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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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4 Stonewood Lane, West Tisbury, MA

Price$989,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32118

  • Residential
  • Square Feet 1992
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.79

This Replica 1760 Saltbox has been nicely designed and built. Many nice features include a great room with cathedral ceiling, skylights, a wood burning fireplace, a Jotul wood stove and french doors that lead to an open deck. The kitchen has plenty of work space and cabinets, butcher block counters and a breakfast bar. A more formal dining room is great for entertaining. Fist floor master with private full bath and access to a back deck and outside shower. The second floor has two additional bedrooms each with it's own full bath. True divided light windows and oak wood floors throughout The full basement includes a laundry room, storage and partially finished game room. There is an enchanting detached bedroom used for summer guests. Nicely landscaped with many mature plantings and perennial gardens.

Listed by Karen M. Overtoom R.E.

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

35 Menemsha Cross roads, Chilmark, MA

Price$650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32160

  • Residential
  • Square Feet 1008
  • Bedrooms 3
  • Bathroom 1
  • Acreage 2.2

FANTASTIC LOCATION. Menemsha Crossroads is a great place to live, a close ride to both town center and beaches and Menemsha. A basic ranch style house with great screened porch is ready for the next owner's ideas. 3 bedrooms and 1 bath, the septic was upgraded a few years ago. NOTE: This includes lots 137 and 138.

Listed by Feiner Real Estate

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

10 Deer Path, Aquinnah, MA

Price$2,475,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32185

  • Residential
  • Square Feet 1903
  • Bedrooms 4
  • Bathroom 2
  • Acreage 8.86

This extraordinary Aquinnah property is located across the street from Moshup Beach with a private grassy path leading the way from house to ocean. The beloved 4-bedroom cottage is situated perfectly to absorb the water views, meadow setting and peacefulness of this truly special spot on the island. Offering rare privacy for this area and a beautiful entrance down a country road bordered by stone walls, the house is set on almost 9 acres with a garden area and detached garage, all in close proximity to the Aquinnah Circle and the Gay Head Lighthouse. The original section of the house was a former Coast Guard Boathouse which was moved to the site in 1938 by the same family who has soaked up the sun and surf there ever since. This property has all the elements to create your summer perfection.

Listed by Tea Lane Associates

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

Black Point Road, Chilmark, MA

Price$325,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32197

  • Land
  • Village South
  • Acreage 0.1

Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, Atlantic Ocean beach lot at Black Point Beach. Exclusively offered.

Listed by Russell Maloney Real Estate

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

62 Pond Road, West Tisbury, MA

Price$1,875,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32187

  • Residential
  • Square Feet 4589
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.8

This custom home is beautifully designed and built for today's living. The main house has a spacious and casual floor plan that offers a design perfect for large families, entertaining and summer guests. Features include a grand living room with cathedral ceiling, granite fireplace, custom built in cabinets and french doors that lead to a covered porch and deck. The fully equipped chef's kitchen has a center island, corian counters, a sun-filled breakfast room and separate laundry/mudroom. The front parlor and formal dining room offer added living for special occasions and entertaining. The first floor master suite has it's own private outdoor patio, an office area, a full bath with soaking tub and shower. The second floor includes 2 spacious bedrooms that share a full bath and a generous family room. Beautiful wood floors, many nice details throughout. The detached garage is finished with a 2nd floor bedroom/studio, kitchenette, heat, a/c and full bath. The grounds are beautifully landscaped with lovely perennial gardens and mature plantings. Carefully sited on 2.80 acres for added privacy with plenty of room for a pool and pool house. Association tennis courts, several walking trails and access to a private dock on the Great Pond for small boating and traveling to the barrier beach. An exception property!

Listed by Karen M. Overtoom R.E.

