Chilmark Homes Above $3M

Scroll down to find current homes above $3M for sale in Martha's Vineyard, MA's town of Chilmark. Look through a variety of listings to find your new home. Register with our site to save your favorite properties, and you can get email updates when new listings match your search criteria.

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277 North Road Chilmark MA

Chilmark, MA277 North Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 35612

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 1

With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the island, but this is yours all unto your own. Almost 70 acres of storied history, seclusion and a mile of stone walls throughout the property exude the authentic character of this long beloved farm in Chilmark. Past the antique post and beam barn, a granite bridge over Roaring Brook leads you to the back meadows and a beautiful ridgeline with strong views of the Vineyard Sound and the Elizabeth Islands. From this rise, the vista over the open meadows surrounding the ridge out to the rolling treetops of the north shore is equally enchanting and a landscape like no other on the island. Ride horses on the extensive trails throughout the property and out to the Sound for a swim. Even on your way to your beach, the Vineyard's past whispers to you as you pass the old brickyard. This is an extraordinary situation in which to create your island estate. This is the place James Cagney loved “beyond words” for the freedom and peace it provided. (PLEASE NOTE: There are 2 houses and a detached bedroom which are not habitable as is.)

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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8 Jethro Lane Chilmark MA

Chilmark, MA8 Jethro Lane

Price$15,000,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Square Feet 7000
  • Bedrooms 7
  • Bathroom 6
  • Half Bath 1

Stunning Chilmark north shore 4 acre waterfront paradise with wonderful sunsets and unique privacy nestled between a large wooded hill and a 200 acre private estate. The 5 bedroom 4 1/2 bath TWO kitchen main house and 2 bedroom (with 2 dormers) 2 bath guest house enjoy dramatic views of the Elizabeth Islands from the Gay Head Lighthouse to Woods Hole from every room. The property is beautifully manicured with an enchanting contour stretching to the bluff overlooking a dreamy private cove and sandy beach. Four cleared acres are very rare on the heavily wooded north shore. Waterfront values on the rugged, elevated and protected Vineyard north shore are attracting more interest after Hurricane Sandy damaged the low elevation fragile south shore NY, NJ and New England coast line. The property is in the highly desirable 335 acre Spring Point community with 38 home sites with 135 acres of common land, 3/4 mile of private beach, 2 tennis courts and endless dirt roads and trails.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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18 Austin Pasture Road Chilmark MA

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS Number 34345

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 3
  • Acreage 16.38

A magical setting on Squibnocket Pond with endless waterviews of Squibnocket Pond, Atlantic Ocean and Nomans Land Island. Perched high up on a hill on over 16 acres of untouched land, sits this inviting Chilmark home that has been crafted to take in the beautiful surroundings and private landscape. The home features wonderful wood throughout, a generous main level with an open living room and a stone fireplace, a built-in window seat, a spacious dining room and a large gourmet kitchen with an over-sized island. The master suite includes a spacious bath and access to a lovely porch overlooking Squibnocket Pond and beyond. A separate guest wing includes 2 additional bedrooms and full guest bath. Oversized windows allow for spectacular waterviews in every direction. The lower level features a comfortable sitting room with a wood stove, 2 guest bedrooms, full bath and access to a one car garage and storage area. Venture down a peaceful footpath to the water's edge and boat, kayak, or paddle board with ease on Squibnocket Pond. With over 16 acres of grounds, this home is sited to take in mesmerizing waterviews and its serene setting is the perfect retreat to create memories for a lifetime.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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100 Beach Plum Lane Chilmark MA

Chilmark, MA100 Beach Plum Lane

Price$8,500,000

Est. Mortgage: $/month

MLS Number 35399

  • Residential
  • Square Feet 2140
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.3

Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was lovingly restored by the current owner and Joseph Dick, a well-known and respected architect on the Cape and Islands. The main house features two bedrooms, two baths, living and dining rooms with water views, fireplace, well-appointed kitchen, outdoor rain shower, and a front porch which provides a front row seat to those magical Menemsha sunsets and the Elizabeth Islands. The guest house has one bedroom and bath, large, open living and dining areas, an ample kitchen, and an outdoor shower. Adjacent to the guest house is a detached, one bedroom cottage. A cottage at the rear of the property contains an office with wide water views and a lower level space currently configured as a personal gym. The last of the five cottages on the property is used for storage of seasonal furnishings. Mature landscaping, specimen trees and lush perennial gardens surround the property and delight the senses with vivid colors and welcoming floral scents. A short stroll on a deeded path takes one to the historic fishing village of Menemsha, it's seafood and craft shops and the calm waters at Menemsha Beach. Click here for video tour of this property.

