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Find charming homes for sale in downtown Martha’s Vineyard. Enjoy the vibrant island lifestyle with these centrally located properties.

Downtown

Downtown Homes for Sale, Martha’s Vineyard | MV Seacoast

Wooded parcel in Vineyard Haven located off scenic Lamberts Cove Road.   Conveniently located to Tisbury Center and neighboring Vineyard Open Land Foundation’s Cranberry Acres.  A recent survey has been completed, identifying right of way and wetlands, all other engineering and permitting is the responsibility of the buyer. A License to Sell issued by the Dukes Probate and Family Court is a requirement for sale.

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0 Lamberts Cove Road

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A must see property located in the heart of Vineyard Haven. This three-bedroom, two bath, colonial style condo boasts expansive living spread over three floors. Completed in 2019, this energy efficient 1682 sq ft home includes a 5 KW solar PV system. The open layout of the first floor includes a modern, galley style kitchen with stainless steel appliances and extensive counter space. The three bedrooms located on the second floor include the primary bedroom with an amazing third floor loft. The loft spans the length of the home and offers distant water views of Lagoon Pond and Vineyard Haven Harbor at opposite ends. The house is surrounded by unbelievable, professionally landscaped yards with ornamental trees, a grape arbor, herb garden, planting beds, cobblestone walls, front and back lawns, and over 1500 sq ft of brick paver walkways and patio spaces. The property is fully fenced and provides the owners with a private oasis in the heart of downtown Vineyard Haven. This is village living at its best! In the back of the home there are two outbuildings. A large 16'x14' insulated/heated workshop with an attached 10'x12' storage room, and a detached 6'x8' garden shed. There is a three-car asphalt driveway at the front of the property and room for additional parking in the courtyard space at the front of the house. The property is a 4 minute (0.2 mi) walk to the Steamship Authority ferry terminal. Just steps from all the shops and restaurants downtown Vineyard Haven has to offer, as well as the MV Museam , and Veterans Park. Located in the Tisbury Waterfront/Commercial District with flexible zoning that allows for residential, commercial, or mixed uses. Additionally, the home is tied into the Tisbury Wastewater system which provides for possible expansion pending town and condo trust approval.

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62 Lagoon Pond Road B

LOT #3 - A 5-lot Edgartown subdivision in an emerging neighborhood! This group of residences will feature over-sized lots with utilities in place. 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 properties will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all of the popular requests such as garage, pool and pool house. The lots are connected to town water and town sewer, and all have an established building/development envelope. The Seller will be improving the area, the entrances and implementing professional landscaping. As you will see, construction is far along on Lot 1, Lot 2 and Lot 5. Lot 3, which is 1.9-acres, is newly offered and ready for your design concept.

65 Division Road

LOT #4 - One of the last lots available in this 5-lot Edgartown subdivision! This group of residences will feature over-sized lots with utilities in place. 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 properties will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all of the popular requests such as garage, pool and pool house. The lots are connected to town water and town sewer and all have an established building/development envelope.  The Seller will be improving the area, the entrances, and implementing professional landscaping. Construction is far along on Lot 1, Lot 2, and Lot 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

63 Division Road

Location, Location, Location. Largest available parcel in State Road commercial corridor with 1.47 acres of land. Fully tenanted on month to month leases including single family house and other buildings. Lots of vacant commercial land, unwooded and ripe for development of some kind. Commercially zoned B-2.

317 State Road

Spend your time on the Vineyard this summer as a homeowner, not a renter.
You haven't missed the boat. And if you live here, you will never miss the boat.
This fully furnished, classic Vineyard-style home can be your home in time for spring.  
This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car. You will never have to worry about steamship reservations again.
You're within walking distance of everything you need—markets with locally grown food, fish, and meats; coffee shops, restaurants, galleries, 
and you can walk to the Steamship Authority terminal.  
This Vineyard classic home is being sold fully furnished down to the lobster pot. All you need to bring is your swimsuit.

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249 State 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

This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design, fosters positive and sustained interaction and relationships among people and the natural environment. The entrance to the home leads across enormous granite steppingstones bridging over expansive reflection ponds with two waterfalls cascading to a lower-level pond. The entry way welcomes one to open and dramatic living spaces with 10 ft ceilings and large expanses of glass facing Vineyard Sound and the surrounding landscape. In the main residence, each of the five-bedroom suites have unique features and connect with the beauty of the outdoors. The lower level of the residence offers amazing, eye-catching living spaces which include state of the art wine cellar, entertainment room, media room, gym and sauna. There is a spectacular glass circular staircase leading to a roof top pool which is surrounded by expansive decks and gardens and offers what is arguably the best place one could choose to watch the sunset each evening. The residence offers countless distinctive features and green technologies including self-sustaining solar energy. Minawetu is essentially a platform for a botanical garden, one with nature and a harmonic part of the island’s environment. Complimenting the property is a detached accessory building with two rooms and two full baths which is designed in harmony with the main house and constructed with the same level of detail. This outbuilding would also be a perfect place for a removed office or studio space. While it’s a short walk to the main residence, it enjoys privacy and it’s owns views over wild flower covered meadows. The landscaping is an incredible blend of open, natural settings complimented by the botanical gardens which grow on and around the house. There is a weathered stone staircase providing easy access to a white sandy beach. There are so many spectacular properties on the island of Martha’s Vineyard, each offering their own incredible features but there truly is no other property that captures the magic of Minawetu.

