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LINK ID: 33574 $3,100,000

Stairway to you own personal private beach and dock
Stairway to you own personal private beach and dockRelaxing sunroomGuest bedroom number 1
Town: Vineyard Haven
Type: Single Family

**RECENTLY INSTALLED 5 BEDROOM SEPTIC ** Rare opportunity to own this vintage, dutch colonial waterfront home situated atop a West Chop bluff offering unparalleled views of Vineyard Haven Harbor, East Chop, and Vineyard Sound. Elevated above a secure bluff, enjoy breathtaking views with your friends and family from every vantage point! This unique property has its own private white sand beach with a private stairway and swimming dock, which was completely rebuilt in the spring of 2015. Enjoy the feeling of seclusion from your oasis within walking distance of shopping, restaurants, the ferry and all that downtown Vineyard Haven has to offer. Also includes a detached one car garage, lush landscaping and grass, mature trees and an extra downstairs toilet and shower for after beach use (not included in 2.5 bath figuring). Owned by a single family since 1955 and while it has been updated over the years, the original charm of this delightful home remains entirely intact. This house could not be replicated today in its current location. Don't miss this opportunity!

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LINK ID: 33561 $4,800,000


magnificent water views across Stonewall PondEnjoy al fresco dining on the 2  water facing decks.out to the Atlantic Ocean.
Town: Chilmark
Type: Single Family

Spectacular waterfront property with private dock on Stonewall Pond. Breathtaking one-of-a kind views across Stonewall Pond out to the Atlantic Ocean as well as stunning views of Quitsa Pond. This magical property is known as the "Lorca" home because the current owners purchased it in 1972 from the Garcia Lorca estate. With modern upgrades, this is a year round home which evokes old Vineyard charm and features water views from almost every room. Built in 1939 "Lorca" was expanded in 1973 and has been been lovingly renovated and maintained over the past 40 years. There are 3 bedrooms and 2 bathrooms, an open living room, kitchen and dining room, an adjacent family room with fireplace and wonderful picture windows to maximize the water views. Dine al fresco on one of the 2 large decks and enjoy magical moon-rises and spectacular sunsets with 360 degree water views from the roof top deck. Stroll down the gently sloping yard to a private dock and enjoy sailing, kayaking, swimming and paddle boarding. Boat from Stonewall Pond under Hariffs Bridge to Quitsa and Menemsha ponds and then out to the Vineyard Sound or take a quiet moment at home to simply relax in the surrounding beauty. The sunrises and sunsets here are breathtaking and watching the moon rise over the pond is spectacular. It's just a short walk (.3 miles), boat or drive to nearby private association Stonewall ocean beach. This is an amazing opportunity to own a very special Chilmark waterfront property that is surrounded by nature. This one-of-a-kind property is part of a 3 home compound also being offered for sale together for $10,300, 000 ( link id 33559) and the other two homes "Lenom/Boathouse" are being offered separately as well for $5,500,000 ( link ID 34994)

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LINK ID: 33559 $10,300,000


The Magnificent views  across Stonewall PondEnjoy al fresco dining on the water facing deck.
Town: Chilmark
Type: Single Family

Spectacular 3 home waterfront Chilmark estate on 5.4 acres with private dock on Stonewall Pond. Breathtaking one-of-a-kind views across Stonewall Pond out to the Atlantic from all 3 homes as well as stunning views of Quitsa Pond. Each of the homes is charming and beautifully maintained, with its own Vineyard history. “Lorca” is sited on a 1.4 acre lot (140 State Rd) while “Lenom” and the “Boathouse” are sited on the abutting 4 acre lot (138 State Rd). These 3 homes are offered together for the first time in over 50 years. Built in 1939, the original "Lorca" home was expanded in 1973 and renovated over the past 40 years. This year round home evokes old Vineyard charm with modern upgrades and features water views from almost every room. “Lorca” has 3 bedrooms, 2 bathrooms, and light open living spaces with wonderful picture windows through which to enjoy views of the pond and the ocean beyond. Enjoy al fresco dining on the water facing decks then walk down a gentle grassy slope to your own private dock on the pond, surrounded by nature. “Lenom” is the second home with 3 bedrooms and 3 baths. Most recently expanded in 1988, the kitchen and dining area were renovated in 2013 and air conditioning was added in 2017. This year round house has a beautiful stone fireplace, a focal point of the open living/dining area, and a rooftop deck that has wonderful 360 degree views of Stonewall and Quitsa ponds. Nestled between “Lorca” and “Lenom”, on the water’s edge, is “The Boathouse”. Built in the early 1970’s as a boathouse it was expanded in the 1980s into an additional home with one bedroom and one bathroom plus loft space, full kitchen, living room and lovely outdoor decks over-looking the pond. Each of these homes, with its own unique vistas and water views, is privately situated. Together they create a family compound that allows both separation and the ability to come together so the whole property can be enjoyed by all. Relax in the beauty or enjoy sailing, kayaking, swimming and paddle boarding. The sunrises and sunsets here are breathtaking and watching the moon rise over the pond is spectacular. Just a short walk, boat or drive to nearby private association Stonewall ocean beach. Boat from Stonewall Pond under Hariffs Bridge to Quitsa and Menemsha ponds and then out to the Vineyard Sound. This is an extraordinary property, exclusively offered as a 3 home estate for $10,300,000 or the two parcels may be purchased separately.

