Chilmark Homes for Sale

MLS ID 35733

• Residential
• Square Feet 1798
• Bedrooms 3
• Bathrooms 3
• Acreage 3.4

Spectacular sunset water views are the focus of this gorgeous property with a zen like feel that fits gently into the stunning landscape. Views from every room over the north shore and Vineyard Sound. The master suite has a wonderful orientation with drop dead views from the bed. Each room has its own access to a private deck or porch. The kitchen is brand new as are all the windows and doors throughout. A gazebo in the yard offers a sanctuary form the home for meditation and solace. Walk the 3/5 mile of private beach, roam the trails and explore the miles of conservation properties nearby. This is a wonderful and intimate home that will bring joy for generations to come. Enjoy it as is or consider modifying it to fulfill your needs. Sellers is motivated.

Listed by Feiner Real Estate

MLS ID 35879

• Residential
• Square Feet 700
• Bedrooms 1
• Bathrooms 1
• Acreage 6.16

Enchanting cottage in the heart of Chilmark. Set hilltop, this home is found in a bucolic setting, surrounded by ancient stone walls, gorgeous trees and a fabulous landscape with flowers, lawn, and much more. The house has been beautifully maintained and features expansive outdoor decks, screened in porch, outdoor shower, and an inviting interior with oak floors throughout. 6+ acres allows for expansion (2.96 acres are under CR) with a 2-car garage on the property as well. Ownership in Chilmark allows access to town residents' only beaches at Squibnocket and Lucy Vincent. Make this your enviable island destination!

Listed by Compass

MLS ID 35860

• Residential
• Square Feet 4431
• Bedrooms 5
• Bathrooms 4
• Half Bath 1

Amazing, dramatic, expansive sunset water view property in the desirable Spring Point Association. Property features a three bedroom main house and a two bedroom, two bath guest house. Sited on 3.6 acres, this association offers deeded, private beach access to Beck's Beach, tennis courts, and walking trails. Main house offers an open floor plan with modern kitchen with pantry, dining area, spacious living room with fireplace, and half bath. Wonderful screened porch off the kitchen that opens onto a new, spacious deck. Two additional patios add great outdoor gathering areas. There is a main level master bedroom with en-suite bathroom, office and access to private deck. The lower level features two additional bedrooms, a full bath, storage area, and spacious garage. The guest house is nicely sited away from the main house and is quite private. There is a large deck, screened porch, living room with fireplace, loft, and two bedrooms each with a private bathroom. In addition, enjoy Lucy Vincent Beach, Squibnocket Beach and all Chilmark has to offer. Quansoo Beach lot also available for separate sale. *square footage of property to be confirmed by town

Listed by Island Real Estate

MLS ID 35814

• Residential
• Square Feet 2500
• Bedrooms 3
• Bathrooms 2
• Half Bath 2

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx.

Listed by Flanders Real Estate

MLS ID 35757

• Residential
• Square Feet 4967
• Bedrooms 6
• Bathrooms 3
• Acreage 63.3

Over 63 acres 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 ID 35612

• Residential
• Square Feet 2914
• Bedrooms 6
• Bathrooms 3
• Half Bath 1

With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the island, but this is yours all unto your own. Almost 70 acres of storied history, seclusion and a mile of stone walls throughout the property exude the authentic character of this long beloved farm in Chilmark. Past the antique post and beam barn, a granite bridge over Roaring Brook leads you to the back meadows and a beautiful ridgeline with strong views of the Vineyard Sound and the Elizabeth Islands. From this rise, the vista over the open meadows surrounding the ridge out to the rolling treetops of the north shore is equally enchanting and a landscape like no other on the island. Ride horses on the extensive trails throughout the property and out to the Sound for a swim. Even on your way to your beach, the Vineyard's past whispers to you as you pass the old brickyard. This is an extraordinary situation in which to create your island estate. This is the place James Cagney loved “beyond words” for the freedom and peace it provided. (PLEASE NOTE: There are 2 houses and a detached bedroom which are not habitable as is.)

Listed by Tea Lane Associates

MLS ID 35593

• Residential
• Square Feet 7000
• Bedrooms 7
• Bathrooms 6
• Half Bath 1

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 Tea Lane Associates

MLS ID 35606

• Residential
• Square Feet 1728
• Bedrooms 3
• Bathrooms 2
• Acreage 0.7

Contemporary year round home set hillside with lovely terraced gardens, patio and glacial rocks. Ample family space on two levels. Bright and fully equipped kitchen opens onto the screened porch for dining alfresco. The en-suite master bedroom opens to private deck. Gas fireplace and central AC. Great location just minutes to Beetlebung Corner and Lucy Vincent Beach.

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

MLS ID 34345

• Residential
• Square Feet 4000
• Bedrooms 5
• Bathrooms 3
• Acreage 16.38

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 Wallace & Co. Sotheby's

MLS ID 35507

• Residential
• Square Feet 770
• Bedrooms 2
• Bathrooms 1
• Acreage 0.2

An opportunity to be right in the heart of Menemsha in one of the most iconic cottages over looking the harbor. This sweet 2 bedroom home has been in the same family for generations and some of you may remember Rasmus Klimm, a famous local figure who displayed his wooden carvings and fishing floats on the shacks on the Harbor. This quintessential 770 square foot Chilmark cottage is right in the middle of it all. Walk to the beach, Dutcher's Dock, The Galley, Homeport, fish markets and of course the famous Menemsha sunsets. Breathe in the simplicity of what this sweet fishing village has to offer. This feels like a genuine escape, with all the summer amenities you need to enjoy Menemsha during the quiet of spring, the warmth off summer and the buzz of derby season. A very special location and opportunity for someone!

Listed by Tea Lane Associates