60 Bartimus Luce Road

This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive views of the South Shore. There are 5 suites all with luxurious bathrooms, closets, and private garden terraces. Additionally, there is an attached carriage house with 3 additional bedrooms, a billiards room and exercise room. The grounds offer a large, stunning pool, a 12 person Jacuzzi, outdoor kitchen, and parking courtyard. There is a high level of finish throughout, a whole house Lutron control system and advanced audio/video. Herring Creek Farm offers direct access to private South Shore beach and over 150 acres of conserved land.

30 Crackatuxet Cove Road

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.

34 Windemere Road

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.

311 East Chop Drive

This conforming 10,108 sq ft lot sits in the middle of a new 3-lot subdivision just minutes to Main Street.  It is approved and ready for nearby town water and sewer connections to accommodate a 4-bedroom residence.  A new private way is in, along with fire hydrants and power lines and the entrance is being improved by MA DOT.  With few Edgartown building lots available, this is an ideal location for your next project.  Note: The adjacent lot on the road is also available for purchase for a special package price of $2.6M.  Double the size of your lot, increase your building area, develop it, or sell it!

3 Ogden Lane

This charming 1942 two bedroom ranch-style home is part of a 3-lot subdivision located just a short walk to downtown.  The conforming lot is connected to town water and sewer, approved for 4 bedrooms. A new private road, Ogden Lane, has been created to allow access to the two lots in the rear.  A buyer can refurbish the existing cottage, expand, or build your Vineyard dream home from scratch.  With limited land listings, this is a great opportunity to be in a very convenient Edgartown location, close to the Village, school, library, bike path, Morning Glory, shopping, etc.  Property is being offered "as-is".  Note: the vacant lot behind is also available for purchase for a special package price of $2.6M for both lots.

87 West Tisbury Road

This conforming 10,169 sq ft lot sits on the road at the start of a new 3-lot subdivision, just minutes to Main Street.  The existing 1940's ranch is connected to town water and sewer, approved for a 4-bedroom residence.  A new private way is in, along with fire hydrants and power lines and the entrance is being improved by MA DOT.  With few Edgartown building lots available, this is an ideal location for your next project.  Note: The vacant lot behind this property is also available for purchase for a special package price of $2.6M.  Double the size of your lot, increase your building area, develop it, or sell it!

East Chop close to beach and town! This 4 bedroom home has it all; great location, wrap around porch, plenty of parking, oversized garage, large shed, walk-out basement, heating system, original hardwood floors. 4 Bedroom Title V passed septic system. Don't miss this opportunity to buy in this desirable neighborhood just a short distance to the beaches, shops, and restaurants of Downtown Oak Bluffs.

11 John Wesley Avenue

Classic turn-of-the Century building in the heart of Circuit Avenue's pedestrian bustle. This well-cared-for building has housed a vibrant clothing store for more than 30 years. There is ample window display space and high ceiling height and a newley created half bath. The expansive second floor, with lofty ceilings and a full bath is ready for creative use. It's finished interior includs skylights,bright living area with french doors to a spacious deck overlooking the charm of the Campground and providing access to two coveted, rear parking places. This seperate entrance creates possibilities for use or rental as professional office or studio space.. A large, clean basement for storage and the potential for expansion add to the appeal and versatility of this marvelous spot.

33 Circuit Avenue

Waterview beach house in Aquinnah! Just a short walking path to the calm and sandy waters of the North Shore beach. Traditional
layout with the kitchen, living, dining room and full bath on the first floor. The living room comes with water views and a cozy
fireplace, and multiple sliding doors that walk out to the wrap around porch. Upstairs the views are increasingly beautiful! Four
bedrooms share a full bath, one of the bedrooms has a fireplace while two have sliding doors that walk out to water view balconies.
The full walkout basement/garage offers plenty of room for a vehicle, extra storage or set up a ping pong table. This bright and
airy home is the perfect Aquinnah retreat.

654 Lighthouse Road

Welcome to this beautifully renovated 4-bedroom, 3-bathroom home nestled on a tranquil dead-end street, offering a spacious .92-acre lot and a fabulous finished basement. This property is the epitome of modern comfort and convenience, where every detail has been thoughtfully considered.
As you approach this charming home, you'll appreciate the quiet serenity of the dead-end street, ensuring minimal traffic and a safe environment for your family, and guests. The nearly one-acre lot provides ample space for outdoor activities, gardening, or simply enjoying the natural surroundings.
Step inside and be captivated by the meticulous renovation that has transformed this property into a haven of contemporary living. The open-concept design welcomes you with a bright and airy atmosphere. The heart of the home is the stunning kitchen, boasting Quartz countertops, and a generous island for both meal prep and casual dining. It seamlessly flows into the dining area and living room, creating a perfect space for entertaining and everyday living. 
The commitment to excellence in this home doesn't stop at the exterior and main living areas. Each of the bathrooms in this property has been completely renovated from top to bottom. These renovations ensure that not only the shared and private spaces are modern and functional but also offer a touch of luxury. 
Upon descending the stairs, you will discover a exquisitely finished basement, elegantly augmenting the available living area on the primary level.
This remarkable property unquestionably demands your attention. Kindly request a comprehensive list of the extensive enhancements available.

