Property for Sale in Chilmark, MA

LINK ID: 35593
Town:Chilmark
Type: Single Family
$15,000,000.00

Property Details

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.

LINK ID: 36458
Town:Chilmark
Type: Single Family
$11,750,000.00

Property Details

NEW LISTING

Pond House LLC is proof that dreams come true. A sublime elevated private setting just steps from the water with a 90 ft deep water dock encourage swimming, kayaking, sailing, boating, fishing et al and enjoying breathtaking views from every room and place on the property. What could be better than tumbling out of bed to waterski, fish off the dock, paddle board or scull at the ready, or swim a mile in fresh seawater cleansed by the tides twice a day. Perhaps, the only activity better is watching from inside or outside the house your young children or grandchildren exploring for clams and paddling around the shoreline in safe calm waters without concern for waves rolling in and out. The house has great charm and character designed to bring the outside in. Last but not least are beautiful sunsets to cap off an active and wonderful day. The creative layout and wrap around upper and lower decks are ideal for memorable entertaining or special quiet time.

LINK ID: 35612
Town:Chilmark
Type: Single Family
$9,500,000.00

Property Details

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

LINK ID: 32237
Town:Chilmark
Type: Land
$9,500,000.00

Property Details

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

LINK ID: 34345
Town:Chilmark
Type: Single Family
$8,900,000.00

Property Details

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.

LINK ID: 35399
Town:Chilmark
Type: Single Family
$7,995,000.00

Property Details

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

LINK ID: 32807
Town:Chilmark
Type: Single Family
$4,195,000.00

Property Details

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.

LINK ID: 36676
Town:Chilmark
Type: Single Family
$4,000,000.00

Property Details

NEW LISTING

With 425 ft of private ocean beach, this offering deserves its reputation as the "ultimate beach house". The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide access to a wide swath of sand that many consider the most beautiful stretch of beach on Martha's Vineyard. The property is being offered mostly furnished. To fully appreciate this extraordinary setting, view the images in the "photo gallery" and watch this drone video: https://vimeo.com/175588276

LINK ID: 25297
Town:Chilmark
Type: Single Family
$3,000,000.00

Property Details

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).

LINK ID: 35757
Town:Chilmark
Type: Single Family
$2,950,000.00

Property Details

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.

LINK ID: 35123
Town:Chilmark
Type: Single Family
$2,795,000.00

Property Details

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.

LINK ID: 36557
Town:Chilmark
Type: Single Family
$2,500,000.00

Property Details

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.

LINK ID: 36499
Town:Chilmark
Type: Land
$1,729,000.00

Property Details

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.

LINK ID: 35538
Town:Chilmark
Type: Single Family
$1,695,000.00

Property Details

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.

LINK ID: 36342
Town:Chilmark
Type: Single Family
$1,500,000.00

Property Details

This charming Chilmark cottage offers unexpected water views of the Vineyard Sound. Private and tranquil, the two bedroom, two bath main house and separate two bedroom guest suite, and garage is nestled in the woods off of Tea Lane on Chilmark's North Shore. The main house features an open concept living space comprised of a great room, open kitchen, and dining area with high ceilings, wide planked hardwood floors, an impressive stone fireplace and a wall of windows looking out onto an expansive view of the Sound. The main house has two bedrooms, both facing the water, and two bathrooms, designed with a warm post and beam style that fits so well in the natural beauty of the Chilmark woods. The property has a spacious two car garage with a guest suite above which offers two bedrooms, a bathroom, and study space. The property has a six bedroom septic in place offering the possibility for expansion. The house was built to be a three season home, but the Seller is currently installing additional insulation and a heat pump. This is a wonderful investment opportunity for a Chilmark Buyer looking for a special view at a great price.

LINK ID: 36279
Town:Chilmark
Type: Single Family
$1,500,000.00

Property Details

You can "see for miles and miles and miles and miles" from this uniquely located Chilmark beach cottage that includes deeded access to 7 acres of pristine South Beach on the Atlantic Ocean! 180 degree water views looking easterly over Chilmark Pond, to the Barrier Beach and beyond and westerly over the Atlantic to Nomans Land. Simply Stunning! Colorful Sunsets! The cottage is a cozy camp with beach stone fireplace; used seasonally. This is a "one of kind" south shore location that is not often available for purchase. Short distance to the shores of Chilmark Pond from the cottage where you can wade across, in the summer, to the boardwalk that leads to your private access to South Beach! Included is an approved septic design for a 3 bedroom system. Buyer is responsible for installation. Enjoy the "camp" as it is or use your vision to rebuild/remodel. A special place on this beautiful island.

LINK ID: 36695
Town:Chilmark
Type: Single Family
$1,475,000.00

Property Details

NEW LISTING

An opportunity to be right in the heart of Menemsha in one of the most iconic cottages over looking the harbor. Why wait on making a move to own this sweet 2 bedroom home which has been enjoyed by the Klimm family for generations. Some of you may remember Rasmus Klimm, a renowned fisherman and local figure who displayed his wooden carvings and fishing floats on the shacks on the Harbor opposite the house. This authentic 770 square foot cottage is what living in Menemsha is all about - a bustling little village that attracts many for its quintessential Vineyard vibe and world famous sunsets. Walk to the beach, Dutcher's Dock, Fish markets, restaurants, art galleries and more. Fish from the beach or jetty or take a charter out deep sea fishing. Keep your boat just steps from the house in the harbor, and 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. Plus the cottage comes with an excellent rental history too!

