Oak Bluffs enjoys a reputation as one of the more active night-life towns on the island. Oak Bluffs also includes the East Chop peninsula, Lagoon Heights and Harthaven. Home to the Historic Gingerbread Houses Wesleyan Grove is a 34 acre National Historic Landmark District located in Oak Bluffs, Massachusetts.  It is also known as the Martha’s Vineyard Campmeeting Association (MVCMA) or the Campgrounds. In 1835 the 35 acre wooded forest were host to a two or three day Methodist religious revival meeting during the summer.  The revival at Wesleyan Grove became an annual event, at first there were nine tents for the attendees, twenty-three years later almost 12,000 people attended and families began bringing their own tents and building rough wooden platforms for them, and finally simple houses were built on these platforms.  These houses were built very simple, the inside walls were also the outside walls, no heat and tiny rooms, but they were built with elaborate gothic flair.

$2,678,000
4 Beds ⋅ 4 Baths ⋅ 22604054 MLS
Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

31 Temahigan Avenue, Oak Bluffs
$2,995,000
4 Beds ⋅ 2 Baths ⋅ 22604007 MLS
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock.

27 Beach Road, Oak Bluffs
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 22603994 MLS
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to cover costs(to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

2 Winemack Street, Oak Bluffs
$1,255,000
3 Beds ⋅ 2 Baths ⋅ 22603967 MLS
Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint. Natural light floods the house from the bank of windows in the living room to the sliding glass doors in the dining area leading to the deck. A spacious garden shed with a front porch and electricity complete the yard. Plenty of room for a nice pool to make those summer days extra special.

11 Stanley Street, Oak Bluffs
$1,225,000
1 Beds ⋅ 2 Baths ⋅ 22603763 MLS
This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, provides flexible space for two additional overnight guests, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious primary bedroom, a large open loft that can serve as an additional living or sleeping area, and a second full bathroom. Adding even more value, the home is equipped with transferable solar panels .

323 County Road, Oak Bluffs
$425,000
73560451 MLS
Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails, town beaches, and ferry landings. Bring your vision, architect, and builder to create a bespoke sanctuary in one of the Vineyard's most vibrant communities.The property is limited to 1 bedroom and has no Title V bathroom limit.

Heather Ln, Oak Bluffs
$1,750,000
3 Beds ⋅ 4 Baths ⋅ 22603069 MLS
GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10' stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, Oak Bluffs
$1,745,000
2 Beds ⋅ 1 Baths ⋅ 22603245 MLS
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.

11 Beach Road, Oak Bluffs
$5,100,000
22602561 MLS
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.

7 Overview Lane, Oak Bluffs
$549,000
22602745 MLS
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 MVC-approved plans by Sullivan & 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.

112 Dukes County Avenue, Oak Bluffs
$1,199,000
3 Beds ⋅ 2 Baths ⋅ 22602630 MLS
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.

47 Winemack Street, Oak Bluffs
$869,000
1 Beds ⋅ 1 Baths ⋅ 22602409 MLS
In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled bathroom with tub shower enclosed shower. 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.

37 Circuit Avenue, Oak Bluffs
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