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69 Island Farms Road

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space.  
The main level boasts a thoughtfully designed floor plan featuring a gourmet kitchen, a spacious living area, and a dining space ideal for entertaining. The primary bedroom suite offers a private retreat with a luxurious en-suite bathroom.

With a 6-bedroom septic in place, the possibilities for expansion are endless. The generous lot size allows for the potential of a garage, guest house, and pool catering to your individual vision. 

Located in the sought-after Vineyard Haven, this home presents a rare opportunity to embrace a lifestyle of luxury and tranquility. The property is located within the Lagoon Watershed and does not require a septic system upgrade. The current system complies with the new town regulations. 24-hour notice is needed for all showings.

46 Red Buoy Lane

The West Tisbury Inn located in the village of West Tisbury. This unique offering includes three buildings on a prominent setting across from the Grange Hall and Town Hall. The Inn’s primary structure, a Victorian style farmhouse which dates to 1784, was totally renovated in 1998. There are seven bedrooms inside, one is a two bedroom suite, and six baths. All have showers and three have whirlpool tubs. The home features light, spacious rooms and modern conveniences. There is an acre of inviting grassy lawn surrounded by beautiful flower gardens, brick patios and an enormous covered porch and 20 x 24 sundeck. Two additional buildings provide more bedrooms and living space. There is plenty of parking for owners and guests. The location in the village offers easy convenience to Alley's General Store, 7A, playground, public library, Artisans Fair and Film Festival, Church, Senior Center, bus stop, Island bike paths and Lambert’s Cove beach.

1070 State Road

This custom Gambrel-style home sits high atop Manaca Hill on Chappaquiddick Island with views of Edgartown Harbor and Katama Bay. The first-floor features hardwood floors throughout, tall ceilings and lots of windows to maximize the views. Enjoy the spacious open kitchen with top of the line appliances, a large center island and soapstone countertops. Perfect for entertaining, the area opens up to a sunny living room with fireplace and French doors leading out to the terrace. A formal dining room, laundry room, powder room and den with custom woodwork complete the first floor. All three-bedroom suites are on the second floor with luxurious private baths. The large, screened porch with fireplace and lounge seating is the perfect spot for morning coffee or a glass of wine before dinner. You will have the pleasure of spending your day on the private association beach just a short walk from the house, and the Chappy Ferry is also nearby for a quick run into Edgartown Village.

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5 Armstrong Lane

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.

21 Island Inn Road 35G

In the heart of Downtown Oak Bluffs this is 1 of 2 penthouse condominiums in the building for sale. Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view of Downtown Oak Bluffs. Sit back and watch the boats come into the harbor at one of the many seating areas or enjoy diner al fresco under the stars. This spacious unit has many custom wooden features including a staircase leading to the rooftop deck creating a storage area and sleep nook with daybed. Take a step down to the comfortable living area. With hardwood floors throughout, the kitchen and dining area are divided with custom cabinetry. The spacious bedroom has an additional alcove area with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. A separate Laundry room is available on the second floor. *Another condominium is available for sale in this building buy both and Save $100,000 of the combined listed price..

37 Circuit Avenue #5

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large enclosed sun porch off the kitchen to enjoy meals and family time and is adjoined by a breakfast nook. Three (3) Bedrooms are located on the upper level. The primary bedroom is complete with a balcony to enjoy sunrises and sunsets. The 4th bedroom is on the first floor next to a full bathroom. The basement is a finished area with an additional living area. The septic system has been upgraded to allow for six bedrooms.

94 Menemsha Inn Road

The Size will Surprise~ Cloud Nine~ Located on a quiet hidden circle with 14 enchanting cottages in the Historic Martha's Vineyard Camp Meeting Association. Steps to Circuit Avenue, beaches, shops, ferries, and restaurants. This YEAR ROUND RENOVATED Charming Cottage is FULLY INSULATED with spray foam and in 2022 Brennan and Co. installed a Daikin Multi Position Air Handler with thermostat to control the system. In addition, Brennan and Co. installed an electric back-up space heater in the fully insulated crawl space that is easily accessible. Convenient on-site parking in stone driveway. Features newer Anderson Windows, primary with full bath, washer /dryer and updated electrical. This property is immaculate, well cared for and ready for new owners! Welcome home!

9 Forest Circle

Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as well as the primary bedroom suite and office on this upper level. This is a great house for entertaining and offers A/C, screened porch, generator, music system, outdoor lighting and other perks. The exterior space features a tennis court, beautiful gardens with water feature, and a cleared meadow, which is several acres in size, surrounded by woodlands. No other houses can be seen from here. A pool is possible and there is plenty of space for this addition. Subdivision potential. Includes Brickyard Beach rights.

49 Gosnolds Way

Final lot remaining in this subdivision. Includes an approved 4 bedroom septic permit. Town water available to each lot, and electricity. There is a $250 annual membership in the Holly Bear Lane Road Association required. Broker has a partial ownership interest in property. Broker is also a builder and can give a land/house package price. Homes in this area recently selling for near $3 million.

