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23 Circuit Avenue Extension, Oak Bluffs
$2,450,000
3 Beds ⋅ 1 Baths ⋅ 22601795 MLS
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,

23 Circuit Avenue Extension, Oak Bluffs

3 Hidden Cove Rd, Oak Bluffs
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 73500165 MLS
Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The sun-filled interior features a living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows. The chef’s kitchen is appointed with stone countertops and Dacor® appliances. The second-floor primary suite boasts a private balcony with pond views and a stylish en suite bath. The garden level provides additional bedrooms and a bonus space with a Murphy bed. Outside, enjoy a bluestone terrace and two levels of decks overlooking a private yard. This move-in-ready home is offered fully furnished with over $80,000 in 2026 summer rental income already secured.

3 Hidden Cove Rd, Oak Bluffs

22 Greenleaf Avenue, Oak Bluffs
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 73355326 MLS
Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect Jaime Weisman. Lovingly maintained by one family for over 27 years, it now awaits its next chapter.Fairview includes three bedrooms, a finished basement for flexible living or work space, and a multipurpose outbuilding that functions as both shed and garage. With off-street parking and a generous yard, the property offers convenience and charm. Just steps from the heart of Oak Bluffs—Illumination Night, Tabernacle concerts, Ocean Park strolls—yet still a private, serene retreat.A rare chance to own a home with incredible views, historic charm, and space to make it your own.

22 Greenleaf Avenue, Oak Bluffs

71 Netock Ave, Oak Bluffs
$1,865,000
4 Beds ⋅ 5 Baths ⋅ 22505098 MLS
On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor primary bedroom with ensuite bath, powder room, and laundry room. Upstairs are three additional spacious bedrooms and two full baths. A new roof, siding, and central air enhance comfort. Outside, enjoy a large back deck, welcoming front porch, and an expansive yard with irrigation, a new sod lawn, lush evergreen and privet hedge borders, plus a classic Vineyard must-have: an outdoor shower. Ideally located near charming Oak Bluffs with its whimsical gingerbread cottages, Flying Horses Carousel, harborfront, quaint shops, dining, and nearby Oak Bluffs Town and Jetties beaches. Buyers and agents please verify all herein.

71 Netock Ave, Oak Bluffs

7 South Meadow Lane, Oak Bluffs
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 73473424 MLS
Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs’ most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood’s peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and all downtown attractions, within easy reach.

7 South Meadow Lane, Oak Bluffs

44 Tiffany Drive, Oak Bluffs
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 22503290 MLS
Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted microwave and oven combination, counter cooktop, breakfast bar with seating, and a built-in desk with glass shelving--perfect for casual meals or entertaining. French glass-pane doors with elegant glass knobs provide classic charm and a graceful flow between the kitchen, dining room, family room, and living room. The family room features a vaulted ceiling with skylights and a striking full stone wall with brick insert for a gas propane stove, while the spacious living room offers a Count Rumford brick fireplace. The first floor also includes a bedroom, full bathroom, and a mudroom, all with beautifully maintained distressed oak and oak hardwood flooring. Upstairs, you will find two spacious bedrooms, including a primary ensuite with Jacuzzi tub, plus a third full bath. Flooring on this level

44 Tiffany Drive, Oak Bluffs

5 Bayes Hill Circle, Oak Bluffs
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 22502540 MLS
Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with timeless elegance. An idyllic covered porch invites you into the home. The heart of the home is undoubtedly the kitchen, which opens to a second living area adorned with a charming wood-burning fireplace--ideal for chilly Vineyard evenings. Just off the kitchen, the deck overlooks a beautifully manicured backyard and a private wooded area, providing a serene backdrop for outdoor gatherings, birdwatching, or simply unwinding. A convenient first-floor laundry room leads out to the 2 car-garage. The second level features a spacious primary bedroom with en suite bath, ample closets, and an attached home office. Three more bedrooms and a shared bath complete the second floor. The finished basement, not included in the square footage, adds an extra layer of versatility, offering a cozy retreat for movie nights, a workout area or a game of pool. (Pool table is included with the sale) Residents of Bayes Hill enjoy access to the association's tennis and pickleball court, and with southern woodland trails right at your doorstep, outdoor adventures await! As a delightful bonus, the sellers are including a 2008 BMW Convertiblea perfect Island car to cruise the picturesque roads of Martha's Vineyard!

