Chilmark MA Real Estate & Homes

MLS Number 36389

• Residential
• Mls Status Active
• Bedrooms 9
• Bathroom 8.5
• Acreage 60.4

One of the largest single residential lots in Chilmark, this exceptional 60 acre offering includes 800 +/- feet of direct, breath-taking Atlantic Ocean front. This Martha’s Vineyard estate offer multiple homes including a new farmhouse, main house and bunk house. A private drive leads you past beautiful farmland, open fields, down past Quenames Pond and over the dune down to the sandy beach. The residences and grounds offer endless options in this simply stunning private oceanfront estate.

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

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 36784

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 1

Spectacular Stonewall Pond and beyond! Experience a sense of privacy and peacefulness while enjoying panoramic ocean & pond views. Each of the three bedroom suites have a connection to an outside space. The master bedroom has extraordinary views and includes an open sitting room and fireplace, as well as a private balcony to take in the sounds of the ocean. The large and open kitchen has recent upgrades with expansive area for dining. Adjacent to the living room is a lovely sitting room currently used as an office. Truly an experience of special living on the Vineyard.

Listed by Julianna Flanders of Flanders Real Estate

MLS Number 38217

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.6

Surrounded by nature, this is a South Shore waterfront sanctuary. The presence of the peaceful placid pond combined with the power of the ocean and the sound of the waves is part of the special experience of living here. It has a particular sense of privacy and peacefulness. Hidden away on a quiet road of lilacs and summer cottages, the yard is defined by stone walls, lush gardens, natural art objects and several outdoor patios. Just beyond the lawn is a sandy path for easy access to the ocean and pond. The feeling inside the tasteful home is one of understated pleasing ambience. There are three bedroom suites and the ability to create a fourth. Each of the bedrooms has a connection to an outside space, two have pond and ocean views and one bedroom includes a sleeping loft space. The large and open kitchen which was recently renovated has a vaulted ceiling and an expansive dining space. Natural light and views of the pond fill the room and glass doors lead to the outdoor patios. The library with fireplace and a wall of windows to the water also serves as a formal dining room. In the living room, the dramatic height and spectacular views of the ocean and pond give you an expansive sense of water. The views from the adjacent sunroom have an intimacy and this room is currently used as an office and sitting room. The primary bedroom suite has extraordinary panoramic views and is a retreat that includes an open sitting room and fireplace as well as a private balcony and bathroom. The character of this property, its authenticity, vistas and connection to the natural landscape all combine to create a truly unique experience.

Listed by Meg Bodnar 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 38491

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

Located in the Tower Farm neighborhood in Chilmark, this property is a masterpiece of light and design. An exceptional new to-be-built 5-bedroom and 5.5-bath modern style beach house nestled among 55+ acres of conservation area. Generously entertain family and guests in the open kitchen/family floor plan lined with oversized windows which overlook the lively outdoor landscape, stone walls and Conservation land beyond. This turn-key home will feature state-of- technology, sustainable materials and solar. The outdoor spaces include expansive decking, outdoor grill kitchen, lavish gardens, and proposed reflecting pool. 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

MLS Number 37882

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 5.5
• Acreage 3.9

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

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

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

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