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 buildings of any size. Water and electric are nearby.

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the possibilities are endless.

This is your opportunity to get in on the ground floor of what will be a stunning, new development --- Lagoon Ridge. Several homes are already in place. This beautiful, wooded parcel is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation lands. This beautiful homesite is waiting for YOU and the construction of your dream home. All utility connections are at the street: electricity, water, and a unique, private, state-of-the art, Amphidrome septic system that services the entire development. It relieves the homeowner of a major concern, functioning as its own sewerage treatment plant. Lagoon Ridge is a well-controlled and planned development with protective architectural review and strong Homeowners Association Covenants. It is overseen by a third-party property management company, First Property Management Co. This particular Lot is extremely private. It is the last Lot on the right at the end of the cul-de-sac and is surrounded on two sides by conservation land. You may select your own home design, subject to architectural review, which ensures that the surrounding homes will be of similar size, design and quality throughout the neighborhood. Further, you may select the contractor of your choice. A two-bedroom home is allowed for the parcel, exclusive of bonus or flex room.

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.

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 past and present owners, this is a rare find — timeless and truly one of a kind.

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.

Welcome to Lagoon Ridge.....Oak Bluffs’ newest and most sought-after neighborhood! Build your 3 bedroom dream home on this lofty setting, 95 feet above Lagoon Pond, featuring sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This exceptional building lot is among the last of the remaining opportunities in this thriving new community. Utilities are already at the site, including town water, electric; and a private Amphidrome wastewater system that will save you the cost and inconvenience of a septic system. Lagoon Ridge borders acres of pristine conservation land with abutting access to scenic biking and hiking trails providing the perfect blend of privacy and outdoor adventure. Located in desirable Oak Bluffs, and central to all down Island towns, this is an active and vibrant community with plenty of construction momentum—don’t miss the opportunity to become part of this attractive neighborhood! Easy to show – contact us today for a private tour of this exceptional offering!“ Price is for lot only, home pictured is a sample of home to be built..call for details.

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 sought-after Oak Bluffs neighborhood.

PRISTINE YEAR ROUND COTTAGE RENOVATED THROUGHOUT ~Welcome to 17 Siloam Avenue, a delightful cottage nestled in the historic Martha’s Vineyard Camp Meeting Association, offering spectacular sunset views of Sunset Lake and the distant harbor from its inviting porches. The current owners have cherished this home year-round for 13 years, and it’s easy to see why. This spacious residence features an open living and dining area that seamlessly flows into a beautifully renovated kitchen, perfect for both family gatherings and entertaining. The first floor also includes a delightful partially renovated bathroom adorned with attractive painted wood beam ceilings, adding a touch of elegance to the space. Venture to the second floor, where you'll find 3 airy bedrooms filled with natural light thanks to the abundant windows. Located just steps away from the harbor, beaches, ferry ports, and all the vibrant attractions that Oak Bluffs has to offer, this cottage is the perfect retreat for those seeking both tranquility and adventure. Don’t miss your chance to own a piece of this picturesque location! Most of the furniture is included and personal items will be removed prior to closing.

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!!

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. 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.

OAK BLUFFS. Situated on an Expansive Corner Lot, this Mighty and Exceptional MOVE IN ready newer home is Packed with upgrades. Open and bright floor plan with oversized windows lets light in even on gloomy days. Attractive and designed for efficiency the Kitchen is outfitted with quartz stone counters and contrasting stone backsplash. The generous composite sink makes sense for pots and pans. Gas Stove. SS Appliances (2025 Refrigerator) Laundry room with ½ bath and Ceiling to floor Custom Cabinets. Primary Bedroom is XL and en-suite with full bathroom and shares room with an office, a walk-in closet as well as a wall-to-wall closet on the opposite side of the room. Covered Front porch to enjoy the beautiful butterfly and hummingbird garden. Also, a fenced in XL patio perfect for outdoor grilling and entertaining or just relaxing. BONUS is the FLEX SPACE provided by the Climate Controlled INSULATED WITH AC & HEAT WORKSHOP on the other side of the house. It has its own driveway which includes a Galvanized carport. BONUS WHOLE HOUSE GENERAC GENERATOR, WATER FILTRATION SYSTEM and WATER PRESSURE BOOSTER system. Full poured Basement with custom closet. Perfectly located within a short walk or bike to the Lagoon for Kayaking and water access. Super location to Buses, Town and central proximity around the island. See 3 pages of Upgrades.

