Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with Dukes County Registry of Deeds in Book 278, Page 144. The plan indicates that it "contains 10,033 sq. ft., more or less". Located in Zone 2, it should meet all criteria to allow for a 1-bedroom septic system. All engineering will be the BUYER'S responsibility.

Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby.

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. The Island Inn is seasonal, welcoming guests from April through October.

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 Martha’s Vineyard Commission–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. Some photos virtually altered for seasonality.

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 Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is inside the Zone II district, which will require a microfast septic system (buyer to confirm). The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 10,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity.

Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either an Enhanced Septic System or Advanced Treatment System, or alternatively, a 2-bedroom home equipped with a Title 5 septic system. Prospective buyers are encouraged to confirm building options and requirements with the Town of Oak Bluffs. Attached documents for buyers review.

Oak Bluffs Buildable Lot – Prime Location This flat 3-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 Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is outside the Zone II district, so a standard Title V septic system should be permissible (buyer to confirm). The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 15,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity.

GOING, GOING… GONE! This is the LAST 3-bedroom lot available in Cluster C. 12 lots SOLD 9 homes already built. Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes. The lot is ready for development with utilities at the site, including town water, electric, and a private Amphidrome wastewater system, eliminating the cost and maintenance of a traditional septic system.Lagoon Ridge borders acres of pristine conservation land with direct access to scenic biking and hiking trails, providing the perfect balance of privacy and outdoor recreation. Ideally located in Oak Bluffs and central to all down-Island towns, this vibrant neighborhood continues to grow with strong construction momentum. Easy to show contact agent for a private tour..

Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue! Title 5 Certification in place for existing one bedroom septic system. Lot is in Zone II and will allow a total of two bedrooms with an advanced treatment system. Land is large enough to have a house and guest house when meeting ZBA requirements or with new Massachusetts Accessory Dwelling Unit law. A short stroll, just one house away, from Wesleyan Park. Close to town, restaurants and all that Oak Bluffs has to offer! Walk to the harbor! This is a little gem, waiting to be polished!! Property is being sold in "As is" condition. Easy to show!!

OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha’s Vineyard’s most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value & BUILDING PERMIT in place for an ADU. Ready to go!!

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 of Downtown Oak Bluffs. Sit back and watch the boats come into the harbor at one of the many seating areas or enjoy diner al fresco under the stars. This spacious unit has many custom wooden features including a staircase leading to the rooftop deck creating a storage area and sleep nook with daybed. Take a step down to the comfortable living area. With hardwood floors throughout, the kitchen and dining area are divided with custom cabinetry. The spacious bedroom has an additional alcove area with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. A separate Laundry room is shared by 2 other units.

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 relaxing or entertaining. Additional highlights include in-unit laundry, dedicated parking, a storage area, a new septic system (2025), and low HOA fees. Ideally located near Farm Neck Golf Club, Felix Neck Wildlife Sanctuary, scenic bike paths, and the down-island towns, this inviting property offers the best of coastal living.

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 with glass enclosed shower, and a large primary bedroom that's over 16'x21'. 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!

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. Enjoy this house as it is or work through the process to create something new. 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.

Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous .69-acre lot. Built in 2014, the property presents an excellent opportunity for a year-round residence, vacation getaway, or investment. The property is being sold as is. Buyers and their agents are encouraged to perform their own due diligence and verify any potential for expansion or additional improvements with the Town of Oak Bluffs. All buyer’s agents must submit proof of funds with any offer.

HEAD START BUILD OPPORTUNITY IN OAK BLUFFS WITH POTENTIAL WATER VIEWS OF THE VINEYARD HAVEN HARBOR. Rare opportunity to secure a prime parcel in a sought-after Oak Bluffs location with valuable groundwork already in place and potential views of Vineyard Haven Harbor. The property features an existing foundation and on-site materials, offering a meaningful head start for buyers looking to build and streamline the construction timeline. Whether you are a builder, investor, or end user ready to create a custom Vineyard home, this offering offers the chance to step into a project already underway -- saving both time and early-stage costs. Set in a well-established neighborhood with strong surrounding property values, this is an ideal location for a thoughtfully designed residence or investment build. A unique opportunity to capitalize on both land value and forward progress in one of Martha's Vineyard's most consistently desirable markets. Plans for the residence under development are expected to transfer with the sale, along with associated approvals, permits, and an approved septic design, offering a clear path forward while preserving flexibility for customization.

