Kelleher Real Estate Services

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.

2 Rockrose Path Chilmark MA 02535

Chilmark, MA2 Rockrose Path

Price$1,288,000

Est. Mortgage: $/month

MLS Number 36863

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 4
  • Bathroom 3

This four bedroom, three bath home with ocean views is located on Rockrose Path off 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, large laundry room and plenty of storage space. Architectural plans are available for renovation or rebuild. Owner motivated to sell. Furnishings available separately. Access to a deeded, private Atlantic Ocean beach at Thumb Cove is also available separately (follow this link: http://vineyard.mylinkmls.com/Listings/36865).

Listed by Russell Maloney of Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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

MLS Number 37977

  • Residential
  • Mls Status Active
  • 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: 2.94% last updated on May 13, 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

MLS Number 36769

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 3
  • Bathroom 2

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: 2.94% last updated on May 13, 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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27 Oyster Lane Chilmark MA 02535

Chilmark, MA27 Oyster Lane

Price$2,700,000

Est. Mortgage: $/month

Active With Contract

MLS Number 37903

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Acreage 9.87

Four bedroom home designed by Hugh Weisman on 6.86 acres with adjacent lot already subdivided to be kept for future use or sold as wanted. One guest house can be built on one of the lots approved by the MV Commission. Large beautiful pond and natural matured landscaping all add to the appeal of this up-island offering.

Listed by Brenda Codding of Up Island Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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

Open House

MLS Number 37095

  • Residential
  • Next Open House: Thu 05/27 12:00 pm. to 2:00 pm.
  • Mls Status Active
  • Village North
  • Bedrooms 3

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: 2.94% last updated on May 13, 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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37 North Abels Hill Road Chilmark MA 02535

Chilmark, MA37 North Abels Hill Road

Price$3,475,000

Est. Mortgage: $/month

Pending

MLS Number 37032

  • Residential
  • Mls Status Pending
  • Village South
  • Bedrooms 4
  • Bathroom 3

An uncommon opportunity in Abels Hill. A sweet year round 4 bedroom home that offers strong south shore Atlantic Ocean and Chilmark Pond views. Renovated in the 90's and well maintained with an easy floor plan that expands out to the large deck and looks over a meadow to the ocean beyond. Wood floors, open beams, high ceilings and so much sunlight! 2 Loft style bedrooms and 2 additional bedrooms on the first floor with a total of 3 bathrooms. The open living space has four sets of glass sliding doors that open to the water views and make this feel like a real vacation home. Central AC plus a mini-split in one of the lofts. There is also a brick fireplace in the living room. Plus a garage to store your on island car. This is a solid year round home in one of the most desirable areas of Chilmark. Private access to the exclusive sandy south shore beach of Abels Hill. Zip around in your boat, kayak and paddle board all across Chilmark Pond and have a game of tennis on the three private courts the association offers.

Listed by Jill Napior of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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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260 South Road Chilmark MA 02535

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS Number 32807

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 6
  • Bathroom 3

Waterview Chilmark estate sprawling over 6.1 acres with deeded access to a dock on Chilmark Pond and private Atlantic Ocean beach access. 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 an 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 multiple 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 extraordinary and rare find in the heart of Chilmark.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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

MLS Number 37278

  • Residential
  • Mls Status Active
  • 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: 2.94% last updated on May 13, 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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31 Tower Lane Chilmark MA 02535

Chilmark, MA31 Tower Lane

Price$7,100,000

Est. Mortgage: $/month

MLS Number 37882

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 5.5
  • Acreage 3.7

An exceptional new 5-bedroom and 5.5-bath single-story modern style farmhouse nestled among 55 acres of conservation area in Chilmark. Generously entertain family and guests in the open kitchen/family floor plan with 10’-foot ceilings. Designed with entertaining and relaxation in mind, this beautiful timeless design offers expansive views that immediately connects you with nature in a private setting. The artfully designed landscape will feature custom planters, a lively outdoor grill kitchen and pool overlooking views of the Conservation Area beyond. Places like landscapes to experience and inhabit; to welcome guests and feel welcomed ourselves in beautiful, comfortable outdoor surroundings. Tower Farm Chilmark invites the senses to a realm of well-being and pleasurability. [Construction to begin 2021]

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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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18 Austin Pasture Road Chilmark MA 02535

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS Number 34345

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 5
  • Bathroom 3

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 Alyssa Halisky of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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 Jethro Lane Chilmark MA 02535

Chilmark, MA8 Jethro Lane

Price$11,995,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 7
  • Bathroom 6.5

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 Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of May 17, 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."

Kelleher Real Estate Services