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South Shore

South Shore Homes for Sale, Martha’s Vineyard | MV Seacoast

Live the beautiful Island Life with this gorgeous condo at an affordable price. This is a delightful one and a half bedroom seasonal condo ( sleeps 6) available for your families use. When you’re not here, the management team will rent and take care of everything for you. Amenities are amazing. There’s a beautiful pool, spacious outdoor area with lots of seating, fire pits, play area &  barbecues.  Right next to the popular Nomads restaurant and walking distance to two ocean beaches, bike paths and buses to towns.
Brokers must accompany clients.

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21 Island Inn Road 35G

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This 3 + acre Lower Makonikey lot with mature trees is a short distance away from a deeded private association beach. A quiet friendly community with protective covenants. The lot has been surveyed and a building envelope has been established. To date no testing or septic design has been performed.

00 Kennebago Avenue - 65-E-1

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS.  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.

0 Eastville Avenue

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!

22 Paddock Road

KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with a full bath and a second-floor primary suite. Outside, you will find a private back deck, beautiful garden and open lawn. The newly appointed Association swimming pool is close by. Located in the highly desirable Katama area, this home sits less than two miles from South Beach and even closer to Edgartown Great Pond. This private community is a hidden gem, ideal for year-round living, a vacation home, or a rental investment.

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17 Meetinghouse Village Way

Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system.

2 Other House Road

Spectacular, private beach lot located just off Moshup Trail. Gated entry, parking rights and a deeded 1/5 acre of beach on the Atlantic. This is not a buildable lot, no structures of any kind are permitted. Lot 7-5

00 Moshup Trail

Exceptional 8 bedroom home with attached artist/fitness barn studios. 
Each bedroom includes a en-suite bathroom.
The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

26 Curtis Lane

Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 

211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each bedroom includes an en-suite bathroom. Spacious kitchen and dining area. The kitchen/dining area includes: 2 refrigerators and 4 freezer drawers, A 5-burner gas stove and oven, 2 dishwashers, 1 microwave. Spacious living room: including 2 sofas and 1 coffee table, finished basement (2,000 square feet), Basement includes: 10 washer/dryers, 1 television and DVD player, 2 small rehearsal rooms, Complimentary Wi-Fi, Outdoor deck with picnic tables.

26 Curtis Lane is an exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

Two more adjacent lots with parking and a yard are also available for purchase upon request.

211 Upper Main Street & 26 Curtis Lane

PRIME 5-ACRE LOT - R20 ZONE EDGARTOWN 
Introducing a rare opportunity to own a piece of the island (currently two parcels) close to all Edgartown has to offer. This spectacular level lot is situated along Edgartown Road and provides the perfect setting to create a private retreat or a potential subdivision. The property borders the Triangle area of Edgartown, with ease of access to public transportation routes. Ideally located just minutes from beautiful beaches, boutique shops, and world-class dining. Please note, that perc tests and utilities are the buyer's responsibility. Don't let this extraordinary opportunity to build slip away!

15 & 27 Pennywise Path

Panoramic Ocean Views can be enjoyed from each level of his thoughtfully built 4 BR home designed for easy Summer enjoyment or 4 Season living. It is wonderful in every way. It is built into the hill, so the first floor feels like a 2nd floor. Downstairs is a large open space to create a family room, or use it the way it is as a home gym/spa with state of the art equipment included. Energy efficient, private, easy access, plenty of outdoor space that has huge potential since the home takes up only 1/3d of the property. Enjoy complete privacy from neighbors or the road, nestled into a hillside where bird life abounds, yet convenient to dining at the Outermost Inn, Lighthouse and cliffs.

The home is lavishly laid out over 2 levels and provides over 3000 ft. of living space. A wall of glass on both levels for the enjoyment of the uniquely insteresting, forever protected vistas across a one of a kind beauty of the pristine fauna and flora of Aquinnah. There is nothing obstructing the views to the horizon with the Elizabeth Islands, and Menemsha hills. Watch the sailboats glide by and relax in style and comfort in this wonderful space. All Aquinnah Beaches are accessible within a short distance. Price has been drastically reduced by motivated Seller! House comes Turn Key for immediate use. Fully furnished and ready to go right now, or Enjoy your first Summer 2025 at this fabulous Vineyard Coastal home.

