“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering exceptional opportunities for swimming, kayaking, and paddleboarding directly from your backyard. The main residence features a welcoming sun porch, an inviting living room anchored by a stone fireplace, and a light-filled primary bedroom with tranquil water views. The updated kitchen and adjoining dining area showcase beautiful brick floors and a built-in window seat. French doors open from the kitchen to a spacious lawn designed for outdoor entertaining, complete with a charming former boathouse reimagined as a unique dining pavilion. A striking spiral staircase leads to an expansive rooftop deck, ideal for sunbathing, entertaining, and enjoying panoramic views of passing ferries and Vineyard sunsets. A separate guest cottage offers two additional bedrooms and a full bath. Additional amenities include a private outdoor shower, a one-car garage with attached office space, and a newly built garden shed. This iconic Oak Bluffs property is just a short bike ride to island beaches and the vibrant shops and restaurants of both Oak Bluffs and Vineyard Haven. A truly magical waterfront property offering the quintessential Martha’s Vineyard lifestyle.

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Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by soaring cathedral ceilings, rich hardwood floors, and a striking hand-cut stone propane fireplace that anchors the open-concept living spaces. The well-appointed kitchen with casual dining area flows seamlessly into a formal dining room and an inviting living room, creating an ideal layout for both everyday living and entertaining. A spacious mudroom offers practicality and convenience after beach days or inclement weather. The primary suite is privately situated on the first floor and features abundant natural light from a bay window overlooking the backyard, a walk-in closet, and an oversized bath complete with skylights and an additional bay window. A front-facing bedroom currently serves as a den or office, offering flexibility to suit a variety of needs. The second level features two generously sized and identical ensuite bedrooms, each offering shower/tub combinations and dual closets for exceptional storage. The partially finished lower level offers an additional 1,957 square feet, presenting remarkable opportunities for customization or expansion. The oversized two-car garage is complemented by approximately 576 square feet of space above, ideal for potential guest accommodations, an ADU, studio space, or a private office. Approvals from the Town are required. Meadow View Farms is known for its convenient and quiet setting, close proximity to the bike path, Farm Neck Golf Club, and more than 200 acres of nearby conservation land with extensive trails. Title V inspection has passed and approved for a five-bedrooms. * "Buyer Agent must be present at all buyer client showings, inspections and walkthroughs unless otherwise agreed to in advance by the listing agent."

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Would you love to live or vacation in a brand-new home on Martha’s Vineyard? We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD! Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood. Easy to show – Call now! To be built with lot purchase $695,000 and building contract approximately $1,550,000. This 3-bedroom dream home is set in an elevated enclave 95 feet above Lagoon Pond, capturing sweeping sky views, colorful sunsets, and refreshing sea breezes. This exceptional home site represents one of the final opportunities in this thriving new community. To be built — The Naushon — features 3 bedrooms, 3.5 bathrooms, and over 2,400 square feet of thoughtfully designed living space. A grand wrap-around covered porch provides a welcoming entry and the perfect place to enjoy morning coffee or cool evening breezes. Inside, the open-concept floor plan connects the chef’s kitchen with spacious living and dining areas—ideal for entertaining family and friends. Each bedroom suite includes a tiled en-suite bath with customizable fixtures and finishes, and the second-floor suites may offer private balconies for added relaxation. Classic Oak Bluffs cottage architecture meets modern comfort and energy efficiency, making The Naushon an ideal year-round or seasonal retreat. Lagoon Ridge offers direct access to conservation lands with walking and biking trails, and nearby Lagoon Pond invites kayaking, sailing, and shell fishing. All utilities—electric, town water, and a private, state-of-the-art Amphidrome wastewater system—are located at the street. This innovative system serves the entire neighborhood, providing convenience and peace of mind. Lagoon Ridge is a covenant-protected community with architectural review and professional management by First Property Management Co. This beautiful home site is ready for the construction of your Vineyard dream home. Eleven lots have sold—only two remain available: 2 Hopes Way and 35 Double Ox.

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Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much opportunity; this house is being sold As-Is.