Oak Bluffs: Home Sweet Home Situated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom and a spacious second-floor primary bedroom with a private deck. The finished basement provides additional living or hobby space. Updates include a 2017 oil burner and Roth oil tank. An inviting outdoor shower completes this well-maintained home, offered furnished and ready for your personal touches. Located in a quiet residential neighborhood close to all that Oak Bluffs has to offer.

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.

Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure year-round storage. Conveniently located near Farm Neck Golf Club, downtown Oak Bluffs, and more. Easy access to all island destinations via County Road and Barnes Road. Perfect blend of practicality and charm for seasonal or year-round use. Flexible leasing, partnership, or investment opportunities available.

Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank flooring, as well as two comfortable bedrooms and access to a screened-in porch, perfect for relaxing summer evenings. Upstairs, you’ll find two extra large bedrooms and a shared bath, providing flexible space for family and guests. The enclosed backyard is well suited for gardening, entertaining, or simply enjoying the outdoors, while the nearby Lagoon town landing offers easy access for kayaking, canoeing, or launching a small boat. Ideally located walking distance to the Lagoon, less than one mile to Farm Neck, and under two miles to the heart of Circuit Ave and all Oak Bluffs has to offer. This inviting home also offers easy bike access to the Oak Bluffs School and Tradewinds. A full, unfinished basement provides excellent potential for future expansion or storage.

PRIME LOCATION! 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 extended shoulder season comfort. 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-min walk to Harbor and Library. Rental history $1000. per night (Not part of the Campground Association). OVER $100,000. GROSS RENT POTENTIAL EXCEPTIONAL! SEE "DOCUMENTS" FOR LONG LIST OF IMPROVEMENTS. AIRBNB HISTORY. $89,000. in rental income booked so far for Summer 2026.

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 open gathering area for family and friends. The French doors to back deck provide additional grilling or sunning opportunities in the warmer months-+ essential outdoor shower. A desirable first floor bedroom is adjacent to a full bath and additionally there’s a very big family room w/access to the side porch. Head up the skylight lit staircase & you’ll find 2 oversized bedrooms w/high ceilings & skylights - each generous enough for sleeping area & sitting/work area. There’s is another full bath w/double vanities and access from each bedroom. Downstairs the full basement is partially finished (bead-board walls) & was previously used as a family rec room w/lots of storage. Definitely a great space to complete!! Landscaped irrigated grounds w/grassy back yard, mature plantings of Rhododendrons, flowers, & a peek at the water add to the ambience of this peaceful neighborhood. Walking the wooden paths spilling over the salt marshes is a Zen-like experience w/just you & the birds singing. You’ll come to kayak racks and dinghy dock - Private Community access to Sengenkontacket Pond. A beautiful spot! Winter boat storage and private community tennis courts are also amenities for this upscale waterfront neighborhood! Priced to SELL! 24 HR NOTICE NEEDED FOR TENANTS PLEASE.

Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room highlighted by an impressive wall of windows that fills the space with sunlight and frames serene views of protected pastoral land. The open-concept kitchen, dining, and living areas are anchored by a striking fireplace, creating an inviting setting for gatherings. Just off the kitchen, a charming, screened porch offers a cozy three-season retreat, perfect for morning coffee or evening relaxation. The main level includes three generous bedrooms and a full bath. while the walk-out basement provides a workshop area with sink and storage room. Outside, the property is thoughtfully landscaped with irrigation with mature rows of Arborvitae trees, giving it a private, park-like feel. A back patio and a detached office offer additional spaces to work, unwind, or take in the peaceful surroundings. Conveniently located, this property is within walking distance of the Oak Bluffs School, the Tradewinds walking trail just across the street, bike paths, and public transit. Downtown Oak Bluffs and the beach are only minutes away- an ideal combination of privacy, convenience, and potential. This lot could provide potential options for future enhancements such as expanded living space, a garage, guest house/ADU… Building possibilities should be explored and reviewed in accordance with town bylaws. Note: The property is being sold as-is, and the buyer will be responsible for replacing the existing septic system.

Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an idyllic open field. This house is perfectly set back off of the small cul de sac. Wonderful location provides easy access to town. This classic cape offers three bedrooms, two baths plus an open loft area. The new kitchen boasts a slider to the deck and pool. A cathedral ceiling in the living room provides a spacious open feeling. Two bedrooms with a full bath complete the first floor. Upstairs is the large main bedroom, a full bath and a lovely loft area. Adding to the allure of this fantastic home is a two room finished basement area. This house has everything one could hope for.

Tucked away in a private desirable Oak Bluffs neighborhood yet only minutes from the charm of downtown and the incredible OB beaches, this home is a wonderful island retreat. The neighborhood is a must see to fully appreciate this property. With four levels of finished living space, it offers room to gather, relax, entertain in any season. Hardwood floors, open concept kitchen and living areas, crackling fireplace set the tone indoors. Step outside and you’ll discover a backyard designed for relaxation or entertaining—mature plantings, a built in exterior fireplace that invites long summer evenings, mahogany deck, brand new cedar fence that adds ultimate privacy and a wood-fired pizza oven ready for family feasts. The paved circular driveway offers plenty of space for the boat! Every corner of the property has been carefully maintained and thoughtfully updated, from the roof (2019) to the windows and doors (2020) to the beautiful cedar fence (2024) and all interior paint (2022), so all you have to do is settle in and enjoy. Here, you can bike into town for morning coffee, spend the afternoon at the beach, and return home to evenings under the stars. This house is move in ready and a rare opportunity in this wonderful neighborhood.

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 comfort and outdoor living. The first floor also includes a bedroom and a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus thoughtfully outfitted with a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use, or a private retreat. Surrounded by beautifully manicured grounds, the property is enhanced by lush plantings and a charming stone wall that adds to its sense of privacy and character. Two garden sheds provide practical storage while complementing the property’s well-kept outdoor spaces. Ideally located in the heart of Oak Bluffs and just moments from MV Regional High School, Performing Arts Center and YMCA, this inviting home offers both tranquility and accessibility, making it a wonderful opportunity to enjoy the very best of Martha’s Vineyard living. Strong rental history!

Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property includes a newly beautifully renovated 2 bedroom 2 bathroom guest house. This guest house is offered fully furnished. This listing documents include a custom landscape design plan. This very large parcel of land is well suited to get started building an investor dream or family compound.

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 Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a full bathroom with tub and storage area. This home and its established gardens have been lovingly maintained, and its location in a delightful neighborhood of highly sought-after East Chop, gives you all that Martha's Vineyard living can offer. Passed Title V Inspection.

Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features abundant counter space and opens to the dining area, with sliding doors leading to a back deck and yard—perfect for entertaining or relaxing.Lovely blue stone patio in the back yard. Radiant heated floors bring cozy comfort to the primary master suite and basement playroom. There is a two-car garage with bonus space above. The driveway parking area has lovely stonework in front of the garage. The furnace was replaced in 2020 and the water heater was replaced in 2024.

Being sold turnkey this modern home has four bedrooms and three full baths. Large windows and high ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the open concept kitchen, living room, dining room. The primary en suite includes full bath, Jacuzzi tub and shower, walk-in closet and dressing area. Three sliders lead onto a large sunny deck from the living area, great for alfresco dining, lounging and entertaining, extending the large living space. A fourth slider accesses the deck from the primary bedroom. Building into the hillside, the builder made use of topography resulting in a third level of fully usable living space. Along with eighteen foot ceilings, multiple windows and glass back door, the basement also includes a third full bath and utility room. This surprising third level would make a fantastic recreation / media room / playroom / home office. This home is being sold in "as is" condition. Located in a private community with wonderful amenities such as tennis, pickleball, mail delivery, freshwater pond, clubhouse, and kayak storage with access to a salt water dock and boat landing. Potential for a boat mooring via the Oak Bluffs Harbormaster! Great central location near Farm Neck Golf Club with easy access to all island Towns, shopping, beaches, restaurants and entertainment.

