Chilmark Real Estate

MLS Number 37589

• Residential
• MlsStatus Active
• Square Feet 2106
• Bedrooms 4
• Bathroom 3

Charming two cottage Chilmark retreat tucked away on Middle Road. Nestled into a rolling hill, the main structure overlooks the quintessential up-island setting: a lower pasture lined with ancient stone walls and mature trees. Completing the main house is a first-floor ensuite master, two additional bedrooms, a dramatic wall of windows, and a sizable deck perfect for summer evenings. The separate one-bedroom guest house offers an idyllic, private refuge with a wood-burning fireplace, ample natural light, and a bonus sleeping loft. Situated on 1.3 acres, this property is in close proximity to all that Chilmark offers- Lucy Vincent Beach, Squibnocket, Chilmark General Store, and an abundance of scenic hiking trails. Renovations have just begun to refurbish this 1973 cottage, making it an excellent opportunity for a buyer to perfect their up-island sanctuary.

Listed by Wallace & Co. Sotheby's

MLS Number 36863

• Residential
• MlsStatus Active
• Square Feet 2100
• 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 Real Estate

MLS Number 36769

• Residential
• MlsStatus Active
• Square Feet 1024
• 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 Flanders Real Estate

MLS Number 37199

• Residential
• MlsStatus Active
• Square Feet 2384
• Bedrooms 4
• Bathroom 3

Menemsha -- one of the most desirable locations on the Island. It is an easy walk to the village and to the beach from this sweetly located property. Set at the end of a private cul-de-sac, this remodeled beach themed, sea view cottage oozes with charm. Three bedrooms and two baths are in the two story main house. The second floor consists of a master suite, dressing area, bathroom, water-view office and bonus room with ample storage. A screened in porch and upper and lower decks point the way to terrific sunsets! A one bedroom one bath guest cottage and outdoor shower complete this property. Agent has an ownership interest in home.

Listed by Kendall & Kendall

MLS Number 37547

• Residential
• MlsStatus Active
• Square Feet 2429
• Bedrooms 5
• Bathroom 4

Perfection off of Middle Road with all of the natural beauty that embodies this part of the island including mature trees, perennial gardens, and old stone walls. A meticulous main house, recently renovated and facing south with sunlight all day long on the deck and in the main living areas. Well designed with three ensuite bedrooms and baths and AC throughout. Open living spaces flow from the kitchen to the dining and living room. A tasteful fireplace centers the living room as a focal point and makes this space so cozy in the off season. A separate guest suite is located across the lawn - with bedroom, full bath, outdoor shower, living room/kitchen with AC. Plus there's a bonus bunk house. This Chilmark home is ready to move right in and enjoy.

Listed by Tea Lane Associates

MLS Number 37327

• Residential
• MlsStatus Active
• Square Feet 1164
• Bedrooms 3
• Bathroom 2

Located near Black Point Beach, this quaint rural setting offers lots of privacy and a wonderful yard for children to play, outdoor games. and mature garden bed. Open Kitchen/living room with soap stone counter tops and an island with granite countertops and storage. Beautiful hardwood floors through out house. Built by South Mountain, this house can be expanded or reduced to guest size, and the property is large enough to create a family compound. Black Point Beach lot available at an additional cost. For virtual tour, please copy and paste this link to your browser https://my.matterport.com/show/?m=uatVdGxkZFg&mls=1?ts=1

Listed by Flanders Real Estate

MLS Number 25297

• Residential
• MlsStatus Active
• Square Feet 1980
• Bedrooms 5
• Bathroom 2

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

MLS Number 37032

• Residential
• MlsStatus Active
• Square Feet 2082
• 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 Tea Lane Associates

MLS Number 35757

• Residential
• MlsStatus Active
• Square Feet 4967
• Bedrooms 6
• Bathroom 4

PRICE CHANGE reflects the addition of 3.9 acres to the existing listing. Large estate 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

MLS Number 37095

• Residential
• MlsStatus Active
• Square Feet 1550
• Bedrooms 3
• Bathroom 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 may have other uses such as a personal residence. It 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 Tea Lane Associates

MLS Number 32807

• Residential
• MlsStatus Active
• Square Feet 2604
• Bedrooms 6
• Bathroom 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 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 Wallace & Co. Sotheby's

MLS Number 37278

• Residential
• MlsStatus Active
• Square Feet 3883
• 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 Real Estate