A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and basement with stylish finishes throughout. Originally crafted in the Victorian era and thoughtfully restored for contemporary living, this home enjoys an unbeatable setting and is steps to beaches, ferries, restaurants, galleries, and all the conveniences of downtown Oak Bluffs.Whether cherished as a year-round residence summer retreat, or a high-demand rental, this Ocean Park home offers exceptional walkability and an unrivaled island lifestyle in one of Oak Bluffs’ most coveted locations. This listing is for Parcel One of the current Deed. The assessed value is yet to be properly recorded.
Courtesy: Anchor Realty of MV
508-696-7777
Downtown Oak Bluffs located in the Copeland District this Victorian home combines historic charm with modern comfort. Offering 6 spacious bedrooms and 3.5 bathrooms, this home provides ample living space for family and guests. Also making an ideal rental property Sleeping 12 comfortably just a block to the restaurants and shops of Circuit Ave. and a couple of blocks to the beach it's the perfect location for leaving your car behind and enjoy the best the Island has to offer at your doorstep. With a three-sided porch overlooking Hartford Park, one of the many grassy parks throughout the historic Copeland district perfect for entertaining, dining al fresco or just relaxing outdoors on the many rocking chairs. Classic design details are paired with thoughtful updates, including heat and insulation creating a residence that is both inviting and functional all year round. This property is ideal for those seeking a home with character, location, and enduring appeal.
An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining room. The kitchen is at the back of the house with the mudroom and side entrance beyond. Enjoy the beautiful natural light in the spacious sun room at the front of the house with French doors leading to the side yard. The property offers charm and potential in a sought-after location. Several updates were completed in 2010 such as a new roof, windows, and siding (see full list in documents section). The property is being sold “AS IS”. There are 2 existing cesspools on site that failed inspection. Per the Oak Bluffs Wastewater Department, the property can tie into Town sewer.
Courtesy: Sandpiper Realty Inc
508-627-3737
Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and abundant natural light throughout, this move-in-ready home blends comfort and style. Ideal for year-round living or seasonal retreat.
Courtesy: Sandpiper Realty Inc
508-627-3737
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.
Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush landscaping with stone walls, specimen trees, and a goldfish pond with a waterfall. Additional amenities include a pool house, a detached one-car garage/workshop, an oversized two-car garage, and a full basement—perfect for extra storage or hobbies. With private access to Lagoon Pond, this park-like property offers the ultimate blend of indoor-outdoor living and tranquility. A rare Vineyard gem designed for entertaining, relaxation, and easy island living.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
NEW CONSTRUCTION ~Welcome to Lagoon Ridge, Oak Bluffs' newest and most sought-after neighborhood. Build your 3-bedroom dream home in this elevated enclave, set 95 feet above Lagoon Pond and capturing sweeping sky views, colorful sunsets, and refreshing sea breezes. This exceptional home site represents one of the final opportunities in this thriving new community.To be built -- The Naushon -- features 3 bedrooms, 3.5 bathrooms, and over 2,400 square feet of thoughtfully designed living space. A grand wrap-around covered porch provides a welcoming entry and the perfect place to enjoy morning coffee or cool evening breezes. Inside, the open-concept floor plan connects the chef's kitchen with spacious living and dining areas, ideal for entertaining family and friends. Each bedroom suite includes a tiled en-suite bath with customizable fixtures and finishes, and the second-floor suites may offer private balconies for added relaxation. Classic Oak Bluffs cottage architecture meets modern comfort and energy efficiency, making The Naushon an ideal year-round or seasonal retreat. Lagoon Ridge offers direct access to conservation lands with walking and biking trails, and nearby Lagoon Pond invites kayaking, sailing, and shell fishing. All utilitieselectric, town water, and a private, state-of-the-art Amphidrome wastewater systemare located at the street. This innovative system serves the entire neighborhood, providing convenience and peace of mind. Lagoon Ridge is a covenant-protected community with architectural review and professional management by First Property Management Co. This beautiful home site is ready for the construction of your Vineyard dream home. Eleven lots have soldonly two remain available. Call for details!
