Sponsored: Real Estate Confidential: The Chilmark story for the rest of us


Real Estate Confidential is a weekly chit-chat about new listings, sales, or other insider info on the Martha’s Vineyard Real Estate market, by Fred Roven, Martha’s Vineyard Buyer Agents. It appears each Friday in The Minute.

A few weeks ago I wrote about properties in Chilmark and focused on luxury homes. I may have given the false impression that was all Chimark has to offer. There is an opportunity to purchase a little bit of paradise for prices similar to down-Island while enjoying Lucy Vincent Beach, one of the “ten best beaches” in America. Some of these homes have been on the market much longer than average and I believe it is because someone looking for reasonably priced homes does not even consider Chilmark. Do not miss the current, and perhaps never to be seen again, pricing opportunities.

The town of Chilmark offers some of the most breathtaking views of unspoiled land, rolling meadows, and brilliant sea. The town center is marked by an historic church, as well as a general store featuring a spacious down-home porch where visitors and natives alike gather throughout the day to feast, chat and share the latest local tidbits. You’ll still find a working sheep farm with sweeping vistas of the Atlantic and just a ways to the north is Menemsha, a picturesque fishing village which, remarkably, has kept much of its old New England character. You will also find a few of the best restaurants the Vineyard has to offer, and mile after mile of ancient stone walls.


For many, Chilmark is all about the beaches.

    • Lucy Vincent Beach is the Chilmark section of South Shore with surf, bluffs and available to Chilmark residents only. Off season you can spend hours walking the beach and enjoying the spectacular cliffs views.
    • Squibnocket Beach is also on the Chilmark section of the South Shore. It is newly expanded and provides some of the best surfing on the island.
    • Menemsha Public Beach is next to Menemsha Harbor. A gentle beach with the clear, bright water that is typical of the North Shore. Menemsha is especially popular as the best place on the island from which to watch a colorful sunset.


  • Great Rock Bight Preserve provides the opportunity to get some hiking in while experiencing incredible Vineyard Sound and Elizabeth Islands views before relaxing on the beach.


So, where can you experience all that Chilmark has to offer?

1 Swan’s Way is a summer home designed for easy care and relaxation and only a mile to Alley’s and a couple of miles to Lucy Vincent. The lawn and gardens are serene and magical, creating a unique and charming enclave. This charming home is designed for utmost privacy, comprised of three individual pods. The main pod contains the central living area with a screened porch, brick hearth fireplace, a bedroom and even loft space for additional sleeping space. The other two pods each contain a bedroom and bath.

The cozy year-round cottage at 33R North Road is surrounded by stone walls and abuts Seven Gates Farm. The property is in a quiet area with a rural Chilmark feel yet just minutes to the North Tisbury shopping area and a few minutes more to fresh fish right off the boat. There is a spacious 500 square-foot wraparound mahogany deck with seating for summer entertaining. For me, the main aspect would be crossing the road to my dog Nico’s favorite hiking trails and views at Waskosim’s Rock Reservation, and the connection to other up-Island trails. This property should certainly be considered for anyone looking for an inexpensive Island investment with substantial summer income.

3 Little Oak Lane provides an opportunity for spectacular sunsets and a water view at a reasonable price — Chilmark living the way it is supposed to be. It’s a gardener’s dream, with newly planted raised perennials in a deer resistant enclosure. The property is steps away from Fulling Mill Preserve with its extensive trail system and dramatic ocean views with the sound of the gurgling brook always in the background. The house is recently updated with new roof, deck, updated bathrooms and kitchen plus heating and AC provided by four mini-splits.

And, what would a trip to Chilmark be without my mentioning my current favorite listing in terms of long term investment value at 26 Kenasaoome Way? I really do not understand why this property has not sold. With the many restrictions in Chimark for new construction, this property at over three acres can be expanded someday to include house, guest house, pool, and barn. The current two-bedroom home and one-bedroom sleeping cottage can provide years of enjoyment while planning the expansion. The property borders on The Grey Barn and Farm with 90 acres of conservation land, and down the road is Quansoo Beach — summer membership required, but enjoyed at will in the off season. Of course Lucy Vincent and the newly enhanced Squibnocket Beach are available to all Chilmark residents and guests.

Click here for a complete list of Chilmark homes for the rest of us

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