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LINK ID: 33391 $14,900,000


Town: Edgartown
Type: Single Family

Magnificent Chappy estate overlooking Katama Bay and surrounded by conservation land. Designed by Patrick Ahearn, this custom residence is perched high on a hill on 5.95 acres with over 180 degrees of unobstructed water views. Built for today’s lifestyle and technology, the property has numerous amenities which include, an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room. Offering over 10,000 square feet of luxurious living space, this home features 8 bedrooms and 11 baths. Truly a rare and unique opportunity to own and enjoy a generational quality estate.

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LINK ID: 33389 $899,000

Nearby Lagoon and Herring Run ladders
Nearby Lagoon and Herring Run laddersNearby Featherstone Art Gallery and Studios.Miles of horseback riding trails.Lagoon parking area and maps.
Town: Oak Bluffs
Type: Single Family

BEST VALUE ON MARTHA'S VINEYARD! HOUSE, BARN, 2 CAR GARAGE on 1.38 ACRES! A convenient central "down-island" location (Oak Bluffs-Barnes Road), complete with a 24' x 30' Horse Barn, Main house and an oversized Garage plus enclosed storage area, all on 1.38 acres of land abutting 35.3 acres of conservation land. Great property for anyone that wants a large lot, abundant storage and a 4 bedroom house, all within a 5 minute drive to town or the Ferry. Much of the value lies in the excellent location, degree of privacy, amount of land, and Brand New 4 bedroom Septic System has just been installed. Very close to Featherstone Art Gallery and the Lagoon Pond Herring Run. Only minutes to the VH Ferry. Please call a minimum of 24 hrs. before a requested showing. House occupied. Dog on premise.

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LINK ID: 33361 $1,590,000

Frontal view of 31 North Street with pleasant landscaped yard.
Frontal view of 31 North Street with pleasant landscaped yard.Formal entrance to the house.Living room to the left of the formal entrance......with room for all to gather.
Town: Edgartown
Type: Single Family

PROXIMITY TO THE VILLAGE - 3 BEDROOM HOUSE AND 1 BEDROOM APARTMENT ABOVE A 2 CAR GARAGE. A short distance to the Village, set in a quiet, private location, with a pleasant landscaped yard, this property is an exceptional offering, with all the elements of an ideal Village home. There is a formal living room to the left of the front entrance for special occasions, but most often used is the spacious den off the side entrance with a wood burning fireplace, with the dining room and kitchen beyond. A full bath with laundry room off the den connects to office space on the first floor. An en-suite master bedroom with walk in closet, along with two guest bedrooms and a bath occupy the second floor. A separate apartment above an ample two car garage is an added feature and can serve a variety of family functions or generate income. If it sounds wonderful, it's because it is.

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LINK ID: 33352 $1,500,000

Aerial View of 2 Swan Neck Road Lot
Aerial View of 2 Swan Neck Road LotAerial View of 2 Swan Neck Road LotAerial View of 2 Swan Neck Road LotAerial View of 2 Swan Neck Road Lot
Town: Edgartown
Type: Land

Waterfront lot on Jacob's Neck Pond with access to Edgartown Great Pond and Land Bank beach on the South Shore. Build your Vineyard home on this private 5.49 Acre parcel. High-end Edgartown neighborhood with substantial homes and privacy. Newly subdivided and surveyed. Natural Heritage & Endangered Species work in progress. (Note: Current assessment not noted because of new lot line change). Adjacent 6.8 acre lot (6 Swan Neck Road) available for purchase.

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LINK ID: 33338 $675,000

The second bedroom has a private bathroom and two closets.
The second bedroom has a private bathroom and two closets.The back deck at the Tashmoo Woods condo looks out over a peaceful wooded area.Large dining space opens onto the kitchen.Entry foyer for the Tashmoo Woods Condo in Vineyard Haven.
Town: Vineyard Haven
Type: Condo