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 make it as cozy in winter as it is bright and breezy in summer. Enjoy easy access to Oak Bluffs Harbor, beaches, restaurants, shops, and all the vibrancy the town has to offer, just moments from your front porch. Ownership includes membership in the MVCMA, providing access to this unique and storied community with its stunning Tabernacle, charming cottages, and welcoming sense of place. Lovingly referred to as Fun Size and Baby Vineyard, by previous and current owners, this is a rare find — timeless and truly one of a kind.
Courtesy: Island Real Estate
508-693-4800
Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. Owners are offering a $25,000 credit at closing to assist with the costs of the new septic system. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations.
Courtesy: Sandpiper Realty Inc
508-627-3737
Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property, affords a private retreat or additional space for family and friends. Nestled in the heart of East Chop--a close-knit, sought-after community--this property is just a short distance from pristine beaches, the active harbor front, and vibrant downtown Oak Bluffs. A happy home, ready to welcome new memories and lasting moments.
Courtesy: Anchor Realty of MV
508-696-7777
Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The basement with over 1100 square feet of addition finished space could have a third bedroom if you install the correct window in compliance for a bedroom. Presently there is a 3 bedroom septic installed. The large yard has a lot of potential. Close to the Oak Bluffs school and town center. bedroom septic system, offering flexibility for future expansion. Outside, enjoy the large yard with plenty of room for outdoor living, gardening, a deck, outdoor shower and lots of room for adding a patio or firepit. Whether you're seeking a year-round residence, vacation getaway, or investment property, this Oak Bluffs gem offers island living at its best central, spacious, and move-in ready.
Courtesy: Island Real Estate
508-693-4800
Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full bath. Enjoy seamless indoor-outdoor living from the expansive wrap-around deck. After a day at the beach, rinse off in the convenient outdoor shower. A spacious, barn-style shed provides ample storage or potential workshop space. Located in the R1 zoning district and also in Zone 2, the property is subject to 20-foot setbacks on all sides. It is a pre-existing, non-conforming lot, so any structural additions will require approval from the Zoning Board of Appeals. The septic system has passed Title V inspection and is certified for two-bedrooms, which aligns with current zoning limits. Conveniently situated near the Lagoon, bike path, Oak Bluffs Elementary School, and the Public Library, this property offers both practicality and charm in a so
Courtesy: Sandpiper Realty Inc
508-627-3737
Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers more than 3,200 square feet of comfortable living space. This home is ideal for those who love to host lively gatherings while providing ample accommodations. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary suite with double walk-in closets and a private ensuite bath. The main living space includes a traditional living room with fireplace that flows easily into the open kitchen and dining space, creating a natural gathering spot. The large screened-in porch extends the living space outdoors and is a true highlight--perfect for unwinding or entertaining under the stars. A second living room or media space offers even more flexibility for work or play. The full basement presents great storage or finishing potential, and there is also an attached two-car garage. Set on a private, landscaped lot, this home offers both convenience and community perks, including association tennis courts and quick access to the bike path. Just minutes to Farm Neck Golf Club and the shops, restaurants, beaches, harbor and all the enjoyment Oak Bluffs has to offer. shops, restaurants, beaches, harbor and all the enjoyment Oak Bluffs has to offer.
Experience the elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s finest beaches. Clad in red cedar clapboard siding with an asphalt roof, the residence sits quietly above and across from Lagoon Pond, where you can enjoy water views and access to fishing, boating, kayaking and paddleboarding. The home is a harmonious balance of indoor comfort and outdoor connection. Inside, the thoughtful spacious design layout includes multiple private suites ideal for guests or multigenerational living, cherry floors and Douglas Fir doors and trim. Elevator, media room, wine cellar, fully equipped gym, lush landscaping, infinity pool, spa and waterfall - this luxury property has it all!
Courtesy: Ocean Park Realty, Inc.