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.

Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace and lovely built-ins, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room for gardens, pets or play. 3 generous sized bedrooms with the primary bedroom having an en-suite bath. There is wood flooring throughout most of the home. Whether you are seeking a year-round residence, a summer getaway or an investment property, this home delivers an exceptional value. Property has a large rear storage shed for added convenience. This is a peaceful and private location yet minutes to the beach, ferries and restaurants! The home currently has a cesspool. Homeowners are working with an engineer to prepare plans for a new septic system. There will be a Buyer credit at Closing towards the new septic. Buyer credit to be determined. Strong rental history. Easy to Show!

Welcome to this spacious and well-appointed home offering 2,128 square feet of comfortable living space, nestled on a generous 0.49-acre lot. Perfect for both everyday living and entertaining, this residence features beautiful hardwood floors throughout the first floor, with wall to wall carpet in the second floor bedrooms adding warmth and timeless appeal. The large open-concept kitchen is the heart of the home, seamlessly connecting to the dining area, living room, and a separate den — ideal for hosting gatherings or simply enjoying family time. The kitchen provides ample counter space, abundant cabinetry, and a island breakfast nook. Upstairs you'll find the primary bedroom suite with a double sink vanity full bathroom. Another full bathroom is off the hall. These oversized bedrooms, each offering plenty of space and natural light, providing peaceful retreats for rest and relaxation. Outside, enjoy the freedom of nearly half an acre — A spacious deck for grilling and outdoor gathering. There's still plenty of room for gardening, recreation, or future additions like a patio, or shed. With its thoughtful layout, generous lot size, and stylish features, this home offers the perfect blend of comfort, space, and potential. Eligible for 3 bedrooms with an enhanced septic system.

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. ***PLEASE NOTE- Seller will either have the wood floors refinished or they will offer a credit at closing for you to have them done.

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.

Oak Bluffs Charmer – Welcome to 9 Bayview Avenue, a 3-bedroom, 2-bath home tucked away on a quiet road in Oak Bluffs. Sited on a level 10,050 sq. ft. lot, this property offers 1,428 sq. ft. of light-filled living space. The main level features a spacious living room, kitchen, and dining area, along with a first-floor bedroom and full bath. Upstairs, two comfortable bedrooms share a full bathroom, providing ample space for family and guests. The basement is partially finished, offering additional flexible space. A unique advantage of this location is the Lagoon Pond access at the end of Bayview Avenue—ideal for fishing, clamming, kayaking, paddleboarding, or simply enjoying a quiet day by the water. Centrally located, this home is just minutes from downtown Oak Bluffs, Farm Neck Golf Club, beaches, and ferry service. Whether you’re looking for a year-round residence, island retreat, or investment opportunity, this property offers the perfect blend of comfort, convenience, and Vineyard charm.

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.

Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul-de-sac on Iron Hill Road is filled with possibilities. This 1.6-acre lot has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. There is a current home on the property is in need of renovations or start fresh and build new! The acreage offers tremendous privacy and backs up to the pasture. The Iron Hill covenants will allow up to 2 horses on the lot. Access to trails and open space give you an up-island feel with proximity to Edgartown, Oak Bluffs and Vineyard Haven.

Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul de sac on Iron Hill Road is filled with possibilities. This 1.6-acre has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. Intended to be a guest house to a future-built main house, the current home is 3-bedrooms and 1.5 baths. Renovate the existing structure or start new and add a building. The acreage offers tremendous privacy and backs up to the pasture. The Iron Hill covenants will allow up to 2 horses on the lot. Access to trails and open space give you an up-island feel with proximity to Edgartown, Oak Bluffs and Vineyard Haven. The property is being offered as-is.