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LINK ID: 33545 $769,000


Town: Chilmark
Type: Single Family

Designed for the utmost in individual privacy, this truly charming home is comprised of three "pods". The central pod houses living/dining room with brick hearth; immaculate kitchen with windows onto the screened porch that let you serve directly onto a dining bar with stools; a roomy bedroom with adjoining bath and a tidy laundry utility room. The other two pods each have their own bedrooms and baths - one of which has a propane "woodstove" and is large enough to hold a dance party! The lawn and gardens are serene and magical, creating a unique and charming enclave, while the location is fantastic - just about a mile away from Alley's General Store for any and all those last minute items - yet only a couple of miles from Lucy Vincent Beach.

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LINK ID: 33535 $11,750,000


Town: Vineyard Haven
Type: Single Family

This three-story shingle-style air conditioned home on Vineyard Sound, an easy walk to the West Chop Club, epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler’s pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens and open lawns. A private path leads to the West Chop Trust’s north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come.

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LINK ID: 33533 $700,000


Town: Chilmark
Type: Single Family

Close to Chilmark Center, this three bedroom, two bathroom home is pleasantly sited on a quiet lane. It is ready for a new owner to repair & refurbish it for the next chapter!

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LINK ID: 33503 $2,950,000

Waterfront Dining
Waterfront DiningBedroomBedroomBedroom
Town: Edgartown
Type: Single Family

Over 10 special acres stretching from Beach Road to the waters of Trapps Pond - all less than a mile away from Edgartown village. This property is sub-dividable (proposed plan available upon request). The cottage at the water's edge is charming, and from just yards away from the deck you can set off to explore the pond by kayak, paddle-board, or dinghy. The birdlife here is extraordinary, and so are the sunsets over the barrier beach from Nantucket Sound. This waterfront property will be the setting of family memories for generations to come.

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LINK ID: 33491 $1,699,000

Center isle
Center isleGreat roomAnother viewGreat room kitchen
Town: Oak Bluffs
Type: Commercial

High End COMMERCIAL BUILDING/APT, in prime B1 In-Town location offering the perfect spot for a year round or seasonal operation and it includes a beautiful, sun-filled, and gracious apartment above. An original Victorian landmark renovated in its entirety in 2012 with the best materials and craftsmanship, and meticulously maintained since then. First floor commercial space has easy access into a spacious open with gleaming hardwood flooring that flows into 2 more ample rooms that can be used for office, storage etc, and into a stylish tiled full bathroom, then down to a full basement with plenty of extra space. The apartment has a great room with high ceilings, lots of glass, hardwood flooring honed granite kitchen counters, Wolf range, Sub Zero fridge, and Miele dishwasher, a cozy dining area along with other intimate settings. A restful bedroom and a full bathroom with separate tub, tiled shower, and marble vanity, and a separate den/study completes the interior, and lastly, a short stairway takes you to the sprawling roof top deck where you can unwind in total privacy.

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LINK ID: 33487 $1,400,000


Town: Aquinnah
Type: Single Family

Long favored by Islanders in search of a quiet life, the community of Aquinnah enjoys a secluded natural setting of bayberry, scrub oak, and ocean vistas. This two bedroom light filled cottage is tucked away on a 4.7 acre lot. Cozy up to the propane woodstove in the kitchen which is the focal point for casual family gatherings or relax in the comfortable living/dining room. Multi levels lead to walk out basement and access to the Circa 1850’s barn with original chestnut beams and antique wood flooring. This barn was dismantled, brought to the Vineyard from Western Mass, and lovingly rebuilt piece by piece by the present owner.

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LINK ID: 33477 $725,000


Town: Chilmark
Type: Land

4.32 rolling acres with stone walls. Deeded walking access to north shore beach. 4-bedroom septic, well, and electric power are all installed. Natural Heritage work has already been completed and permit is in hand. The access and building site was recently brush-cut for easy access.

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LINK ID: 33452 $179,000

good sized Bedroom 
Condo sleeps 5 total
good sized Bedroom 
Condo sleeps 5 totalWatch the kids in the pool from your condospacious pool area for familygreat pool
Town: Edgartown
Type: Condo

BEST LOCATION in Edgartown Commons! OVERLOOKING the POOL, you can watch the kids from your living room! This highly sought after unit is a money maker with it's first floor location. Attractively decorated and upgraded. This one bedroom condo sleeps 5 people! Stay for a few weeks with the family and let the on-site management team rent out the other weeks. Located right in the village of Edgartown for restaurants, boutiques, harbor and beaches. GREAT RENTAL INCOME!

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LINK ID: 33393 $1,525,000

Lower Makonikey home with water views and acess to the association's private beach.
Lower Makonikey home with water views and acess to the association's private beach.Rear Exterior, wrap around decks and walk-out basement.Landscaped front exterior.Views across the Vineyard Sound.
Town: Vineyard Haven
Type: Single Family

Enjoy stunning water views from every room of this charming three bedroom Vineyard Haven home. Tucked away off lower Lambert's Cove Road, this post and beam styled house is nestled on over three acres in Lower Makonikey and boasts substantial views of Vineyard Sound from the first and second level. There are many sweet interior details including three fireplaces, a loft space, and a fully finished walk out basement which provides additional living space. The property also offers access to the association's private North shore beach. The house has been thoughtfully maintained by the current owner including new skylights, roof, downspouts, red cedar shingles and new roof. The graceful trees behind the home have been regularly topped and pruned to maintain the broad, deep view. The property offers ample outdoor spaces with deck and patio overlooking gently wooded land, open lawn space, as well as lovely plantings .

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313 - 324 of 415 Listings