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382 Lighthouse Road

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 Barnes Road

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!

30 Sengekontacket Road

You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around mahogany decking. Views are also seen from the large, first floor, primary bedroom with en-suite bath. Descend to the lower level, where three additional bedrooms await—two of which have water views. The larger of the three bedrooms has walk out access to a patio with an adjoining flower and vegetable garden. A large bathroom, laundry and utility room complete the lower level. The property is further enhanced by stone walls and mature landscaping, creating a picturesque setting. A workshop/studio with full basement, plumbing, electricity and a wood stove is located at the rear of the property. A new Land Bank/Sheriff's Meadow property currently under development will provide access to Squibnocket Pond and one of the most beautiful beaches on the island and is located just across the street.

4 Nomans Watch Road

PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed Katama, just 4 minutes to Main Street in Edgartown. PLEASE NOTE: Locus shown in first photo is approximate. Refer to attached documents for complete survey.

26 Mill Hill Road

Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The Lightkeeper’s Inn, this historic Inn was said to be home to Henry Lyman Thomas, one of the last lightkeepers of the Edgartown Lighthouse.  The property is unique in that it offers onsite parking, which is a rarity on Martha’s Vineyard. Currently operated as an Inn, this property may be converted to a single family residence with the required proper permitting and approvals. It is conveniently located close to Edgartown Ferry, Edgartown Lighthouse, and minutes from N. Water Street, which offers shopping and restaurants.

25 Simpsons Lane

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!!

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26 Winthrop Avenue

Private Atlantic Ocean beach lot located on the serene coastline of Aquinnah on Martha's Vineyard.  This exceptional beach lot offers a rare opportunity to own a piece of prime oceanfront. Located just off of Moshup Trail is private gated access to your own designated parking area. From there, a picturesque boardwalk meanders through native flora and opens onto a sandy path leading directly to the water's edge. The sandy ocean beach offers panoramic views of the Atlantic Ocean. Don't miss your chance to own a piece of Martha's Vineyard's coveted coastline.

WELCOME to this turn-key CHAPPY COMPOUND!  This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable nets.  Game on!  All of this is set upon three acres of private, expansive land with distant WATER VIEWS! 

The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location!

This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping.

The Workout & Game Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. 

The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large.  

The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Workout & Game Barn.  The interplay between the Workout & Game Barn, Pool House, Pool and abutting Tennis and Pickleball Courts makes this Chappy Compound fun and playful! Strong Rental History.

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72 Chappaquiddick Avenue

East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to call East Chop, a close-knit community only a short distance from the harbor and downtown Oak Bluffs, home!

33 Clay Avenue

Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on property is a detached 304sq. ft. garage/cottage.

9 Galway Road

Set atop a hill overlooking Menemsha, Quitsa and Squibnocket Pond sits this stunning home. A masterful combination of up-island elegance, fine craftsmanship and expert design sets this contemporary apart from other high end homes. Being sold completely turn key, this house was built  with the finest of materials and finishes  and with entertaining in mind. Large  living room with magnificent fireplace, state of the art kitchen and screened in porch overlooking the pool. The family room adjacent to the guest bedrooms offers another entertainment space while affording privacy. This home is at harmony with its natural surroundings, while at the same time sophisticated and extremely comfortable. A bonus pool house with bathroom, lounging area and kitchenette is surrounded by extensive gardens and patio area. A meditation pond at the entry of the house sets the Zen mood as you approach this enchanting home. Easy to show.

515 State Road

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.

8 School House Village

Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is in an area of several multimillion-dollar homes and will accommodate a house, guesthouse, and swimming pool. The neighboring 3.2-acre lot (48.5), which includes 60 ft of water frontage on Vineyard Sound, is also available for purchase. Note: The lot is most easily accessed via Chappaquiddick Ave, where the cleared area is easily visible on the left.