Calling water and boating enthusiasts. Solid Cape-style home one block from Sailing Camp Park, water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. A few thoughtful updates would make this home shine. Come take a look.

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.

East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, 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. 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. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include crown molding and attention to detail, new kitchen and bathroom (with handicap accessible shower) with Italian Carrara subway tile, classic and timeless, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. House keeping available at owners discretion. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

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. 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. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, new kitchen and bathroom with Italian Carrara subway tile, classic and timeless, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. New hot water tank 2023. House keeping available at owners discretion. If owner desires, the propane fireplace may require a new propane tank exclusively for the fireplace independent of generator, inspection and approval of town and fire department, prior to operation. CO detector required. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

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. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, new kitchen and bathroom with Italian Carrara subway tile, classic and timeless, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. House keeping available at owners discretion. Hot water on 80-gal. tank, metered and prorated. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located within the highly sought-after B1 Zone, this residence has been cherished as a family home while also providing the potential for commercial endeavors. The property features a well-designed floor plan that includes four bedrooms—one conveniently located on the first floor—along with a full bathroom, two half bathrooms, a laundry storage area, an eat-in kitchen, and a cozy living room. The home is adorned with stunning wood flooring throughout, bright and airy rooms with original windows, a new hot water on demand system, and a charming front porch, perfect for leisurely afternoons. With its four bedrooms and prime in-town location, this property offers substantial rental potential, making it an exceptional opportunity for both personal enjoyment and investment.

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).

LOCATION! YEAR ROUND HOUSE!INVESTMENT PROPERTY!STARTER HOME! A comfortable home in an established, East Chop neighborhood, this four bedroom, two bathroom house is located within walking distance to the Harbor, downtown Oak Bluffs, and the Oak Bluffs Ferries. There is easy access to shops, family entertainment, and the beach. This home provides a welcoming porch and a spacious backyard patio for relaxation and gatherings. There is large first floor bedroom. The downstairs has an open living room, kitchen, and dining area plus a laundry and mud room near the rear exit. There is a bathroom on the first floor. There are three bedrooms on the second floor and a full bathroom. The house was painted and renovated in 2014 when the heating system and hot water heater were upgraded.The stainless steel appliances in the kitchen were recently purchased.There is an available rental history. Some furnishings are included. The 4 Bedroom septic passed its Title V Certification. Easy to show. A must see!

Bright, Open Living, Steps from the Lagoon! Spacious and sun-filled, this charming 3-bedroom, 2-bath home offers effortless single-level living. As you enter the home, you're welcomed by a spacious sitting area that seamlessly flows into an open-concept living room, dining area, and modern kitchen—perfect for entertaining and everyday living. A separate home office or den provides additional flexible space, making this 2,015 sq ft residence live large. Set on a generous 11,000 sq ft corner lot, the home features sliding glass doors off the living room that open to the deck—perfect for enjoying the beautifully landscaped yard and embracing outdoor living. A detached two-car garage offers added convenience and great storage space. Ideally located just across the road from Lagoon Pond, you’ll enjoy west-facing views overlooking the Lagoon and Vineyard Haven Harbor. Whether you're sipping morning coffee, kayaking, canoeing, clamming, or soaking in the stunning sunsets, you'll relish the very best of life just steps from the water. Carefree coastal living at its finest—ideal as a year-round residence, a serene holiday getaway, or vacation rental.

Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted microwave and oven combination, counter cooktop, breakfast bar with seating, and a built-in desk with glass shelving—perfect for casual meals or entertaining. French glass-pane doors with elegant glass knobs provide classic charm and a graceful flow between the kitchen, dining room, family room, and living room. The family room features a vaulted ceiling with skylights and a striking full stone wall with brick insert for a gas propane stove, while the spacious living room offers a Count Rumford brick fireplace. The first floor also includes a bedroom, full bathroom, and a mudroom, all with beautifully maintained distressed oak and oak hardwood flooring. Upstairs, you will find two spacious bedrooms, including a primary ensuite with Jacuzzi tub, plus a third full bath. Flooring on this level includes tile and laminated wood, with many rooms recently painted for a fresh, updated feel. A bonus room currently, used as an office with laminated flooring is ideal for a home workspace. Above the attached two-car garage is a private one-bedroom apartment with a separate entrance, open-concept kitchen/living area, full bath, and a small private porch. The home’s total square footage includes this apartment and the bonus room. Multiple sliders and a rear door lead to a slate stone patio accented by a cultured stone wall, surrounded by mature trees for a serene, private setting. Ample parking is available in the driveway and by the garage.

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. With four levels of finished living space, it offers room to gather, relax, entertain, and create memories in every 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 celebration and entertaining—mature plantings, a built in exterior fireplace that invites long summer evenings, 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. SHOWINGS BEGIN MONDAY 10/20

Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with timeless elegance. An idyllic covered porch invites you into the home. The heart of the home is undoubtedly the kitchen, which opens to a second living area adorned with a charming wood-burning fireplace—ideal for chilly Vineyard evenings. Just off the kitchen, the deck overlooks a beautifully manicured backyard and a private wooded area, providing a serene backdrop for outdoor gatherings, birdwatching, or simply unwinding. A convenient first-floor laundry room leads out to the 2 car-garage. The second level features a spacious primary bedroom with en suite bath, ample closets, and an attached home office. Three more bedrooms and a shared bath complete the second floor. The finished basement, not included in the square footage adds an extra layer of versatility, offering a cozy retreat for movie nights, a workout area or a game of pool. (Pool table is included with the sale) Residents of Bayes Hill enjoy access to the association's tennis and pickleball court, and with southern woodland trails right at your doorstep, outdoor adventures await! As a delightful bonus, the sellers are including a 2008 BMW Convertible—a perfect Island car to cruise the picturesque roads of Martha’s Vineyard!

Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor** This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from around the globe and ferries arriving at port, all in the company of your favorite guests. This picturesque setting is enhanced by the delightful scent of vibrant Rugosa roses that adorn the sandy landscape. Experience the unique convenience of storing your paddleboard, kayak, windsurfer, and other watercraft right in your backyard, allowing you to indulge in refreshing swims at your leisure. There is potential for mooring a motor or sailboat. This property epitomizes the classic Martha’s Vineyard experience—creating timeless memories. Additionally, it has a solid rental history. Please note, our information suggests that the adjacent lot is un-buildable; however, we recommend verifying this with the town.

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.

THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground utilities and town water in place and each lot has been approved for up to six bedrooms per Oak Bluffs Board of Health. A peaceful and private setting abutting conservation land and trails for hiking, walking and biking! Don't wait to be part of this lifestyle!

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.

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.

East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the "Tivoli", features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this 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. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. Hot water on 80-gal. tank, metered and proated. House keeping available at owners discretion. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

East Chop Water Front Luxury Condominiums -- This 2-bedroom, 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. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include high end finishing, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. House keeping available at owners discretion. Hot water on 80-gal. tank, metered and prorated. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard and a heated above-ground pool with deck! The large detached two-bay garage has a new attached studio with full bath, laundry, kitchen and a private deck. Newer exterior cedar shingles and trim, and a new 4 bedroom septic installed. Equidistant to each down-Island village, it resides within a mature neighborhood with attractive curb appeal.

