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.

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.

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.

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 rare 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. Ready to go!!

An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining room. The kitchen is at the back of the house with the mudroom and side entrance beyond. Enjoy the beautiful natural light in the spacious sun room at the front of the house with French doors leading to the side yard. The property offers charm and potential in a sought-after location. Several updates were completed in 2010 such as a new roof, windows, and siding (see full list in documents section). The property is being sold “AS IS”. There are 2 existing cesspools on site that failed inspection. Per the Oak Bluffs Wastewater Department, the property can tie into town sewer.

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: 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, 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. Three generous sized bedrooms with the primary bedroom having an en-suite bath. There is oak 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. “The homeowners have completed the new septic system plans with their engineer. The owner is also coordinating directly with the installer, and the new system will be installed at the owner’s expense. Strong rental history. Easy to show!”

Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features include a large primary bedroom, a convenient first-floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower—perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and natural light throughout, this move-in-ready home blends comfort, character, and charm. The floor plan offers privacy between the 3 oversized bedrooms. Ideal for year-round living or a seasonal retreat.

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.

Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the island’s favorite attractions. Step inside to find a bright and open 1,500 sq. ft. main level, featuring a seamless flow between the kitchen, dining area, and living room — ideal for entertaining or relaxing with family and friends. The modern kitchen boasts updated finishes and ample space for gatherings. A wood burning stove provides a cozy atmosphere and heat on winter nights. The primary suite includes a private en suite bath, while the second bedroom is conveniently located near the hall bathroom. Downstairs, the semi- finished lower level adds over 1,100 sq. ft. of additional living space — perfect for a family room, home office, gym, or guest area. With the installation of an egress window, this level could accommodate a third legal bedroom. The home is already equipped with a three-bedroom septic system, offering flexibility for future expansion. Outside, enjoy the large yard with plenty of room for outdoor living, gardening, a deck, outdoor shower and lots of room for adding a patio or firepit. Whether you’re seeking a year-round residence, vacation getaway, or investment property, this Oak Bluffs gem offers island living at its best — central, spacious, and move-in ready.

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.

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.

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!

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.

Meadowview Farms — This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace into the kitchen and dining space, while a large screened-in porch creates an exceptional setting for gatherings and outdoor enjoyment. A huge second-floor bonus room provides flexible space for media, recreation, or home office use. Additional highlights include a full basement, attached two-car garage, landscaped lot, association tennis courts, and convenient access to the bike path. Just minutes to Farm Neck Golf Club and all that Oak Bluffs has to offer.

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.

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon Pond. Enjoy sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This outstanding building lot is among the last remaining opportunities in this thriving community. Utilities are already at the site, including town water, electric, and a private Amphidrome wastewater system, saving you the cost and inconvenience of a septic system. Lagoon Ridge borders acres of pristine conservation land, with easy 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 active and vibrant community is experiencing significant construction momentum. Don’t miss the chance to be part of this attractive neighborhood! Call for details and to schedule a tour of existing homes in Lagoon Ridge. Price is for the lot only; the home pictured is a sample of what can be built. Contact us today for a private tour of this exceptional offering!

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$700,000 and building contract $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.

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 which has 1.957 square feet. A future office, media room, or workout area awaits. The two car garage is large and has an additional 576 square feet of 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.

UNIQUE IN-TOWN INVESTMENT opportunity in the heart of Oak Bluffs. This COMMERCIALLY ZONED B1 property offers flexibility and a strong existing rental history. Built in 2017, the MULTI-FAMILY building combines modern efficiency with an unbeatable location — just a short stroll to Oak Bluffs harbor, the Inkwell Beach, art galleries, shopping on Circuit Avenue, restaurants, the Historic Flying Horses Carousel and MVCMA campground. The FRONT HOUSE features a spacious light filled living room & modern kitchen with stainless steel appliances, half bath and laundry room. Go Upstairs to 2 bedrooms & Full bath. Six foot high Basement underneath. A BRIGHT, ENERGY-EFFICIENT ATTACHED YEAR-ROUND COTTAGE (UNIT B), offers approximately 350 square feet of thoughtfully designed living space. The unit features a first floor bedroom, living area, full kitchen with quartz countertops, tile flooring throughout, a full bathroom, and in-unit laundry. Additional highlights include a crawl space, maintenance-free composite decking, a shared brick patio, and an outdoor shower shared—perfect for easy, comfortable year-round living and enjoying the Vineyard Lifestyle. THE DETACHED REAR COTTAGE (UNIT R) offers approximately 600 square feet of living space, including the loft, with high vaulted ceilings, exposed wood beams, and an abundance of natural light throughout the open living and dining areas. The kitchen features granite countertops, a glass accent tile backsplash, and Stainless steel appliances. A first floor bedroom and full bath open out to a fenced-in area and private enclosed outdoor shower. Additional highlights include a roomy loft area, full size in-unit laundry, and a bluestone patio surrounded by beautiful landscaping. This is a charming and efficient year-round retreat. UPGRADES INCLUDE: 41 solar panels installed in July 2021, state-of-the-art energy-efficient utilities, and low-maintenance composite decking. The structure is insulated with 1.5-inch closed-cell foam on the walls and 3-inch closed-cell foam on the roof and interior walls, ensuring year-round comfort and reduced energy costs. Additional features include energy-efficient heat and A/C pumps throughout and ENERGY-COMPLIANT windows. A RARE BLEND OF COMMERCIAL ZONING, MODERN CONSTRUCTION, and a LOCATION PRIME WALK-TO-TOWN— ideal for investors or those seeking both income potential and in-town convenience. Don’t miss this opportunity to own a RARE OAK BLUFFS GEM—a truly exceptional property.

Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush landscaping with stone walls, specimen trees, and a goldfish pond with a waterfall. Additional amenities include a pool house, a detached one-car garage/workshop, an oversized two-car garage, and a full basement—perfect for extra storage or hobbies. With private access to Lagoon Pond, this park-like property offers the ultimate blend of indoor-outdoor living and tranquility. A rare Vineyard gem designed for entertaining, relaxation, and easy island living.

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 2026 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

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 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.

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.

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!

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.