MIDDLETOWN - One of Middletown's historic buildings is up for sale.

The building, at 7793 Main St., was put on the market through Dominion Real Estate a couple of months ago by owners Lisa and Terry Shaffer. The asking price is $269,900.

The Shaffers purchased it in May 2014 after the death of its then-owner Leo Bernstein. It had sat empty since his death in 2008, Lisa Shaffer said.

“I hate to sell it. I love it,” she said.  “Almost 300 years this building has been here. As I looked at deeds, I realized I was a temporary custodian.”

The building was standing while people talked of independence and the Revolutionary War. It was standing as blood was spilled during the Civil War.

Lisa Shaffer said that when she walked into the charming building, her expression was one of amazement.

The Shaffers hosted events and parties in the historic home, including collaborating on some events with the Wayside Inn, which is next door. They also operated an escape room that was managed by their son Jason. 

Lisa Shaffer said she would like to see someone purchase the building who will preserve it and maintain it.  It can be used as a residence or for commercial space since it is zoned for both.

Bernstein had previously said the building was built sometime between 1724-1732. Shaffer said archeologists estimated it had been built sometime around the 1750s to 1760s. That means it is probably one of the oldest buildings in Frederick County and could predate the founding of Frederick County in 1743.

The building, because of past renovations and work, does not qualify to be on the National Registry of Historic Homes, but still retains original components like window sills and floors. There was a major renovation done by Bernstein as recently as 1985, Lisa Shaffer said.

During her time owning the building, she did research trying to put the pieces of its history together.

One of the earlier deeds she has found in her research transfers the property to Ezer Ellis, who purchased the property on July 7, 1801, for 37 pounds from Jost and Elizabeth Kuter.

Lisa Shaffer said the building is commonly referred to as Larrick’s Tavern - not to be confused by the Wayside Inn's bar that is named Larrick's Tavern – but she has found no official confirmation that her building was ever a tavern. 

It was, however, in the Larrick family. It was deeded in 1897 to Augusta Larrick, who later married and became become Augusta Smith.

Lisa Shaffer stressed her research is not complete and she is still trying to fill in the gaps. It is possible she may still find that it was a tavern, which was common in the area at the time.

The most well-documented former owner of the property is Robert Bailey.

Lisa Shaffer found where Bailey documented his life in a book first printed in Richmond in 1822 titled “The Life and Adventures of Robert Bailey. From his Infancy to December 1821.”

He wrote it as a means of making money after he lost everything and spent time in a debtors prison a couple times during his nomadic life. Bailey often traveled around Maryland and in Virginia. He was a  gambler, which he referenced as banking.

“I have won in the course of my banking upwards of half a million of money, all of which is gone from whence it came,” he wrote in his book.

Bailey also was enamored with running for Congress. He liked the finer things, too – nice clothes, pocket watches, property and furniture, and women, including a mistress, Ann Turnbull.

“I bought a situation near Winchester, adjoining Middletown, Frederick County, I finished it off in the nicest manner, built barns and other outhouses, I was at the time entirely clear of debt. I called it Bailey’s retirement and fully intended to end my days at this spot with Mrs. Turnbull,” he wrote.

That was in 1812, Lisa Shaffer said.

But he never retired on the spot with Turnbull, or anyone else. He would, at various times in his life, be forced to sell off or turn over most everything, including his furniture, fine suits and watch, to settle debts.

When he had nothing, he would end up in debtors prison.

Bailey and Turnbull split when he fell in love with 16-year-old Lucy Harris. Despite Turnbull’s pleas to return to her, Bailey refused to leave the girl. Bailey and Harris would have two children.

Bailey again in his life found himself with nothing and in debtors prison while Harris was incarcerated at a local jail until Bailey managed to once again secure his debts.

It was after Bailey and Harris were released he decided to write his autobiography.

Contact Melissa Topey at mtopey@nvdaily.com