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Chilmark Real Estate

The visual trademark of Chilmark, just west of West Tisbury, might well be the stone walls that wind their way through rolling fields and forests, recalling the day when vast expanses of the Island landscape were open land, devoted to sheep farming. You’ll still see a working sheep farm if you look south from the South Road across the fields of Allen Farm to sweeping vistas of the Atlantic.

Chilmark has two important town centers. One, at a place called Beetlebung Corner for the trees there, has its library, school and town hall.There is also the charming Chilmark General Store where everyone gathers in the summer for chats and lunch.  Just a ways to the north is Menemsha, a picturesque fishing village which, remarkably, has kept much of its old New England character. While there you will want to buy fish right off the dock at Larsen's Fish Market. The beach at Menemsha draws people all summer long, and is especially popular for its colorful sunsets and one of the few places on the east coast where the sun sets over the sea.

92 Kings Highway Chilmark MA 02535

Chilmark, MA92 Kings Highway

Price$1,450,000

Est. Mortgage: $/month

Pending

MLS Number 37915

  • Residential
  • Mls Status Pending
  • Village South
  • Bedrooms 4
  • Bathroom 2

Set in the heart of Chilmark's largest continuous trail system off King's Highway, this comfy, bright and airy contemporary home is a great place to enjoy your Vineyard lifestyle. This great vacation home was designed with high ceilings, a wonderful stone fireplace and an open floor plan . There are 4 spacious and bright bedrooms, 2 updated baths and an unfinished basement area with workbenchand storage ready for your personal touch. The spacious deck wraps around 2 sides of the house and there is a smaller private deck off the master bedroom. There are literally miles of trials in every direction for great walking, mountain biking or adventures in the woods. The centralized location is midway between Alleys and the Chilmark beaches.

Listed by Jim Feiner of Feiner Real Estate

$
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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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40 Blueberry Ridge Lane Chilmark MA 02535

Chilmark, MA40 Blueberry Ridge Lane

Price$1,500,000

Est. Mortgage: $/month

Pending

MLS Number 37977

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 3.7

Located in the beautiful Blueberry Ridge Association off North Rd, this traditional 4-bedroom home delights us with many appealing upgrades. The spacious, eat-in chef's kitchen is clearly the heart of the home. Decks on both the front and back of the house provide attractive transitional areas to relax and enjoy the quiet country setting abutting Sheriff's Meadow property. This is a great year-round home or the vacation home that is nicely located for easy access to Menemsha and the center of town. Of course, this house provides entree to the beautiful Chilmark south shore beaches as well. Major full house renovations done in 2011, additional upgrades in 2015.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Tabor Hills Chilmark MA 02535

Chilmark, MA22 Tabor Hills

Price$1,695,000

Est. Mortgage: $/month

Pending

MLS Number 38274

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 3.1

Beautifully kept three bedroom contemporary home, set amongst 3 acres of rolling Chilmark land. The first floor is all wood floors, a spacious first floor master bedroom, with large bathroom and walk-in closet space as well as an open layout plan for the living/dining and spacious kitchen area all add to the comfort of this home. Enjoy dinners on the screened in porch, or reading a back on the back deck overlooking the large yard and wooded surroundings. A First floor laundry area, a half bathroom, a small office area, as well as a 2 car garage complete the first floor. Upstairs you will find 2 more large bedrooms that share a full bathroom. This home gets amazing light, the living room is lined with windows, making it a wall of glass to enjoy the Chilmark landscape. This home has a 5 bedroom septic in place, yet it is only a 3 bedroom home so the potential already exists to add more bedrooms either by finishing the walk out basement area, an addition or a detached bedroom, so many options!

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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239 State Road Chilmark MA 02535

Chilmark, MA239 State Road

Price$2,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 36769

  • Residential
  • Village North
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.5

A Charming summer home with magnificent, uninterrupted views of Menemsha Pond, Vineyard Sound, and on a clear day the Elizabeth Islands, in the distance. The property comes with access to Short Beach; a private beach 10 minutes away by foot and just a few minutes by car. The beach comes with small boat launching rights. The house has great cross breezes on warm days and a fireplace for when it's chilly. It has been in the same family for over 60 years and has been called "Windhover" based on the Gerard Manley Hopkins poem by that name. The property is on what is now considered an undersized lot, but is grandfathered in for zoning purposes. Property is located close to State Road, but has extensive privacy with natural brush surrounding the perimeter.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Drive Way Chilmark MA 02535

