Chilmark Homes for Sale

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

MLS ID 35387

• Residential
• Square Feet 3776
• Bedrooms 5
• Bathrooms 4
• Half Bath 1

55 Bijah's Way is a custom designed post and beam home built by well-known and respected island builder Heikki Soikkeli. Sited on 3 private acres, this home features 5 bedrooms, 4 ½ baths, screened porch, 2 decks, fireplace, generator, and an attached two car garage. Native plantings, sweeping lawns, a lengthy stonewall, scattered glacial erratics, as well as specimen trees including red maples, beetlebungs, oaks, hollies and pines enhance the landscape. The first floor of this home features an open living and dining room, fireplace, screened porch, and a well appointed kitchen. There are two first floor bedrooms; the master suite with walk in closets and an outdoor shower and a second bedroom and bath. The second floor of this home contains three bedrooms, one of which is separate and accessed by its own staircase providing space for an au pair, in-laws, or an office. There are two bathrooms found on the second floor as well. Closet space is ample throughout the home. This property borders 50+ acres of land held under conservation restriction, and miles of walking and hiking trails can be found nearby. Neighborhood community tennis courts are available. Chilmark residents enjoy the ocean beaches of Lucy Vincent, Squibnocket, and Vineyard Sound beach at Menemsha.

Listed by Russell Maloney Real Estate

MLS ID 35294

• Residential
• Square Feet 2106
• Bedrooms 4
• Bathrooms 3
• Acreage 1.3

House and guest house on a hilltop sanctuary. The mid-century modern main house designed by Ronald Gourley offers open-living space with a glorious wall of windows that bring in dramatic light throughout the day. Main house has a first floor en suite master with private office space. Two upstairs bedrooms are connected by a loft hallway. The one-bedroom guest cottage is privately tucked away down the hill. Both houses offer expansive decks and outdoor showers. The large lower yard is hidden from the main road and surrounded by stone walls. Mature landscaping offers privacy and solitude.

Listed by Feiner Real Estate

MLS ID 35279

• Residential
• Square Feet 1719
• Bedrooms 3
• Bathrooms 3
• Acreage 5.4

Bright and airy retreat on Black Point complete with key to Black Point Beach. Set on 5.4 acres off Black Point Road in Chilmark, this charming cottage brings an immediate feeling of peace and levity. One can hear the ocean and walk, ride or drive to Black Point Beach as a key to this private south shore beach is included. The layout of the house is intelligent with an entry that brings one into an open and bright living, dining and kitchen area, as well as a screened porch and an open deck. The upper level offers a master bedroom and bath with water views, while the downstairs level offers another bedroom, full bathroom and living area. There is also a substantial independent garage with a newly finished bedroom and bath above. The current owners renovated both structures inside and out to include new appliances, heating and cooling systems, new roofing, an upgraded septic and so much more. They have enjoyed the property as is, but this generous lot has potential to support another home.

Listed by Tea Lane Associates

MLS ID 34559

• Residential
• Square Feet 2444
• Bedrooms 5
• Bathrooms 2
• Acreage 6.7824

Vintage stone cape-style home, originally built in 1941 by renowned Chilmark builder, Roger Allen. This charming stone house was created using Chimark stones. A five bedroom home situated on a beautiful private 6.78 acre lot off North Road close to Menemsha. This extraordinary property abuts acres of Land Bank agricultural conservation property and is being offered for the first time in over 75 years. Within close proximity to Trustees of Reservations Menemsha Hills Preserve, a short drive to Land Bank Great Rock Bight preserve, Menemsha Beach and sunsets galore! This charming stone home welcomes you as you approach the property. A bright and cheery sun room addition lets you enjoy the spacious yard with ancient stonewalls and magnificent trees. Update this unique and charming home or use your imagination to make it the home of your dreams, close to Menemsha yet a world away! To top it off there is a spacious two-car garage with attached workshop. Title V septic system recently installed. This property is very unique and must be seen to appreciate its value. Pictures do not do it justice. Being sold "as is". There is an easement for grazing cattle on a portion of the lot, please call listing broker for further information.

