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LINK ID: 44725 |
NEW LISTING |
| 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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LINK ID: 36712 |
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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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LINK ID: 44395 |
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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 | ||
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LINK ID: 42465 |
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| SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha's Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and connection to the outdoors. The main living spaces are both dramatic and inviting, with high ceilings, skylights, and walls of glass that frame the ever-changing water views. A central staircase and classic columns define the space, with a decorative stone fireplace providing a natural focal point and warmth. A true chef's kitchen is equipped with stainless steel appliances, expansive stone counter space, custom cabinetry and an oversized island. A wet bar featuring a beverage refrigerator and ice maker enhances the entertaining flow, while a more casual dining area provides a comfortable setting for hosting. The home includes three spacious ensuite bedrooms. The primary suite is privately situated and enjoys water views, direct access to the pool terrace, and a luxurious bath with soaking tub, double vanity, and glass-enclosed shower. Two additional en suite bedrooms are located on the second level, along with an open sitting area that overlooks the main living room below. Designed with entertaining in mind, the lower level features a billiards/game room, den, bonus room, kitchenette, wine storage, and flexible room for a gym or additional use. Outdoor living is a highlight of this fabulous property, with a heated pool and spa set within a bluestone terrace, and an outdoor kitchen area ready for your custom design and choice of appliances. This space is perfect under the open sky with multiple areas for lounging. The calm Lagoon waters are just steps away and offer ideal conditions for swimming, paddling, boating, and clamming, with the ability to secure a mooring. The Lagoon is known for some of the best steamers, littlenecks, and cherry stones on the Island. In fact, there is a huge clam bed in the Lagoon right behind the house off the private beach. Offered furnished, with a proven strong rental history, this property also enjoys a 2-car garage and is a rare offering combining privacy, comfort, and exceptional waterfront living. | ||
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LINK ID: 43452 |
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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 | ||
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LINK ID: 44341 |
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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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LINK ID: 44172 |
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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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LINK ID: 44237 |
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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 | ||
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LINK ID: 44208 |
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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 | ||
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LINK ID: 44234 |
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| Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through | ||
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LINK ID: 44615 |
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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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LINK ID: 44316 |
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| Farm Neck Golf Club - Undeveloped Water View Parcel with MembershipA truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha's Vineyard residence.Included with the property is a highly coveted Farm Neck Stockholder Membership certificate, an extraordinary privilege that bypasses the current 16+ year waitlist and is seldom available in conjunction with a land offering. The parcel provides an opportunity to design and build a custom island home tailored to your vision. Whether a refined seasonal retreat or a legacy compound, the setting offers both privacy and access to the full Farm Neck lifestyle: championship golf, tennis, association dock, and a vibrant, established community.The property has been staked to reflect both boundary lines and the designated building envelope. Buyers are responsible for their own due diligence; please consult a qualified land engineer to confirm the potential bedroom count. | ||
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LINK ID: 44528 |
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| Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built residence offers the perfect blend of sophistication and refined Vineyard style.The spacious floor plan offers over 3,200 square feet of living space, highlighted by a first-floor primary suite, an open-concept great room with high ceilings and oversized windows, gourmet kitchen with pantry, dining area, mud room with laundry and seamless indoor-outdoor living. A screened porch and covered porch are perfect for summer entertaining and relaxed evenings after a day at the beach.The second floor features two additional bedroom suites, a loft-style gathering area or office, dedicated laundry, and a flexible bonus space ideal for media room, fitness space or office. An attached two-car garage provides ample storage for vehicles, bikes, and beach gear.Crafted with high-end materials and attention to detail, this is a terrific opportunity to own a custom, to-be-built home in vibrant Oak Bluffs. Enjoy easy access to beaches, sailing, golf, restaurants, shops, ferry ports, and all the attractions that make the Vineyard a premier vacation destination. | ||
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LINK ID: 42895 |
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| Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home's original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs. | ||
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LINK ID: 44347 |
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| Classic Vineyard charm meets modern luxury. Set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space, a gourmet kitchen, multiple entertaining areas, a screened porch, and a separate one-bedroom guest apartment above the garage. Renovations include two new kitchens (one in the apartment), 4.5 new bathrooms, 4-bedrooms (two ensuite), all new windows and new flooring on first floor. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace to the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. The first floor includes one of the ensuite bedrooms and a large screened in porch off the dinning room. The 2nd floor includes two large bedrooms (one ensuite), a second full bathroom and new washer/dryer. The attached 1-bedroom apartment includes living/dining/kitchen area, washer/dryer, heat/AC and sits above a large 2-car garage with mud room and lots of storage space. To the side of the garage is a large separate bonus/variable use room with heat/AC that could be used as an office or game/family room. Property includes a spacious rear patio and deck with access off both the kitchen and screened in porch, as well as an outdoor shower and parking for several cars in the driveway. The lot is large enough in this R3 zone for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Please note: Newly seeded lawn areas have been touched up and furniture in several rooms is virtually staged and noted in photos. Title V septic passed inspection 5/12/25 and in-ground propane tank pressured tested in 2025. | ||