1 Holly Bear Lane

This waterfront 4 bedroom 2.5 bath quality custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and the primary bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. A large building envelope allows room for expansion should a new owner desire. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Welcome to 12 Mae Avenue, where laid-back island living meets timeless allure. This 3-bed, 2-bath gem boasts 1,700 square feet of pure Martha's Vineyard charm. Nestled in the sought-after Lagoon area of Oak Bluffs, this home offers breathtaking panoramic views of the serene Lagoon from nearly every angle. Step inside to discover the first floor, where a full bathroom and three generous bedrooms await, including an inviting primary bedroom with its own ensuite bathroom. As you make your way through the home, you'll find yourself drawn to the rear door, leading you to a covered porch adorned with not one, but two, roomy porch swings. Ascend to the second floor, where the magic continues. A spacious living room welcomes you with its lofty vaulted ceilings, creating an airy and inviting atmosphere. Adjacent, the dining room and kitchen beckon, offering the perfect space to entertain and create culinary delights while taking in the stunning views that surround you. Step outside through one of three large sliding glass doors to the upper porch, where automatic awnings provide shade for the ample outdoor dining and entertainment space. Whether you're hosting a lively gathering or simply unwinding with a glass of wine as you soak in the sunset, this outdoor oasis is the perfect extension of the home's charm. With its ideal location only steps from the Lagoon and close to downtown Oak Bluffs and offering picturesque vistas, 12 Mae Avenue is the quintessential Martha's Vineyard retreat. Whether you're seeking a peaceful getaway or a year-round haven, this home offers a classic charm with a touch of vintage allure, providing an opportunity to upgrade or renovate to match your unique style. Don't miss your chance to make this island paradise your own. This home also represents a good investment opportunity with a solid rental history. Furnishings available for separate purchase / negotiation.

12 Mae Avenue

Explore this colonial style home in the ideal Edgartown Estates neighborhood. The upside-down layout maximizes lush tree views and privacy. The main living area awaits—a bright cathedral-ceilinged room that seamlessly blends kitchen, dining, and lounging spaces. Two separate decks with sliding doors off dining and living area perfect for summer gatherings with a fireplace to anchor the open layout. The first floor has French doors into the den—a versatile space for work or guest overflow. Three bedrooms including the primary bedroom with private porch and private bath. The property has a one car garage with two built-in storage sheds. The location of this home is ideal, nestled conveniently off the bike path and close to both town and South Beach.

30 Deacon Vincent Way

THIS IMMACULATELY MAINTAINED AND UPGRADED HOME WITH GUEST COTTAGE AND NEW SEPTIC IS A RARE FIND! Situated on a quiet cul-de-sac and located only minutes from downtown Vineyard Haven, with its unique shops, restaurants, entertainment, markets, beaches, and more…. this five-bedroom home is MOVE-IN-READY! The owner has added many upgrades and renovations, including a charming studio guest cottage and finished walk-out basement.  Among the many newer renovations and replacements are: New Nitrogen mitigating Septic System, new Andersen windows, exterior doors and skylights; Irrigation system; Mini splits/Heat and AC installed throughout (in addition to the existing baseboard hot water heat); Hot water heater; All light fixtures replaced; All decks replaced with IPE lumber;… and more! The beautifully landscaped back yard, accented with statuesque Leyland Cypress trees, sprinkled with a variety of other tastefully placed shrubs and trees, creates a perfect island getaway in your own back yard.  Other features include solar panels, outdoor shower and hot tub!  Entering the front door, you’re greeted with a bright living and dining room area, kitchen with beautiful wood dining counter and beyond the kitchen, is the first-floor bedroom with a full bath across the hall with laundry room and new Samsung washer and dryer.  Moving back to the dining area –the double glass patio door opens to an immaculate and spacious 27 x 18 stone patio which flows into the spacious greenery. Beyond the patio, to the left, is the sweet guest cottage studio with kitchen and mini-split.  The “everyday” side entrance opens to a mudroom with convenient built-ins and coat hooks for easy storage.  Going up - the second floor boasts two spacious bedrooms and hall bath with skylight.  Both bedrooms feature custom built-ins as well as roomy closets with extra storage, cathedral ceilings and skylights for star gazing enthusiasts. The finished walk-out basement, including a sizeable fourth bedroom, full bath, generous family room (with upgraded large well window) and additional laundry area with more storage, completes this Vineyard GEM. A MUST SEE!!

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191 Spring Hill Road

Historic 4 bedroom Victorian Cottage and Guest House. Recently renovated Victorian Cottage on a 1/2 Ac lot in East Chop with a brand new oversized guest cottage. The 4 Bedroom Main House has been thoughtfully re-engineered to support a thorough remodel or to be used as the cottage that it is. A summer home to many over the years, the current owner has spent considerable time updating the engineering under and throughout the home in order to support any new construction. A new kitchen, insulation and new bathroom are some of the updates addressed as well as the design and build of a fully winterized and insulated guest house. Careful consideration was given to the authenticity of elements of history and style, with re-purposed hardware, wood doors and original flooring creating a sense of stepping back in time to simpler times. House is being sold as-is.

