Can we take a peek? Inside a 12-acre Chilmark Estate

Trespassing on the best Island properties (with permission).

The whimsical town of Chilmark — with its undulating landscape of twisted vines and sheep grazing in hilly pastures — has captured the hearts and imaginations of artists, musicians, farmers, nature lovers, and folks with imaginations more vast and vibrant than a Menemsha sunset.

Driving down Old Farm Road in Chilmark, the lichen-covered stone walls that lace along the sloping shoulder can lead you to all sorts of hidden worlds that highlight the creativity of those who live in town.

One such world, a 12-acre estate that boasts some of the most distinctive topography (and architecture) I’ve seen on Martha’s Vineyard, illustrates perfectly how somebody’s ambition can evolve and eventually morph into a one-of-a-kind labor of love.

The property owner and the man behind the most recent iteration of the space was able to give Vineyard Visitor a tour of the sprawling eden.

The property abuts more than 300 acres of Roth Woodlands and Waskosim’s Rock and Tiasquam Valley Reservations, which stretch uninterrupted from North Road to Middle Road (crank that music — the neighbors can’t hear you).

You’d hardly know it pulling off Old Farm and into the driveway of the small but comfortable post-and-beam guest house, but the real highlight of the up-Island wonderland sits at the back of the lot.

Just hover over the property on Google Maps and you’ll see what I mean when I say this gleaming structure stands out among other buildings in the area that may rival its size.

Topped with solar panels that provide convenient shading, and outfitted with a state-of-the-art temperature control system, a 2,800-square-foot architectural greenhouse rises up from the ridge that bisects the land.

If it were made of stone and adorned with intricate religious symbols, you might assume it to be an ancient cathedral nestled in the Chilmark woodlands. But the endlessly fascinating greenhouse might be likened more to an alien spaceship, with how advanced the technology is that keeps it running, and how entering into the shimmering cruciform almost makes it seem as though you’ve set foot on another planet.

According to the property owner, the greenhouse is one of the first in America to use solar panels to provide all the electricity to heat and cool the space.

Designed by the Rough Brothers — a premier greenhouse designer and manufacturer — the unique structure holds a variety of rare plants (and, currently, a man cave). A simple bathroom and shower is also included in the greenhouse.

Rough Brothers also dreamed up and built the National Botanical Gardens in Washington, D.C., and the MIT University and Huntington Garden and Museum.

The owner explained that, although the greenhouse could be used to grow food commercially seven months out of the year, it also serves as a great residential space or guest house for visiting family and friends.

“The possibilities with the greenhouse are really endless. It could be a rec room, a man cave, a living space, or a major growroom. Whatever you can think up,” the owner said.

The first owner of the property was a farmer-artist who wanted to clear a meadow for grazing his horses. He kept the horses in a primitive barn, and planted fruit and vegetable gardens on either side of the sloping ridge.

Now, the barn that once held horses and tack has been refitted into a cozy residential space right next to the massive greenhouse.

Both residential buildings on the property feature exposed wood, which lends to the homely feel. The living barn has a beautiful old metal tub, which I found to be a personal highlight.

About 300 yards of stone walls criss-cross either side of the ridge, and the entire space is wrapped up in blueberry bushes, which the owner believes might be vestiges of the old Tea Lane blueberry farm.

Even before the trees and bushes are in full bloom in Chilmark, the quietude and privacy provided by the dense vegetation and rolling landscape are unmatched.

“When you can’t see something in the winter, you know you’re not going to be able to see it in the summertime when all the green comes out,” the owner said. Additionally, the vast expanse of conservation land sits right in the backyard of the property — perfect for long walks and other adventures.

According to the property owner, the space has gone through a number of evolutions. At one point, the greenhouse was being used as an indoor sculpture garden. Now, part of it is used as a nice place to relax and watch some television.

“You could probably even put a basketball hoop in here,” the owner laughed. “The opportunities here for anyone with an imagination, and how someone might manifest their visions within this space are really boundless.”

Is there an Island home that you’re curious about? Email We’ll see if we can make the connection and take a peek.