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Oak Bluffs
0 California Avenue, Oak Bluffs MA 02539

LINK ID: 42933
Town: Oak Bluffs
Type: Unimproved Land
$495,000.00

Property Details

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 1 bedroom for this lot. Water and electric are nearby.

47 Circuit Avenue # 1A, Oak Bluffs MA 02557

LINK ID: 42759
Town: Oak Bluffs
Type: Commercial
$525,000.00

Property Details

This commercially zoned property enjoys plenty of foot traffic in the heart of Circuit Avenue’s pedestrian activity. The space is bright and cheery with great natural light. Currently set up as a hair salon with access to a shared half bath, the space can be transformed to fit other specific needs including retail or office space. The property offers an opportunity for a piece of commercial/retail space or as an excellent rental investment property.

0 Barnes Road, Oak Bluffs MA 02557

LINK ID: 42701
Town: Oak Bluffs
Type: Unimproved Land
$530,000.00

Property Details

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.

0 Worcester Avenue & Olinda Avenue, Oak Bluffs MA 02557

LINK ID: 43015
Town: Oak Bluffs
Type: Unimproved Land
$575,000.00

Property Details

Location, Location, Location. Rare Opportunity to own a 10,000 sq ft South facing level corner lot on a paved road that may accommodate up to 3 bedrooms with Board of Health approval. A sandy beach on Lagoon Pond is just a short stroll (about 1500 ft.) .....enjoy the beach, walk your pet, watch the stunning sunsets, and GREAT shell fishing . How nice would little necks on the half shell or baked scallops sound for dinner! Have a boat? With permission from the Oak Bluffs Harbormaster, you could be steps away from your own private mooring. A convenient bike path nearby links your access to miles of safe paved trails leading to downtown Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury and 6000 acres of the State Forest. Martha's Vineyard Hospital and Oak Bluffs Elementary School are a 5 minute drive away. This established neighborhood is perfect for both vacation or year round living. The seller is working on securing an engineer to begin the process for a survey, perc test and septic design. Easy to show...

35 Temahigan Avenue lot 5, Oak Bluffs MA 02557

LINK ID: 43050
Town: Oak Bluffs
Type: Unimproved Land
$595,000.00

Property Details

Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future house can possibly have up to seven bedrooms and have up to three floors. Include on the property is a small antique garage. A recent appraisal values the lot at $850,000. There are plans available for a six bedroom, five bath house. So in addition to a six bedroom house, it may be possible to build a one bedroom guest house or possibly a pool. Listing agent has an owner's interest in the subject property.

47 Circuit Avenue # 1B, Oak Bluffs MA 02557

LINK ID: 42760
Town: Oak Bluffs
Type: Commercial
$600,000.00

Property Details

Great opportunity for commercial space in a thriving business district with plenty of street parking and a storefront and side entrance. Office / Studio / Retail ~ Your choice! The space is versatile and is currently set up as a large open space with 2 dressing rooms, a large storage room in the back, and a shared half bath. If you are looking for a different layout, the space can easily be reconfigured to fit your specific business needs. With move-in-ready space and a fabulous location, this is an exciting opportunity to own a piece of commercial/retail space, whether for your own business or as an excellent rental investment property.

56 Holmes Hole Road, Oak Bluffs MA 02557

LINK ID: 42990
Town: Oak Bluffs
Type: Unimproved Land
$699,000.00

Property Details

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.

25 Oak Avenue, Oak Bluffs MA 02557

LINK ID: 42761
Town: Oak Bluffs
Type: Unimproved Land
$699,000.00

Property Details

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot. According to the engineer who has percolated the lot, it will allow a FIVE (5) bedroom regular septic system. The Board of Health have stated there are no Board of Health issues or limitations with this property and are deferring to the engineer’s opinion, It may be possible to have more than Five (5) Bedrooms. Water and Electricity are all ready at the site. There's also a small house on the property, built in 1900, and a dilapidated garage. Property is being sold in 'As is" condition. If BUYER chooses to remove the house and garage it will be at their expense. Retaining the footprint of the garage has value as it could possibly be rebuilt in place. Buyer should clarify with relevant town officials. Easy access to harbor, town, shops, restaurants, Oak Bluffs Ferry, Sunset Lake, Campground cottages, Oak Bluffs Library. PRICED BELOW ASSESSED VALUE.