5 Bayes Hill Circle, Oak Bluffs

3 Kims Way, Oak Bluffs
$1,188,000
3 Beds ⋅ 2 Baths ⋅ 73478102 MLS
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.

3 Kims Way, Oak Bluffs

61 Ocean Avenue Unit 4, Oak Bluffs
$1,185,000
1 Beds ⋅ 1 Baths ⋅ 73521487 MLS
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. 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 with 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.

61 Ocean Avenue Unit 4, Oak Bluffs

96 Manchester Avenue, Oak Bluffs
$1,125,000
3 Beds ⋅ 2 Baths ⋅ 22600161 MLS
New Interiors Coming Soon - Nestled in a quiet neighborhood less than two miles from the heart of Circuit Avenue, this contemporary cape-style home is ready to welcome you. A charming farmer's porch invites you into a spacious living area with cathedral ceilings and an open-concept design that seamlessly connects the kitchen, dining, and living spaces--perfect for gathering with family and friends. The main level features a convenient first-floor bedroom and a full bath with laundry. Upstairs, you'll find a large primary bedroom with ample storage, a cozy second bedroom, and a shared full bath. The lower level offers an additional 400 sq. ft. of finished space--not included in the listed square footage--plus a generous unfinished area for all your storage needs. Step outside through sliding doors off the dining area to a private backyard oasis, complete with a coveted oversized outdoor shower--an island favorite. Set on a generous corner lot with a gentle slope, the property provides easy access to downtown, the school, bike path, and beautiful local beaches. Whether you're seeking a year-round residence or a seasonal retreat, this delightful home is the perfect fit.

96 Manchester Avenue, Oak Bluffs

21 Butler Avenue Unit 1, Oak Bluffs
$1,035,000
3 Beds ⋅ 2 Baths ⋅ 73552744 MLS
Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with modern comfort. Two-car off-street parking—an exceptional Campground amenity—adds convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away. The 1,135-square-foot home features painted wood floors, abundant natural light, vintage details, and flexible living spaces for gathering, guests, or a home office. Unlike many Campground cottages, it is fully winterized with a four-zone heat pump system providing efficient heating and air conditioning, plus a propane on-demand water heater. Significant improvements include updated electrical and lighting, newer appliances, kitchen built-ins, foundation work, and a sealed, dry crawlspace. Outside, the fenced yard, expanded brick patio, shade sails, cooling fan, outdoor television, and large storage shed create a private retreat rarely found in the Campground.

21 Butler Avenue Unit 1, Oak Bluffs

21 39G Island Inn Road, Oak Bluffs
$487,500
1 Beds ⋅ 2 Baths ⋅ 22600497 MLS
Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live music are just a short walk from your condo.This is an end unit with beamed wood ceilings, a comfortable living room with a gas fireplace and sliders that lead to the patio. The primary bedroom has a half bath and a generous closet with extra storage space. The kitchen has been updated with granite counter tops. The recently updated full bathroom has a walk-in shower. A bonus 'sleep alcove' has twin beds (with new mattresses) and both a closet and owners closet. Picturesque grounds include gardens and green areas, a heated community pool, 3 clay tennis courts, bbq areas with fire pits, a children's playground, and a management office with resident manager apartment. This association is pet friendly. Shared washers and dryers and function rooms. There is ample parking on the property for owners. Gulph Creek Hotel management, on site, provide exceptional rental and management services for guests and owners. Their responsibilities include housekeeping, maintenance and rental bookings. Live or rent - the options are yours. There is an assessment. Please inquire. The Island Inn is seasonal, welcoming guests from April through October.

21 39G Island Inn Road, Oak Bluffs

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