Welcome to 39 Iron Hill Rd, Oak Bluffs (Martha’s Vineyard)—a private multifamily colonial within Iron Hill Farm, near Island Alpaca, Island Grown Initiative, miles of trails, and access to Duarte’s Pond, with convenient proximity to Vineyard Haven and Oak Bluffs beaches and amenities. The 4,334± sq. ft. property offers 5 BR / 5.5 BA in total. Main residence (4BR/4.5BA) features two ensuite primary bedrooms, two additional bedrooms with a shared bath, plus an additional full bath and powder room. The attached 1BR/1BA apartment includes private entrances, a living room, kitchen, laundry, private deck, and central air—ideal for rental income, guests, or multigenerational living. Circular driveway, four-plus-car garage capacity, and ample parking. Room for a pool and detached garage can be as a potential ADU (permits required). Community Access to Duarte’s Pond. Enjoy trails, nature, and wildlife—even keep a horse (buyer to confirm allowances).

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home offers convenience and charm. Don't miss the opportunity to own this fantastic property.

Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to shops, restaurants, beaches, and ferries. . The commercial zoned land has been approved for several different situations from housing to store fronts. Come take a look at all this property has to offer.

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 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. Call for details!

Downtown Oak Bluffs an investment opportunity awaits at the top of Circuit Ave. Dual zoned this is two properties in one. An existing 6 bedroom 3.5 bath Victorian home in the popular Copeland District a couple blocks to the beach even closer to restaurants shops and entertainment. On town sewer it’s ideal for weekly rentals. The other side of the property facing Circuit Ave. is zoned Commercial giving you a wide arrange of business opportunities several ideas have been previously approved. An ADU dwelling is also another possibility While waiting for permitting you can easily lease up to 9 parking spaces (see attached plan). Calling all investors this property is priced to sell.

Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and hand-cut stone propane fireplace, a kitchen featuring granite countertops, Wolf range, and an undercounter wine cooler. A casual dining area at one end of the kitchen, and inviting living room offer the perfect space to entertain. Rounding out the first floor, the primary bedroom has a large walk-in closet, soaking tub, and bay window looking out over the backyard. The second first floor bedroom is currently being used as a TV room. The second level has two sizable ensuite bedrooms with ample closet space and skylights. Highlights of the home include radiant heat, hardwood floors, firepit, large yard and plenty of room for expansion. Even more opportunity for expansion is found in the partially finished lower level. A future office, media room, or workout area awaits. The two car garage is large and has additional space above offering options for additional guest quarters. Meadow View Farms is quiet and private with walking trails and association tennis. The property has mature plantings and is close to both the bike path and over 200 acres of conservation land with hiking trails. Title 5 inspection passed for a 5 bedroom septic. This home is move in ready and is perfect for year-round living. This home would also make a desirable summer vacation retreat.

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The unattached studio complete with loft, full bath, AC and 2 additional garage spaces 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 2 wood-burning fireplaces, new mini-split units, 2 outdoor showers, optional base-board heating and hardwood floors throughout. Enjoy Association amenities like tennis, pickleball, kayak racks, 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.

East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most importantly, the modern comforts today's lifestyle demands. Set on a generous, level parcel, with an existing seven-bedroom septic system—providing ample opportunity for future expansion and customization. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're just minutes from the harbor and vibrant downtown Oak Bluffs. A true island compound—rooted in tradition, yet ready for what comes next.

Motivated Seller!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location. FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four bathrooms. You can own a one of a kind 180 degree Panoramic water view of Vineyard Haven harbor with breathtaking sunsets from the rooftop entertainment area. Host epic cocktail parties while watching Steamship ferries and sailboats glide by. Originally built by Shaw Norris (whaling captain) in 1859, this Greek Revival home has a very interesting history This house has been thoroughly renovated with new roof, new siding, new trim and all mechanical systems replaced. Imagine the convenience of TWO first floor ensuites. One has original architectural features including an original hearth, while the other has an exclusive entrance with access to a very private patio porch. The first floor has an intelligent open floor plan that is perfect for entertaining as well as a gourmet kitchen that opens to a very intimate outdoor dining area. A second-floor lounge opens onto a spacious upper recreation area. The privacy of this idyllic setting is ensured as two sides of the property are surrounded by landbank property. This property is perfect as an investment or as a generational family treasure. Broker has an owner's interest in the property.