25 Oak Avenue, Oak Bluffs MA 02557

LINK ID: 42766
Town: Oak Bluffs
Type: Single Family Residence
$699,000.00

Property Details

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the exiting building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) as it’s not in a Board of Health area of concern - Consult your engineer - the Seller has already been through the lengthy process with the Martha's Vineyard Commission to receive approvals to knock down the house and has succeeding in obtaining that approval. According to the engineer who percolated the lot, the lot will allow a FIVE (5) BEDROOM regular septic system. The Board of Health have stated there are no Board of Health issues with this property and are deferring to the engineer's opinion. Water and Electricity are already at the site. Property is being sold in 'As is" condition. If BUYER chooses to remove the house and garage it will be at their expense. Retaining the footprint of the garage has value as it's a preexisting non conforming location on the lot and therefore could be rebuilt in place, Buyer to clarify with relevant town officials. Easy access to harbor, town, shops, restaurants, Oak Bluffs Ferry, Sunset Lake, Campground cottages, Oak Bluffs Library. Front porch for relaxing on a Summer evening. Easy to show! PRICED BELOW ASSESSED VALUE.

7 Highland Avenue, Oak Bluffs MA 02557

LINK ID: 42382
Town: Oak Bluffs
Type: Unimproved Land
$750,000.00

Property Details

BUILD YOUR DREAM HOME ON MARTHA'S VINEYARD! This almost 20,00sq ft of BUILDABLE land is nestled in the private quiet neighborhood of East Chop. Do you want to live conveniently close to downtown Oak Bluffs, the ferry terminal, beaches including Inkwell Beach, the Flying Horses Carousel, Ocean Park, tennis courts, and more? This parcel may accommodate a 7-bedroom home (see perc test letter in documents) and when you're not using it for personal enjoyment this parcel is in the #1 rental location on Martha's Vineyard making it an excellent investment. Town water is accessible on Coral Ave. The seller's agent is related to the seller.

17 Siloam Avenue, Oak Bluffs MA 02557

LINK ID: 43209
Town: Oak Bluffs
Type: Single Family Residence
$829,000.00

Property Details

COMING SOON~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 three comfortable 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. First Showing May 17th

26 Winthrop Avenue, Oak Bluffs MA 02557

LINK ID: 42248
Town: Oak Bluffs
Type: Single Family Residence
$899,000.00

Property Details

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!!

8 Rock Avenue, Oak Bluffs MA 02557

LINK ID: 43217
Town: Oak Bluffs
Type: Single Family Residence
$899,000.00

Property Details

Experience the charm of this exquisitely renovated Victorian Gingerbread Cottage, nestled within the historic Martha's Vineyard Camp Meeting Association. Just moments away from Oak Bluffs Harbor, ferry terminals, art galleries, restaurants, public beaches, and vibrant shopping areas, this cottage offers an unparalleled location next to all of Oak Bluffs' picturesque parks. This rare gem features two side yards adorned with vibrant landscaping, enhancing its curb appeal. Step inside to discover a breathtaking chef’s kitchen, designed with chic shiplap walls and custom cabinetry. Recent updates include a brand-new roof, modern electrical and plumbing systems, a state-of-the-art HVAC system, and energy-efficient, high-quality Blomberg appliances. The cottage showcases gleaming hardwood floors throughout, complemented by a fresh coat of paint and designer finishes that add a touch of elegance. This three-season home is move-in ready, making it the perfect place to enjoy a fantastic location where everything is within walking distance.