Two Historic Oak Bluffs Cottages - Prime Location – Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout. Built at a time when automobiles were rare, these homes were sited with ease of access in mind. Though they have no driveways, convenient on-street parking is always available—local residents often find it easier to stroll, or bike, into town than drive. Both homes are separately deeded, giving you the flexibility to own them jointly or individually, and the ability to create a compound with rental options. They are fully furnished and move-in ready, with a long history of use as rentals and community housing. Whether you're looking for a full-time residence, income-generating property, or a flexible retreat for extended family or friends, these cottages provide a unique and practical setup—ideal for dual living or multi-generational use. Set against a backdrop of cool breezes and peaceful surroundings, these modest yet solidly built mirror image cottages feature warm, weatherproof interiors, ground-level entries, and ensuite bathrooms. While they may not compare in size to modern builds, their simplicity is part of their charm—and their history is unmatched. The Hughes family, who once lived here, famously hand-dug full basements in both homes in the late 1920s—a remarkable feat in a neighborhood where most homes sit on crawl-spaces. This added space offers valuable storage, office, or expansion options rarely found in similar homes of the era. With a strong local school system, a welcoming neighborhood, and the charm of yesteryear combined with present-day comfort, these homes are an ideal place to put down roots, invest in community, or create a home-away-from-home. Keep them as they are, or add your own touches.

A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invites you to experience the essence of Oak Bluffs! The main house, dating back to the 1850s, has been well maintained, preserving its period architectural details while incorporating modern updates, including an updated kitchen with a walk-in pantry. At the heart of the home, a classic stone fireplace anchors the living and dining areas, creating an inviting gathering space. On the second floor, the primary suite gives a sense of grandeur and charm, with a vaulted ceiling, chandelier and multiple closets. The bathroom includes a soaking tub and separate water closet. Two more bedrooms and a shared full bath provide comfortable accommodations for family and visitors. The second floor is thoughtfully centered around a laundry area, complete with an additional third shower for added convenience. The guest cottage is a sweet retreat~ built in 1999. The first floor features a full kitchen, living room, and half bath, along with a convenient stackable washer and dryer. Upstairs, the second floor offers a one-bedroom layout with an adjoining dressing room or office area that leads to a full bath. Hardwood floors run throughout and forced hot water heating allows for comfortable year-round use. The guest house and the main house share the rear deck, and an outdoor shower that's perfect for island living. The properties are connected to town sewer and equipped for year-round use with a heating and A/C Viessmann system for efficiency. When in bloom, blue hydrangeas frame the properties, enhancing their classic Vineyard charm. Both homes feature quintessential front porches, ideal for greeting neighbors and enjoying the island community. This an opportunity to become a part of this enduring legacy and create lasting memories for generations to come. With a strong rental history, this property presents a great investment opportunity too!

Would you love to live or vacation in a brand-new home on Martha’s Vineyard? We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD! Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood. Easy to show – Call now! To be built with lot purchase $695,000 and building contract approximately $1,550,000. This 3-bedroom dream home is set in an elevated enclave 95 feet above Lagoon Pond, 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 utilities—electric, town water, and a private, state-of-the-art Amphidrome wastewater system—are 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 sold—only two remain available: 2 Hopes Way and 35 Double Ox.

