Oak Bluffs Massachusetts homes for sale starting at Fifty Thousand Dollars

$13,200,000 - Oak Bluffs, MA

150 East Chop Drive Oak Bluffs, MA - Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves.

$10,500,000 - Oak Bluffs, MA

47 E Chop Drive Oak Bluffs, MA - East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 3.) Or convert to condominiums, paperwork has been completed but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 7-BR main house plus 1-BR guest cottage, includes a 106 ft dock with water/electric for 8 slips and a 40' T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, all new heating/AC mini-splits, and new exterior security cameras.

$4,500,000 - Oak Bluffs, MA

267 Barnes Road Oak Bluffs, MA - Enjoy waterfront living at its best with 163' of Lagoon frontage, including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the water ~ boating, swimming, kayaking, clamming, and more. Savor the views from almost every room of the house, designed to accommodate family and friends with ease, and comfortable living. It is rare to find a home in a setting like this on Martha's Vineyard. Tucked away off Barnes Road in a remote locale, close to many Island favorites. The main level, with high ceilings and large windows, enjoys natural light and provides spectacular water views from all angles. A wood-burning fireplace and wet bar set the tone of the living room, and a more formal sitting area is focused on the views. There is a half bath, a dining room, and a large eat-in kitchen with access to the patio. Two additional rooms with a private deck and full bath are cleverly located in a separate wing of this floor and can be used as an office or den. Unique to the second floor is a wraparound deck and screened porch overlooking the Lagoon. The primary suite has a wood-burning fireplace, walk-in closet, and a generous en suite bath with direct access to a private deck overlooking the Lagoon. There are two additional spacious en suite bedrooms on this floor which also enjoy fabulous views. If you are looking for a quiet retreat, a second covered porch at the front of the house is the place for you. Have fun transforming this 2,000-square-foot walk-out basement with a full bath to fit your needs. Being sold furnished, this is the ultimate Vineyard Experience. First Floor: The welcoming, sun-filled foyer captures the essence of this home. From the moment you walk in, you are captivated by the remarkable ceiling height and dramatic views of the Lagoon. The living room, adjoining sitting room, and dining room create the perfect space for entertainment. The eat-in kitchen is on the right, with access to the patio. If you are looking for a quiet space, the left wing offers a full bath and two rooms for either an office, den, or overflow. Second Floor: The primary suite with a wood-burning fireplace, walk-in closet, and large bath occupies the entire left side of this floor. Enjoy the amazing views with access to the upper deck. Two large ensuite bedrooms, also with delightful views and access to the deck, are located on the right side. Basement: New flooring and interior painting were recently completed, offering many options for this space. A full bathroom and laundry are on this floor.

$3,250,000 - Oak Bluffs, MA

63 Bayes Hill Rd Road Oak Bluffs, MA - Picture yourself in this beautifully designed custom home offering the ultimate in privacy. The first floor has an open floor plan which includes the dining room, kitchen, wet bar, and living space. Bypass siding doors separate the living space from the dining and kitchen. Experience the ultimate in culinary luxury with a gourmet kitchen featuring custom cabinets, high end appliances, and ample counter space with beautiful granite counter tops. The primary bedroom is located on the 1st floor away from the kitchen and living area. Surround yourself with 15 foot ceilings and lovely built in bookshelves, and a mid 1800's style rolling ladder to reach the top shelves. The primary bedroom also features a private bath, large walk in closet and attached office space which has access to the back deck. The 2nd floor has 3 bedrooms, two full bathrooms and an extra room for your office or entertainment area. The finished basement has a full bath, and mudroom with access to the garage and dedicated storage. This area also has potential for a game room as well as a gym space.

$3,100,000 - Oak Bluffs, MA

23 Circuit Ave Extension Oak Bluffs, MA - Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound-a setting that captures the very best of island living. From your front yard, watch ferries come and go, boats drift through the harbor, and enjoy the stunning backdrop of open water stretching toward Vineyard Sound. This is a property that puts you right in the middle of everything, while still offering the charm and character of a classic island home. Zoned B-2 Commercial, the opportunities are truly endless. Continue the legacy of a successful tourist-oriented business like the longtime Anderson Bike Rentals, create a new commercial venture, or reimagine the property as your personal dream home. Whether you renovate the existing structure or build from the ground up, you'll benefit from one of the most visible and vibrant locations in Oak Bluffs. Walk to everything-ferries, beaches, the marina, restaurants, movies, shopping, Ocean Park concerts, the OB fishing pier, and the beloved Oak Bluffs Fireworks. This is a must-see, legacy property with rare potential in a location that can't be beat. Very easy to show. Pre-approval or proof of funds required with all offers.

$2,999,000 - Oak Bluffs, MA

34 Massasoit Avenue Oak Bluffs, MA - This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to shops, restaurants, beaches, and ferries. Come take a look at all this property has to offer.

$2,500,000 - Oak Bluffs, MA

10 Wood Duck Way Oak Bluffs, MA - Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large windows throughout, offering an abundance of natural light. The first-floor primary has an ensuite bath, a walk-in closet with generous shelving, and direct access to the deck. Upstairs is the second bedroom with ensuite bath and walk in closet. Extra storage is found in the attic space. The versatile loft space overlooks the living room and is a perfect spot for a home office, play area, or reading nook. The lower level includes two guest bedrooms, full bathroom, laundry room, additional storage and second refrigerator, as well as a family room that opens to the stone patio and outdoor shower. The exceptional views and grounds serve as an oasis of privacy, complete with well-maintained flower beds and lush plantings. Association members have access to the dock and clubhouse.

$2,495,000 - Oak Bluffs, MA

16 Atlantic Avenue Oak Bluffs, MA - East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most importantly, the modern comforts today's lifestyle demands. Set on a generous, level parcel, with an existing seven-bedroom septic system-providing ample opportunity for future expansion and customization. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're just minutes from the harbor and vibrant downtown Oak Bluffs. A true island compound-rooted in tradition, yet ready for what comes next.

$2,445,000 - Oak Bluffs, MA

4 High Meadow Lane Oak Bluffs, MA - Classic Post & Beam set in Meadow View Farms This bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf range, and wine cooler. There is a casual dining area off the kitchen and a formal dining room. The spacious first floor primary bedroom has a large walk-in closet, soaking tub, and bay window looking to the backyard. The other bedroom is currently being used as a TV room. The second level has two sizeable ensuite bedrooms with ample closet space and skylights. Highlights of the home include radiant heat, hardwood floors, firepit, large yard and room for expansion. More opportunity is found in the partially finished lower level. A future office, media room, or workout area awaits. The two car garage is large and has additional space above offering options for additional living space. Meadow View Farms is quiet and private with walking trails and association tennis.

$2,375,000 - Oak Bluffs, MA

30 Sengekontacket Road Oak Bluffs, MA - Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main level features a living area with a wood-burning fireplace, a spacious kitchen, and a screened-in porch with cathedral ceilings, perfect for dining while enjoying the beautiful views. The primary suite is situated on the second floor and boasts French doors that open to a small deck, allowing you to take in the expansive scenery. The lower level includes three bedrooms, each with French doors leading to a lower deck, and they share a full bathroom. The Sengekontacket Association, established in 1971, encompasses 93 acres and provides a variety of amenities including tennis and pickleball courts, an Association Clubhouse situated on Wiggy's Pond, and a boat ramp with kayak storage on Sengekontacket Pond. Homeowners can consult the Harbor Master for a mooring in Major's Cove, where the Association dock is located. Fully renovated in 2007, this property is ready for you to enjoy!

Oak Bluffs, Massachusetts listings for sale

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