1 Cottage Park, Oak Bluffs MA 02557

LINK ID: 42887
Town: Oak Bluffs
Type: Single Family Residence
$925,000.00

Property Details

The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs within the historic Martha's Vineyard Camp Meeting Association. Located on a pedestrian street, you'll be mere steps away from the shops and restaurants of Circuit Ave., Ocean Park, and the Oak Bluffs beaches. This cherished three-bedroom, three-bathroom cottage seamlessly blends vintage charm with modern comforts. Step up to the inviting covered front porch that is perfect for entertaining and alfresco dining. Enter through the scrolled double screened doors and enjoy a spacious parlor, a newly crafted, fully equipped kitchen and a first floor primary bedroom with ensuite bath. Vintage windows, shutters, and classic built-ins preserve the charm of a bygone era, while thoughtful renovations ensure comfortable living. Not to mention an outdoor shower to wash off after a day at the beach! On the main floor, new tongue and groove pine floors lead throughout the first floor of this charming home, including into the first floor primary bedroom, with king size bed and large closet. The remodeled kitchen boasts all new appliances, cabinets and quartz counter tops. Insulated walls and electric baseboard heating provide four seasons of main floor living. The second floor is updated with designer grade, wall-to-wall carpeting. On this level is a second, primary bedroom, a guest bedroom and a newly added second floor bathroom. There is a large storage area for extra convenience and an overflow room. This home is being offered turnkey with some exclusions. Please visit https://www.mvcma.org/ for cottage owner information.

37 Circuit Avenue # 5, Oak Bluffs MA 02557

LINK ID: 43000
Town: Oak Bluffs
Type: Condominium
$935,000.00

Property Details

Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood floors, air-conditioning, custom built-in with a open yet divided living area, a sleep alcove and wood staircase to the rooftop deck. The large bedroom has a sunny nook with a opening skylight. This condo is ideal for a year-round living, an escape from the city getaway, or would make a great vacation rental with no car needed.

37 Circuit Avenue # 4, Oak Bluffs MA 02557

LINK ID: 42973
Town: Oak Bluffs
Type: Condominium
$985,000.00

Property Details

Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit. The interior with it's custom wooden features and ships ladder to the deck gives it a nautical feel. It's surprisingly spacious with a living area, dining and separated kitchen. The primary bedroom is over 16' x 21'. Just off the hall is a tiled bathroom with glass enclosed shower and another bedroom. This space is perfect for year-round living or makes a great summer rental property with it's ideal location. No need for a vehicle with in-town living, beach, and access to all the Ferries within a few blocks.

50 Canonicus Avenue, Oak Bluffs MA 02557

LINK ID: 42877
Town: Oak Bluffs
Type: Single Family Residence
$995,000.00

Property Details

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. 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.

249 County Road, Oak Bluffs MA 02557

LINK ID: 42866
Town: Oak Bluffs
Type: Single Family Residence
$1,050,000.00

Property Details

This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy easy access to Oak Bluffs’ vibrant Main Street, stunning beaches, and the ferry, making it an ideal spot to experience all the best of down-island living. The property is being sold as-is. Fiduciary responsibilities apply.

130 Wing Road, Oak Bluffs MA 02557

LINK ID: 42834
Town: Oak Bluffs
Type: Single Family Residence
$1,099,000.00

Property Details

This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and bus routes. The home is sited on a conforming lot in the R2 zone. The interior features all new paint, freshly finished wood floors and all new matching appliances including washer & dryer. There is a working, masonry wood-burning fireplace that has been inspected and has a new damper installed. The roof and sidewall shingles were replaced in 2023. This home also includes an oversized, detached, one-car garage perfect for additional storage. Expansion is possible. The sale includes a 3 bedroom septic system design. The existing two-bedroom septic system passed inspection this year. Also included in this sale are architect's plans for a three-bedroom home with attached garage and a 16' x 32' pool. This property is remarkably adaptable to a variety of purposes accommodating your present needs and future dreams!

70 Carol Lane, Oak Bluffs MA 02557

LINK ID: 42456
Town: Oak Bluffs
Type: Single Family Residence
$1,250,000.00

Property Details

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.

