A historic Stockbridge home that wouldn't sell becomes an Airbnb opportunity for owners

STOCKBRIDGE — The big yellow house on Main Street across from the town library has been a private residence for notable local families since it was built in 1845.

Now, after four years of unsuccessful attempts to sell the property, including the carriage house behind the house, the Henderson family, owners since 1975, has shifted gears.

"Everybody said it's way too big, we don't want to take it on," owner Jack Henderson recalled. Even a series of price cuts from $1.35 million to $600,000 (just for the main house) failed to entice a buyer. The town's valuation of the entire property is $1.4 million, according to Principal Assessor Michael Blay.

"To this day, I still can't understand why somebody hasn't snatched it up," Henderson said. "We thought it would go like hotcakes. But at this point, I'm kind of glad it didn't."

That's because Henderson and his business partner Pam Loring decided to renovate and upgrade the interior into a luxurious, multiunit vacation home rental property now being listed on Airbnb.

Loring owned the Morgan House in Lee with her husband, James, from 2008 to 2016 and Pamela Loring Gifts on Main Street from 1994 to 2006. The couple also owned the Devonfield bed-and-breakfast in Lee from 2000 to 2005.

Henderson is a son of the late Robert Henderson and of Aleva Henderson, 91, a resident of Kimball Farms in Lenox, whom he described as a former "grand dame of Stockbridge." He moved back home from Concord after retiring from his Boston-based career as an environmental engineer who designed water treatment plants.

A full-time ski instructor at Jiminy Peak Resort in Hancock, Henderson lives in the carriage house at the rear of the property.

Henderson and Loring were introduced last August by a mutual friend. After Loring took her first walk through the house, she called it "fantastic, unbelievable. This would make such a great Airbnb!"

"I've thought the same thing for the last year and a half," Henderson recalled telling her. But he had been "totally overwhelmed" by the prospect of redecorating and refurnishing the entire house.

Loring explained that an Airbnb rental property is "self-sufficient, people can check themselves in and out. You don't have to be there, it doesn't tie you down as much as a B&B does. I think Airbnb is ascending while B&Bs have plateaued."

So far, Stockbridge has not explored any potential restrictions or regulations on short-term vacation rental homes.

Henderson and Loring downplayed other advantages of the online short-term rental phenomenon, such as non-taxation of guest stays and no regimen of health and safety inspections as required at inns and B&Bs. But Henderson acknowledged that state and possible local taxation are on the way, "and we've figured that in."

Besides, Loring pointed out from personal experience that running an inn or B&B "is like having an infant you can never leave alone, you always worry. With an Airbnb, you don't have those restrictions."

Henderson described his property as "geared toward the short-term rental market, but it's very conceivable that we could rent this out for the summer, or more, to somebody."

The house has now been reconfigured to include six bedrooms in three separate units — the three-bedroom "Henderson Suite," the two-bedroom "Hawthorne" unit and a one-bedroom "Holmes" apartment. Renters can access the home's screened-in outdoor patio in season.

Several sets of weekend guests have already stayed at 39 Main, where the current off-season, introductory rate for a one-bedroom unit with a living room, bathroom and full kitchen was listed on Friday at $125 on Airbnb. Either Henderson or Loring, who lives two miles away, will be available to guests on-site or by text and phone, and so will Tim Miller, a former manager of The Inn at Shaker Mill Farm in Canaan, N.Y., who lives nearby and has been assisting with renovations and painting.

"We want to attract business," Henderson explained, "but we don't want to price ourselves too low because it's a high-end place." Peak-season rates are projected to range from $250 and up for the one-bedroom and around $400 for a two-bedroom unit.

Explaining how she transformed the house into a rental property, Loring pointed out to a visitor that "every single thing you see here was not here, nothing." After joining the project last August, her mission was to acquire furniture, furnishings and other appointments.

"Pam has been just remarkable," Henderson commented. "During the four years the house was on the market, I expected it would sell at any moment, so I didn't do any ongoing maintenance, interior or exterior." But he decided a year ago that he couldn't defer maintenance any longer, such as painting and minor carpentry.

Henderson described the cost of the property's renovation as "a lot of money," but declined to offer specifics.

For furnishings, Loring visited area antique shops, Sisters Used Furniture in the Great Barrington village of Housatonic, Flourish Market, which sells vintage furniture in West Stockbridge and Finders Keepers in Lee, finding "great stuff and putting it all together to make something that looks good in this house. Our big splurge was a dining room table and rug from Paul Rich & Sons in Pittsfield."

An imposing-looking chandelier and comfortable dining room chairs were acquired from Habitat for Humanity ReStore in Pittsfield. "Instead of spending $400 or $600 on a chandelier, we got it for $18," said Loring. Books lining the shelves in the living room came from tag sales.

According to the Stockbridge Historical Society, the house was built by Pilling & Sons for Daniel R. Williams and his family around 1845 to 1850 — he became president of the Housatonic Bank on Main Street from 1865 to 1899, Later, Williams relocated the bank's original front door to his home, where it still stands as the main entrance.

Subsequent owners included Charles E. Hull, a prominent fuel, hay and feed dealer in the early 1900s, and then Eugene T. and Clara M. Rose, who were given a permit by the town in 1948 to operate the Rose Coffee House and inn. In 1960, the house was acquired by Dr. Edward Knight, a general practitioner who used a portion of it as his office, waiting room and X-Ray lab. He also put on a two-bedroom addition at the rear of the house.

By combining a historic setting with contemporary amenities, Henderson is optimistic that the property "overlooking Norman Rockwell's Main Street" will enjoy a prosperous revival as a landing place for visitors seeking to recapture the aura of the past that the town assiduously cultivates.

Clarence Fanto can be reached at cfanto@yahoo.com or 413-637-2551.


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