Chilmark MA Real Estate & Homes

MLS Number 35593

• Residential
• Square Feet 7000
• Bedrooms 7
• Bathroom 6
• Half Baths 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 Number 32237

• Land
• Village North
• Acreage 69.2

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.

Listed by Tea Lane Associates

MLS Number 35612

• Residential
• Village North
• Square Feet 2914
• Bedrooms 6
• Bathroom 3

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 Number 34345

• Residential
• Village South
• Square Feet 4000
• 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 Wallace & Co. Sotheby's

MLS Number 35399

• Residential
• Village North
• Square Feet 2140
• Bedrooms 4
• Bathroom 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 renovated and 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. Expansion of the main house is possible with permitting. The property has been approved for a five bedroom septic system (see listing broker for conditions). 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. A video tour of this property can be found here: https://vimeo.com/video/358902170

Listed by Russell Maloney Real Estate

MLS Number 19770

• Residential
• Village South
• Square Feet 2300
• Bedrooms 4
• Bathroom 1

Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from your door. First level of home is a large living area with kitchen all fronted by a large screened in porch. There is also another area that serves as bedroom or could also be used as a den or office space. Upper level has 3 bedrooms, large living room, full bathroom and loft space - great for the young ones. This home is great for entertaining and offers some of the most spectacular views in Chilmark. Enjoy sunset views over the pond...or swim off of the private sandy beach area on the pond which is great for young swimmers and for launching kayaks...All of this just within a short distance of Squibnocket Beach. To view a virtual tour, please copy and paste the following link into a new tab https://my.matterport.com/show/?m=Kz61UjgogyS&brand=0

Listed by Flanders Real Estate

MLS Number 32807

• Residential
• Village South
• 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 25297

• Residential
• Village South
• Square Feet 1927
• 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 35757

• Residential
• Village North
• Square Feet 4967
• Bedrooms 6
• Bathroom 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 Number 35123

• Residential
• Village North
• Square Feet 4100
• Bedrooms 4
• Bathroom 3

This property exudes fine craftsmanship and a well rounded experience with pool, privacy and Menemsha Pond access nearby. Located in the Flanders Lane area near Menemsha, this post and beam home was built with only the best materials - red oak timberframe, quarter sawn red oak floors, radiant heat, Alaskan yellow cedar shakes, copper gutters and mahogany barn doors. It is solid, and elegant. This property needs to be experienced to be appreciated fully. The living spaces are generous and customized with built-ins. The bedrooms are large and private from each other. The 1000 s.f. garage and workshop space has radiant heat and beautiful timberframe structure and is ready for conversion to a first floor master suite, a rec room or whatever needs suit you. There is a new heated, Gunite saltwater pool which connects to the stone patio and the expansive lawn and gardens beyond. This is truly a hidden treasure.

Listed by Tea Lane Associates

MLS Number 36499

• Land
• Village South
• Acreage 3.02

In the Quansoo area of Chilmark, three unspoiled acres with views and full access to Tisbury Great Pond. Ownership includes membership to Old Fields association with deeded access to 2- acre private beach on Tisbury Great Pond, perfect for kayaking, paddleboarding, sailing or take a quick ride in your motorboat to the south shore and play in the surf. The property is approved for six-bedroom septic. This is a rare opportunity to create your own Island sanctuary.

Listed by Point B Realty LLC

MLS Number 35538

• Residential
• Village South
• Square Feet 2100
• Bedrooms 4
• Bathroom 3

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