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LINK ID: 36870 |
PRICE CHANGE |
| LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES.Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history.Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous accommodations for family, friends, and guests. From the EXPANSIVE ROOFTOP entertainment deck, enjoy sweeping 180-degree water views of Vineyard Haven Harbor | ||
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LINK ID: 44300 |
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| Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom.Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together a combined total of just over an acre of land. Included is Deeded Access, via a boardwalk to Brush Pond, with more wonderful views. Directly in front of the property lies a sandy beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf and a host of activities. This property offers both tranquility and convenience in one of Martha's Vineyard's most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for purchase separately. Excellent Rental History. Rentals in place for 2026 Summer Season! | ||
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LINK ID: 44579 |
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| Classic Oak Bluffs Victorian Steps from Beach, Harbor and Town.. Built in 1875 by famed architect Samuel Pratt, this Classic Oak Bluffs Victorian offers a rare opportunity to own a piece of Vineyard history just one block from the sandy beach. Located moments from the harbor, ferries, shops, restaurants, and all the attractions of downtown Oak Bluffs, this warm and welcoming four-bedroom home captures the essence of in-town coastal living. Enjoy sparkling water views from the expansive wrap-around porch with solid mahogany flooring and the private second-floor balcony while taking in the sights and sounds of Oak Bluffs. Rich in historic character, the home features spacious living and dining areas, an eat-in kitchen, a cozy sitting/TV room, and four second-floor bedrooms filled with natural light. The beautifully landscaped gardens and outdoor gathering spaces create the perfect setting for relaxing after a day at the beach. Listen to the ferry horns in the distance, stroll to town for dinner or shopping, and experience the convenience of one of Oak Bluffs' most desirable in-town locations.Recent improvements and features include two mini-split heating and cooling units (2021), a wrap-around porch rebuilt in 1999 with solid mahogany flooring, a second-floor balcony, cedar shingle exterior, replacement of the west-side cedar shingles and exterior painting in 2019, asphalt roof (2012), Harvey vinyl replacement windows (2002), updated kitchen and bathroom flooring (2012), updated electrical wiring (2012), electric hot water, outdoor shower, town water and sewer, and off-street parking for two vehicles.This property also offers excellent investment potential with a strong established rental history and existing 2026 rental bookings in place. Buyers could generate immediate income while enjoying personal use of this exceptional Vineyard property. Combining historic significance, water views, thoughtful updates, proven rental performance, and an exceptional location, this Samuel Pratt-designed Victorian is a truly special Oak Bluffs offering. Partially insulated this is a 3 Season Home. Rentals in place call agent for an appointment. | ||
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LINK ID: 43898 |
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| “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 comfor | ||
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LINK ID: 42967 |
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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. | ||
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LINK ID: 43866 |
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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 and 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 | ||
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LINK ID: 44349 |
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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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LINK ID: 44652 |
NEW LISTING |
| 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 with direct access to Inlkwell Beach. | ||
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LINK ID: 44113 |
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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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LINK ID: 44718 |
NEW LISTING |
| 33 Tia Anna Lane has so much to offer; a charming, bright, renovated main and guest house on a half-acre in Oak Bluffs with proximity to town and walking distance to Lagoon Pond for swimming, fishing, boating and sunset enjoyment. The property is ready to enjoy, offering a turn-key home on a quiet side street as well as a detached guest house with it's own yard and deck. The inviting main house has been thoughtfully updated and renovated and features a generous yard with lovely plantings, a wrap-around deck, screened porch, and finished basement. Inside there's a large, well appointed kitchen and separate pantry/laundry, a spacious living room, powder room, and generous first floor primary bedroom with en-suite bath. The second floor offers a guest room, and substantial office/bonus room and another full bathroom. This house lives much larger than it looks! The main home is being offered furnished with a few exclusions. This property is a great opportunity for comfortable living or rental investment. | ||
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LINK ID: 44018 |
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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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LINK ID: 44054 |
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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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LINK ID: 44077 |
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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 | ||
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LINK ID: 44641 |
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| Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop.Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the rare opportunity to own a slice of waterfront paradise.Designed for relaxed seaside living, the home features a bright, open living area filled with natural light, a eat-in kitchen, and two comfortable bedrooms that provide a peaceful escape after a day by the water. Expansive windows frame spectacular ocean vistas, while a spacious open porch is ideal for morning coffee, sunset dinners, or simply enjoying the ever-changing seascape.Whether you're looking for a vacation getaway, or an investment property, this cottage offers timeless coastal charm in an unbeatable location. Just imagine what you could build on this magnificent property. | ||
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LINK ID: 44518 |
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| Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch | ||
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LINK ID: 44671 |
