$1,501,326Average Value$952Average Price per Sq Ft37Homes For Sale
Historic Black vacation destination
Oak Bluffs is known for its whimsical gingerbread houses, port of entry to Martha’s Vineyard and storied history as a summer refuge for Black Americans. This down-island town, in the geographic northeast of the island, is where tourists exit ferry boats during the summer high season, a phrase typically shortened to just "during season" by beach town locals. It's where gray-shingled beach houses look out into the Nantucket Sound, where people buy T-shirts and fresh doughnuts along Circuit Avenue and where the wind blows so hard that it’s easy to see why Massachusetts considered installing wind turbines on Cape Cod to create renewable energy.
Driving north into the center of Oak Bluffs over the bridge featured in “Jaws,” a concrete wall blocks ocean access on the right, and gray, weather-worn shingled houses sit on the left overlooking the water. Unlike buttoned-up Edgartown, where the white paint on picket fences is always fresh, shorefront Oak Bluffs homes feel like they’ve been kissed by the beach, as if the rumbling Nantucket Sound waves washed over the whole town at some point without causing damage.
Oak Bluffs has been a summer haven for the Black community for generations. In 1912, island property owner Charles Shearer, born enslaved in Virginia, opened Shearer Cottage, an inn catering to Black families who were not welcome elsewhere. The resort did well and operates today as the Inn at Shearer Cottage. In a 2023 essay for Martha’s Vineyard Magazine about the island as a reprieve for Black Americans, the writer Bijan C. Bayne described Martha's Vineyard as a “race machine” that instantly removed the prejudices that Black people face in their daily lives, where they could just be, and relax, without having to worry. “It was a place where I didn’t have to think about my complexion every day, and where my friends were far less likely to be judged by theirs,” Bayne wrote. Still, the island’s population is predominantly white. The population of Dukes County is 89% white, 5% Black, nearly 4% Hispanic or Latino and 1.4% Asian. Every year in August, Oak Bluffs hosts the Martha’s Vineyard African American Film Festival and a fireworks show.
The Overton House is a historic landmark just a short walk from downtown Oak Bluffs.
Visitors flock off the ferry and into the streets of Oak Bluff.
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Flying horses and live bands at a dive bar
The commercial district in Oak Bluffs is steps from where visitors exit ferry boats during season. It’s a relaxed area where pizza parlors, ice cream shops and clothing stores do business on the ground floor of what look to be residential buildings. Just before season starts in May, the town is flooded with construction workers and painters putting the finishing touches before all the tourists come. Construction workers come from off-island spots like New Bedford, says Lisa Lucier, owner and broker of Anchor Realty in Oak Bluffs. “If you got to the boats at 3 or 4 p.m. when they’re done for the day, they’re full of people getting on with their lunch box or whatever they’ve got with them,” she says.
Cafes like Aalia’s serve breakfast and coffee to caffeine-deprived customers. Aalia’s has a handful of small indoor tables and some seats by the window, not nearly enough to fit the lines of 80 or so people that stretch out the front door during season. Linda Jean’s Restaurant is open year-round, serving jerk chicken, oxtail and quarter-pound lobster rolls. The Flying Horses Carousel, which originated in Coney Island, is the oldest platform carousel in the U.S., and it sits inside a tiny red building near a median sign welcoming people to Oak Bluffs.
On nights and weekends, there’s the Ritz Café. It’s a dive bar and live music venue where people come for shows and Tuesday night karaoke. On Wednesdays, local bands like Johnny Hoy & the Bluefish crowd into the side of the joint and play bluesy dance music. The bar pours beers from breweries like Allagash and Maine Beer Co. The Sweet Life Café, an upscale eatery, is open year-round.
Grab the brass ring for a free ride at Flying Horses Carousel in Oak Bluffs
Listen to live music at Aalia’s in Oak Bluffs.
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Whimsical Victorian homes in Martha's Vineyard town
Across from the town beach is Ocean Park, a rolling, hilly park. It’s vast and open, overlooking the shoreline, and people walk through it via paved pathways and sit on benches. Whimsical Victorian homes with turrets and front porches surround the park, but the truly fantastical Oak Bluffs homes are at the Martha’s Vineyard Camp Meeting Association. This historic district of about 300 homes started as a summer religious camp for Methodists, who lived in tents and eventually built cottages. Known as “gingerbread houses,” the cottages come in bright colors like blue, pink and purple and have names like “the Purple Lady.” Property owners lease their land, Lucier says, and about five or six gingerbread houses hit the market per year. “I just sold one, the last one I think that sold, maybe in February. It’s two houses and it sold for $700,000. It needed a lot of work. It was built in 1897,” she says.