A wonderful opportunity to purchase a property in Tashmoo Woods, a private community of single family homes and condominiums on more than 100 acres in Vineyard Haven. This well appointed townhouse is bright, open and spacious with large windows, a fireplace, and a cathedral ceilings. The sun-filled living room opens onto a raised deck with a peaceful view of the surrounding woods. The condominium also features a charming eat-in kitchen, separate dining area, full bathroom, and cozy bonus room (currently being used as a home office) on the main level. A master suite and guest bedroom, both with ensuite bathrooms and ample closet space make up the second floor. Adding to the living space is a finished walkout basement, currently being used as a family room and space for overflow guests. This home was built as part of Phase One of Tashmoo Woods, which means it offers additional features like charming built-in shelving and a full walk out basement. Central air, a garage, and outdoor shower are other features of the unit. The home has been well cared for and has a strong rental history. The association boasts a community pool, tennis courts, a private boat landing and dock onto Lake Tashmoo, walking trails and access to both town and association beaches. Nearby is Mink Meadows Golf Club and the port of Vineyard Haven for dining and shopping. The Property Owners Association takes care of the condo exterior, the roads, and community spaces (pool, tennis courts, beach access) so you can enjoy all the Island has to offer with less of the stress of property ownership.

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LINK ID: 33322 $1,325,000


Large fenced in backyard.Great roomMaster
Town: Chilmark
Type: Single Family

Classic features blend seamlessly with modern sensibilities in this expanded Cape Cod-style home. With double the square footage of the original and updated for the 21st-century lifestyle (including a first-floor master suite), this home is perfect for year-round living or as an all-seasons Vineyard retreat. The property adjoins acres of untouched woods, providing ample privacy, while remaining easily accessible throughout the year on a town-maintained paved road. First floor consists of formal living room with fireplace, separate dining room, master suite with large sitting room and private screened-in sunroom, laundry room, additional bedroom and bath, kitchen, 650 sq. ft. mahogany deck for outdoor entertaining, and sun-filled, 530 sq. ft. great room with 14' ceiling, exposed antique beams and radiant floor heating for the ultimate in winter comfort. Second floor contains two large bedrooms with cozy dormer alcoves, and full bath. Oversized two-car garage with built-in work bench. 1500 sq. ft. basement provides lots of storage space, additional refrigerator and freezer, and second laundry room. The many updates and improvements include new well, architectural-shingle roof, cedar-siding shingles, HVAC, Title V septic system, top-quality insulation, upgraded electrical and plumbing, and energy-efficient Marvin windows and French doors throughout. This home is turn key. Beautifully furnished right down to the grand piano!

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LINK ID: 33320 $6,350,000


Town: Aquinnah
Type: Single Family

Perched above Menemsha Pond, this exquisite new five-bedroom home combines state-of-the-art construction with all the elements for the ideal Vineyard experience including some of the best water views on the island, Menemsha Pond access via walking path, heated Gunite pool, and the privacy and protection of abutting conservation land with no building allowed between this house and Menemsha Pond. This substantial and tasteful home with contemporary style has been thoughtfully designed into the surroundings. Only the finest craftsmanship and materials were used including Lutron lighting, Will Parry custom doors, local custom cabinetry, walnut floors, and two solar flowers which track the sun as a 5kw system. With an open floor plan for everyday living and plenty of room to expand when entertaining guests, this smart layout includes all bedroom/bathroom suites and a dedicated gym or yoga room with full bathroom. Flowing from the indoors out, through the screened porch and expansive deck, to the rolling landscape beyond, stone walls and pathways lead you from the main house to the detached guest suite and on to the pool and pool house where sliding cedar barn doors reveal an outdoor kitchen area and indoor changing room and bathroom. From there, the walking path to the pond awaits. Deeded view easement and deeded pond access with beach usage included. This section of Menemsha Pond is lovely and shallow, where little ones could spend hours playing safely and being entertained by the wildlife. Seller currently has two moorings on the pond and will transfer. Additionally, Aquinnah home ownership gives you Philbin Beach on the south shore and dog-friendly Lobsterville beach on the north shore. This is a rare opportunity for new high-end construction and an unparalleled combination of elements creating an experience that is truly the best of up-island living!

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LINK ID: 33303 $3,500,000


partial View of Kitchen in Main houseMain HouseCaretaker cottage, pool house and main house beyond
Town: Chilmark
Type: Single Family

This is a unique property like no other! Located off of Middle Road on over 63 acres (much of which are conservation restricted), this amazing property has been used as a family compound. Offering an architecturally designed main house, a charming guest house, a caretaker's cottage, additional outbuilding as well as an unfinished in ground pool and pool house. This property, while exceptional, it is in need of maintenance and updating. Being sold "as is", this property needs to be seen to be appreciated.