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.

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2024 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

Arrive by land or sea to 311 East Chop Drive, a truly rare offering that combines panoramic water views in nearly every direction. Perfectly positioned between Vineyard Haven Harbor, Vineyard Sound, and Crystal Lake, this iconic East Chop residence—known as “The Sandpiper”—offers 100 feet of private beach, a 125-foot dock, and an additional mooring, all just minutes from the restaurants, shops and attractions of Oak Bluffs and Vineyard Haven. Completely renovated from top to bottom, this two-story waterfront haven blends the charm of its 125-year history with the modern conveniences of today. Expansive glass sliders and bay windows capture the ever-changing seascape, while hardwood floors, whitewashed beadboard, and a beach-stone fireplace infuse timeless coastal character. With four bedrooms and two and a half baths, the home offers generous space for family and friends. The fully appointed kitchen with breakfast bar invites casual dining and easy gatherings, flowing effortlessly to multiple outdoor spaces designed for relaxation and entertaining. A fenced beach-stone patio and brick terraces lead to a car barn with expansion potential, an outdoor shower, and seaside gardens blooming with rosa rugosa and native grasses. Whether arriving by boat or by car, 311 East Chop Drive offers an unparalleled combination of privacy, convenience, and coastal beauty—an exceptional Vineyard retreat where every day feels like a seaside escape.

Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry, high-end appliances, stunning granite countertops and generous counter space for cooking and hosting in style. Outdoor enthusiasts will appreciate private access to over 200 acres of trails right from your back yard.

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.

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

This 4-bedroom / 3-bath home lies in the middle of East Chop at the highest point on the bluff offering expansive views of Vineyard Sound. The home features a large clear story living room with fireplace, a family room/kitchen also with fireplace, a huge screened porch opening up to a large deck area and a first floor bedroom with private bath. The 2nd floor offers two guest bedrooms and a master bedroom with large deck that share two baths. There are entrances on two roads, the grounds are nicely landscaped and there is a garage that could be used for a number of usages.

Live the Dream on Martha’s Vineyard! Whether you're seeking a year-round residence or a seasonal escape, this is a once-in-a-lifetime opportunity to own a piece of paradise. 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. Tucked away off Barnes Road in a secluded enclave, yet close to beloved Island spots, this residence is a masterclass in comfort and elegance. Nearly every room in this spacious, 4046 square foot home is designed to showcase the water’s beauty, making it perfect for entertaining or simply unwinding with loved ones. The main level boasts soaring ceilings, oversized windows, and uninterrupted Lagoon views. A cozy wood-burning fireplace, stylish wet bar, and formal sitting area set the tone for relaxed sophistication. 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 - ideal for a home office, den, or overflow guest suite. On the upper level, the primary suite is a sanctuary unto itself, featuring a fireplace, walk-in closets, spa-like en-suite bath, and direct access to 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 - perfect for morning coffee or evening cocktails. If you are looking for a quiet escape, you will enjoy a second covered porch at the front of the house. The recently refinished 2,000-square-foot walk-out basement includes a full bath and laundry - ready to be transformed into your personal gym, studio, or media room. Sold fully furnished, this home is ready for you to move in. Dive into the ultimate Vineyard lifestyle - boating, swimming, kayaking, clamming, and soaking in the serenity of the sea.

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. THESE LOTS ARE ALREADY SUBDIVIDED. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling. Septic permits in place for two lots. Lot #1 - 147.2 (45,782sq.ft.) Permit in place for an APPROVED 6 Bedroom Septic System; Lot #2 - 147.3 - (31,320sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #3 - 147.4 - (34,824sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #4 - (52,451sq.ft.) 6 Bedroom Septic System Designed, NOT YET submitted; Lot #5 - (45,074sq.ft.) - Permit in place, APPROVED for a 4 Bedroom Septic System. Lot # 5 - May have access directly from Wapello Street. Ten (10) Bedrooms have been approved. Applications for an additional Twelve (12) Bedrooms are in process. Lot#2 - Application for 6 bedrooms. Lot#3 - Application for 6 Bedrooms. Lot #4 is undetermined at this point. Access may be allowed via Sunset Road or Eastville Avenue. Water is available via Sunset Road, at the property. Electricity is on site. Buyer is responsible for verifying any and all information on this property.