The gingerbread houses sit one next to the other, circling a park, an outdoor tabernacle and the United Methodist Church of Martha’s Vineyard. Parking is limited. Elsewhere, on skinny paved streets near the beach, sit gray-shingled beach cottages, and the town also has Cape Cods and farmhouses in rural neighborhoods. Home prices range from about $800,000 to $8.4 million.
Incredible craftsmanship can be seen in this victorian Oak Bluffs home.
A row of fantastical Oak Bluffs homes are found in Martha’s Vineyard Camp Meeting Association.
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After school activities and health care services
Locals can walk on a sandy pathway along the Nantucket Sound, where they can look out into the water and smell the fresh ocean air as the waves crash at their feet. They can ride bikes over the bridge that connects Oak Bluffs with Vineyard Haven. They can go to one of many beaches with assertive waves, like Inkwell Beach or Oak Bluffs Town Beach on the Nantucket Sound, or Eastville Beach on Lagoon Pond. Away from the center of town, teenagers practice their tricks at the skate park across from Martha’s Vineyard Regional High School and hang out after school at the YMCA.
Mass General Brigham Martha’s Vineyard Hospital, the island’s main health care facility, sits within Oak Bluffs. The hospital has an emergency room, an intensive care unit, cardiology services and more. The affiliation with Mass General Brigham has helped the island, says Lucier. The partnership gave Martha’s Vineyard Hospital access to a broader continuum of care, and doctors within the Mass General Brigham health care system can transfer. Lucier says she had cancer and received most of her treatment on-island. She only had to go to Boston for surgeries. “That was so much part of the care, because if you have to get in a car, drive to the boat, take the boat back home, that would have probably did me in,” she says.
Joseph Sylvia State Beach offers miles of coastline for residents of Oak Bluffs.
Catch your dinner from Oak Bluffs Fishing Pier in Oak Bluffs.
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Blue Ribbon high school on Martha's Vineyard
Each Martha’s Vineyard town has a public elementary school. Oak Bluffs Elementary School serves prekindergarten through eighth grade and has a B-rating from Niche. Martha’s Vineyard Regional High School serves the entire island and has a B-plus from Niche. The high school has about 700 students and is a two-time National Blue Ribbon School award winner.
Oak Bluffs Elementary School received an overall B rating from Niche.
Martha's Vineyard Regional High School got a B+ for academics by Niche.
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Ferrying around during season
During season, ferry boats shuttle passengers between Oak Bluffs and Nantucket, Woods Hole and North Kingstown, Rhode Island. The year-round ferry to the island is in nearby Vineyard Haven. Driving to Vineyard Haven takes 10 minutes, the ride to the center of Edgartown is 15 minutes and Martha’s Vineyard Airport is 15 minutes away.
The ferry steams past Dockside Beach in Oak Bluffs
Cape Air makes it easy for Oak Bluffs residents to get on and off the Island.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Oak Bluffs
US
Homicide
3
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
1
4
Motor Vehicle Theft
1
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Oak Bluffs Demographics and Home Trends
On average, homes in Oak Bluffs, Marthas Vineyard sell after 88 days on the market compared to the national average of 55 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,295,000, up 13% from the median home sale price over the previous 12 months.
The ambience of this tranquil Waterfront community will inspire you immediately. This spacious 3 bedroom w/oversized family room home is affordably priced. The sun shines in the charming living room w/ brick fireplace, Palladian side windows, Rennai gas monitor & attractive hardwood floors. The ample chefs kitchen extends w/L shaped counter & snack bar. The dining area is adjacent creating an
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
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
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
Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The
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
Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features
COMING SOON: HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes throughout. Community amenities include a private boat dock, walking trails, pickleball and tennis,
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 —perfect for
This beautifully updated four-bedroom, two-bath home combines thoughtful design with quality craftsmanship. The open floor plan features reclaimed wood floors and custom built-in cabinetry. The stunning kitchen with handcrafted cabinets and stainless steel appliances features slate flooring from Vermont and PaperStone® countertops. Every detail was intentionally chosen, as the owners lovingly
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
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—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an
Turnkey modern home with 4 bedrooms and 3 full baths, filled with natural light from large windows and soaring ceilings. The first floor offers three bedrooms and a full bath with double sinks, while warm oak and maple floors are accented by cherry stairs and custom built-ins.The open-concept second level features a spacious kitchen, living, and dining area, along with a private primary en suite
**SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor
Allison Cameron ParryDouglas Elliman Real Estate - Nantucket
Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and
Allison Cameron ParryDouglas Elliman Real Estate - Nantucket
**SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and
Allison Cameron ParryDouglas Elliman Real Estate - Nantucket
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.
THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.
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