14 High Meadow Lane, Oak Bluffs MA 02575

LINK ID: 42472
Town: Oak Bluffs
Type: Single Family Residence
$1,449,000.00

Property Details

MEADOW VIEW FARM/OAK BLUFFS - This sun-drenched, contemporary reverse-style home has 3 levels of living space. Well-maintained over those years, this 3+ bedrooms, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open kitchen, dining and living areas with cathedral ceilings and 3 sliding doors allow for the sunshine to fill the home. Open the sliders to the expansive deck and you greatly increase the living space on the upper level. A powder room completes the upper level. The first floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck. There are 2 more spacious bedrooms and a shared bath. Venture down to the above-grade lower-level and enjoy the family room, reading nook, and bonus room which adds an additional 350 sq. ft of finished space. There is also a large storage/utility room with a second power room. This space opens to the 1-car garage. Like every true island home, there is an outdoor shower. Plenty of additional storage under the deck. Air conditioning on the upper level and the first floor primary bedroom. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind the house, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis, open meadows, and even mail delivery. The septic has passed the Title V inspection for 3 bedrooms. An interested buyer should speak to an engineer about expanding the size of the septic to accommodate more bedrooms or adding a pool. The home has been well-maintained throughout its single-family ownership.

47 East Chop Drive Unit 5, Oak Bluffs MA 02557

LINK ID: 43068
Town: Oak Bluffs
Type: Condominium
$1,495,000.00

Property Details

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.

47 East Chop Drive Unit 2, Oak Bluffs MA 02557

LINK ID: 43085
Town: Oak Bluffs
Type: Condominium
$1,495,000.00

Property Details

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.

47 East Chop Drive Unit 1, Oak Bluffs MA 02557

LINK ID: 43141
Town: Oak Bluffs
Type: Condominium
$1,495,000.00

Property Details

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.

46 Kennebec Avenue, Oak Bluffs MA 02557

LINK ID: 43137
Town: Oak Bluffs
Type: Single Family Residence
$1,590,000.00

Property Details

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.

8 School House Village, Oak Bluffs MA 02557

LINK ID: 42630
Town: Oak Bluffs
Type: Single Family Residence
$1,690,000.00

Property Details

Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors lead to a large deck, perfect for outdoor entertaining. The open kitchen and dining room are at the back of the house and enjoy direct deck access. There is a half bath off the living room. The primary suite with a full bath, and 2 additional bedrooms that share a full bath, complete the second floor. An exceptional feature of this property is the apartment with comfortable living space and a private entrance and deck. The location is ideal with easy access to the bike path, YMCA, high school, and state forest, and centrally located to all the down-island towns! Easy to show and being sold mostly furnished, this property is ready for immediate use.

66 Brush Pond Road, Oak Bluffs MA 02557

LINK ID: 42739
Town: Oak Bluffs
Type: Single Family Residence
$1,699,000.00

Property Details

**Charming Vineyard Waterfront Cottage in Oak Bluffs** Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the iconic Drawbridge, this cozy retreat provides the ultimate setting for both relaxation and outdoor enjoyment. Inside, natural light pours into the open-concept living, dining, and kitchen areas, creating a bright and airy space designed with comfort in mind. The spacious kitchen flows seamlessly into the dining area, where you can enjoy meals with a view or sip a morning coffee while taking in the serene landscape. The living room offers a cozy space to unwind, while large windows frame the breathtaking vistas and invite the outdoors in. Step outside onto the surrounding patio, where you'll find plenty of seating to enjoy the tranquil surroundings. Adirondack chairs and patio furniture provide the perfect spots to watch the sunset over the water—an experience you won't want to miss. Lush greenery, vibrant flowers, and mature trees create an idyllic outdoor oasis. Whether you’re seeking a peaceful retreat or a place to entertain, this Vineyard cottage offers it all. The combination of its charming interior, spectacular views, and serene outdoor spaces make it a true haven. Ideal for a vacation home or year-round residence, this property is a rare find in Oak Bluffs. Don't miss the chance to call this waterfront beauty your own! This property is a great income producer, with a very strong rental history.