16 Atlantic Ave

In search of buyers to enjoy boating, swimming ,fishing, kayaking, paddle boarding living waterfront on Vineyard Haven Harbor! Watch the ferries passing to Woods Hole, the Black Dog Sail Boats and view spectacular sunsets over West Chop and beyond!  Quintessential two bedroom Vintage Cottage with private sandy ,rose-covered beach as your backyard. The true value is the scarcity of oceanfront properties available in this price range on the Island.  There exists a strong rental history in place (Rental rate starting at $3,000. wkly.) and a vacant non-buildable lot abuts this property to increase your privacy. New roof 2024 and Town Sewer hook up is available. Enjoy as a waterfront charming retreat, as a boathouse or while planning a renovation !

11 Beach Road

This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below. The property is located in a very conservative minded, private area abutting Katharine Graham’s Mohu estate.

104 & 111 Old Herring Creek Road

Rocco's Pizza in the Tisbury Marketplace...an Iconic Island Eatery and Definitely Some of the Best Pizza on the Island!   For Sale is this "Turn-key" business along with the 2 commercial condominiums totaling 1309 sq.ft., which the business occupies. There is also a water view roof-top deck, with an additional 500 (+-) sq. ft.  of space and plenty of seating. This a rare opportunity to own a highly 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 new owner upon an application and approval from the Town of Tisbury. Property has 3 half-baths, 2 sets of stairs to access the upper deck, water views from first and second floors, along with convenient parking. It is located adjacent to the new Vineyard Wind Headquarters on Beach Road, along the Tisbury Waterfront area. This area is in the midst of a revitalization.  NOW... is the perfect time to make your investment! Financials and an Inventory List are available upon request.

79 Beach Road B13 and B14

Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation.

Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with soaring ceilings. A staircase leads to a second-level landing area and a third level that extends across the entire structure. This additional space effectively doubles the square footage, totaling approximately 6,000 square feet. The barn offers endless possibilities, from completely renovating it into a massive 6-bedroom home to hosting large events or accommodating extensive storage needs. It must be seen to be fully appreciated.

There is a driveway to the property directly off Moshup Trail and an expansive backyard meadow perfect for a larger new house, a pool, or a large play area. Additionally, the property includes a charming 2-bedroom, 1.5-bathroom cottage with beautiful hardwood floors, providing an immediate, cozy living space.

With the existing 6-bedroom septic system in place, you have the flexibility to completely renovate, rebuild, or expand to meet your specific needs. The potential this property holds is limited by your imagination only. Don't miss the opportunity to make this unique property in Aquinnah your own, and create a custom retreat that perfectly suits your lifestyle.

9 Moshup Trail

Interior photos coming soon!! Here is your opportunity to build your family compound in the heart of Katama! Located 1.5 miles from Downtown as well as South Beach and right near the bike path, this property offers easy access to all things Edgartown! Short Walk or Bike ride to Field Club as well. This level, square half-acre lot sits on a quiet side street and currently has a garage/guest house in the back corner of the lot and the property can also support a main house with a 4 bedroom septic in place. There is the potential for 5 bedrooms with town approvals and an upgraded septic system.

7 Marthas Way

This beautiful wooded 4.12 acre parcel of land is peaceful and serene, and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. The large, flat building envelope on this parcel offers many siting possibilities, the ability to create a meadow and open gardens or keep a more wooded feel, and the land is grandfathered for a possible guest house. The sought after Plum Bush Point neighborhood is located between two large conservation preserves, the 91-acre Short Cove Preserve and the 173 acre-Sepiessa Point Reservation. Launch your kayak or small boat from the Sepiessa Point Reservation just around the corner. This is a wonderful piece of land in a special location…private and close to nature yet convenient to West Tisbury town center and centrally located on the island, essentially equidistant from here to Menemsha Harbor, Edgartown Main Street and Tisbury Main Street. This property provides natural beauty and easy access to all the Vineyard has to offer, including access to Lambert's Cove Beach. Spend your day hiking miles of walking trails or exploring the waters and beaches of the South Shore, Tiah’s Cove and Tisbury Great Pond, and then come home to your private and quiet country retreat.

25 Plum Bush Point Road

Stunning Building Lot in Vineyard Haven!

Discover this beautiful 1/3-acre building lot on Tashmoo Avenue, nestled in the serene Baylis Woods community. This prime location offers easy access to Main Street, the Harbor, Owen Park, and Lake Tashmoo, as well as nearby boating and tennis facilities.

Enjoy leisurely bike rides around West Chop or explore the picturesque beaches and trails of the Martha's Vineyard Land Bank. With ample space to build both a main residence and a guest house, this lot is perfect for creating your dream home. Plus, a preliminary septic design has already been approved for a 6-bedroom home, streamlining the building process.

Baylis Woods is a charming subdivision of custom homes, all within walking distance to the vibrant Village area of Vineyard Haven. Don’t miss this exceptional opportunity!

00 Tashmoo Avenue

Katama location! Approximately 1.5 miles to South Beach as well as the center of town. Very close to a bike path for easy access to all that Edgartown has to offer. This level lot already has a lawn with mature trees on it. Should be able to build a four bedroom house. Buyer should confirm this with the Board of Health.

