Chilmark Homes For Sale

Chilmark is arguably the island’s most beautiful town with rolling rural landscape sandwiched between gorgeous beach-lined coasts to the north and south. Many of the lovely homes for sale in Chilmark are properties lined with classic stone walls across several acres. Real estate in Menemsha, Chilmark’s historic fishing village is very popular thanks to the picturesque sunsets, nearby beaches, and great restaurants. 

Homes for sale in Chilmark are a great investment, whether you are looking for a vacation home or a place to live year-round. At Coldwell Banker Landmarks we specialize in helping buyers find the perfect real estate on Martha’s Vineyard. Our team has decades of experience in the local real estate market, so contact us to get started.

Learn more about Chilmark.

18 Spruce Gate Road

Price$7,500,000

Est. Mortgage: $/month

MLS ID 34218

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

The best and most coveted location on Martha's Vineyard - Squibnocket Ridge. Set within a private, gated +/- 500 acres community that includes over 300 acres of conservation land, extensive private waterfront on Squibnocket Pond and the Atlantic, and only 12 homes, this turnkey offering melds modern construction and comforts with an idyllic farm-like setting. Stately and elegant, the property residence abuts extensive conservation fields and 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 the feel of a traditional New England farmhouse, with multiple gables and cedar shingles defining the facade. The living space centers on a gorgeous open chef's kitchen, winged on two sides by entertaining or living room spaces. 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 within the kitchen, and high-end millwork and material are on display throughout the home. A sense of warmth exudes from the dramatic post & beam ceilings, along with the rich cherry flooring in nearly every room. The master suite is set perfectly on the first level at the home's southern end, and four additional bedrooms are found on the opposite side of the main living area. 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 and the Google assistant. The landscape of the property was thoughtfully designed, highlighting ancient stonewalls on the property borders and views of the ocean and open fields abutting the parcel. Along with gracious lawns, flower beds and a beautiful 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 a spacious back deck for sunning or dining al fresco, a superb screened porch with outdoor fireplace, and a fire pit - ideal for summer evenings or nighttime star-gazing. Ownership in Squibnocket provides access to miles of trails, multiple accesses to Squibnocket Pond, and driving access with parking to the exclusive owners-only beach, which is home to some of the most stunning dunes and sandy beachfront on the Atlantic seaboard. An enchanting property where beauty truly abounds!

Listed by Wallace, Peyton of Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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51 State Road

Price$1,200,000

Est. Mortgage: $/month

MLS ID 34181

  • Residential
  • Square Feet 2600
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 2

Walk to Town, Library and Chilmark Store from this newly built classic Vineyard Colonial situated in a peaceful serene setting with established plantings that provide plenty of privacy all around. 3 bedrooms, 2.5 baths, open plan kitchen , dining and living and family rooms with gleaming wood floors. The back patio/deck overlooks the ancient stone walls and a charming detached studio with large deck provides many possibilities. Peeks of the Atlantic, Chilmark landscape and the Chilmark Church steeple gives this property a charming village feel.

Listed by Conroy, Rebecca V of Conroy & Company R.E., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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1 Azalea Lane

Price$8,250,000

Est. Mortgage: $/month

MLS ID 34126

  • Residential
  • Square Feet 2511
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 1

Rarest of the rare - Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for the completed product. Note that the images shown are of the house BEFORE renovation. Detached garage.

Listed by Jenkins, Mark of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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61 Stonewall Road

Price$2,750,000

Est. Mortgage: $/month

MLS ID 34058

  • Residential
  • Square Feet 2537
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 4.5

Stonewall Association, one of the premier waterfront neighborhoods in Chilmark, is the location of this brilliant renovation. A wall of beautiful windows across the entire length of the house, white tile and light hardwood floors, create a delightful and stylish home. The renovation, completed this year, adds a clean, modern aesthetic that complements the strong post and beams of the original design. The 4.5-acre property is largely cleared providing a sweeping lawn and a setting for a whimsical outdoor dining gazebo. An Atlantic Ocean beach is the main allure of the neighborhood and this property is well situated for access to the beach and all the pleasures of Chilmark. Whether you are a fun-loving beach person or academic recluse, this property has broad appeal to a gamut of tastes. Motivated sellers.