11 Beach Road, Oak Bluffs MA 02557

LINK ID: 43197
Town: Oak Bluffs
Type: Single Family Residence
$1,790,000.00

Property Details

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, pending approval from the Harbormaster. 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 unbuildable; however, we recommend verifying this with the town.

22 Paddock Road, Oak Bluffs MA 02557

LINK ID: 42294
Town: Oak Bluffs
Type: Unimproved Land
$1,850,000.00

Property Details

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!

35 Tuckernuck Avenue, Oak Bluffs MA 02557

LINK ID: 43161
Town: Oak Bluffs
Type: Single Family Residence
$1,895,000.00

Property Details

Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience. As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a generous covered porch and lovely historic details. The living areas are perfect for both cozy family gatherings and entertaining guests. Large windows with architectural shutters throughout the home invite abundant natural light, creating a warm and welcoming atmosphere. Outside boasts an outdoor shower, patio area and a garage! Situated in a highly sought-after neighborhood, this property combines an ideal location whether you’re looking to enjoy the local activities of Oak Bluffs or seeking a peaceful escape, this home offers the best of both worlds. With its open layout and inviting design, this wonderful residence is more than just a home—it's a lifestyle. (Home is being sold as-is).

34 Paddock Road, Oak Bluffs MA 02557

LINK ID: 40763
Town: Oak Bluffs
Type: Unimproved Land
$1,950,000.00

Property Details

The Preserve - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two sides. The lot will support 6 bedrooms, has been perk tested and is ready for you to build your ultimate Vineyard compound.

2 Farm Path, Oak Bluffs MA 02557

LINK ID: 42860
Town: Oak Bluffs
Type: Single Family Residence
$1,995,000.00

Property Details

"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 pool! 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.

47 East Chop Drive Unit 4, Oak Bluffs MA 02557

LINK ID: 43078
Town: Oak Bluffs
Type: Condominium
$1,995,000.00

Property Details

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.

47 East Chop Drive Unit 3, Oak Bluffs MA 02557

LINK ID: 43096
Town: Oak Bluffs
Type: Condominium
$1,995,000.00

Property Details

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.

4 Dempster Park, Oak Bluffs MA 02557

LINK ID: 43106
Town: Oak Bluffs
Type: Single Family Residence
$2,285,000.00

Property Details

East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. The 1st floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio. Completing the first floor is a kitchen and bedroom with half bath. Second floor includes three additional bedrooms, one ensuite plus another full bathroom. The second floor also has full plumbing, electrical and venting in the large hall closet for another washer and dryer. In addition, the second floor has additional storage that runs the length of the front of the house that is accessible from the two front bedrooms. Full unfinished basement includes two large storage areas, washer/dryer and a large additional room that could be a family room or large studio/workshop. Property includes spacious rear patio, outdoor shower, and parking for several cars on the front of the property. The yard has been nicely landscaped. Rental income approx. $7,000/wk in season. Available for showings with 24-hour notice.

30 Sengekontacket Road, Oak Bluffs MA 02557

LINK ID: 42694
Town: Oak Bluffs
Type: Single Family Residence
$2,375,000.00

Property Details

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main level features a living area with a wood-burning fireplace, a spacious kitchen, and a screened-in porch with cathedral ceilings, perfect for dining while enjoying the beautiful views. The primary suite is situated on the second floor and boasts French doors that open to a small deck, allowing you to take in the expansive scenery. The lower level includes three bedrooms, each with French doors leading to a lower deck, and they share a full bathroom. The Sengekontacket Association, established in 1971, encompasses 93 acres and provides a variety of amenities including tennis and pickleball courts, an Association Clubhouse situated on Wiggy’s Pond, and a boat ramp with kayak storage on Sengekontacket Pond. Homeowners can consult the Harbor Master for a mooring in Major’s Cove, where the Association dock is located. Fully renovated in 2007, this property is ready for you to enjoy!

