Chilmark MA Real Estate & Homes

MLS Number 36699

• Residential
• Mls Status Active
• Village South
• Bedrooms 6
• Bathroom 5

Perfectly sited on a slight bluff overlooking upper Chilmark pond to the Atlantic. Kayak or canoe from your dock to the private beach access. Superbly appointed , this 6 bedroom custom built home offers the finest in craftsmanship and materials including Lew French stone work and patios. There are few words that can adequately describe the feeling that exists in this location. The roar of the ocean and the glorious sunrises, the privacy, the view of nature’s world serene and safe. Exclusively offered.

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

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

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

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.

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

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

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

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 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 Robert Kenney of Tea Lane Associates

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

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