LINK ID: 36441
Town:Chilmark
Type: Single Family
$1,450,000.00

Property Details

Beautifully kept three bedroom contemporary home, set amongst 3 acres of rolling Chilmark land. The first floor is all wood floors, a spacious first floor master bedroom, with large bathroom and walk-in closet space as well as an open layout plan for the living/dining and spacious kitchen area all add to the comfort of this home. Enjoy dinners on the screened in porch, or reading a back on the back deck overlooking the large yard and wooded surroundings. A First floor laundry area, a half bathroom, a small office area, as well as a 2 car garage complete the first floor. Upstairs you will find 2 more large bedrooms that share a full bathroom. This home gets amazing light, the living room is lined with windows, making it a wall of glass to enjoy the Chilmark landscape. This home has a 5 bedroom septic in place, yet it is only a 3 bedroom home so the potential already exists to add more bedrooms either by finishing the walk out basement area, an addition or a detached bedroom, so many options!

LINK ID: 36272
Town:Chilmark
Type: Single Family
$1,250,000.00

Property Details

On a quiet country road in Chilmark, this bright and airy contemporary home offers recent, extensive renovations including new kitchen, bathrooms, HVAC and decks. This is a great vacation home with open layout, high ceilings, stone fireplace, walls of windows, skylights and large wrap-around deck for outdoor living. There are four spacious bedrooms with a private deck off the master. Includes plans for a detached garage designed into the hillside with guest suite above. Hiking and biking trails all around. Great location equidistant to Lucy Vincent beach and Alley's!

LINK ID: 34809
Town:Chilmark
Type: Single Family
$1,050,000.00

Property Details

Unique opportunity to enjoy the Vineyard the way it use to be on this lovely country lane just steps from the Homeport and Menemsha Pond. Nestled in among vintage cottages this charming, fully renovated home offers all of the amenities buyers are looking for in an expanded Cape with three floors for entertaining family and summer guests. The home offers a beach theme design with its white beadboard wainscoting and offers rich wood floors, ceramic tile floors and baths. The home includes three spacious bedrooms and three full baths as well as a cozy sun room off the kitchen and a large finished basement. Winter water views from upstairs. This location offers your family and guests the unique ability to walk to a day at the beach, watch a Menemsha sunset, go to dinner and never have to get into a car or struggle to find a coveted parking space. Most Furnishings Included. There is over 600 additional sq feet of living space on the lower level that is not included in the square footage listed. Check out the 3D Virtual Tour.

LINK ID: 36663
Town:Chilmark
Type: Single Family
$997,000.00

Property Details

NEW LISTING

Quintessential waterfront cottage overlooking Martha's Vineyard's hottest surf destination on the south shore. What a great place to spend some time and enjoy this classic and wonderful home listening to the sounds of the surf and sea. This home has had years of great use and can be used now until it's time to move or rebuild it. 3 comfortable bedrooms and a delightful kitchen lead to a living room centered around a great field stone fireplace with views from every room. The property may be used as is for some time and then be converted into a private beach access ideal for surfers and beach goers alike.

LINK ID: 33477
Town:Chilmark
Type: Land
$725,000.00

Property Details

4.32 rolling acres with stone walls. Deeded walking access to north shore beach. 4-bedroom septic, well, and electric power are all installed. Natural Heritage work has already been completed and permit is in hand. The access and building site was recently brush-cut for easy access.

LINK ID: 34844
Town:Chilmark
Type: Land
$675,000.00

Property Details

Three acre vacant lot with second story waterviews abutting conservation land. Enjoy pastoral and pond views along with beautifully restored stone walls from your building site. Lot is fully engineered with well and utilities in place with rights to nearby tennis courts. Just bring your plans.

LINK ID: 17138
Town:Chilmark
Type: Land
$675,000.00

Property Details

This private three acre lot enjoys North shore waterviews, substantial building envelope, privacy from abutting Waskosim's Rock Reservation, beautiful stonewalls, and pondviews. This is a rare offering of one of only a few lots in an area of pastoral and ecologically protected land in Chilmark. Fully engineered. Well and utilities on site. Property includes rights to the two tennis courts nearby on Old Farm Rd which are all weather sandy green carpet surface similar to har-tru.

LINK ID: 36647
Town:Chilmark
Type: Land
$595,000.00

Property Details

A beautiful 4.2-acre piece of land at the top of Hammett Lane. This is a very special spot with gently undulating woodlands punctuated by lichen-covered boulders. The property can support 6 bedrooms, based upon perk test results. In addition to site work by Sourati Engineering, all NHESP work has been completed. No other homes can be seen from the proposed location of the main house which adds to the desirability of this piece of land. Please check the documents section for a site plan showing the location of the ideal home site. The entrance to Great Rock Bight beach is just half a mile from Hammett Lane. Menemsha, Beetlebung Corner, and Lucy Vincent are all a short distance away.

LINK ID: 34926
Town:Chilmark
Type: Land
$495,000.00

Property Details

A smart opportunity to own a lovely 2.2 acre south facing parcel off South Road. There is an approved 6 bedroom septic design and access to power allowing for an easy property to develop. Birdsong, glacial boulders and nature all around. Cleared paths and site and easy to show A well located private piece of land to build your new home in Chilmark!

LINK ID: 33176
Town:Chilmark
Type: Land
$165,000.00

Property Details

Enjoy access to lovely stonewall Beach, south shore Atlantic beach with great swimming and fishing! - not a buildable lot.

LINK ID: 35677
Town:Chilmark
Type: Land
$150,000.00

Property Details

Escape the crowds and take advantage of this opportunity to own a private beach lot at the Atlantic Ocean and Stonewall Pond. Stonewall Beach is centrally located between Lucy Vincent and Squibnocket and easily accessed, just 2 minutes off State Road. Enjoy sailing, kayaking, swimming on the pond and sunbathing and surfing at the ocean. Parking is available. This is not a buildable lot.
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