Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with strong rental history!

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LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN ROWLEY COTTAGE, Unit 62 at 131 N Water Street in Edgartown, a 895-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after an extensive restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a cooktop, microwave, and refrigerator/freezer. Both bedrooms are well proportioned, and the two full bathrooms are designed for everyday ease. An outdoor shower enhances the coastal lifestyle. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Rowley Cottage, Unit 62 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

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This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick’s most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird’s-eye views capture the natural beauty that surrounds you. Thoughtfully renovated throughout, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality—an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres of pristine conservation land, featuring scenic trails, abundant wildlife, and direct ocean beach access. Whether you’re seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque delivers it all. With an impressive rental history and consistent bookings during both summer and shoulder seasons, it stands out as a premier opportunity in today’s market. This home is more than just an address—it’s the essence of Chappy living.

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Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home. Conveniently located just off the bike path, and only a mile to the desirable South Beach, the location doesn’t get much better than this. Property is being sold “as is”. Buyer is responsible for the research on how to make this pre-existing, non-conforming property conform to today’s building and zoning requirements.

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Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth, character, and enduring craftsmanship. The spacious 4-bedroom, 3-bath home features soaring cathedral ceilings, wide pine floors, a mudroom with built-in storage cubbies, and a generous office/media/playroom complete with custom desks and bookcases. Sun-filled living spaces feel both open and inviting, while a striking brick fireplace anchors the living room — the perfect gathering place after a day at the beach. The property also includes a charming guest cottage, outdoor shower, and large shingled shed, all thoughtfully positioned within a beautifully private setting abutting conservation land. Expansive front and rear decks invite outdoor living, entertaining, and quiet moments immersed in the natural beauty of Chappaquiddick. Thoughtfully updated for comfortable year-round living, the home includes central heating and air conditioning, a whole-house water filtration system, heated mudroom and bathroom floors and energy-efficient solar panels that help keep annual utility costs remarkably low. Located just three miles from the heart of Edgartown, the property is a short walk to Katama Bay, where kayaks and sailboats may be stored, and only 1.5 miles from the pristine shores of Wasque and East Beach. Property Highlights * Distinctive post-and-beam architecture * 4 bedrooms | 3 bathrooms * Separate one-bedroom guest cottage with outdoor shower * Large shingled storage shed * Sprinkler system * Private lot abutting conservation land * Spacious yard with exceptional privacy

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Imagine owning your own beach house on Martha’s Vineyard, ready for summer fun. Perched atop a rise that captures sweeping views over the property, floods interiors with natural light, and opens to a spectacular night sky, this furnished move-in-ready home delivers the Vineyard lifestyle you've been imagining — with room for everyone. Over 2,600 square feet (not including the walk-out basement) unfold across four levels, beginning with a dramatic 30-foot vaulted foyer bathed in sunlight. The fully renovated chef's kitchen features Sub-Zero paneled refrigerator, luxury stainless steel appliances, and stone counters, opening onto a favorite gathering place in the heart of the home - a custom banquette with built-in window seats that easily seats 10. A formal dining room, oak floors, a wood-burning stone fireplace once featured in Architectural Digest, and a view-facing living room with balcony set the tone for effortless entertaining. The primary suite features a walk-in closet and en-suite bath, complete with a sunken tub and double vanity. Two additional bedrooms share a full bath. A sculptural spiral staircase rises to a loft lounge with glass doors to a private balcony — perfect for stargazing or savoring the serene setting — plus two bonus rooms for overflow guests. The walk-out lower level(an additional 900 s/f not included in the s/f), with custom stained concrete floors and new Andersen French doors, adapts easily as a lounge, home office, or gym. Overall, the home is well-maintained, lightly used, with regular renovations and upgrades, including a HydroViv water filter system. The expansion potential is exceptional: a sewer connection option allows growth to seven bedrooms, with room for a guest house, pool, and pool house. Seller is offering $25,000 at closing for the sewer tie-in. There is flex space within the existing floor plan ready for additional bedrooms. Minutes to Vineyard Golf Club, Morning Glory Farm, South Beach, Edgartown Village, and scenic bike paths.

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A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between. Gather around the custom firepit under a canopy of stars, soak in the sauna and cold plunge after a day on the water, or simply unwind on the porch as the island quiets down around you. The three-bedroom main house offers warm, open living spaces, while the two-bedroom guest house — with its covered porch, back deck, and outdoor shower — keeps guests close but comfortably their own. Recent renovations include extensive landscaping, new features, exterior paint, select Vineyard Decorators furniture, plus stainless steel appliances. Move-in ready and offered turnkey with few exclusions for immediate enjoyment. Everything here is geared toward living well outdoors. An oversized garage with furnished loft space provides room for the gear and the gang. Chappy's beaches, hiking trails, Slip Away Farm, and the Community Center are all just minutes away — but with a place this special, you may never want to leave. Offered turnkey with no rentals in place - ready for summer fun!

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LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 94 at 131 N Water Street in Edgartown, a 730-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a microwave, and refrigerator/freezer. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Huxford Cottage, Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

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Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed floor plan with a spacious kitchen, large center island, walk-in pantry, and garden access. The dining area, with an enamel pellet stove, opens to the expansive deck, while the sunken living room offers cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. A first-floor bedroom and full bath provide flexibility for guests. Upstairs are a primary suite with den or office space and half bath, plus two additional bedrooms and a full bath. Outside, enjoy established gardens, a spacious deck, and an outdoor shower. The basement provides storage and overflow space. Town sewer allows expansion up to seven bedrooms, adding significant future potential in this desirable Edgartown location.

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Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on this property if garage, pool or more square footage is wanted, this lot offers the space.

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LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all the popular requests such as a 3-car garage, pool and pool house. The oversized lots are connected to town water and town sewer and all have an established building/development envelope. Substantial new construction homes are up on surrounding lots 1, 2, and 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

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Turnkey Katama Retreat – Welcome to this beautifully appointed, fully furnished home, offering the perfect blend of relaxed coastal living and effortless ownership. With a strong rental history and thoughtful upgrades throughout, this property is an exceptional opportunity as a year-round residence, vacation escape, or income-producing investment. At the heart of the outdoor experience is a 19-foot heated swim spa with current and attached Jacuzzi, set into a stunning wood deck. The surrounding outdoor spaces are equally inviting, featuring an outdoor shower, a bluestone fire pit patio, dining area, multiple decks, and wooded privacy that creates a peaceful atmosphere. Inside, the kitchen and dining area with cathedral ceilings provide an airy and welcoming gathering space with an abundance of natural light. Stainless steel appliances, granite countertops, and modern finishes complement refreshed interiors and new maple floors upstairs. Recent improvements include a new roof, renovated bath, updated landscaping, and numerous interior enhancements—ensuring true turnkey convenience. The thoughtfully designed layout includes a primary bedroom with a private balcony and two first-floor bedrooms with a shared full bath for convenient accessibility. Town sewer connection allows for expansion up to six bedrooms, offering added long-term value. Ideally located, a short distance to South Beach, Edgartown Village and Morning Glory Farm, this property captures the very best of Katama living. Move-in ready and ready to enjoy from day one—this is a rare opportunity to own a truly turnkey home in one of Martha’s Vineyard’s most sought-after locations.

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