveted location. An exciting opportunity to own in one of Oak Bluff's iconic settings!

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A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

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The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an expansive deck, a pergola with a fireplace, and an elevated gazebo overlooking meticulously manicured grounds. Versatility is at the heart of this unique compound. With three kitchens, the home easily accommodates use as a spacious single-family residence or as three separate living quarters—ideal for multi-generational living, hosting extended guests, or generating rental income. Additional highlights include a 10-bedroom septic system in place - allowing for future expansion, an oversized three car garage, and solar. Come experience the very best of Island living.

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This exceptional waterfront estate offers unmatched panoramic views from house and guest house with extraordinary privacy on a nearly two acre setting rarely found in this coveted Oak Bluffs location. Commanding sweeping vistas of Lagoon Pond, Vineyard Haven, Hines Point, the iconic drawbridge, Vineyard Sound, and even distant views of Cape Cod. The property includes a renovated three-bedroom main residence and a two-bedroom guest house, each thoughtfully oriented to capture the ever changing light over the water. The main home offers a spacious open layout with generous living, dining, and sitting areas, ideally suited for entertaining and family gatherings and all with stunning views of the water. A large, bright kitchen serves as the heart of the home, while the living room, dining room, primary bedroom and two elevated decks provide front row seats to boating activity, wildlife, and some of the most spectacular sunsets on the island. The primary bedroom is a serene sanctuary with floor to ceiling water views that feel truly immersive. A second main level bedroom also has water views and its own full bath. On the lower level, a bedroom suite includes a comfortable sitting area with a TV, and spacious full bath. The guest house is a retreat unto itself, offering equally stunning water views from kitchen, living room and private porch. Its large primary bedroom features ample space, while the additional bedroom is a cozy, private nook. Outdoors, the estate’s expansive grounds offer a rare combination of beauty, privacy, and direct waterfront access. Private steps lead to the property’s own sandy beach and mooring, where guests can enjoy swimming, boating, kayaking, paddle boarding, fishing, or simply savor the extraordinary natural beauty. An amazing variety of birds, including osprey complete the scene out on the water. The property also borders 14 acres of conservation land with scenic walking trails, enhancing the sense of seclusion, privacy and connection to nature. This is a truly remarkable island estate that has had only 3 owners in the past 65 years. This is a generational opportunity to enjoy and improve this family compound with unforgettable views, refined living spaces and unparalleled waterfront setting.

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Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane presents a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views of the 7th fairway and 8th tee box, across to Sengekontacket Pond, offering a serene backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. This is a unique chance to create a bespoke Vineyard estate tailored to modern living while honoring the property’s heritage. Ideally located within close proximity to the clubhouse, restaurant, pro shop, and tennis courts, the home offers seamless access to the best of the Farm Neck lifestyle. While offering a tranquil and private setting, the property is just minutes from boutique shopping, fine dining, the harbor, and ferry terminal—providing both seclusion and convenience. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included with the offering is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

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A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and guests that have enjoyed dramatic sunsets, spectacular August fireworks and evening strolls to town for generations. This historic home retains its Victorian character while having been carefully maintained and updated over the years. Recent improvements include a Title V septic, all new windows, ducted mini-splits for heat/AC throughout the house plus two propane monitors and outdoor shower. Lastly, there is parking for three cars in the parking area behind the house -- a big plus in the heart of downtown.

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This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor includes a private guest bedroom with its own bath, while the second floor offers two additional guest bedrooms and a generous primary suite with access to a large deck. These rooms share two well-appointed bathrooms. With dual road access, thoughtfully landscaped grounds, and a versatile garage space, this home provides both comfort and flexibility in a prime location.

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