Chilmark Homes for Sale

MLS ID 35624

• Residential
• Square Feet 900
• Bedrooms 2
• Bathrooms 1
• Acreage 0.2

A quintessential Chilmark cottage offering gorgeous water views of Quitsa and Menemsha Ponds, access easements to both the Pond and Atlantic, and much more! The home's renovated interior is recently refreshed, cute and charming, just right for your summer retreat. The exterior has undergone extensive upgrading, including a new roof completed in 2019. Also with an excellent rental history, this property offers a rare combination of proximity to beaches, views, and charming indoor/outdoor living spaces. An outstanding waterview offering - welcome to your up-island getaway!

Listed by Compass

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. Some of you may remember Rasmus Klimm, 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 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. Special location and opportunity !

Listed by Tea Lane Associates

MLS ID 35538

• Residential
• Square Feet 2100
• Bedrooms 4
• Bathrooms 3
• Acreage 1.6

This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of 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 (under construction), and plenty of storage space. This property is being sold with access to a private Atlantic Ocean beach, Thumb Cove, and access to a dock on Chilmark Pond for launching of a small boats, kayaks, and paddle boards. This home is being sold "as is"....bring your architect and builder for renovation and expansion plans! Furnishings available separately.

Listed by Russell Maloney Real Estate

MLS ID 35429

• Residential
• Square Feet 1920
• Bedrooms 5
• Bathrooms 5
• Acreage 0.5

This classic Chilmark home offers 4 bedrooms, 3 fireplaces, 4 full baths plus outdoor shower on a lovely parcel with stonewalls and mature plantings. The living room and kitchen each have fireplaces, and the dining room has a fireplace and a bay window. Additionally, there's a detached studio with the 5th bedroom, 5th bath, a studio space and a garage. The property abuts Menemsha Hills Trustees' land preserve with 211 acres of vista, water views and walking trails leading to Vineyard Sound. The trail head is steps away. Many recent improvements include full a/c by mini-splits, new bamboo floors throughout the entire house, new exterior shingles, new roof, skylights and many new windows. The spacious master bedroom has an en suite full bath with large skylight, walk in closet, and a large sliding glass door leading to a private balcony overlooking historic Chilmark stonewalls. Easy walk to Menemsha Hills Reservation and only a mile from Menemsha!

Listed by Tea Lane Associates

MLS ID 35318

• Residential
• Square Feet 2300
• Bedrooms 4
• Bathrooms 3
• Acreage 6.16

Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019.

Listed by Flanders Real Estate

MLS ID 35399

• Residential
• Square Feet 2140
• Bedrooms 4
• Bathrooms 3
• Acreage 3.3

Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was lovingly restored by the current owner and Joseph Dick, a well-known and respected architect on the Cape and Islands. The main house features two bedrooms, two baths, living and dining rooms with water views, fireplace, well-appointed kitchen, outdoor rain shower, and a front porch which provides a front row seat to those magical Menemsha sunsets and the Elizabeth Islands. The guest house has one bedroom and bath, large, open living and dining areas, an ample kitchen, and an outdoor shower. Adjacent to the guest house is a detached, one bedroom cottage. A cottage at the rear of the property contains an office with wide water views and a lower level space currently configured as a personal gym. The last of the five cottages on the property is used for storage of seasonal furnishings. Mature landscaping, specimen trees and lush perennial gardens surround the property and delight the senses with vivid colors and welcoming floral scents. A short stroll on a deeded path takes one to the historic fishing village of Menemsha, it's seafood and craft shops and the calm waters at Menemsha Beach.

Listed by Russell Maloney Real Estate