NOW SHOWING! 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, all conveniently located near Oak Bluffs and the Island’s other towns. Designed to accommodate family and guests with ease, the home features a sun-filled living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows, skylights, and glass doors leading to the deck. The chef’s kitchen is appointed with gorgeous stone countertops, custom cabinetry, and Dacor® appliances. The second-floor primary suite includes space for a sitting area or office, a private balcony, and a stylish en-suite bath with a soaking tub and glass-enclosed shower. The garden level offers additional bedrooms, baths, and bonus space with a murphy bed for overflow guests. Outside, enjoy the serene pond views from the bluestone terrace with grilling area or from two levels of spacious decks overlooking the private yard. An attached one-car garage provides storage for and island car, beach gear and more. This property is being offered with all furnishings and over $80,000 in 2026 rental income for Summer, 2026. Don’t miss this special move-in-ready offering in one of Oak Bluffs’ most sought-after communities.

Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and 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, both inside and out. The detached studio complete with loft, full bath, AC and 2 additional garage bays below, is a private retreat for work, art, music, yoga or even for spill-over accommodations. The Chef’s kitchen boasts handcrafted cabinetry, naturally beautiful soapstone countertops, a professional Viking gas range and Miele dishwasher. The bathrooms feature custom built vanities with luxurious marble countertops and wainscoting surrounds each wall. Outside, a Zen-inspired garden, flowering hydrangea plants and a newly rebuilt oversized deck are perfect for small or large gatherings. Additional features include an elevated deck accessed from the living and dining areas, 2 wood-burning fireplaces, one being in the primary bedroom, newer mini-split units, 2 outdoor showers, optional base-board heating and hardwood floors throughout. Enjoy the Association amenities of tennis, pickleball, kayak racks, a community dock and moorings for larger boats. To truly make this a seamless transition to “Vineyard Life” the seller is open to including a Boston Whaler, a small sailboat, and an inflatable zodiac in the sale.

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A groundvfloor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together they are a combined total of just over an acre of land. Included is Deeded Access via a boardwalk leading to Brush Pond, with wonderful views. Directly in front of the property lies a sandy State Beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf & a host of activities. This property offers both tranquility and convenience in one of Martha’s Vineyard’s most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for separate purchase. Excellent Rental History. Rentals in place for 2026 Summer Season!

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, shopping, Ocean Park concerts, the OB fishing pier, and the beloved Oak Bluffs Fireworks. This is a must-see, legacy property with rare potential in a location that can’t be beat. Very easy to show. Pre-approval or proof of funds required with all offers.

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, shopping, Ocean Park concerts, the OB fishing pier, and the beloved Oak Bluffs Fireworks. This is a must-see, legacy property with rare potential in a location that can’t be beat. Very easy to show. Pre-approval or proof of funds required with all offers.

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, the 3-bedroom home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, a new kitchen, updated baths, and stylish finishes throughout. New windows and doors throughout complete this extensive renovation. 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. Also, the assessed value is yet to be properly recorded. Seller is actively correcting this issue. *Agent is related to Seller.

Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs.

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

Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s Vineyard residence. Included with the property is a highly coveted Farm Neck Stockholder Membership certificate, an extraordinary privilege that bypasses the current 16+ year waitlist and is seldom available in conjunction with a land offering. The parcel provides an opportunity to design and build a custom island home tailored to your vision. Whether a refined seasonal retreat or a legacy compound, the setting offers both privacy and access to the full Farm Neck lifestyle: championship golf, tennis, association dock, and a vibrant, established community. The property has been staked to reflect both boundary lines and the designated building envelope. Buyers are responsible for their own due diligence; please consult a qualified land engineer to confirm the potential bedroom count.

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 expansive deck, a pergola with a fireplace, and an elevated gazebo overlooking meticulously manicured grounds. Versatility is at the heart of this unique compound. With three kitchens, the home easily accommodates use as a spacious single-family residence or as three separate living quarters—ideal for multi-generational living, hosting extended guests, or generating rental income. Additional highlights include a 10-bedroom septic system in place - allowing for future expansion, an oversized three car garage, and solar. Come experience the very best of Island living.

