Sponsored: Real Estate Confidential: my personal 2020 favorites (all in Chilmark)


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

I started out selecting homes for this week’s column with a focus on attributes that I would want in any home I were to buy. In my search, I drew a circle around the entire Island and included minimum needs of at least several acres of land, wide views across farm fields or water, and at least one fireplace. I did not consider the price (although in retrospect it might have been a good idea). Fortunately or unfortunately, the results gave me an average price of $7 million and, choosing my four favorites, brought me to homes all in Chilmark. I have often thought Chilmark would be my next move and this search affirmed it.

So, why Chilmark? 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 a picturesque church, as well as a general store featuring a spacious down-home porch where visitors and natives alike gather throughout the day, and my home away from home, The Chilmark Tavern. The visual trademark of Chilmark might well be the stone walls that wind their way through rolling fields and forests, recalling the day when vast expanses of the Island landscape were open land, devoted to sheep farming. 

These houses are definitely not for every Martha’s Vineyard buyer. They range from one of the last of their kind — “summer of  ’42” cottages — on the South Shore to a 70-acre farm on the North Shore complete with a 1700s post and beam barn; from well-maintained antiques to homes already renovated and in move-in condition. Most likely because of cost considerations, none of these very desirable homes will be mine, but they could be yours.

Approaching 277 North Road with its sweeping entrance through an expansive farm field, past a mile of stone walls throughout the property and, past the antique post and beam barn plus 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. Standing on a rise deep into the 70-acre property and taking in the breathtaking views helps you understand why James Cagney loved this place “beyond words” for the freedom and peace it provided. This is an extraordinary situation in which to create your Island estate. 

100 Beach Plum Lane is a compound of shingle-clad seaside cottages with commanding views of Vineyard Sound high on a bluff overlooking the village of Menemsha. The “summer of ’42” main home has been renovated and restored by the current owner and a well-respected local architect, and includes a front porch which provides a front row seat to those magical Menemsha sunsets and the Elizabeth Islands. In addition to the main house is a guest house, a detached one-bedroom cottage, and a cottage currently used as an office and personal gym. 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.

Island treasures like 260 South Road, built in 1688, will not be available forever as those homes are renovated or re-built. The South Shore used to be dotted with weathered Capes and this provides a unique opportunity for a new owner to carry on the proud legacy of this home’s historic past. This waterview estate on six acres has access to Chilmark Pond and an Atlantic Ocean beach on paths through an open field past stone walls. Known as The James Allen House, this home with multiple fireplaces has been lovingly maintained by the same family for generations. A rare find in the heart of Chilmark.


For views that go forever on an ever changing South Shore with the power of Atlantic Ocean waves rolling onto your 425 feet of private beach, nothing compares to 11 Azalea Lane. Perched high on a bluff adjacent to Lucy Vincent Beach, this grand estate is unmatched in location, quality and design.

No luxury has been overlooked in this ultimate beach house, completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. Many Islanders consider this stretch of beach the most beautiful on Martha’s Vineyard.


For the rest of this Real Estate Confidential and house photos, click here.

Click here for more information and a list of my 2020 favorites


For more Real Estate Confidentials click here.