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Our Martha's Vineyard Real Estate Listings

Landmarks Real Estate has current, prestigious real estate in Martha's Vineyard. Search through our listings, and we can help you find your new permanent home or vacation getaway. From waterfront homes to seasonal rentals, we have the expertise to help you. Save the listings you love when you sign up for an account, and you can get email notifications when similar properties are posted. 

Please contact us online or call 508-693-6866 with questions or to visit any of the Martha's Vineyard properties in person.

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311 East Chop Drive

Price$2,250,000

Est. Mortgage: $/month

MLS ID 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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92 Main Street

Price$2,100,000

Est. Mortgage: $/month

MLS ID 34789

  • Residential
  • Square Feet 6330
  • Bedrooms 7
  • Bathrooms 6
  • Half Bath 1

The Captain Dexter House, ca. 1843, has a storied history. Originally owned by one of the Island whaling captains, this home has had several iterations, including the most recent in 2004 when a 3 story addition completed the restoration of this charming historic residence set in the heart of the seaside village of Vineyard Haven. The restoration included the preservation of the original architectural details while bringing the home into the present century with the addition of the country kitchen including a large center island and top of the line appliances, informal dining area and family room with a fireplace and access to the garden patio. Conveniences include a walk-in pantry, powder room and full bath, and laundry room. Formal and informal living areas can be found throughout the house as well as seven bedrooms and six and one-half baths. There are five working fireplaces including the master bedroom suite. All mechanical systems have been completely updated including central AC. Exterior living areas feature a balcony off the second floor sitting area, covered porch with views of the harbor, newly fenced bluestone patio with mature plantings, tiered perennial gardens and private parking for 3 cars. Theater, restaurants, boating and the beach are within footsteps of this gracious in-town residence. Walk to the library and elementary school. Offered fully furnished with a list of exclusions, attached. Substantial rental history.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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37 Madaline Lane

Price$700,000

Est. Mortgage: $/month

MLS ID 34444

  • Residential
  • Square Feet 1560
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

Making your way to school, ferry and all the conveniences of downtown will be a breeze from this super-bright and inviting home on a barely trafficked dead-end lane. Built in 2000, the house is charmingly appointed, smartly laid out and impeccably maintained. Maple floors, oversized windows and a handsome wood stove are among the quality finishes. And what a relaxing backyard you'll enjoy from your deck and patio. Mature lilacs, butterfly bushes, hydrangea, a showy Rose of Sharon and a host of perennials burst forth in color, in season. The parcel is generous enough to add a detached garage and, with town approvals, perhaps an apartment above? A Title V 3BR septic system is in place. If replaced by an enhanced system, the property can qualify for additional bedrooms, per the Tisbury BOH.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$35,000 to $60,000

Rental ID 116963

  • RTR Vacation Rental
  • Lease $35,000 to $60,000
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 6

Luxurious Edgartown waterfront estate with award-winning infinity pool surrounded by 150 acres of conservation land. This quintessential summer escape offers views, location and lifestyle. Deluxe amenities abound in this 8,000 sq ft custom built compound, the main house includes four bedrooms and five baths. A fully equipped gourmet kitchen with top of the line appliances and beautiful stone fireplace with sitting area add the perfect touch. Private guest quarters located above the garage includes separate bath, kitchen and living area. Elegant craftsmanship and attention to detail throughout the design of this home, everything state of the art. The bluestone patio, custom built stone gas grill, entertainment bar and sink and professionally landscaped grounds add to your summer outdoor entertaining. It s everything that you and your family could possible need for a spectacular Vineyard experience.

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$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$20,000 to $40,000

Rental ID 116578

  • RTR Vacation Rental
  • Lease $20,000 to $40,000
  • Village Edgartown
  • Bedrooms 6
  • Bathrooms 5

Elegant waterfront home on Eel Pond with private pool and carriage house suite. Spacious open interior with great attention to detail and full of amenities. Beautiful grounds and large patio area for outdoor entertaining. Located in desirable Edgartown, convenient to downtown area - boutique shopping, restaurants, galleries, cinema and harbor stroll.

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$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$25,000 to $30,000

Rental ID 133977

  • RTR Vacation Rental
  • Lease $25,000 to $30,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

The house itself is spacious with elegant details, state of the art systems, and an attractive floor plan. Craftsmanship quality in this 5,400 square foot home is everywhere, from the kitchen, with its granite counters, center island with copper counter, custom cabinetry, and tile floors & backsplash. To the living areas and bedrooms, that include heart pine flooring, high-ceilings with exposed wood beams, wainscoting and moldings. And, the bathrooms, with their high-end fixtures, tile flooring and custom elements. The kitchen includes a Sub-Zero refrigerator, eight-burner, gas, Viking, stovetop, and two Bosch dishwashers. Heating/AC system includes a Viessmann boiler, forced hot air heat and air conditioning, and radiant heat in the lower level. Floor plan includes a number of bonus areas, table tennis room, media/TV room, wine cellar with brick floor and cedar paneling; two master suites, and an open main level that centers on the living room, which includes cathedral ceilings, fieldstone fireplace, and egress to exterior decking. Many rooms with water views. This beautiful home features all of the finest amenities as well as a heated pool for outdoor entertaining and enjoyment and just recently put tennis court.

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$
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$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$30,000 to $30,000

Rental ID 132316

  • RTR Vacation Rental
  • Lease $30,000 to $30,000
  • Village Aquinnah
  • Bedrooms 4
  • Bathrooms 3

This Martha’s Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. This new 4 bedroom 3.5 bath home overlooks the Vineyard Sound with breathtaking panoramic views out to the Elizabeth Islands. With state of the art decor and interior furnishings, guests will enjoy environmentally sensitive, energy-efficient, and sustainable design. Just a short path to the private sandy beach, a great fishing spot and perfect for families with younger children. An outdoor shower, jacuzzi and sauna complete this spectacular, modern home.

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$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$10,965 to $26,500

Rental ID 116998

  • RTR Vacation Rental
  • Lease $10,965 to $26,500
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 5

Located in one of the most exclusive associations on the Vineyard, this five bedrooms home offers some of the most stunning water views the island has to offer. This home includes spacious decks, vaulted ceilings, and all the amenities one expects in a premier property. Tenants have access to both the association and homeowners beaches.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$22,000 to $25,000

Rental ID 123611

  • RTR Vacation Rental
  • Property Name Chilmark -
  • Lease $22,000 to $25,000
  • Village Chilmark
  • Bedrooms 4

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$15,000 to $25,000

Rental ID 116916

  • RTR Vacation Rental
  • Lease $15,000 to $25,000
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 4

The Dexter House is part of a spectacular two house waterfront compound situated on the historic Edgartown harbor. The complex is lovingly crafted from the finest materials, fabrics and hardware. Wonderful bright airy living, kitchen, dining loft overlooking the old harbor with spectacular views of Chapaquidick and Vineyard Sound. You can dine, sunbathe or just watch the world go by on solid teak furniture out on the adjoining deck. State of the art electronics, digital satellite and high speed internet access available. A slip for up to a 17 ft boat and one parking space is included.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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