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An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless beauty of Martha’s Vineyard converge. This 1.87-acre homesite represents the final opportunity to build within this exclusive community, offering underground utilities, town water, and Board of Health approval for up to six bedrooms. Enjoy a peaceful and private setting with direct access to conservation land and miles of scenic walking and biking trails. Ideally located just minutes from downtown Oak Bluffs, pristine beaches, Oak Bluffs Harbor, ferry terminals, and Farm Neck Golf Club, this exceptional property offers an unparalleled blend of privacy, convenience, and enduring value. Whether envisioning a year-round residence or a seasonal Island retreat, this is the opportunity to create a legacy property in one of Martha’s Vineyard’s most sought-after communities.. Easy to Show ! Call Agent for a tour!

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Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the harbor, while enjoying the privacy of a quiet residential neighborhood. Over the past decade, the property has benefited from extensive improvements, including a four-bedroom septic system, energy-efficient mini-split heating and air conditioning, updated windows, renovated bathrooms, irrigation, an outdoor shower, and countless additional upgrades that reflect exceptional pride of ownership. Fully booked for the 2026 summer season, the property provides immediate rental income from day one while offering exceptional flexibility for future personal use or continued investment. The property is fully rented for the 2026 summer season. Showings are available only on scheduled turnover days.

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Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath. Sliding doors open to a deck and patio with manicured lawn. Moments to downtown, beaches and ferries.

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Quintessential Waterview Farm! Built as a year round house with all the charm of the original cottages, this well-loved family home awaits a new generation. The sunny, open floor plan has two bedrooms and a full bath on each level and plenty of room to spread out. The skylit kitchen is cleverly tucked into a corner of a large gathering area for dining and relaxing, with a rounded wall of glass that spills out to the deck and large, private yard. A sunken living room features a fireplace and stairs to a loft seating area. The structure was built in 1978 and is fully winterized, with a partial basement and forced air heat. The south facing, half-acre lot abuts a peaceful and forever wild 8 acre meadow, creating a private oasis in every season. A path across the lane ambles through another large wildflower meadow to the private association beach. Tucked between Farm Neck and Felix Neck, Waterview Farm features a natural landscape with 22 acres of common land and an accessible sandy beach and dock, boat storage areas and the possibility of a mooring. Start enjoying this unique property as it is while you dream of ways you can make it even better!

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Your opportunity in Sengekontacket! Being sold turnkey. This modern home has four bedrooms and three full baths. Large windows and high vaulted ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the kitchen, living room and dining room. The primary en suite includes full private bath with Jacuzzi tub and shower, walk-in closet and dressing area. Three sliders lead onto a large sunny deck from the living area, great for alfresco dining, lounging or entertaining, extending your living space. The fourth slider accesses the deck from the primary bedroom. The full finished basement has eighteen foot high ceilings, multiple windows and glass back door. The basement also includes a third full bath and utility room. This surprising basement would make a fantastic recreation, media room, playroom, dance studio, or home office. This home is being sold in "as is" condition. Located in a private community with wonderful amenities such as tennis, pickleball, mail delivery, freshwater pond, clubhouse, and kayak storage with access to a salt water dock and boat landing. Potential for a boat mooring via the Oak Bluffs Harbormaster. This is a great central Island location near Farm Neck Golf Club, with easy access to all island Towns, shopping, beaches, restaurants and entertainment.

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Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property includes a newly beautifully renovated 2 bedroom 2 bathroom guest house. This guest house is offered fully furnished. This listing documents include a custom landscape design plan. This very large parcel of land is well suited to get started building an investor dream or family compound.

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Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features abundant counter space and opens to the dining area, with sliding doors leading to a back deck and yard—perfect for entertaining or relaxing.Lovely blue stone patio in the back yard. Radiant heated floors bring cozy comfort to the primary master suite and basement playroom. There is a two-car garage with bonus space above. The driveway parking area has lovely stonework in front of the garage. The furnace was replaced in 2020 and the water heater was replaced in 2024.

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Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double the living space on the upper level. There is also a powder room on the upper level. The main floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck; that level offers 2 more spacious bedrooms and a shared bath. Venture downstairs to the above-grade lower level and enjoy the family room, reading nook, and bonus room. There is also a large storage/utility room with a second powder room. Like every true island home, there is an outdoor shower. Plenty of additional storage is under the deck. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind it, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis courts, and pastoral meadow views. Strong year-round rental history! The home is being sold "as is".

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