22 Greenleaf Avenue, Oak Bluffs MA 02539

LINK ID: 43058
Town: Oak Bluffs
Type: Single Family Residence
$2,390,000.00

Property Details

Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill the sky with color and a front-row seat to the town’s iconic fireworks display. This home’s unique architectural style nods to the area’s beloved gingerbread cottages, blending classic Vineyard character with thoughtful design by Island architect Jaime Weisman. The home has been lovingly maintained for over 27 years by one family, and now offers a wonderful opportunity for the next chapter. Fairview includes three bedrooms, a finished basement that offers flexible space for relaxing, entertaining, or working from home, and a multipurpose outbuilding that doubles as a shed and garage. With off-street parking and ample yard space, the property provides both convenience and charm. Though located just steps from the vibrant energy of Oak Bluffs—like Illumination Night, concerts at the Tabernacle, and strolls through Ocean Park—Fairview remains a serene retreat, offering privacy and tranquility. This is a rare chance to own a home that combines unbeatable views, a storied location, and the opportunity to update and personalize a treasured piece of Martha’s Vineyard.

79 Circuit Avenue, Oak Bluffs MA 02557

LINK ID: 42960
Town: Oak Bluffs
Type: Single Family Residence
$2,400,000.00

Property Details

Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities for a business and would also be ideal for a live/work situation or seasonal rental. With its large welcoming front porch and inviting secret garden for hosting family, friends and customers, this property has been cherished by many over the years. For 25 years, Oak Bluffs’ institution Good Dog Goods has operated out of the first floor and 2nd floor office space and been the main tenant. There is also a one-bedroom apartment, including a balcony with commanding views over Circuit Avenue is the perfect spot for people watching. This amazing home is looking for the next entrepreneurial spirit to take the reins and steward a true gem of a property.

79 Circuit Avenue, Oak Bluffs MA 02557

LINK ID: 42958
Town: Oak Bluffs
Type: Commercial
$2,400,000.00

Property Details

Historic classic Victorian located at the gateway to the Oak Bluffs Business district with frontage on Circuit Avenue and 5 off street parking spots. The layout offers incredible opportunities for a business and would also be ideal for a live/work situation or seasonal rental. With its large welcoming front porch and inviting secret garden for hosting family, friends and customers, this property has been cherished by many over the years. For 25 years, Oak Bluffs’ institution Good Dog Goods has operated out of the first floor and 2nd floor office space and been the main tenant. There is also a one-bedroom apartment, including a balcony with commanding views over Circuit Avenue is the perfect spot for people watching. This amazing business opportunity is looking for the next entrepreneurial spirit to take the reins and steward a true gem of a property.

4 High Meadow Lane, Oak Bluffs MA 02557

LINK ID: 42967
Town: Oak Bluffs
Type: Single Family Residence
$2,495,000.00

Property Details

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.

16 Atlantic Avenue, Oak Bluffs MA 02557

LINK ID: 43061
Town: Oak Bluffs
Type: Single Family Residence
$2,495,000.00

Property Details

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.