Listed by Hancock Real Estate

MLS ID 19789

• Residential
• Square Feet 2384
• Bedrooms 4
• Bathrooms 3
• Acreage 0.2

Menemsha -- one of the most desirable locations on the Island. It is an easy walk to the village for a fish sandwich and a swim at the beach from this sweetly located property. Set at the end of a private cul-de-sac, this remodeled beach themed, sea view cottage oozes with charm. Three bedrooms and two baths are in the two story main house. The second floor consists of a master suite, dressing area, bathroom, water-view office and bonus room with ample storage. A screened in porch and upper and lower decks point the way to terrific sunsets! A one bedroom one bath guest cottage and outdoor shower complete this property. Agent has an ownership interest in home.

Listed by Kendall & Kendall

MLS ID 35123

• Residential
• Square Feet 4100
• Bedrooms 4
• Bathrooms 3
• Half Bath 1

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 ID 34278

• Residential
• Square Feet 3194
• Bedrooms 4
• Bathrooms 4
• Half Bath 1

This impeccably built home is set on 3 private acres off of Old Farm Road in Chilmark. Open and light, the 4 bedroom house has an intelligent design that works well for quiet time or company. Upon entering one appreciates the sizable spaces that connect the living room, dining area, well appointed kitchen and study. The cathedral ceilings, large fireplace, and stunning glass doors ensure that you have everything you need in the center of the house. The left wing includes a master bedroom suite and sitting area that overlook the gardens and lush lawn, while the second floor offers another generous master bedroom suite. There are also two lovely bedrooms and one corresponding bathroom. Each room has its own orientation viewing the pool, or gardens- like an English country house with all the modern conveniences... The in ground pool was designed by Rosbeck and is nicely separated from the house but enjoys a refined pool house with full bath and outdoor shower. There is also a detached garage that continues the aesthetic while beautiful flowers, grasses and other plantings tie the property together and deepen the relationship of the structures to the land... This is a perfectionist's dream....must be experienced...

Listed by Tea Lane Associates

MLS ID 34988

• Residential
• Square Feet 3770
• Bedrooms 4
• Bathrooms 4
• Acreage 3

A Large commanding residence set hilltop off Middle road with outstanding water views of the Atlantic and glimpses of Chilmark Pond. Inviting common room with cathedral ceilings, fireplace and gourmet kitchen seamlessly flows to the screened porch and lounging deck. Each wing of the house is comprised of a master bedroom en-suite including two additional bedrooms with private baths. Whether spread out in the family/media room, deck or porch this expansive home can accommodate the largest of families. Special and private with access a short walk away to Fulling Mill Brook Preserve offering 60 acres of walking trails

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

MLS ID 35095

• Residential
• Square Feet 1476
• Bedrooms 3
• Bathrooms 2
• Half Bath 1

This rare Chilmark waterfront setting is on three acres of graceful land featuring a light-filled home with an intelligent one level layout. Kayak from the private pond front beach to the Atlantic, or enjoy paddle boarding, shell fishing and the sunset right in your front yard. The current home is open and bright, the master suite has its own wing and the two additional bedrooms and bath are on the other side. The house is centered by an open concept kitchen, dining and living room area with a fireplace, and views to the water. The screened porch and extensive decking offer further areas to gather, and the grounds have lovely old oaks and a rolling lawn.This property supports 6 bedrooms and is the perfect palate for a substantial and thoughtful water front home. The property captures intimate pond views, as well as views to the Atlantic Ocean and Quansoo beach. The Island's Great Ponds, over ten acres in size, are salt ponds, and considered some of the best fishing and boating spots on Martha's Vineyard. The Tisbury Great Pond is on the south shore and separated from the ocean by a barrier beach that is opened seasonally to achieve the balance of salinity necessary for the native oysters, clams and many species of fish. For those seeking a quiet and tranquil escape with a quintessential and expansive Martha's Vineyard water view, it doesn't get much better than this. See broker for further details about beach access.

Listed by Tea Lane Associates