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| Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26. | ||
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LINK ID: 44469 |
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| Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26. | ||
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LINK ID: 44199 |
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| Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio | ||
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LINK ID: 44374 |
PRICE CHANGE |
| This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located within the highly sought-after B1 Zone, this residence has been cherished as a family home while also providing the potential for commercial endeavors.The property features a well-designed floor plan that includes four bedrooms | ||
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LINK ID: 44213 |
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| Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is. | ||
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LINK ID: 44475 |
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| THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-terre is convenient to long stretches of beach, numerous shops, great and varied restaurants and the vibrant life of Oak Bluffs in the summertime. This is a completely renovated and updated Unit with high end finishes including solid mahogany doors and mahogany counter top center island. The property is beautifully landscaped and can be enjoyed year-round. It includes a coveted, off-street parking space. From the French doors in the Unit, you walk out onto a private, second floor, 7' x 21' porch from which you have a front row seat to watch the Oak Bluffs fireworks, band concerts in the gazebo and all the summer festivities on Ocean Park. This is a rare opportunity to own a genuine piece of American history that cannot be duplicated. | ||
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LINK ID: 44033 |
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| $100,000 PRICE REDUCTION !!! You cannot get all these amenities in another property in this price range!! Hidden Cove Waterfront community is a peaceful tranquil neighborhood. This spacious 3 bedroom w/oversized family room home is VERY affordably priced. The sun shines in through skylights and the charming living room has big windows and a brick wood burning fireplace. There's attractive Palladian side windows, Rennai gas monitor and fantastic hardwood floors. The ample chefs kitchen extends w/L shaped counter and snack bar. The dining area is adjacent creating an open gathering area for family and friends.French doors to back deck provide additional grilling or sunning opportunities in the warmer months and essential outdoor shower.A desirable first floor bedroom is adjacent to a full bath and additionally there's a very big family room w/private entrance and private side porch.Head up the skylight lit staircase and you'll find 2 oversized bedrooms w/high ceilings and skylights - each generous enough for sleeping area and sitting/work area. There's is another full bath w/double vanities and access from each bedroom.Downstairs the full basement is partially finished (bead-board walls) and was previously used as a family rec room w/lots of storage. Definitely a great space to complete!!Landscaped irrigated grounds w/grassy back yard, mature plantings of Rhododendrons, flowers, and a peek at the water add to the ambience of this peaceful neighborhood.Walking the wooden paths spilling over the salt marshes is a Zen-like experience w/just you and the birds singing. You'll come to kayak racks and dinghy dock - Private Community access to Sengekontacket Pond. A beautiful spot!Winter boat storage and private community tennis courts are also amenities for this upscale waterfront neighborhood! Don't miss this GREAT VALUE!! easy to show-sold as is | ||
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LINK ID: 44658 |
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| Discover the charm of this inviting single-story ranch with a large, finished basement, perfect as a vacation retreat or year-round home. Extensively renovated, this charming 3-bedroom, 1.5-bath home offers comfort and effortless living. The finished basement adds nearly another 1000 SF of living space with a spacious TV room and game area for extra entertainment, while the welcoming back deck and enclosed outdoor shower make it easy to unwind after a day at the beach. Recently installed solar panels add significant energy efficiency. Set on a landscaped corner lot, the home is close to Lagoon Pond, where you can swim, shellfish, boat, and take in unforgettable sunsets. The location is close to Farm Neck Golf Club and downtown Oak Bluffs, with easy access to Island beaches, dining, and attractions. With strong rental bookings for 2026, this home is also a smart investment opportunity. | ||
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LINK ID: 43914 |
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| Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure year-round storage. Conveniently located near Farm Neck Golf Club, downtown Oak Bluffs, and more. Easy access to all island destinations via County Road and Barnes Road. Perfect blend of practicality and charm for seasonal or year-round use. Flexible leasing, partnership, or investment opportunities available. | ||
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LINK ID: 43457 |
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| Welcome to # 0 Temahigan Ave and Dover Street, Oak Bluffs.Build Your Martha's Vineyard Dream Home.Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha's Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a possible future pool.Located in the sought-after Eastville area, where many homes enjoy beautiful water views, this lot offers the potential to capture stunning views of Vineyard Sound and beyond from a thoughtfully designed home. Create a custom residence that embraces all the beauty and lifestyle Martha's Vineyard has to offer.Enjoy a short walk to Eastville Beach, where you can take in spectacular sunsets, watch the ferries come and go, and experience the charm of island living.Just a short drive away, you'll have access to everything that makes Oak Bluffs so special | ||
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LINK ID: 44490 |
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| Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system. | ||
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LINK ID: 44108 |
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| Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle. | ||
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LINK ID: 44649 |
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| Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This thoughtfully planned neighborhood will feature distinctive architect-designed residences, creating a refined and cohesive community setting. Approved for connection to the neighborhood's private Amphidrome | ||
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LINK ID: 44599 |
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| Located within the historic Martha's Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking | ||
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LINK ID: 44714 |
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| Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process.The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development.Subject to the Town of Oak Bluffs' zoning regulations and permitting requirements, the property offers the potential for a main residence and a guest house, with a combined maximum of six bedrooms.Whether you're envisioning a year-round residence, a seasonal getaway, or an investment property, this parcel presents an outstanding opportunity to build in one of Martha's Vineyard's most sought-after communities. | ||