With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the rear of the property, a private guest house—affectionately known as The Nest—has undergone a similar transformation and offers a private escape. Adjacent to the main home, the charming bunk house completes the ensemble, perfectly complementing this unique and inviting expansive compound. Though the wraparound porch invites you to linger with its endless ocean views, the nearby beaches, boutique shops, acclaimed restaurants, and the contagious energy of Circuit Avenue and the Harbor are all steps away, offering something for everyone to enjoy. For those seeking flexibility, the home’s established rental history further highlights the desirability of both the property and its coveted location. An exciting opportunity to own in one of Oak Bluff's iconic settings!

SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and connection to the outdoors. The main living spaces are both dramatic and inviting, with high ceilings, skylights, and walls of glass that frame the ever-changing water views. A central staircase and classic columns define the space, with a decorative stone fireplace providing a natural focal point and warmth. A true chef’s kitchen is equipped with stainless steel appliances, expansive stone counter space, custom cabinetry and an oversized island. A wet bar featuring a beverage refrigerator and ice maker enhances the entertaining flow, while a more casual dining area provides a comfortable setting for hosting. The home includes three spacious ensuite bedrooms. The primary suite is privately situated and enjoys water views, direct access to the pool terrace, and a luxurious bath with soaking tub, double vanity, and glass-enclosed shower. Two additional en suite bedrooms are located on the second level, along with an open sitting area that overlooks the main living room below. Designed with entertaining in mind, the lower level features a billiards/game room, den, bonus room, kitchenette, wine storage, and flexible room for a gym or additional use. Outdoor living is a highlight of this fabulous property, with a heated pool and spa set within a bluestone terrace, and an outdoor kitchen area ready for your custom design and choice of appliances. This space is perfect under the open sky with multiple areas for lounging. The calm Lagoon waters are just steps away and offer ideal conditions for swimming, paddling, boating, and clamming, with the ability to secure a mooring. The Lagoon is known for some of the best steamers, littlenecks, and cherry stones on the Island. In fact, there is a huge clam bed in the Lagoon right behind the house off the private beach. Offered furnished, with a proven strong rental history, this property also enjoys a 2-car garage and is a rare offering combining privacy, comfort, and exceptional waterfront living.

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 main residence and a two-bedroom guest house, each thoughtfully oriented to capture the ever changing light over the water. The main home offers a spacious open layout with generous living, dining, and sitting areas, ideally suited for entertaining and family gatherings and all with stunning views of the water. A large, bright kitchen serves as the heart of the home, while the living room, dining room, primary bedroom and two elevated decks provide front row seats to boating activity, wildlife, and some of the most spectacular sunsets on the island. The primary bedroom is a serene sanctuary with floor to ceiling water views that feel truly immersive. A second main level bedroom also has water views and its own full bath. On the lower level, a bedroom suite includes a comfortable sitting area with a TV, and spacious full bath. The guest house is a retreat unto itself, offering equally stunning water views from kitchen, living room and private porch. Its large primary bedroom features ample space, while the additional bedroom is a cozy, private nook. Outdoors, the estate’s expansive grounds offer a rare combination of beauty, privacy, and direct waterfront access. Private steps lead to the property’s own sandy beach and mooring, where guests can enjoy swimming, boating, kayaking, paddle boarding, fishing, or simply savor the extraordinary natural beauty. An amazing variety of birds, including osprey complete the scene out on the water. The property also borders 14 acres of conservation land with scenic walking trails, enhancing the sense of seclusion, privacy and connection to nature. This is a truly remarkable island estate that has had only 3 owners in the past 65 years. This is a generational opportunity to enjoy and improve this family compound with unforgettable views, refined living spaces and unparalleled waterfront setting.

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs 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. The main living room features a dramatic floor-to-ceiling stone fireplace, premium fir-clad ceiling, and extends into a generous screened porch with accordion doors overlooking the garden. The dining room, with views of Lagoon Pond, opens directly to the sunlit pool deck, infinity pool, spa and waterfall - perfect for summer entertaining! The lower level offers a show-stopping media room with a 12ft overhead projector, massive sofa to comfortably seat 9 people, wine cellar, bar, kitchenette, bathroom and fully-equipped gym. Elevator goes to the main level and lower level.