Listed by Bradley, Cassie of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

Price$9,995,000

Est. Mortgage: $/month

MLS ID 34036

  • Residential
  • Square Feet 3888
  • Bedrooms 6
  • Bathrooms 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, Julianna of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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96 Menemsha Cross Road

Price$950,000

Est. Mortgage: $/month

MLS ID 33992

  • Residential
  • Square Feet 1546
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Meticulously maintained Cape style home and 2 car garage is move in ready! This home is charming and offers a lovely setting. This home has had tremendous updates in recent years; some of which include new kitchen, new furnace, new roof, upgraded insulation and so much more! A master bedroom and full bathroom on the first floor with spacious living room, small office, updated kitchen and a formal dining area that is surrounded by large windows to allow the room much natural light. Three additional bedrooms and a full bathroom upstairs. The well manicured and mature plantings that surround the house add more appeal and character to this home. A simple distance to Menemsha and also to Chilmark center and Lucy Vincent beach. With a wonderful rental history as well!

Listed by Flanders, Julianna of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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10 Rumpus Ridge

Price$750,000

Est. Mortgage: $/month

MLS ID 33533

  • Residential
  • Square Feet 1000
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.5

Close to Chilmark Center, this three bedroom, two bathroom home is pleasantly sited on a quiet lane. It is ready for a new owner to repair & refurbish it for the next chapter!

Listed by Flanders, Julianna of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

Price$4,375,000

Est. Mortgage: $/month

MLS ID 33963

  • Residential
  • Square Feet 2018
  • Bedrooms 4
  • Bathrooms 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 Kelly, Michelle of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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114 Middle Road

Price$2,250,000

Est. Mortgage: $/month

MLS ID 33858

  • Residential
  • Square Feet 3951
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

New Price! This masterfully-crafted home completed in 2010 was built with the highest quality materials, finishes, and mechanics. There is custom paneling, mill work, and cabinetry gracing each and every room. Start with the open concept floor plan - enter first the foyer with a coat closet, powder room, and gorgeous staircase. Then the living room with cathedral ceiling and impressive stone fireplace, a lovely dining area, and a spectacular chef's kitchen with top-tier appliances - Wolf stove top and microwave, 2 Viking ovens and warming drawer, Fisher Paykel refrigerator, dishwasher, and dryer. Off the living room is the master bedroom suite with its own library with fireplace, dressing room with fireplace, and stunning bathroom with a claw-foot soaking tub, double vanity, and tiled shower. Off the kitchen is the year-round sun room or den, a butler's pantry, laundry, and 2-car heated garage. Upstairs you have 2 more bedrooms each with high-end bathrooms. Outside there are stone walls and patios and a charming fountain - all designed for relaxing. Plus a deck perfect for outdoor dining. It should be noted there is a 4-bedroom septic system so the den could be used as a bedroom if desired. The stylish furniture can be purchased separate from the house sale. So many options at this unique home. It's a must see!

Listed by Gilstad, Idalyn of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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130 South Road

Price$1,150,000

Est. Mortgage: $/month

MLS ID 33794

  • Residential
  • Square Feet 2746
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 2.3

Once a two story barn, this 2200 square foot space was converted to a 3-br residence some years ago and still retains much of its original character. Formerly known as the Fenner barn, the exposed beams, trusses and original wood walls and ceiling were thoughtfully preserved to retain the antiquity and essence of the original Barn. An open style living concept, the residence offers two sunrooms, open kitchen/living dining area with stone fireplace and a main level master bedroom. Two more bedrooms on the second floor and another loft style living area with book cases and another stone fireplace - known as 'the music room'. Surrounding gardens and mature plantings on 2.3 acres complement the simplicity and charm of the interiors. A 1-br guest house (556 sf) at the rear of the property offers additional sleeping space for guests, family or an income producing property.

Listed by Kelly, Michelle of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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