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

233 Great Plains Road, West Tisbury, MA

Price$695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32092

  • Residential
  • Square Feet 1600
  • Bedrooms 2
  • Bathroom 2
  • Acreage 1.5

On a lovely parcel down Great Plains Road is a 2 bedroom log cabin style cape home. Open living kitchen area with a great covered porch and privacy. Also on this lot is a recently renovated studio apartment atop a beautiful one bay detached garage. The studio has beautiful new French doors and is bright and airy. Features includes full bathroom, spacious deck, washer/dryer hook up and separated driveway from main house. This is a great set up for an at home business or overflow space. A truly great opportunity to own in a great neighborhood in West Tisbury.

Listed by Flanders Real Estate

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

55 Charles Neck Way, West Tisbury, MA

Price$850,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32136

  • Residential
  • Square Feet 1653
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.6

Long Point area Contemporary house with an open floor plan, oversized deck and large screened in porches on two levels. Enjoy the cool summer breezes off the upstairs deck to the open living-dining-kitchen area. The cathedral ceiling enhances the bright open space where most of the family and friends gather. In the off-season enjoy the wood burning wood stove and the cedar lined sauna. On a level 1.6 acre parcel, there is plenty of room for outdoor activities, a pool, garage, or house expansion up to 3 more bedrooms with town approvals and septic upgrade. Family occupied so minimum 24 hr. notice for all showings. Being sold mostly furnished.

Listed by Sandpiper Realty

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

6 Red Gate Farm Road, Aquinnah, MA

Price$12,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32134

  • Land
  • Village South
  • Acreage 40.56

Nestled on the shores of picturesque 603±-acre Squibnocket Pond, this pristine, one-of-a-kind 40.56±-acre waterfront retreat looks southeast over the open expanse of calm waters and winding coastline to the Atlantic Ocean beyond the dune-fringed barrier beach that stretches between the pond and the ocean. Two potential homesites on the extensive acreage include one tucked by the 1,009±-foot shoreline of this tranquil oasis, an unspoiled natural refuge for bountiful wildlife in a landscape of breathtaking four-season beauty, featuring many varieties of trees and plants. Also enjoying deeded access to the ocean by boating over the pond, as well as by car, the property has been held by the same family for nearly 40 years as part of the Red Gate Farm compound. The rare setting on the coastline of Aquinnah, the westernmost outpost of Martha's Vineyard, is prized for its unparalleled peace and privacy.

Listed by Wallace & Co. Sotheby's

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

8 Red Gate Farm Road, Aquinnah, MA

Price$15,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32135

  • Land
  • Village South
  • Acreage 75.64

Offering priceless peace and privacy, this rare and pristine 75.64±-acre oceanfront haven sprawling across 1,060± feet of private beachfront has been held by the same family for nearly 40 years as part of Red Gate Farm. The vast acreage and exquisite dune-fringed sands give the sense of a world apart in an idyllic landscape which has remained virtually unchanged over the centuries. Perched on a southwest-facing ridge, the potential homesite commands glorious views to the ocean's brilliant blue waters and sunsets in the midst of this sublime seaside paradise of pastoral coastal heathlands and high dunes. Trails meander through the lush age-old landscape of iconic beetlebung, oak, and beech trees in the splendid solitude of this truly extraordinary property, a natural habitat for abundant wildlife. The serene setting is located in Aquinnah, the Vineyard's westernmost outpost, nestled on a peninsula surrounded by the Atlantic Ocean and Vineyard Sound.

Listed by Wallace & Co. Sotheby's

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

1 Seahorse Lane, Aquinnah, MA

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32133

  • Residential
  • Square Feet 2411
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.6

Spectacular views from this A-frame home sitting atop a hill on Lighthouse Road. Views from almost every room look toward Menemsha, Vineyard Sound and/or The Elizabeth Islands. Expansive decks encompass the first level of the home. Windows and sliders surround the two living areas and kitchen. There are two spacious bedrooms and a full bathroom on the second floor, both with wonderful water views. The Third floor, accessible by a spiral staircase, makes for a cozy third bedroom with amazing views. This home has a great rental history. Property being sold furnished.

Listed by Tea Lane Associates

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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