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LINK ID: 33283 $799,000


Town: Oak Bluffs
Type: Single Family

A must see hidden gem this home lies on 1.52 acres featuring over 100k of reclaimed antique stone work. Located in a very private setting down island, 10 minutes from ferry and 15 minutes from beaches, this home has the feel and tranquility of being up island. The main house offers 3 bedrooms 2 baths with an airy and open floor plan. Beautiful reclaimed wide antique oak flooring as well as other artistic touches truly gives this home the authentic feel of Marhtas Vineyard. An attatched 1400 sq ft 2 story addition with beautiful large stain glass windows ( 4x6ft ) is ready to be easily finished and offers an opportunity to almost double the homes square footage at 2900 sq ft. In addition to added living space it would also make a great home office or artist studio.The property setting is on high ground and overlooks a 9 acre pasture with rights to graze two horses. Access to Little Duarts Pond also accompanies ownership. This property is a great opportunity as a rental/investment home with the additional opportunity to add substantial value with finished addition. Difficult to capture this home in pictures, truly a must see !! And ,YES !, the clock works and keeps perfect time. It is fully modernized with a gps unit for accuracy.

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LINK ID: 33242 $1,290,000

Spacious and gracious dining room
Spacious and gracious dining roomDining room with large windowsDining room with built in buffet and double sided cabinets that open from both the kitchen and dining roomBedroom that opens to finished space over the garage which could be used as a walk in closet, home office or play room
Town: Edgartown
Type: Single Family

Island living at it’s best, straight off The Boulevard! The moment you pull into this manicured property you are welcomed home. This home lives comfortably with it’s layout and oversized rooms. Left of the front entry is a gracious dining room with abundant windows to allow the natural light to filter in. To the right of the front entry is a large living room with open stairway, and entry to the cozy den which features a wood burning fireplace. The den opens to a screened in porch with a slate floor and views of the gardens. Back in the kitchen one finds views overlooking the yard where alfresco dining can take place. The kitchen has a unique feature in that it has a built-in buffet countertop and row of cabinetry with doors that open from both the kitchen and the dining rooms, peek-a-boo cabinets which allow easy access to plates and stemware from both the kitchen and dining room, a very clever design element. The first floor also features a bath with shower stall; whereas the second floor features two full baths. On the second floor one finds the master-en-suite which features a newly renovated, sleek, sophisticated white bathroom, a walk in closet and entry to a private outdoor upper deck. Three guests rooms, a laundry area and finished space over the garage also adorn the second floor. This home also features an oversized attached two car garage and detached shed. The property is close proximity to the waters edge of Sengekontacket Pond. A truly MUST SEE property to appreciate all it has to offer.

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LINK ID: 33239 $1,649,000


Town: West Tisbury
Type: Land

Tisbury Great Pond ~ A superb parcel that stretches from Thumb Cove to Middle Cove. Six lushly treed acres with direct water frontage on Thumb Cove. Enjoy access to the Pond and boat to a pristine south shore barrier beach for swimming and beaching, recreational fishing and shell fishing. Tisbury Great Pond and its many coves offer some of the best waters for kayaking and boating on the island. Privacy and nature abound. Proximate to hundreds of acres of Trustees of Reservations Conservation land/Long Point Wildlife Refuge.

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LINK ID: 33183 $1,050,000

Another world
Another worldOver 3 acres of beautiful landBeautiful Oyster PondBoating
Town: Edgartown
Type: Land

One of the few remaining building sites still available in the coveted Oyster Pond Area. This site is a beautiful , easy to build on parcel, with several beautiful knolls , much hard wood and several prime spots to build and achieve , quiet enjoyment, and privacy. Adjoining acres of conservation. The best part is the ability to construct several structures , including, a full guest house, for a total of 8 bedrooms , if desired.. Here is really the best part ; just steps away, are deeded rights to beautiful Oyster Pond, opening up so many of summer activities . Sailing , kyaking , shell fishing ,swimming , boating etc..A value at this price and a wonderful place to either summer or live year round.

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325 - 336 of 415 Listings