11 Beach Pebble Road

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench, offering stunning water views of Vineyard Sound and the Elizabeth Islands. Ideally located just steps from Gray's Beach and dock, this is one of the most picturesque properties in Seven Gates Farm. The Seven Gates Farm community consists of 45 homesites on 1,600 acres with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails for walking and horseback riding. Residents of Seven Gates Farm also enjoy exclusive access to 1.5 miles of private beach, two piers, and two tennis courts. This rare opportunity allows you to become part of a remarkable community, once an assembly of farms, that remains dedicated to the preservation and stewardship of the land.

85 North Reservoir Road

Welcome to this delightful 4-bedroom, 3-bathroom home, perfectly situated in a highly desirable location where convenience meets tranquility. Just a short stroll from town, restaurants, Tashmoo Landing, and tennis courts, this property offers the ideal combination of lifestyle and leisure.

Step onto the covered front porch and into a warm, inviting space featuring two living rooms—one on each floor—providing flexibility for entertaining or quiet relaxation. The first-floor primary bedroom with an ensuite bathroom ensures comfort and accessibility, while the additional bedrooms offer plenty of space for family and guests.

There is a lovely screened-in porch, perfect for enjoying morning coffee or evening breezes. The large backyard is a private oasis, complete with an outdoor shower, blue stone patio, fire-pit and plenty of privacy.

Additional features include a full basement, large 1/2 acre lot that offer a variety of possibilities  to expand including a guest house and/or a garage making this property a rare find with exceptional versatility.

Whether you’re looking for year-round living, a vacation retreat, or an investment opportunity, this home checks all the boxes. With its unbeatable location, you’re just steps from everything that makes this area special.

Don’t miss the chance to make this your own—schedule a showing today!
Showings begin Friday January 17th.

54 Lake Street

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.

47 Circuit Avenue 1B

Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design details. There is a stunning swimming pool area as well as detached guest quarters. The property was once part of an equestrian estate and there is an 8-stall barn with turnout shed that is the subject of a Stan Murphy painting. Privacy to the north is assured thanks to many dozens of acres of conservation land.

140 Merry Farm Road

Village dreams come true…
STUNNINGLY CRAFTED, **this four-bedroom five bath property in Edgartown Village with Garage is truly a rare find! Situated on a corner lot just two blocks north of Main Street and two blocks from the Harbor, it features walking convenience and luxury in one package. 

Main and second floors combine over 3,400 square feet of spacious, elegant living.  The partially finished lower level abounds with an additional 1891 sf, opening even more possibilities for unique customization to suit any lifestyle.

Three of the four bedrooms are en suite with all four quarters well separated, adding wonderful privacy from the next.

The show-stopping central staircase with its grandeur and contour adds a touch of elegance to the home, complemented perfectly by the warmth and sophistication of the maple inlay flooring, which is comfortably radiant heated throughout all three floors.

Despite its proximity to the bustling village life, the thoughtful sound-proof design allows for quiet relaxation when desired. The abundance of French doors not only brings in natural light but also seamlessly connects indoor and outdoor living spaces, enhancing the overall inviting atmosphere of the home.

Overall, this superb Edgartown Village property offers exceptional location with a unique blend of charm and elegance, making it a wonderful investment for those seeking a truly special home in the highly desirable Village of Edgartown.

62 North Summer Street

LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all the popular requests such as a 3-car garage, pool and pool house. The oversized lots are connected to town water and town sewer and all have an established building/development envelope.  Substantial new construction homes are up on surrounding lots 1, 2, and 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

63 Division Road

Coveted Down Harbor!
This 3-bedroom 2-bath home sits in the Down Harbor association in a prime Katama location. This charming home is an entertainer's delight with a spacious yard, a large deck, an outdoor kitchen, pool, and recently built pool house with 2 outdoor showers, 1/2 bath and  a storage shed. This home features vaulted ceilings, exposed beams, and a bright kitchen with a breakfast bar open to the dining area. The living room is bathed in natural light with 2 oversized sliding doors to the deck overlooking the pool and outdoor kitchen.  A bonus loft offers additional living space.  The current homeowners have gone through the approval process for an attached garage with room above, for a maximum bedroom count of 4 on the property.
Enjoy exclusive homeowner rights to the association's private beach, dock and mooring field, all rare and desirable amenities. 
Located between downtown Edgartown and South Beach, this property is perfect for beach lovers and outdoor enthusiasts looking for a retreat with easy access to biking and walking paths. Don't miss out on this prime coastal living opportunity!   
*Offered fully furnished, less a few owner exclusions*

4 Down Harbor Road

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.

