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Martha's Vineyard Up Island Real Estate

Scroll down to browse all Martha's Vineyard Up Island real estate for sale. You will find a variety of listings, including luxury homes, waterfront properties, summer rentals, and much more. Contact us if you have questions or would like to tour a listing.

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7 Maple Hill Road, Aquinnah, MA

Price$3,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32431

  • Residential
  • Square Feet 3527
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.85

This Contemporary home is tucked into the dunes off Moshup Trail and offers the most incredible South Shore ocean views. Deeded beach rights are just a stroll away. There is a total of 3527 square feet of living space, 4 bedrooms and 3 full baths. The open floor plan includes a spacious living/dining room with cathedral ceiling and fireplace, a modern kitchen with granite counters, all offering expansive ocean views all around. The spacious deck with hot tub are perfect for out door entertainment. The guest wing, separated from the main house by a screened-in porch, includes 2 bedrooms and a loft that share a full bath. The first floor master and private bath have cathedral ceilings and a fireplace. The second floor features a second floor den/office space, a 4th bedroom, full bath and a roof deck protected from the ocean breezes. To top it off, a 3rd floor tower with windows all around offering views of the South Shore, Gay Head Cliffs and the Lighthouse. New Heating and A/C. Sited on almost 3 acres of privacy and seclusion, there are mature plantings, perennial gardens, stone walls and your own pond with a charming bridge that takes you on walking trails throughout. Truly an enchanting property.

Listed by Karen M. Overtoom R.E.

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Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Clambelly Road, Chilmark, MA

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32609

  • Residential
  • Square Feet 1876
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.5

This charming Chilmark cottage offers unexpected water views of the Vineyard Sound. Private and tranquil, the two bedroom, two bath main house and separate two bedroom guest suite, and garage is nestled in the woods off of Tea Lane on Chilmark's North Shore. The main house features an open concept living space comprised of a great room, open kitchen, and dining area with high ceilings, wide planked hardwood floors, an impressive stone fireplace and a wall of windows looking out onto a surprisingly broad view of the Sound. The main house has two bedrooms, both facing the water, and two bathrooms, designed with a sweetly rustic post and beam style that fits so well in the natural beauty of the Chilmark woods. The property has a spacious two car garage with a guest suite above which offers two bedrooms, a bathroom, and study space. The property has a six bedroom septic in place that has passed Title V offering the possibility for expansion. The Seller has scheduled tree maintenance this fall to broaden the view. Currently, the house is a three season home, but the Seller has an estimate for installing insulation and heat while maintaining the charm and look of the interior, roughly $50,000. This is a wonderful investment opportunity for a Chilmark Buyer looking for a special view at a great price.

Listed by Tea Lane Associates

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

137 Quansoo Road, Chilmark, MA

Price$4,850,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32538

  • Residential
  • Square Feet 1476
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3.2

This rare 3.20 acre waterfront setting captures intimate Tisbury Great pond views, as well as views to the Atlantic Ocean and Quansoo beach. Access the beach by boat or from the Quansoo parking area. The current home is light and bright with an intelligent layout that is all one level, the master suite has its own wing and the two additional bedrooms and bath are on the other side. The house is centered by an open kitchen, dining and living room area with a fireplace, and views to the water. The screened porch and extensive decking offer further areas to gather, and the grounds have lovely old oaks and a rolling lawn.This property supports 6 bedrooms and is the perfect palate for a substantial and thoughtful water front home. See broker for further details about beach access.

Listed by Tea Lane Associates

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

102 Kings Highway, Chilmark, MA

Price$600,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32554

  • Land
  • Acreage 3.05

Gently sloping and wooded lot off King's Highway. Nice building site ready for your new Chilmark home. Well is installed and septic plan is being permitted.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

11 High Meadow Lane, Chilmark, MA

Price$749,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32599

  • Land
  • Village North
  • Acreage 3.02

Three acre lot with second story waterviews with privacy abutting conservation land. Property owns the view easement. Enjoy pastoral and pond views along with beautifully restored stone walls from your building site. Lot is fully engineered with well and utilities in place with rights to nearby tennis courts. Just bring your plans!

