Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

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.

Simplify Your House Hunt - Register with us to save your favorite Martha's Vineyard properties and receive notification when similar listings hit the market. 

r=1-10
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 3.5 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 that share a full bath. The first floor master with fireplace and private bath have cathedral ceilings. A first floor laundry room is just off the kitchen. 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, a partial basement and oversized garage. 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.

{$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 2017-11-02

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 2017-11-02

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$4,650,000The 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 2017-11-02

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
  • Village South
  • 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 2017-11-02

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 2017-11-02

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 2017-11-02

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$778,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32110

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

Stylish Contemporary ranch. Features include a dramatic 11' cathedral ceiling in living room w/ a corner gas fireplace w/black marble mantle, custom lighting. Eye-catching kitchen with gray cabinets, quartz counters and Island. Stone ceramic tile in both the kitchen and dining rooms, ceramic and subway tiles in the bathrooms, hardwood floors in all other rooms, glass door knobs. Master bedroom w/ en suite bath with ceramic glass counter top and sink. Two additional bedrooms share another stylish bath. Another feature includes a 10' x 14' enclosed porch/room that will be insulated and heated suitable for den or in home office with separate entrance. Completing the exterior setting one finds charming flower boxes, a wrap around mahogany deck in the front and side of the house. Sod lawn with 2 zone irrigation. Ample parking in front and side of yard. Decorative fencing w/plantings throughout the exterior of the house. 10'x10' Nantucket shed, pre dipped tea green shingles. Attention to details is evident...simply charming! See Specifications on renovations in Documents.There is room for a garage and 800 sq.ft. accessory apartment on the lot. Must be a yr. round resident for apt, requires special permit. and upgrade of septic. Title V Septic. Well tank and expansion tank replaced. JC Murphy has a financial interest in the 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 2017-11-02

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 offering views of Vineyard Sound, rests this 21-acre compound with association beach access. The stately historic 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 2017-11-02

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 2017-11-02

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

315 Great Plains Road, West Tisbury, MA

Price$699,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32515

  • Residential
  • Village Central
  • Square Feet 1419
  • Bedrooms 3
  • Bathroom 2

This idyllic location is close to the bike path and across the street from protected lands. Set among a delightfully landscaped yard is this cozy, very well maintained home. This one owner home shows pride of ownership in all the recent updates from new roof, shingles and boiler to the meditation garden. A three season porch and a fully finished basement add additional living space. There is an option to join pool and tennis court membership. This is one house that is really adorable and ready for new buyers! Move right in! There is a 4 bedroom septic system now with the potential for up to 6 bedrooms total. Recent updates include new wood siding, new roof, and a Viseman heating system.

Listed by Karen M. Overtoom 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 2017-11-02

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