9 Marthas Way

This waterfront Edgartown Great Pond compound abounds with rare features. Set in a coveted, private location on Turkeyland Cove, the 4.8 acre parcel includes two full sized homes, custom pool with pool house, +/- 400 feet of waterfront, outstanding views, and a private beach lot on the Atlantic. The main residence sits right on the shoreline, with four bedrooms and beautiful quality throughout. The second home, built in 2010, is set back from the waterfront - still with water views - with 2556 sf, two bedrooms, three car attached garage, and full basement. The property is tied together gracefully with extensive plantings, landscaping and custom fence/gateways. The pool area is an oasis unto itself, with two outbuildings supporting the L shaped gunite swimming pool. Open lawns lead easily to the waterfront, where you have access by boat to the Atlantic beach or other recreation on these pristine waters. Held by the same owner for over 30 years, this property is an opportunity not to be missed.

74 Turkeyland Cove Road

PANORAMIC VIEWS OVERLOOKING VINEYARD HAVEN HARBOR, VINEYARD SOUND and CAPE COD SHORELINE! A ONCE in a lifetime opportunity to own a BRAND NEW, FRESH, FABULOUS and FREE-STANDING Condo with over 1500 square feet of contemporary living space with lots of glass and natural light. The Chef's kitchen features Bosch appliances including a bonus 5 burner gas stove. This modern entertainer with soaring ceilings and sweeping views is the best of island living! Features include an attractive corner gas fireplace (not complete) with glass door and beautiful 5" Luxury Plank tile flooring. Designed for comfort and convenience each of the en-suite bedrooms are located on the first floor and the primary has French doors to the Mahogany deck and outdoor shower all with active harbor views. The second comfortable bedroom is located on the first floor adjacent to the full tiled bath/shower with views too! You can't beat this location steps to Ferry Ports and Main Street with all the boutique shops, galleries, and restaurants! Watch the ferries come and go and never miss a departure! An absolute must-see!

26 Union Court 7

Own a Piece of Architectural History...
This splendid home was designed by the award-winning Architect, Robert D. Orr Jr., and originally featured in House & Garden magazine. Each unique aspect of this home possesses its own creative details and charm. "Island Fortress” as it was named by the magazine, has a variety of architectural features that have been expanded upon, creating a unified whole, enriching the experience of its myriad spaces. The many angles, curves, and inclusion of numerous windows maximize the enjoyment of daily living, allowing you to fully appreciate the views from the interior and exterior spaces throughout. This remarkable, one-of-a-kind home, features 1,275 square feet of living space, over 1,300 square feet of mahogany decking on three separate levels, and a tower with a wall of windows. The main level on the second floor is designed for you to “live in the tree-tops”. You will find an open eat-in kitchen with access to a 100+ square-foot deck for outdoor dining, and newer, stainless-steel appliances. The home features a sizable living area with a wall of large windows, a dramatic, twelve-foot ceiling to the level above, with two sunny bedrooms, and 1-1/2 baths. The top floor has yet another large sunny deck, and a gorgeous, scenic tower-room, set apart from the rest: a perfect, quiet space for an office or serene retreat for a yoga studio. Imagine the numerous possibilities of the expansive deck on the lower level. It features 30+ square feet of mahogany decking and access to an enclosed laundry area and utility closet. The home is move-in ready with newer electric, wall-board, paint, and energy-efficient, spray-foam insulation. Enjoy your own “Island Fortress”, a terrific opportunity to own one of the most unique properties on Martha's Vineyard. Location: Conveniently located on a quiet street off the Edgartown/Vineyard Haven Road and just two miles to the town’s center, it is not far from the island’s public schools; 2.5 miles to Martha’s Vineyard Regional High School and 2.3 miles to Edgartown Elementary School, and the new Edgartown Library. It has easy access to the Island Ferry Terminals, the Island Transit bus-lines, and plenty of off-street parking, a perfect location for homeowners or investors, alike. R20 zoning: Home is positioned on the lot to allow for a large garden. Expansion potential

31 Ninth Street North

Historic classic Victorian located at the gateway to the Oak Bluffs Business district & adjacent to the historic Martha’s Vineyard Camp Meeting Association. 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 nearly 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.

79 Circuit Avenue

Immersed in the picturesque setting of Oak Bluffs on Martha's Vineyard, Fairview on Greenleaf Avenue, one of only ten homes in this coveted location, harmoniously blends historical charm with coastal serenity. This cherished family home holds a special place in the hearts of its owners, with roots tracing back to childhood memories and the family's Rochester, NY home on Fairview Crescent.

Architecturally designed to echo the local gingerbread cottages, an addition seamlessly integrates with Oak Bluffs' historical aesthetic. The highlight? A rooftop deck, offering unparalleled views—the highest point on Greenleaf Ave—overlooking Lakeside Park, the rejuvenated Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound beyond. This commanding viewpoint makes Fairview the ideal spot for enjoying the annual Oak Bluffs fireworks display and glorious sunrises.

For over 27 years, Fairview has been a sanctuary of family memories, lovingly maintained and enjoyed by multiple generations. It features three bedrooms and a finished basement that provides additional flexible living space. See the included photos to envision how the lower level would look with furniture and a traditional staircase. The spacious backyard and the large multipurpose building, which functions as both a shed and garage, add to the property's charm and utility. The large lot includes ample parking off of Gorham Ave.

Located on a peaceful side street, Fairview enjoys proximity to the heart of Oak Bluffs' vibrant community life, including traditions like Illumination Night, concerts at the Tabernacle, and walks to Ocean Park. Yet, it offers a quiet retreat, close to all the town's amenities without being in the midst of the hustle and bustle.