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LINK ID: 44342 |
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| Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town.The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard | ||
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LINK ID: 44252 |
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| Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience | ||
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LINK ID: 44276 |
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| In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it! | ||
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LINK ID: 42877 |
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| Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. Enjoy this house as it is or work through the process to create something new. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations. | ||
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LINK ID: 44245 |
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| Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck | ||
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LINK ID: 44275 |
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| In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view of Downtown Oak Bluffs. Sit back and watch the boats come into the harbor at one of the many seating areas or enjoy diner al fresco under the stars. This spacious unit has many custom wooden features including a staircase leading to the rooftop deck creating a storage area and sleep nook with daybed. Take a step down to the comfortable living area. With hardwood floors throughout, the kitchen and dining area are divided with custom cabinetry. The spacious bedroom has an additional alcove area with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. A separate Laundry room is shared by 2 other units. | ||
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LINK ID: 44062 |
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| OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha's Vineyard's most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value and BUILDING PERMIT in place for an ADU. This could be yours! Ready to go. | ||
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LINK ID: 42248 |
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| This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in compliance with Massachusetts ADU regulation - 760 CMR 71.00. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue! Title 5 Certification in place. Lot is in Zone II and will allow a total of two bedrooms with upgrade to an advanced treatment system. Just one house from Wesleyan Park or stroll to Harbor and Town. Empty and easy to show. | ||
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LINK ID: 44425 |
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| Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter | ||
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LINK ID: 44502 |
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| Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications. | ||
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LINK ID: 44640 |
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| Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete the kitchen. The home has two comfortable bedrooms and one full bath. Enjoy seamless indoor-outdoor living from the expansive wrap-around deck. After a day at the beach, rinse off in the requisite Vineyard amenity, the outdoor shower. A barn-style shed provides an enormous amount of storage or it can be a workshop space/she-shed. Conveniently located near downtown, access to the Lagoon, bike path, the hospital, public library and more, this property offers both practicality and charm in a sought-after Oak Bluffs neighborhood. An adorable home to make your own.The septic system has passed Title V inspection and is certified for two-bedrooms. Located in the R1 zoning district and in Zone 2, the property is subject to 20-foot setbacks on all sides. It is a pre-existing, non-conforming lot, so any additions to the structure will require approval from the Zoning Board of Appeals. | ||
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LINK ID: 43296 |
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| GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD 9 homes already built.Welcome to Lagoon Ridge Oak Bluffs' newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready for development with utilities at the site, including town water, electric, and a private Amphidrome wastewater system, eliminating the cost and maintenance of a traditional septic system.Lagoon Ridge borders acres of pristine conservation land with direct access to scenic biking and hiking trails, providing the perfect balance of privacy and outdoor recreation. Ideally located in Oak Bluffs and central to all down-Island towns, this vibrant neighborhood continues to grow with strong construction momentum. Easy to show contact agent for a private tour.. | ||
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LINK ID: 43507 |
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| Oak Bluffs Buildable Lot - Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the Oak Bluffs Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is outside the Zone II district, so a standard Title V septic system should be permissible (buyer to confirm).The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 15,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity. | ||
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LINK ID: 43836 |
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| Nestled in the heart of the historic Martha's Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs' campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort | ||
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LINK ID: 43517 |
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| Oak Bluffs Buildable Lot - Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the Oak Bluffs Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is inside the Zone II district, which will require a microfast septic system (buyer to confirm). The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 10,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity. | ||
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LINK ID: 44094 |
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| Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha's Vineyard's most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park.This level lot includes an existing poured concrete foundation and Martha's Vineyard Commission-approved plans by Sullivan and Associates Architects for a classic Vineyard-style, 2.5-story mixed-use building. The design includes ground-floor commercial space and two one-bedroom residential apartments, creating three rentable units in total.With plans in place and foundational work already completed, the property offers a clear path forward as a mixed-use development or, alternatively, the opportunity to construct a traditional two-bedroom residence in downtown Oak Bluffs. Some photos virtually altered for seasonality. | ||
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LINK ID: 42933 |
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| Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby. | ||
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