10 Wood Duck Way, Oak Bluffs MA 02557

LINK ID: 43163
Town: Oak Bluffs
Type: Single Family Residence
$2,500,000.00

Property Details

Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy’s freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large windows throughout, offering an abundance of natural light. The first-floor primary has an ensuite bath, a walk-in closet with generous shelving, and direct access to the deck. Upstairs is the second bedroom with ensuite bath and walk in closet. Extra storage is found in the attic space. The versatile loft space overlooks the living room and is a perfect spot for a home office, play area, or reading nook. The lower level includes two guest bedrooms, full bathroom, laundry room, additional storage and second refrigerator, as well as a family room that opens to the stone patio and outdoor shower. The exceptional views and grounds serve as an oasis of privacy, complete with well-maintained flower beds and lush plantings. Wander down to the water’s edge where Wiggy’s Pond can be enjoyed year-round. Launch kayaks or a paddleboard, cool off in the summer with a dip, drop in a line and fish, or ice skate in the winter. A detached two car garage and a garden shed provide ample storage and more possibilities. The Sengekontacket Community offers numerous amenities to support an active lifestyle. Association members have access to the dock and clubhouse, which can be reserved for small gatherings. Additionally, there are tennis/ pickleball courts, greenbelt trails, and water enthusiasts will appreciate the convenient access to Sengekontacket Pond. This home is ready for occupancy and offered fully furnished (there is a small exclusion list). Whether you're looking for an investment property or seeking a permanent residence, this Oak Bluffs home makes every day feel like a retreat.

71 Netock Avenue, Oak Bluffs MA 02557

LINK ID: 43171
Town: Oak Bluffs
Type: Single Family Residence
$2,650,000.00

Property Details

On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor primary bedroom with ensuite bath, powder room, and laundry room. Upstairs are three additional spacious bedrooms and two full baths. A new roof, siding, and central air enhance comfort. Outside, enjoy a large back deck, welcoming front porch, and an expansive yard with irrigation, a new sod lawn, lush evergreen and privet hedge borders, plus a classic Vineyard must-have: an outdoor shower. Ideally located near charming Oak Bluffs with its whimsical gingerbread cottages, Flying Horses Carousel, harborfront, quaint shops, dining, and nearby Oak Bluffs Town and Jetties beaches. Buyers and agents please verify all herein.

111 Eastville Avenue, Oak Bluffs MA 02557

LINK ID: 36870
Town: Oak Bluffs
Type: Single Family Residence
$2,798,000.00

Property Details

Not to be missed!! 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.

34 Windemere Road, Oak Bluffs MA 02557

LINK ID: 40654
Town: Oak Bluffs
Type: Single Family Residence
$2,950,000.00

Property Details

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.

23 Circuit Avenue Extension, Oak Bluffs MA 02557

LINK ID: 43212
Town: Oak Bluffs
Type: Single Family Residence
$3,100,000.00

Property Details

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.

311 East Chop Drive, Oak Bluffs MA 02557

LINK ID: 43084
Town: Oak Bluffs
Type: Single Family Residence
$3,250,000.00

Property Details

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

34 Massasoit Avenue, Oak Bluffs MA 02557

LINK ID: 42580
Town: Oak Bluffs
Type: Single Family Residence
$3,500,000.00

Property Details

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.

34 Massasoit Avenue, Oak Bluffs MA 02557

LINK ID: 42756
Town: Oak Bluffs
Type: Commercial
$3,500,000.00

Property Details

Circuit Ave. Commercial Property Build your own commercial building of your dreams on the last B1 undeveloped commercial property on Circuit Avenue's main strip. The commercial land had previously approved development plans including mixed use with commercial store front and apartments or condos above. Located on the corner of Circuit Ave and Massasoit Ave. this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms. With a large warp around porch the spacious home has a lot to offer from Employee housing to a bed and breakfast. The commercial zoned land has been approved for several different situations from housing to store fronts. Easy to show.

63 Bayes Hill Road, Oak Bluffs MA 02557

LINK ID: 42800
Town: Oak Bluffs
Type: Single Family Residence
$3,500,000.00

Property Details

Picture yourself in this beautifully designed custom home offering the ultimate in privacy. The first floor has an open floor plan which includes the dining room, kitchen, wet bar, and living space. Bypass siding doors separate the living space from the dining and kitchen. Experience the ultimate in culinary luxury with a gourmet kitchen featuring custom cabinets, high end appliances, and ample counter space with beautiful granite counter tops. The primary bedroom is located on the 1st floor away from the kitchen and living area. Surround yourself with 15 foot ceilings and lovely built in bookshelves, and a mid 1800's style rolling ladder to reach the top shelves. The primary bedroom features a private bath, large walk in closet and attached office space which has access to the back deck. The 2nd floor has three bedrooms, two full bathrooms and an extra room for your office or entertainment area. The finished basement has a full bath, and mudroom with access to the garage and dedicated storage. This area also has potential for a game room as well as a gym space. The back yard has private access to over 200 acres of trails. Please see attached document of updates and renovations.