Chilmark, MA8 Drive Way

Price$2,650,000

Est. Mortgage: $/month

MLS Number 38298

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 4.7

Middle Road Water View: This fabulous location, just off Middle Road, and not far from Beetlebung Corner, offers views of the lush countryside extending south to the blue waters of the south shore. The residence, designed by noted architect Milton Klein, has modern lines, a minimalist white interior with bleached bamboo floors, a wall of glass sliders with southern exposure and a high ceiling in the Great Room which encompasses living, dining and kitchen. The main level master suite has a separate office space and en suite bathroom. Off the Great Room is a large deck also leading to the screened porch which has access from the kitchen. The lower level floor plan has a family room with built in cabinets for storage and media, glass sliders out to deck and 2 outdoor showers, 3 guest bedrooms, a full bathroom plus powder room, closet laundry room, and utility room. The house is designed with plenty of built-in drawers and cabinets. The 4.7 acre site provides plenty of room for expansion. It is less than two miles to Lucy Vincent Beach and less than 1 mile to the Chilmark Store. Mini-Split A/C in Great Room and Master Bedroom. House heated by both Gas FHW and Electric, and also receives good solar gain from south side. See attached deed for covenants and view maintenance.

Listed by Patty Kendall of Kendall & Kendall

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 and 130R South Road Chilmark MA 02535

Chilmark, MA130 and 130R South Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 37946

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.3

Nestled on South Road in Chilmark is this eclectic, rustic yet newly renovated house and guest house ....Formerly known as "The Fenner Barn" the original home was once a two story barn dating from 1900.  The current owners embarked on a renovation which would keep the authentic feel of this original barn, but bring a modern utilitarian vibe to the traditional New England antique building.   A metal seam roof was added, large windows, industrial lighting and concrete counters were stylishly combined with natural materials such as the beautifully refinished original floors, whitewashed wood, exposed beams and stone walls. The comfy, casual main family home has a large primary bedroom and bath on the first floor as well as an open kitchen/breakfast room, dining, living area with beautiful hardwood floors, and exposed beams with a large fireplace centering the space.  Two newly added large square double height windows that look out to the yard help to bring nature into this home.  There are two additional screened in porches off of which help to give this home a great indoor/outdoor flow. Upstairs to the second floor great room , new oversized windows help to create great light. This room has exposed white-washed beams and trusses, two bedrooms and a bath and den/office in the loft above.   Floor mounted AC mini splits provide the heating and cooling and there are new appliances throughout. The exterior of the home has been treated with a Japanese style process called Shou Sugi Ban. This technique will maximize the longevity of the rough milled pine and gives it a bold contrast to the red metal roof.   The sprawling outdoor space with quintessential Chilmark stone walls, a great patio with fire pit and play area, plus an amazing stand alone outdoor shower constructed of stone, wood and metal. The property has an impressive assortment of established trees and lawn area that separates the main home from the sweet one bed guest cottage with full bath and second outdoor shower.  Beyond this is the basketball court, storage sheds and paths that connect through to hiking trails to the south shore and and other ancient ways.

Listed by Jill Napior of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Middle Road Chilmark MA 02535

Chilmark, MA135 Middle Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 37541

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 2
  • Acreage 7.1

A quintessential 1950s cottage situated on the highly sought after area of Middle Road in Chilmark. Consisting of a main house, guest house, garage and storage shed on 7.1 total acres. Would make a great family compound. A Landbank walking trail abuts property. Property is being sold "AS IS." Septic upgrade plan completed, but not installed.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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129 Chilmark MA 02535

Chilmark, MA129

Price$3,250,000

Est. Mortgage: $/month

MLS Number 37095

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 3
  • Bathroom 3.5

Beauty, privacy and stunning imagination describe the 12 acre estate with 325 yards of ancient stone walls weaving through a meadow landscape with an extraordinary 2,800 sq ft architectural Greenhouse supported by a charming post and beam 925 sq ft guest house and a 600 sq ft beautiful comfortable living barn. Designed like a cross, this advanced high-tech contemporary Greenhouse resembles a cathedral with a soaring angular roof line in perfect symmetry. It was built by Rough Brothers, the preeminent and largest manufacturer of greenhouses world wide. Rough does extensive research and designs systems and controls for conservatories, public and private gardens, US Dept of Agriculture and Forestry, major universities, Projects completed for NY Botanical Gardens, National Botanical Gardens in Washington DC, MIT University and Huntington Garden and Museum. Equipped with the most advanced temperature control system, it houses dozens of exotic and rare plants, trees, grasses, vegetables and flowers. The 12 acres have beautiful meadows, endless trees, dense brush and hundreds of healthy mature heirloom blueberry bushes. The property abuts the 300+ acres of Roth Woodlands and Waskosim's Rock and Tiasquam Valley Reservations extending uninterrupted from North Road to Middle Road.