9 Weston Avenue

In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, two up and one down, share bathrooms on each level. An outdoor shower,  screened porch and outdoor decks make the indoor / outdoor transition comfortable. This property has an excellent rental history, or make it your island getaway or year round home. Offered turnkey, As Is.

6 Gerts Way

"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.

2 Farm Path

Perfectly sited on a knoll with expansive water views at the head of the Lagoon, it is a few short steps to the private sandy shore for swimming, kayaking or continue down the pond out to open water. Designed by the owner's architect father (Nembhard Culin a renowned watercolor artist,) it worked as a solar-heated house for over 40 years. The non working hot air solar collectors have now been turned into a photovoltaic system so it is now 100% renewable electric. The award winning organic garden is being revived by the resident caretaker.

126 Border Road

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore.

Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

64 Squibnocket Farm Road

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming, sailing, and relaxing with friends or family are just a few of the daily dalliances of time spent on Chappy. There is simply no better place to relax and unwind.

9 North Neck Road

This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room, dining space, and kitchen. Glass doors throughout the space lead to a large deck, offering a peaceful view of the private backyard. Recent updates include fresh landscaping and various interior improvements. With Long Point Beach just down the road and access to the exclusive Lambert’s Cove Beach, this home is the ultimate Island retreat. Whether you choose to enjoy it as is or explore its expansion potential, this property is a true gem.

108 Charles Neck Way

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.

150 East Chop Drive

Welcome to a stunning blend of contemporary elegance and charm nestled in the heart of Edgartown. This exquisite water view residence offers 3 spacious bedrooms and 4 luxurious bathrooms, encompassing a generous amount of meticulously designed living space.

The luxurious and versatile interior boasts a modern, move-in ready design, with a gourmet kitchen and recently renovated spaces. Whether you're seeking a private retreat, a space to entertain or an investment property, this home caters to all your needs.

Additional amenities include a spacious garage with studio above that is perfect for extra guests; and a charming outdoor living space with a stone patio. Property is a short walk over to the public boat launch!

99 The Boulevard

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard. The property feels quintessentially Chilmark with ancient stone walls and mature plantings. The detached guest quarters features a spacious bedroom, full bath, kitchenette eating area, and a garage. Menemsha Hills Reservation is your backyard - 211 acres described by its Trustees as follows: "Menemsha Hills was shaped by thousands of years of glacial advance and retreat. Today an array of mini-environments comprise a rugged, pleasant landscape: low wetlands, woodland groves leading to a hilltop, wind-blasted coastal plains, a rocky ocean edge, and 308-foot Prospect Hill." Not to mention - Menemsha sunsets are a short distance away!

345 North Road

Spectacular 20.8 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1.5 mile wide main pond and barrier beach to the ocean beyond. The handful of well pruned trees on the property enhance the water views. The sophisticated and charming quality house was built by Andrew Flake, arguably the finest Vineyard builder over the last 40 years. Mark Hutker created an innovative design with an arc shape nautical theme so every room faces the water. The 3 second floor bedrooms enjoy large balconies and the first floor primary bedroom with separate sitting area opens to a nice deck and quiet garden sanctuary. The hand made luxury kitchen cabinetry and extensive woodworking were done by Smallbone, a British Company noted for time honored design and craftsmanship. Adding to this estate, reflecting decades of careful planning and development, is a lovely private pool and pool house, 4 room guest suite over the garage with large balcony, two stone wall enclosed specimen fruit tree meadows, a large field circled by a grand stone wall, an idyllic lily pond and 2 miles of private trails. Keep boats and small craft on your mooring at waters edge for a short trip to the 3,000 ft Boldwater private barrier beach. Boldwater is 38 homesites on 450 acres with 150 acres of conservation and abuts approximately 1,500 of additional conservation land and a few large estate. A most remarkable rural area convenient to town and the airport. (14.4 abutting acres with grand meadow on 3 Jacobs Neck Rd is available for purchase separately)