98 Farm Neck Way, Oak Bluffs MA 02575

LINK ID: 43207
Town: Oak Bluffs
Type: Unimproved Land
$3,700,000.00

Property Details

Farm Neck Golf Club – Undeveloped Water View Parcel with Membership. A truly rare opportunity to own one of the last remaining undeveloped lots within the prestigious Farm Neck Golf Club community. This exceptional parcel offers sweeping water views of Sengekontacket Pond and the Vineyard Sound, providing a stunning backdrop for your future island home. Included in this offering is the highly coveted Farm Neck Stockholder Membership certificate—a privilege that avoids a 16+ year current waitlist and is rarely available with property sales. With no restrictions on bedroom count, this lot offers the freedom to design and build the Martha’s Vineyard retreat of your dreams. Whether you envision a serene getaway or an elegant compound, this is your chance to experience the exclusive Farm Neck lifestyle, complete with championship golf, tennis, association dock, and a welcoming community. Buyers are responsible for their own due diligence. Please consult a land engineer to confirm the final bedroom count.

28 Beach Road, Oak Bluffs MA 02557

LINK ID: 42946
Town: Oak Bluffs
Type: Single Family Residence
$3,750,000.00

Property Details

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

9 Weston Avenue, Oak Bluffs MA 02557

LINK ID: 42664
Town: Oak Bluffs
Type: Single Family Residence
$3,950,000.00

Property Details

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.

267 Barnes Road, Oak Bluffs MA 02557

LINK ID: 43025
Town: Oak Bluffs
Type: Single Family Residence
$4,500,000.00

Property Details

Enjoy waterfront living at its best with 163’ of Lagoon frontage, including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the water ~ boating, swimming, kayaking, clamming, and more. Savor the views from almost every room of the house, designed to accommodate family and friends with ease, and comfortable living. It is rare to find a home in a setting like this on Martha’s Vineyard. Tucked away off Barnes Road in a remote locale and close to many Island favorites. The main level, with high ceilings and large windows, enjoys natural light and provides spectacular water views from all angles. A wood-burning fireplace and wet bar set the tone of the living room, and a more formal sitting area is focused on the views. There is a half bath, a dining room, and a large eat-in kitchen with access to the patio. Two additional rooms with a private deck and full bath are cleverly located in a separate wing of this floor and can be used as an office or den. Unique to the second floor is a wraparound deck and screened porch overlooking the Lagoon. The primary suite has a wood-burning fireplace, a walk-in closet, and a generous en suite bath with direct access to a private deck overlooking the Lagoon. There are two additional spacious en suite bedrooms on this floor which also enjoy fabulous views. If you are looking for a quiet retreat, a second covered porch at the front of the house is the place for you. Have fun transforming this 2,000-square-foot walk-out basement with a full bath to fit your needs. Being sold furnished, this is the ultimate Vineyard Experience.

7 Overview Lane, Oak Bluffs MA 02557

LINK ID: 43001
Town: Oak Bluffs
Type: Unimproved Land
$5,100,000.00

Property Details

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.

385 Barnes Road, Oak Bluffs MA 02557

LINK ID: 43040
Town: Oak Bluffs
Type: Single Family Residence
$5,995,000.00

Property Details

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!

47 East Chop Drive, Oak Bluffs MA 02557

LINK ID: 43065
Town: Oak Bluffs
Type: Single Family Residence
$10,500,000.00

Property Details

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.

150 East Chop Drive, Oak Bluffs MA 02557

LINK ID: 42039
Town: Oak Bluffs
Type: Single Family Residence
$13,200,000.00

Property Details

Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home, it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

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