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 full 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.

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.

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

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!

Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this exceptional residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living. At the heart of the home lies an expansive great room with soaring cathedral ceilings, rich paneling, and detailed millwork. Flooded with natural light from an array of dormers and oversized windows, the space is warm and welcoming. Three sets of French doors open to a bluestone terrace, complete with multiple seating areas and a heated, saltwater pool—an idyllic setting for al fresco dining, entertaining and lounging. The chef’s kitchen overlooks both the dining area and the great room, creating a seamless flow for everyday living and hosting. Each wing of the home is thoughtfully arranged: one side features a cozy secondary living room or study and a luxurious primary suite with a spa-like bath and custom dressing room. The opposite wing houses three generously sized guest bedrooms, each with cathedral ceilings, walk-in closets, and ensuite baths. Additional highlights include a welcoming side entrance with a well-designed mudroom and a separate laundry room, and a finished lower level offering a media room, full bath, and ample storage. Custom built-ins, refined finishes, and architectural details are found throughout, enhancing the home's timeless character and sophistication. Surrounded by beautifully landscaped grounds and mature plantings, the property offers a rare sense of seclusion. The Preserve is a highly sought-after neighborhood with walking trails that connect to conservation land, and easy access to the bike path, Farm Neck Golf & Tennis, and all down-island towns.

EXQUISITE WATERFRONT RETREAT WITH POOL AND SUPERLATIVE SUNSETS. Luxurious island living awaits at this stunning private waterfront retreat, set on a private 125-foot stretch of sandy beachfront. Three floors of living space totaling 5,400+ square feet, seamlessly blend casual elegance with indoor-outdoor living. Enter through the grand foyer to discover dramatic interiors with soaring ceilings, skylights, and floor-to-ceiling windows that capture breathtaking water views. The open staircase and stately columns add grandeur, while a handsome stone fireplace and custom built-ins provide warmth and sophistication. The gourmet kitchen is a dream for cooks and entertainers alike, featuring custom cabinetry, stone countertops, and stainless appliances. An expansive kitchen island and a wet bar with beverage refrigerator and ice maker enhance the entertaining experience. Adjacent, a spacious dining area with custom built-ins is perfect for memorable gatherings. This home offers three generously sized bedrooms and 4.5 elegantly appointed bathrooms. The primary suite is a sanctuary of comfort, with tranquil water views and access to the pool area for seamless indoor-outdoor living -- plus a spa-like bath with double vanity, soaking tub and glass walk-in shower. The second floor features an open lounge area overlooking the living room, complete with built-in bookshelves flanked by two spacious bedrooms each with en suite bath. The lower level is an entertainer's paradise, featuring a family/TV room, entertaining kitchen, wine cellar room, billiards/game room and room for an in-home gym area. Step outside to a world of leisure and relaxation. The heated pool, with a built-in whirlpool spa and bluestone terrace, is ideal for warm summer days. An outdoor kitchen invites alfresco dining, while a hammock offers a peaceful afternoon retreat. The lagoon waterfront, with stairs to a sandy beach, provides calm waters for swimming, kayaking, and paddleboarding, and the ability to secure a mooring. This home is a true gem, offering an unparalleled lifestyle of luxury and tranquility. The property is being offered with furnishings and boasts an impressive rental history of over $250,000 in income for 2025. Experience the magic of sunsets over the lagoon from your own slice of paradise!

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 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.

East Chop waterfront – Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 3.) Or convert to condominiums, paperwork has been completed but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 7-bedroom property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, all new heating/AC mini-splits, new exterior security cameras and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Furniture included depending on price. Private outdoor shower with dressing area. On town sewer.