Chilmark Homes for Sale

Types of homes in Chilmark include waterfront estates with private docks, cozy beach cottages, Cape styles, and more. The community is home to the fishing village of Menemsha, Squibnocket Beach, and Peaked Hill, which is the Island’s summit. Find homes for sale in Chilmark below.

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260 South Road

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS ID 32807

  • Residential
  • Square Feet 2604
  • Bedrooms 6
  • Bathrooms 2
  • Half Bath 2

Waterview Chilmark estate sprawling over 6.1 acres with access to Chilmark Pond and an Atlantic Ocean beach. Known as The James Allen House, this historic home has been lovingly maintained by the same family for generations. The landscape is like no other with stonewalls, various species of trees, expansive lawn, and a open field with paths that lead you to Chilmark Pond and beyond. The classic floor plan of the main house offers multiple living spaces with 3 bedrooms, several fireplaces, and beautiful waterviews. This property features mulitple other buildings including a 2 bedroom guest cottage, 1 bedroom bunkhouse, garage and garden shed. This is a unique opportunity for a new owner to carry on the proud legacy of this home's historic past. An extraodinary and rare find in the heart of Chilmark.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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27 Clambelly Road

Chilmark, MA27 Clambelly Road

Price$2,600,000

Est. Mortgage: $/month

MLS ID 35814

  • Residential
  • Square Feet 2500
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 2

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx. To view a virtual tour, please copy and paste the following link in a new tab https://my.matterport.com/show/?m=eDWoDdeXtXk?ts=1

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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27, 30, 31 Tower Lane

Chilmark, MA27, 30, 31 Tower Lane

Price$2,950,000

Est. Mortgage: $/month

MLS ID 35757

  • Residential
  • Square Feet 4967
  • Bedrooms 6
  • Bathrooms 3
  • Acreage 63.3

Over 63 acres in Chilmark. As you turn off of Middle Road you are met by a cobblestone driveway that leads you through 7+acres of conservation land and up to the towering Carriage House archway that is the entryway to this majestic property. Emerging through the archway you are greeted by a unique assemblage of structures including the contemporary main house, guest house, and studio. These are surrounded by old stonewalls and newer detailed stonework that creates a harmonious balance between old farmland and new modern design. The Main House contains 4-bedrooms, large open living space and a rooftop deck. The nearby Guest House with 2-bedrooms and full kitchen overlooks raised bed gardens and rolling hills. Also located on the property is another 2-bedroom cottage with a full kitchen and an unfinished pool with pool house. On the far side of the property is over 45 acres of conservation land including portions of the Tiasquam River, all creating the utmost in privacy. There is potential to build one more single-family home on a portion of the property, or simply update the existing structures and enjoy the pristine land that surrounds you. The options for this property are many and varied.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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277 North Road

Chilmark, MA277 North Road

Price$12,500,000

Est. Mortgage: $/month

MLS ID 35612

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathrooms 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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, MA8 Jethro Lane

Price$15,000,000

Est. Mortgage: $/month

MLS ID 35593

  • Residential
  • Square Feet 7000
  • Bedrooms 7
  • Bathrooms 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: 3.73% last updated on Dec 12, 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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3 Fulling Mill Road

Chilmark, MA3 Fulling Mill Road

Price$995,000

Est. Mortgage: $/month

MLS ID 35606

  • Residential
  • Square Feet 1728
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.7

Custom built home set hillside with lovely terraced gardens, patio and glacial rocks. Ample family space on two levels. Bright and fully equipped kitchen opens onto the screened porch for dining alfresco. The en-suite master bedroom opens to private deck. Propane heat, fireplace and central AC. Great location just minutes to Beetlebung Corner and Lucy Vincent Beach.

Listed by Conroy & Company R.E., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS ID 34345

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathrooms 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: 3.73% last updated on Dec 12, 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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2 Creek Hill Road, Menemsha

MLS ID 35507

  • Residential
  • Square Feet 770
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.2

An opportunity to be right in the heart of Menemsha in one of the most iconic cottages over looking the harbor. This sweet 2 bedroom home has been enjoyed by the Klimm family for generations. Some of you may remember Rasmus Klimm, a renowned fisherman and local figure who displayed his wooden carvings and fishing floats on the shacks on the Harbor opposite the house. This authentic 770 square foot cottage is what living in Menemsha is all about - a bustling little village that attracts many for its quintessential Vineyard vibe and world famous sunsets. Walk to the beach, Dutcher's Dock, Fish markets, restaurants, art galleries and more. Fish from the beach or jetty or take a charter out deep sea fishing. Keep your boat just steps from the house in the harbor, and breathe in the simplicity of what this sweet fishing village has to offer. This feels like a genuine escape, with all the summer amenities you need to enjoy Menemsha during the quiet of spring, the warmth off summer and the buzz of derby season. A very special location and opportunity for someone and comes with an excellent rental history too!

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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2 Rockrose Path

Chilmark, MA2 Rockrose Path

Price$1,695,000

Est. Mortgage: $/month

MLS ID 35538

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 1.6

This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of Meetinghouse Road in Chilmark. This heated, year round house is sited on one and a half acres in a private setting with a large front yard and easy to care for landscaping. The open living room, dining area and kitchen have direct views to the Atlantic. The master bedroom and bath also have ocean views. The lower level of the home has one bedroom and one full bath (under construction), and plenty of storage space. This property is being sold with access to a private Atlantic Ocean beach, Thumb Cove, and access to a dock on Chilmark Pond for launching of a small boats, kayaks, and paddle boards. This home is being sold "as is"....bring your architect and builder for renovation and expansion plans! Furnishings available separately.

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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68 Meeting House Road

Chilmark, MA68 Meeting House Road

Price$1,725,000

Est. Mortgage: $/month

MLS ID 35318

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 6.16

Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019. For virtual tour, please copy and paste in a new tab the following link: virtual tour https://my.matterport.com/show/?m=XwSejuiNXGN&brand=0

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 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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