Noteworthy is the involvement of Island architect Jaime Weisman in the addition, ensuring thoughtful design and execution. Fairview isn't just a home; it's a gateway to a lifestyle enriched by the enchantment of Oak Bluffs, celebrated for its historic landmarks and coastal charm. It represents a rare opportunity to continue a legacy of creating memories in a setting that combines the best of Martha's Vineyard's natural beauty and cultural richness.

22 Greenleaf Avenue

Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district & adjacent to the historic Martha’s Vineyard Camp Meeting Association.  Create a single-family home or convert 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 nearly 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.

CHARMING CHILMARK- This sweet, bright, sunny home comes with deeded access to Chilmark Pond and South Shore Beach access. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches.
The location is also convenient, centrally located, and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern.
This three-bedroom post and beam has an efficient Viessmann heating system and a mini-split for AC. The three-acre lot has been thoughtfully landscaped, providing a serene and picturesque setting. Additionally, per Chilmark zoning regulations, there is potential for expansion, allowing for a total of 3,500 square feet and up to six bedrooms with the necessary permits and an upgraded septic system. If a pool is on the wishlist, there is also room for that with a special permit. This property has a lot of opportunities to create your vision, enjoying all Chilmark has to offer.

5 Meeting House Road

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges. Main house has two bedrooms, 2 1/2 baths, private office, expansive fireplaced living room, spacious kitchen/great room, oversized mudroom and large deck. Guest House over 2-car garage features two bedrooms, two full baths and lovely sitting room. LISTING AGENT IS RELATED TO OWNER. **No AC in living room of main house.

12 Tamarack Lane

The 80's are back in this comfortable family "Home". Clean, well maintained by the talented builder owner. Space with good sized bedrooms and plenty of storage and closets. Newly updated 2nd Floor Full Bath is ready for your finishing touches, not finished. The exterior is nicely planted with many summer flowers and greenery. Easy access to Cronig's Market, The Mansion House Pool and Health Center, our own Lagoon Pond, the famous "Chicken Alley" thrift shop and of course Main St., with all of it's Shops, Restaurants as well as the Vineyard Playhouse ! It's a gem in a haystack !!

31 Davis Street

An exceptional waterfront opportunity on the Tisbury Great Pond with two homes and a permitted dock where one can keep a boat, and motor out to the south shore Atlantic sandy beach. There are strong views of the water from both the main home and guest house where one can enjoy the abundant bird and pond life, fishing and tranquility that this coveted location offers.
The air conditioned main home has four bedrooms and two full, plus one half bathrooms.  There's a screened porch on the the south westerly corner - a perfect spot for sunset!  There's also a bonus den/sunroom with wet bar on the south side of the home.  The layout is all on one level, plus there's a huge unfinished basement and back up generator for both homes. 
The two bedroom, two bathroom guest house has a three bedroom septic and nice separation from the main home plus lovely water views from the farmers porch.  A new roof, windows and cedar shingle siding were completed in Spring 2024. 
Both homes offer existing infrastructure to live in now, renovate or ultimately rebuild the home of your dreams, with virtually unobstructed views of the pond that are ready to enjoy. 
Conveniently close to West Tisbury village, Alleys and to Edgartown/West Tisbury Road.

104 Pond View Farm Road

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. Super sunny lot that is fully engineered and ready to go. Single-family dwelling plus an 800sq ft guest house allowed by special permit, plus a detached bedroom and accessory dwellings according to the Chilmark by-laws. Great location in Chilmark, close to the Nashaquitsa town boat landing, Chilmark Town Center, and Menemsha. A dream location for Chilmark lovers. The lot offers interesting topography allowing for a lower-level walk-out basement facing south for maximum sunlight and additional living square footage.  A rare opportunity in Chilmark to own land in Chilmark in this association. Build/design package for a new owner will allow for ease in the development process.

4 Cedar Lane

This rare, unparalleled building opportunity sits on Squibnocket Farm, one of the island’s most private and spectacular locations. Squibnocket Farm consists of approximately 500 acres of forever-protected conservation land, with private access to over 2 miles of beautiful dunes and sandy beach. The 5-acre building site overlooks stone walled conservation fields and beyond to the island’s South Shore. The building envelope has been thoughtfully planned to maximize privacy, views, and to enjoy the pristine natural beauty that Squibnocket Farm affords.

2 Round Pond Road

NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to work from home. Step out from the living room to a covered porch, deck and outdoor shower. Off the main floor an open stairway leads to the lower level with 2 large bedrooms with full size windows and access to a partially covered patio. A large double section bath is shared by both bedrooms. Perfectly located a short distance off South Road the property offers easy access to both down island and up island.

4 Bartlett Woods

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres.  An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby.
Association covenants allow up to two horses.

51 Head of the Pond Road

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. Second floor waterviews over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling , plus a detached bedroom and accessory buildings allowed according to the Chilmark by-laws. Great location in Chilmark, close to the Nashaquitsa town boat landing, Chilmark Town Center, and Menemsha. A dream location for Chilmark lovers. The lot offers interesting topography allowing for a lower-level walk-out basement facing south for maximum sunlight and additional living square footage. A rare opportunity in Chilmark to own land in Chilmark in this association. Build/design package for a new owner will allow for ease in the development process.