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

22 Bridge Lane, West Tisbury, MA

Price$1,795,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32576

  • Residential
  • Village Lambert's Cove
  • Square Feet 4245
  • Bedrooms 4
  • Bathroom 2

QUINTESSENTIAL ISLAND LIVING: LAMBERT'S COVE COUNTRY ESTATE. Set on a quiet country lane, across a wooden bridge and amid 3.3 private and bucolic acres -- this gorgeous estate-like property is set within a picture postcard setting of stone walls, rolling lawns and beautiful lush perennial gardens. Charm abounds inside the home as well . . with classic New England styling and architectural details like custom millwork and paneling, carved wooden archways, custom built-ins, cozy window seats, warm hardwood floors, four fireplaces and so much more. The first floor of the Main House is comprised of multiple living spaces each evoking a different mood and sense of purpose for spending quiet time alone or gathering family and friends together for treasured memories. Behind an arbored gate, the home features a perfect backdrop for outdoor living and entertaining anchored by a large mahogany deck with arbor, a custom stone terrace with English flower and herb gardens, and steps that lead down to a hot tub for nights spent relaxing at home under a beautiful starlit sky. The detached Carriage House offers the perfect place for an office, studio or accommodations for visiting friends or family. You'll feel miles away from everything, but highly-coveted Lambert's Cove Beach and miles of walking/hiking trails are nearby -- and Vineyard Haven's year-round village center and ferries are just a short drive away! This meticulously maintained, one-of-a-kind property also boasts an extended list of recent updates and upgrades (see attached documents). There are also possibilities for expansion as the property will support up to five bedrooms. Sheer bliss!

Listed by Point B Realty LLC

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 Nomans Watch Road, Aquinnah, MA

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32561

  • Residential
  • Village South
  • Square Feet 2000
  • Bedrooms 3
  • Bathroom 2

Near top of 100' high hill of glacial till and clay, facing south, overlooking Squibnocket Pond, its dune scape, Atlantic Ocean and Noman's Island. Panoramic winter view. Neighbors share maintenance of road.Huge glacial huge rock.Abuts Onansis property, Vineyard Conservation. Top quality materials, overbuilt with oversized floor joists, tall ceilings, top quality oak floors, maple trim, over sized Anderson windows

Listed by Gay Head Realty

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

142 Otis Bassett Road, West Tisbury, MA

Price$799,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32110

  • Residential
  • Village Central
  • Square Feet 1316
  • Bedrooms 3
  • Bathroom 2

This house has been completely rebuilt from the carrying beams, new floor joists, to the exterior w/ all new interior. New roof, 30 yr. pre dipped shingles, new energy star rated Harvey windows and custom entry doors. Livingroom has 11' cathedral ceiling, gas f.p., 5 wall sconces, all hardwood floors , black marble mantle on gas fire place.Gas fha & A/C. Tile and hardwood floors. Stone ceramic tile in dining area and kitchen w/custom cabinets, quartz counter tops and Island. Subway tiles in the bathrooms w/stone and glass counter tops, ceramic floors. Bonus of 10' x 14' three season enclosed porch w/ceiling fan and garden window. Mahogany wrap around deck. 10' by 10' Nantucket shed. Well tank replaced and expansion tank. Title V septic. Private, set on almost an acre of woods. 2 zone irrigation system, sod in front and side near deck, accent fence w/ lanscaping and flower boxes. Quality constructed, worry free, for years to come! Easy to show. Please note: You are looking at an outdated town assessment. Property will be reassessed Jan. 1 for next fiscal year. Perfect house for a retirement couple or a buyer ready to sell their big house and get into a easily maintained property.

Listed by Hughes & JC Murphy R.E.

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

371 Indian Hill Road, West Tisbury, MA

Price$1,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32305

  • Residential
  • Village Lambert's Cove
  • Square Feet 3267
  • Bedrooms 7
  • Bathroom 4

Tucked quietly away, atop Indian Hill, rests this 21-acre compound with association beach access. The stately Greek revival, which overlooks an expansive open field framed by stone walls, offers five bedrooms and endless potential. A two bedroom guest cottage, with private gardens, over-sized stone shed and separate studio provide all the additional space you've been looking for. Abutting conservation, and located a mile away from both Cedar Tree Neck Sanctuary and access to an exclusive hidden cove with sandy beach on Vineyard Sound. A sincerely special offering.

Listed by Sandpiper Realty

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

222 Pond Road, West Tisbury, MA

Price$1,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32378

  • Residential
  • Village South Shore
  • Square Feet 2573
  • Bedrooms 4
  • Bathroom 3

Custom built four bedroom home, located in the highly desirable Deep Bottom Pond Association, affording both tennis and deeded access to Tisbury Great Pond. The property lives large, offering ample living spaces, screened in porch and finished basement area. The private setting, conveniently located to Long Point Reserve and providing access to Lambert's Cove Beach, is truly a must see!

Listed by Sandpiper Realty

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.