$1,529,659Average Value$1,021Average Price per Sq Ft52Homes For Sale
Historic 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.
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 85 days on the market compared to the national average of 57 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,424,500, up 30% from the median home sale price over the previous 12 months.
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features 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
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
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 — featuring upgraded systems and finishes that
Welcome to # 0 Temahigan Ave & 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
Welcome to # 0 Temahigan Ave & 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
Build your Martha's Vineyard dream home on this exceptional 1.068-acre parcel in Oak Bluffs. This offering includes approved plans for a six bedroom septic system, saving valuable time in the building process. A topographic/boundary map and soil test included, providing a solid foundation for planning your future home. Subject to the Town of Oak Bluff's zoning requirements and permitting, this
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—creating an inviting connection between indoor
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 -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
Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and
Lisa SheehanBerkshire Hathaway HomeServices Robert Paul Properties
Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living
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
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
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
AVAILABLE SUMMER 2026: JULY 12-AUGUST 9. 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
Allison Cameron ParryDouglas Elliman Real Estate - Nantucket
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.
**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. 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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