32 Stonewall Road

Stonewall is a beloved area of Chilmark with private south shore beach access, well maintained roads and a supreme location for easy Chilmark living. Well located close to the Community Center, Chilmark Store, Quitsa Pond, Lucy Vincent Beach and Squibocket Beach. This property is being offered with two separate abutting lots totaling over 6 acres. 32 Stonewall has second-floor water views facing westward towards sunsets and Squibnocket Point. This parcel will allow for a single-family dwelling and accessory buildings (barn, garage, detached bedroom). The second lot (4 Cedar Lane) has the potential for a house and guest house, garage, barn, and detached bedroom. Both lots have a gentle southern slope allowing for a walk-out lower level where a buyer can gain additional square footage for living space. The potential square footage by right for the two main homes and a guest house is 7925 square feet of living space. This combination of acreage allows for a compound with  parking at Stonewall Association’s quiet and pristine Atlantic Ocean Beach. Both parcels are offered fully engineered with wells installed and septic designs forthcoming. This is a tremendous opportunity to acquire land in Chilmark where you can create exactly what you want while enjoying the privacy and amenities that Stonewall offers. A design-build package is available to a Buyer.

32 Stonewall Road and 4 Cedar Lane

This exquisite waterfront sanctuary boasts breathtaking views and serene surroundings on Katama Bay. The enchanting home offers ample space for comfortable living both indoors and outdoors. As you step through the front door, you are greeted by an airy and light-filled interior, flanked with windows, that seamlessly blend with the beauty of the outdoors. The spacious living area is perfect for hosting gatherings. The highlight of this home is the expansive porch where you can enjoy your morning coffee while taking in the picturesque views of the waterfront. Imagine relaxing here as you watch the sunset over the tranquil waters. Upstairs, you will find the inviting bedrooms, each offering a peaceful retreat at the end of the day. The primary suite is a true oasis with its own private balcony overlooking the water, creating the perfect spot for relaxation.  Located in a highly desirable waterfront community on Chappy and just a short distance to Edgartown Village. Don't miss this rare opportunity to own a waterfront gem that offers a lifestyle of comfort, beauty and a unique opportunity to build your Chappy compound!—sold as is.

74 & 75 Jeremiah Way

The historic town of Vineyard Haven was known as the home of ship builders, where many large schooners were built over the years. There still exists a ship builder in Vineyard Haven, Gannon & Benjamin Marine Railway is located right next to the Black Dog. This quaint town was called Holmes Hole until 1871. Spring Street which runs right up from Main St is one of the oldest streets in Vineyard Haven. This is where this lovely house, which was built by the owners in 2013, sits large on it's lot. The location is the best of two worlds; close enough to town that in 5 minutes you can be walking along Main St shopping at all the local stores, or having lunch at one of the restaurants or just sitting on a park bench eating an ice cream cone. If you need to catch a ferry, that is a 10 minute walk. And yet, most of the time you are far from the "Maddening Crowd" tucked away at 128 Spring Street. The house has a large living room with a mantel fireplace, spacious kitchen, dining room, half bath, mud room, and an attached in-law apartment, which can have many uses depending on the needs of the new owner. The second floor of the house has a master bedroom ensuite, and 3 other ample bedrooms with another full bath. The basement is partially finished with an exterior access. This house is perfect for a family, or anyone who loves living close to the historic village of Vineyard Haven. Interesting note: behind the house on a separate lot is a 1 bedroom Guest House with a 4 bedroom septic, which means the the Guest House could be added onto or a separate house could be built. This would be a separate purchase.

128 Spring Street

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

On approximately .40 of an acre this 21 year old home has much to offer. In a very convenient location close to the
Farm Neck golf course,  O.B. elementary school, and a land bank conservation property - the 72 acre Tradewinds Field Reserve dog park. Two decks provide summertime fun and the walk out basement with bath offers an opportunity to finish off more living space. An excellent floor plan lends itself to entertaining.

10 Nunes Way

Waterview and waterfront property that is protected from the elements and set amongst some of the finest homes in Makonikey! Complete with fully approved plans by Moskow Linn Architects for a new 4 bedroom home with pool and 2 bed. carriage house, this private compound includes three existing dwelling structures that were originally built in 1974, 1981 and 1985. There is a northerly view of Vineyard Sound from the home site, along with ready access to an exceptionally sandy north shore beachfront (approx 100 yards from the home site via 50% ownership in 39 Beach Pebble Rd). Take the plans and build as designed or customize as you see fit! An incredible opportunity to create your dream escape in an exceptionally private and tranquil setting.

26 Chappaquiddick Avenue

UNDER CONSTRUCTION: Coastal inspired Katama Gambrel with swimming pool and pool house conveniently located to both downtown and beaches. Completion Spring 2025. Designed by architect Sasha Robinson White and executed by Dubin Construction. Some customization still available including optional addition of up to 3000 sf finished basement with 6th bedroom and/or attached two car garage with finished guest quarters. Pool will be approx. 16’ by 36’ gunite with integrated hot tub/spa and bluestone patio for seating. Exquisite finishes and generous proportions throughout the home. Designed as a hub for all Martha's Vineyard activities in summer or year-round, this is an exceptional home to be cherished by multiple generations. Architect plans and finish details available upon request.

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