Listed by Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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53 Wequobsque Road Chilmark MA 02535

Chilmark, MA53 Wequobsque Road

Price$4,250,000

Est. Mortgage: $/month

MLS Number 38565

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5

This magnificent waterfront home sited on 6.4 acres sits atop the dramatic Wequobsque cliffs. On Chilmark's coveted South Shore, this home boasts ownership of over 350 feet of private beach with access from your staircase in the backyard. The home has a 5-bedroom and 4-bath wing. Attached by a screened-in porch, is the large gathering kitchen with ceiling beams, tall columns and an open, airy design. Enjoy meals in the dining area with ocean views. Dine on the large outdoor deck facing the Ocean. On the west side of the property sits the barn with a half bath and a loft that can be used as an office or extra sleeping area. There is wet bar, ping-pong table, large screen TV and sofa. There's space to install a wood stove. The home has a new full basement and HVAC system. A very large one car garage below the barn completes the property. This is your opportunity to own your dream home on the waterfront on Chilmark's South Shore.

Listed by Grace Hagerty of Grace Hagerty Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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53 Wequobsque Road Chilmark MA 02535

Chilmark, MA53 Wequobsque Road

Price$4,250,000

Est. Mortgage: $/month

MLS Number 38570

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 6.4

Waterfront in Chilmark with Private Ocean Beach. This home on 6 acres nestled atop the magnificent Wequobsque Cliffs on Chilmark's south shore was built by one of the island's finest builders, John Early Construction. The home enjoys views of the Atlantic Ocean and private ownership of over 300 ft of white sand beach (Note: Seller has installed brand-new beach stairs.) There are 5 bedrooms spread over 4000 square feet with several separate living spaces including the "party barn" that makes up the west wing of the property. Look no further if your dream is to own a home waterfront on Chilmark's south shore. Click the "Documents" tab for full architectural plans including floor plans.

Listed by Andrew McElhinney of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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17 High Mark Chilmark MA 02535

Chilmark, MA17 High Mark

Price$4,900,000

Est. Mortgage: $/month

Pending

MLS Number 37278

  • Residential
  • Mls Status Pending
  • Village South
  • Bedrooms 7
  • Bathroom 5

17 High Mark, built in 1928, sits atop Highmark Hill near the center of Chilmark. There’s a plaque on the wall in the kitchen commemorating the original owner, architect, builders and neighbors of this estate which reads 'High Mark House – Abode of Ennobling Vision'. This unique Chilmark property is now exclusively offered for the first time in 49 years. Spread across 10.4 acres, the property consists of two parcels. The first parcel is 6.7 acres in size and holds the living quarters. The second parcel is 3.7 acres in size and provides a wide buffer to the main homesite or a suitable lot for further development. Structures on the larger parcel include the main house, guest house, detached bedroom, artist studio or playhouse, in ground pool with outdoor shower and dressing room, tennis court, detached two car garage and long shed workshop. Water views to the Atlantic Ocean, Menemsha Pond, and Nomans Land are seen from many of the rooms of the main house and guest house. The grounds hold specimen plantings in a park like, private setting with wide and long front and rear yards. The main house has both primary and guest bedroom suites, living room with large fireplace, dining room with ample seating for ten, office and gallery, kitchen and laundry room. The lower level has a library/media room (or another bedroom), full bath, utility room, cedar closet and multiple storage rooms. The guest house is 800 square feet with 3 bedrooms, full bath, an eat in kitchen and laundry. The detached bedroom is the perfect bunk house with views to the Atlantic. It is rare to find an estate property in Chilmark that has the features of this compound already in place . Many of the existing amenities found on this property (guest house, pool, etc.) allow for immediate enjoyment without special zoning permits and years of in town residency. Ample acreage provides room for building expansion or relocation.

Listed by Russell Maloney of Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$5,200,000

Est. Mortgage: $/month

MLS Number 38183

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Elise LeBovit of Gay Head Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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"Based on information submitted to MA_LINKMV as of July 28, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."

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