32 Boldwater Road

Spectacular 35 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1 1/2 mile wide main pond and barrier beach to the ocean beyond.  The handful of well pruned trees on the property enhance the water views.  The sophisticated and charming quality house was built by Andrew Flake, arguably the finest Vineyard builder over the last 40 years.  Mark Hutker created an innovative design with an arc shape nautical theme so every room faces the water.  The 3 second floor bedrooms enjoy large balconies and the first floor primary bedroom opens to a nice deck and quiet garden sanctuary.  The handmade luxury kitchen cabinetry and extensive woodworking were done by Smallbone, a British Company noted for time honored design and craftsmanship.  Adding to this estate, reflecting decades of careful planning and development, is a lovely private pool and pool house, 4 room guest suite over the garage with large deck, two stone wall enclosed specimen fruit tree meadows, a large field circled by a grand stone wall, a idyllic lily pond and two miles of private trails.  Last but not least, are 14+ subdividable acres. Keep boats and small craft on your mooring at waters edge for a short trip to the 3,000 ft Boldwater private beach.  Boldwater is 38 homesites on 450 acres with 150 acres of conservation and abuts approx. 1,500 acres of conservation lands and a few large estates.  A most remarkable rural area convenient to town and the airport. (** The 20.8 acre 32 Boldwater Road waterfront property can be purchased without the abutting 14+ acres at 3 Jacobs Neck Road for $8,550,000)

32 Boldwater Road, 3 Jacobs Neck Road

Handsome, newly created large level parcel of land in Chilmark! Bounds are in, lot lines are flagged and brush cut, as well as a bit of the lot interior so that you can appreciate the size and orientation of the parcel. Well will be installed and perc test completed soon. Quenames Road is off South Road, a short hop to West Tisbury village center with Alley's General Store, the Town's fabulous library, 7A takeout, and movies and performances at the Grange; while your Chilmark address affords access to the Town's Lucy Vincent and Squibnocket Beaches! *Lot Subdivision is too new for the land to have been separately assessed. This is the 3 acre southerly portion of what had been identified as 45 Quenames Road.

00 Quenames Road

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.

47 Circuit Avenue 1A

Rocco's Pizza Restaurant located in the vibrant Tisbury Marketplace. This is an Iconic Island Eatery open year-round! For Sale is this "Turnkey" business along with the 2 commercial retail condominiums totaling 1309 sf, which the business occupies. There is also a water view roof-top deck consisting of an additional 500(+-) sf. with plenty of seating. OWNER IS OPEN TO CREATIVE FINANCING WITH THE OPTION OF PURCHASING THE BUSINESS ONLY AND LEASING THE REAL ESTATE PORTION WITH AN OPTION TO PURCHASE THE REAL ESTATE IN THE FUTURE. This is a rare opportunity to own a successful and well-established island business. Sale includes all equipment, commercial appliances, furnishings, fixtures, and recipes. Owner currently holds a Beer and Wine Permit which is transferable to the buyer upon application and approval from the Town of Tisbury. Property has 3 half-baths, 2 sets of stairs to access the upper deck. There are water views from the first and second floors, along with an abundance of convenient parking. A very desirable location, along the Tisbury Waterfront area which is in the midst of a revitalization. NOW is the perfect time to make your investment. Inventory List and Financials are available upon request.

79 Beach Road B13 and B14

Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third bedroom and a generous semi-private loft complete with a closet. This versatile loft area is perfect for creative flex space, ensuring everyone has their own retreat. The full basement offers ample ceiling height, presenting a fantastic opportunity for future refinishing or renovation. Imagine the possibilities: a home gym, entertainment room, or additional living space. Step outside the kitchen onto the expansive deck, perfect for al fresco dining and entertaining. The large backyard, complete with a vegetable and flower garden, sprawls over 1.1 acres. Nestled in a serene setting, this home combines comfort, functionality, and potential, making it the perfect place to create lasting memories. Don't miss the chance to make this charming Cape your own!

46 Old Coach Road

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

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.

Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open concept kitchen with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep and dining area, and 2 queen Murphy beds - perfect for guests. Enjoy exclusive access to a private community beach and boat dock and community tennis / pickleball courts, enhancing the home's resort-style living experience. Landscaped grounds with irrigation, outdoor enclosed shower, 2 pea gravel fire-pit areas, bocce ball court, two decks with water views, hot tub, gas grill connection off the kitchen area and ample parking. Primary bedroom has a deck, walk-in closet and steam shower. Located just a short distance from downtown Oak Bluffs and right on the bike path - don't miss this exceptional coastal retreat!

6 Marthas Park Road

TURKEYLAND COVE: 3-ACRE ESTATE-SIZED PARCEL IN KATAMA.  This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. An idyllic Katama lifestyle awaits . . . with mornings spent walking or beachcombing along the windswept shores of South Beach or spent swimming and picnicking at Norton Point. For time on the water the property offers easy access to the Edgartown Great Pond from Wilson's Landing where you can enjoy kayaking, paddle boarding or taking a motorboat across the pond to enjoy the sand and surf at the Land Bank barrier beach. This expansive property offers the opportunity to enjoy all the best of Katama living with easy access to Edgartown Village shops, restaurants and more. IMPROVEMENTS: NHESP approvals already obtained and clearing has been done inside the approved building envelope. There is a new electric service off Slough Cove Road, a new well has been installed and 4-bedroom septic design has been approved by the Edgartown Board of Health.  Architectural plans available for separate purchase ($75,000) with a gorgeous modern farmhouse.

9 Turkeyland Cove Road

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime location for watching incredible sunsets over the pond to the ocean beyond and strolling into town for beach-going, fishing, boating, shopping, and dining. The layout and flow of the spaces feature captivating views from many vantages, and all new windows enhance natural light and views. The refined palette and materials reflect the natural surroundings and match the experience of Menemsha living. With modern forced air cooling and heating and a fully insulated structure, the property can be enjoyed year-round. Additionally, the ground level suite is the ideal complement to the two upper floors, providing a private retreat for family and friends. A turnkey ocean-view offering, the Salt Shack presents a rare opportunity to enjoy a stunning escape to the authentic fishing village of Menemsha.

10 Mollys Way

10 Molly's Way

A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and a kitchen with doors leading out to a welcoming screened porch. This home features a primary bedroom suite  and a guest bedroom suite on the first level. Two additional guest bedrooms complete second floor. The exclusive Boldwater Association offers tennis courts, a boat landing on the Edgartown Great Pond, and a private South Shore sandy Atlantic Ocean beach. The Edgartown Great Pond is great for kayaking, paddling and boating.

4 Boldwater Road

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven’s most quiet and quaint neighborhoods.  With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also features a renovated garage with a finished second level, perfect for a creative studio. Inside, the home exudes warmth and elegance, with wide pine flooring, custom craftsmanship, and intricate wood detailing on the ceilings. The spacious living room, centered around a gas fireplace, is both inviting and stylish. The sunlit kitchen, equipped with top-of-the-line appliances and refined finishes, includes a cozy window seat that adds to its charm. The primary bedroom suite offers a serene retreat, complete with a private tile bath and access to a 2nd-floor deck. The three additional bedrooms are equally comfortable and well-appointed, providing ample space for guests. The finished lower level expands your living space further, ideal for a home theater, gym, or playroom. Spend your days soaking in this privacy that this tranquil abode provides, or take advantage of its ideal location to access the hustle and bustle of downtown Vineyard Haven where you can enjoy various galleries, shops, and fine dining.  This location is also convenient to Owen Park Beach, West Chop and Mink Meadows Golf Club.

36 Tashmoo Avenue

TURN KEY READY 37 Knoll Drive, nestled in the heart of Katama, on a quiet sandy road,  This charming 3-bedroom, 2 full bath home offers 1,232 square feet of cozy living space, including 520 S.F. of finished basement. Located on a generous 16,552 square foot lot. This home is offered "turn key" move in or rent out ready. ( 1 exception Dining Rm Table)

Step inside to discover an open living and dining area, complete with an original wood-burning fireplace and a delightful bow window that fills the space with natural light. Oak floors throughout this home. The kitchen boasts stainless steel appliances & sleek stone counters and opens onto a deck that leads to your private backyard—perfect for summer barbecues or a quiet morning coffee.