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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138 & 138B State Road Chilmark MA

Chilmark, MA138 & 138B State Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 34994

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4

An amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. This year- round home has been lovingly maintained over the years and AC was added in 2017. A lovely cathedral height living room is punctuated with an in impressive stone fireplace for cozy winters and glass doors and three large picture windows to maximize the views and summer indoor/outdoor living and entertaining. The open kitchen was expanded and renovated in 2013 and has views over Nashaquitsa and there's also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. There are three comfy bedrooms and three baths plus an outdoor shower. The "Boathouse" guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the waters edge. A full kitchen, bathroom and living room with ample sleeping spaces make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. This one-of-a-kind property is part of a 3 home compound also being offered for sale together for $10,300, 000 ( link id 33559) and the third home "Lorca" is being offered separately for $4,800,000 ( link ID 33561)

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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18 Spruce Gate Road Chilmark MA

Chilmark, MA18 Spruce Gate Road

Price$7,750,000

Est. Mortgage: $/month

MLS Number 34218

  • Residential
  • Square Feet 3700
  • Bedrooms 5
  • Bathroom 3
  • Half Bath 1

Squibnocket Farm, Martha's Vineyards' only exclusively gated private community is further enhanced by the private 450+ acre Squibnocket community with over 1.5 miles of pond front, over 2 miles of ocean front, 300+ acres of conservation land and shared with only 12 other homes. This turnkey offering melds modern construction and comfort with an idyllic farm-like setting and directly abuts 17 acres of conservation land. Stately and elegant, the property residence sprawls peacefully amid surrounding natural beauty. The home was designed and built by Soikkeli & Company, a well-known luxury contractor on the Island. The exterior design evokes traditional New England farmhouse style, with multiple gables and cedar shingles defining the facade. The living space centers on a gorgeous chef's kitchen - soapstone counters, custom farm sink, all new top of the line appliances and fixtures, and a charming pantry are just a few of the outstanding elements found within. Two living rooms flank the kitchen on either side, and the master suite is set perfectly on the first level at the home's southern end. Four additional bedrooms are found on a northerly wing, as is the two-car garage. Views of the ocean, Squibnocket Pond, Noman's Land, and open fields are readily available from many rooms. The house is wired for sound and includes smart home features such as Nest learning thermostats for the AC and heating systems, and sound controlled by HEOS. The landscape of the property was thoughtfully designed, highlighting ancient stonewalls on the property borders. Along with gracious lawns, flower beds and an organic vegetable garden, the property offers nearly 3 acres of fenced pasture as well as permits for a pool and horse barn. Outdoor living areas to enjoy include an expansive back deck, a superb screened porch with outdoor fireplace, and an outdoor fire pit - ideal for summer evenings or nighttime star-gazing. Ownership in Squibnocket Farm provides access to miles of trails, multiple accesses to Squibnocket Pond, and access to the exquisite homeowners beach, which is home to some of the most stunning sandy beachfront and dunes on the Atlantic seaboard. Squibnocket Farm is a paradise that must be seen to fully experience - a rare enclave of privacy and calm.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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22 Quitsa Lane Chilmark MA

Chilmark, MA22 Quitsa Lane

Price$9,995,000

Est. Mortgage: $/month

MLS Number 34036

  • Residential
  • Square Feet 3888
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. The main house offers a large gourmet kitchen, amazing patio space for outdoor dining, quaint bedrooms and several entertainment and gathering space. The recently constructed guest annex and garage space is tastefully done with room for overflow family and friends.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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21 Squibnocket Road Chilmark MA

Chilmark, MA21 Squibnocket Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 33963

  • Residential
  • Square Feet 2018
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated with many tasteful, modern enhancements and sustainably-sourced materials, and yet retains some of the most charming elements of its past. The airy floor plan offers a family-friendly open kitchen, living and dining area, a master bedroom, and a guest wing with three more bedrooms. The lower level is finished, adding about 1350 square feet of space including a spacious 30' x 20' recreation room and laundry room. The property is surrounded by stone walls, a bluestone patio facing the Atlantic, and a path to the Pond (with rights to build an elevated walkway and kayak rack). Originally known as the Hilly Mayhew House, this property was for over 80 years the haven for the international modernist painter Vaclav Vytlacil and his family. He created hundreds of seascapes and harbor scenes of the Vineyard, many of which can still be found on the island and around the world. Walk to the beach, kayak in the pond, or just sit out on your patio watching the day unfold, osprey fish and surfers ride the waves.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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11 Azalea Lane Chilmark MA

Chilmark, MA11 Azalea Lane

Price$5,200,000

Est. Mortgage: $/month

MLS Number 30618

  • Residential
  • Square Feet 3750
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

With 425 ft of private ocean beach, this offering deserves its reputation as the "ultimate beach house". The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide access to a wide swath of sand that many consider the most beautiful stretch of beach on Martha's Vineyard. To fully appreciate this extraordinary setting, view the images in the "photo gallery" and watch this drone video: https://vimeo.com/175588276

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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15 Lake Road Chilmark MA

Chilmark, MA15 Lake Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number 25297

  • Residential
  • Square Feet 1927
  • Bedrooms 5
  • Bathroom 2
  • Half Bath 1

Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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135 State Road Chilmark MA

Chilmark, MA135 State Road

Price$5,750,000

Est. Mortgage: $/month

MLS Number 19770

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathroom 1
  • Half Bath 1

Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from your door. First level of home is a large living area with kitchen all fronted by a large screened in porch. There is also another area that serves as bedroom or could also be used as a den or office space. Upper level has 3 bedrooms, large living room, full bathroom and loft space - great for the young ones. This home is great for entertaining and offers some of the most spectacular views in Chilmark. Enjoy sunset views over the pond...or swim off of the private sandy beach area on the pond which is great for young swimmers and for launching kayaks...All of this just within a short distance of Squibnocket Beach.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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