508-693-4210
FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf Club. This exceptional property is situated between the 7th and 8th fairways and is just a short walk to the clubhouse restaurant, tennis courts and pro shop. For water enthusiasts there is the opportunity to have a mooring, with Harbor Master approval, off the private beach on Sengekontacket Pond giving you direct boating access to Nantucket Sound. Although this historic home features 5 bedrooms with 4.5 bathrooms and lots of intimate spaces, there is still plenty of room on the property for expansion of the main residence......with the existing detached garage/apartment, this country estate is truly an Island treasure that will provide lots of recreational enjoyment for family and friends throughout the years.
Courtesy: Anchor Realty of MV
508-696-7777
Oak Bluffs -East Chop-Close to the ocean. Two 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.
PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED INSIDE AND OUT. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new heat/AC systems for year-round comfort. Recently installed professionally landscaped grounds offer curb appeal and outdoor enjoyment, complete with shower and patio furniture for al fresco dining and relaxing. Also included are ALL FURNISHINGS and a handy owner’s shed for extra storage. An exceptional value just moments from downtown Oak Bluffs and Beaches. 5 minute walk to Harbor and Library. Rental history $1000. per night. (Not part of the Campground Association).
Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite.The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additional bedrooms, create ample space for guests to luxuriate and relax. Lower level includes game room and gym. Outside, enjoy a sprawling lawn, decks, lush landscaping, and two outdoor showers. Close to East Chop Beach Club, Tennis Club, Yacht Club, Ferry, and Oak Bluffs shops. Be the envy of all you see!
Courtesy: Island Real Estate
508-693-4800
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.
Courtesy: MV Luxury Homes, LLC
973-789-1264
East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water (see floor plans). The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include crown molding, new kitchen and bathroom (with handicap accessible shower) both with Italian Carrara subway tile. Occupancy beginning Nov. 1st, 2025. New condominium pending buyer approval of condo docs.
Courtesy: MV Luxury Homes, LLC
973-789-1264
East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service and house keeping available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condo documents. Available for showing with 24-hr notice until June 15th, thereafter Satruday's 10-12.
Courtesy: MV Luxury Homes, LLC
973-789-1264
East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with fireplace, dining area and a private covered front porch over-looking the water (see floor plans). The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service and house keeping available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval. Available for showings with 24-hr notice until June 15th, thereafter Saturday's 10-12.
Courtesy: MV Luxury Homes, LLC
973-789-1264
East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock with water/electric for 8 slips and a 40' T at the end for a 9th boat; Each condo unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service available. Sold with furniture depending on price. Occupancy available beginning Nov. 1st, 2025. Available for showing with 24-hr notice until June 15th, thereafter Saturday's 10-12.
Live the Dream on Martha’s Vineyard! Step into a world of coastal luxury with 163 feet of pristine Lagoon frontage, complete with your own private sandy beach. Nestled on 1.25 acres of lush, landscaped paradise, this rare gem offers sweeping lawns, panoramic water views, and breathtaking sunsets. Nearly every room in this spacious, 4046 square foot home is designed to showcase the water’s beauty. The main level boasts soaring ceilings and uninterrupted Lagoon views. The eat-in kitchen opens to a sun-drenched patio, while a separate wing offers two versatile rooms with a private deck and full bath. On the upper level, the primary suite is a sanctuary unto itself, featuring a fireplace, en-suite bath, and a private deck overlooking the Lagoon. Two additional en-suite bedrooms share the same stunning views and access to a wraparound deck and screened porch. The refinished walk-out basement includes a full bath and laundry. Sold fully furnished, this home is ready for you to move in.
Courtesy: Today Real Estate
508-790-2300
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.
Oak Bluffs is located in Massachusetts. Oak Bluffs, Massachusetts has a population of 5,284. Oak Bluffs is more family-centric than the surrounding county with 39.56% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Oak Bluffs, Massachusetts is $94,545. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Oak Bluffs is 40.4 years.
The average high temperature in July is 78.9 degrees, with an average low temperature in January of 22.7 degrees. The average rainfall is approximately 47.4 inches per year, with 24 inches of snow per year.