The primary bedroom features a full en-suite bath, while two additional bedrooms share a separate full bath. Wood floors and paneling add warmth and character throughout the home, and central A/C ensures comfort on those hot summer beach days.

Recent updates include a freshly painted interior in 2025, a new roof in 2020, & renovated baths with new fixtures in 2015. The finished 520 S.F. area of the basement, completed in 2019, offers a fantastic space to watch the game or get some work done using the space as a home office.

Located just a short bike ride from the Katama Kitchen, Katama Store and beautiful South Beach. This beach home is perfectly positioned for enjoying all that the Katama area has to offer. Just a 25-minute bike ride or a 5-minute drive to Edgartown's vibrant main street.

This is a fantastic opportunity for both year-round living or rental income (rental history available). Don't miss out on this gem in a neighborhood of beautifully renovated homes. Town water runs in front of this property on Knoll Drive. Possible expansion of an additional bedroom with upgraded septic & town water. Edgartown approvals would be necessary. Title 5 passed on the existing Septic.

37 Knoll Drive

Sublime hillside site with old growth trees and walking easement to 16' of sandy lagoon pond beach.
This property is in the lagoon pond water shed and will require a NitROE denitrification component on the septic system. All information should be verified by the Vineyard Haven Building Department and Board of Health.

Upon entering through the charming side door, you're welcomed into a beautifully screened sun porch – the perfect spot to relax and soak in the surroundings. This inviting space leads to a sprawling, light-filled chef’s kitchen, designed for both culinary creativity and social gatherings. Adjacent to the kitchen, a warm and welcoming living room awaits, featuring a convenient half bath and access to a cozy first-floor bedroom. Just to the right, you’ll discover a second ensuite bedroom, offering both comfort and privacy for guests or family.

From the hallway, a staircase leads to the upper level, where two additional, spacious bedrooms each come with their own well-appointed bathrooms, creating a serene and private retreat.

A second door off the living room opens to the lower level, where you’re greeted by a partially finished entertainment haven, complete with a pool table – an ideal space for relaxation and recreation. Further down the hall, to the left, is the media room, a cozy setting perfect for movie nights. Across from the media room, you’ll find a convenient half bath that leads into a laundry room with direct access to the backyard, blending functionality and convenience seamlessly.

32 Norton Orchard Road

EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well cared for neighborhood with over 70 acres of association common land. The property provides room to grow with a 6 bedroom septic system in the ground, and the lot has an open, sunny and bright feel to it. Surrounding gardens delight with a series of perennials, which bloom through spring and summer. The location is convenient to a variety of desirable amenities. Long Point Beach and Wildlife Preserve, numerous Lank Bank conservation trails, Black Sheep Gourmet, The Fish House, MV Airport, Vineyard Golf Club and Morning Glory Farm are all nearby. Walks, hikes and bike rides await your exploration. With options galore, it's easy to envision your Martha's Vineyard lifestyle starting here!

21 Coffins Field Road

Colonial historical home with over 1,650 square feet of living space, plus 457 square feet of finished basement space, featuring 3 bedrooms ( TITLE V approval 5 bedrooms) and 2 bathrooms all in a highly desirable location, convenient , yet private and tranquil. Located just 0.5 miles from downtown Vineyard Haven, enjoy easy access to Main Street, Owen Park, VH Ferry and Tisbury School. The expansive yard offers plenty of space for entertaining, gardening, play areas, or potential expansion with required town approval. TITLE V Inspection passed, NOT situated in the TISBURY WATERSHED! Recent upgrades throughout the home ensure modern comfort, with a detailed list of improvements. This home offers excellent potential—perfect for both year-round living and seasonal retreats. Don’t miss the opportunity to make this beautiful property your own!

110 Daggett Avenue

Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living room is open to the tiled eat-in kitchen area and the hallway leads to a pantry, full bathroom and two first floor bedrooms. The second floor offers a full bathroom and two generously sized bedrooms. The interior has been completely painted and sparkles brand new with new paint on ceilings, walls, windows, doors, baseboard heaters, and all trim. Brand new carpeting in the first-floor hallway and bedrooms. Do not miss the opportunity to purchase this great investment!

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