Historic LI homes for sale: Redcoats, secret rooms and underground passageways

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Finding a home with a history isn’t hard on Long Island, but discovering one with an action-packed tale is rarer. Three homes currently on the market have backgrounds worthy of stories told around a campfire.

The former Tyler-Jayne Tavern in Setauket

This house was once an 18th century tavern.
(Credit: Veronique Louis)

The former Tyler-Jayne Tavern in Setauket, not only was the site where four men were killed by British soldiers during the Revolution, but it also may have been frequented by the Culper spy ring, whose missions helped Gen. George Washington gather intelligence during the Revolutionary War. Now a private home, the house is listed for $699,900 in April 2017.

Photo taken around 1920 of a Setauket home
(Credit: Three Village Historical Society)

Built around 1750, the tavern would have been a welcome sight for visitors, with its multiple bedrooms and three fireplaces. Lodgers either could rent a room or, for a lower fee, unfurl their bedroll and hit the floor. Its first proprietor was John Tyler, who ran it during the nation’s dangerous early days. Morris Jayne took over around 1800 and became known for holding “fetes,” or local parties, at the site.

This Setauket house, a former tavern, is listed
(Credit: Coach Realtors)

The tavern, now a private home, was cut in half, moved up a hill and reassembled in 1890.

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This Setauket house, a former tavern, is listed
(Credit: Coach Realtors)

Beverly Tyler, historian for the Three Village Historical Society (and no relation to John Tyler), speculates that since the inn was on the main thoroughfare at the time — North Country Road — it, along with the Roe Tavern in East Setauket, probably was visited by members of the Culper spy ring. There were plenty of auxiliary spies working for the organization on Long Island, making it likely they met at the Setauket tavern, she says. Nothing was ever written down, but of course documenting it would have been dangerous.

This was the main room of the tavern.
(Credit: Veronique Louis)

The Culper spy ring leader, Abraham Woodhull, noted in a secret letter that “there were more than three hundred British soldiers stationed in the area. Written accounts say that among the four men killed in 1777 by British soldiers looking for deserters was an innocent bystander, a young man named Arthur Smith. He and his friend, Zophar Hawkins, were in the tavern when the soldiers arrived. The soldiers shot at them as they fled. They killed Smith, but missed his companion.

This Setauket house, a former tavern, is listed
(Credit: Coach Realtors)

Michael O’Dwyer, a real estate broker who uncovered a walled-off fireplace during his residency there from 1996 to 2006, couldn’t verify there are bullet holes still visible in the tavern. “But there are many holes in the old beams,” he says.

A copy of an old ball ticket that
(Credit: Veronique Louis)

A copy of a ticket to a "military ball" that was held at the former tavern.

Old Brookville house built in 1680

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

Although not as violent, the background of the Old Brookville home for sale also is historically colorful. The wood-shingled Georgian Colonial dates back to 1680, making it one of the oldest homes on the North Shore. It is for sale for $1.25 million.

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This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

Christina Lyon, a commercial artist, bought it in 1983 and has guarded its architectural highlights ever since — things like its wide-plank oak floors and the 18th century high-style Dutch door with its lion’s-head knocker. Interior doors in the house at some point were lengthened by adding a strip of wood at the bottom to accommodate taller, modern-day residents, and they remain that way today.

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

The home’s first owner was Henry Townsend, scion of a well known family who was occasionally jailed for entertaining Quakers, who were persecuted at the time. In the 1920s, it became the summer home of a famed architect and one-time Old Brookville mayor, William Lawrence Bottomley. The architect, known for, among other things, building stately homes in Richmond, Virginia, and the River House co-ops building in Manhattan, renovated the original saltbox structure, adding a wing and an extensive garden, turning it into a manor.

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

A 1926 architectural article about the residence described a secret room hidden by a panel beside the fireplace that led via narrow stairs to a small, windowless chamber between the first and second floors. This supposedly was where previous families hid their valuables to keep them from being taxed, first by Dutch authorities and later the British. The room was eliminated during a renovation.

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

Later, the panel was turned into a bookcase that once included a lever (now an empty hole) that released the door leading to the stairs, Lyon says. The bookcase was nailed shut at some point by another owner.

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

A small, square entrance to a tunnel that led to the woods is still visible in the basement, although the outside part of the tunnel was filled in years ago. This, according to lore, was a quick escape route for runaway slaves staying at the house while traveling along the underground railroad.

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This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

Alexandra Parsons Wolfe, executive director of the Society for the Preservation of Long Island Antiquities, says she is familiar with the residence. “Properties like these are authentic documents that connect us to the past,” she says. “They embody stories that resonate, and that’s what’s important about them.” Leaving will be hard for Lyon, who has lived there for nearly a quarter-century.
“I look out the window at the allée of trees in front and think that a long time ago carriages used to come up to the house along there. I love every bit of it, but it’s a lot to take care of,” she says.

A Searingtown house with 1740s roots

This historic home at 10 Old Homestead Way
(Credit: Coldwell Banker Residential Brokerage)

The third house for sale is in Searingtown. This is a Dutch Colonial reconstructed in 1926 from timbers taken from an abandoned 1740s farmhouse in Queens. It is listed for $1.789 million.

This historic home at 10 Old Homestead Way
(Credit: Coldwell Banker Residential Brokerage)

A description from the Society for the Preservation of Long Island Antiquities in 1994 called the house one of the last remaining estate properties in North Hempstead that “retains the form and character as well as many period details in the interior of an early 18th century farmhouse.”

If this tavern could talk

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

$699,900
LOCATION: 2 Tavern Way, Setauket
LISTING HISTORY: On the market for six weeks
TAXES: $13,585
WHAT’S FOR SALE: This is a four-bedroom, 2.5-bath historic, former tavern with a modernized, eat-in kitchen, a formal dining room and two basements, both with an outside entrance. It sits on 2.3 acres.
BIT OF HISTORY: The house, which predates the Revolutionary War, has beamed ceilings and three oversized fireplaces that were the main source of heat in those times.
LISTING AGENT: Barbara Gray with Coach Realtors at 631-255-1592.

Hidden features revealed over time

This historic home at 1257 Cedar Swamp Rd,
(Credit: Realty Connect USA/Russell Pratt)

$1.25 MILLION
LOCATION: 
1257 Cedar Swamp Rd., Old Brookville
LISTING HISTORY: On the market previously; recently re-listed
TAXES: $37,505
WHAT’S FOR SALE: This is a renovated Georgian Colonial with six bedrooms, two full and two half-baths, a large, modernized eat-in kitchen, formal dining room and a basement. It has a master bedroom and four oversized fireplaces. In back is a detached three-car garage and a two-story, 2,500-square-foot guest cottage. The home sits on 2 acres and shares a bog pond with a neighbor.
BIT OF HISTORY: This is one of the oldest homes on the North Shore. At one time, it had secret doors and passageways. It has wide-plank oak floors, beamed ceilings and a Dutch door at the entrance.
LISTING AGENT: Adam Peters with Realty Connect USA L.I. Inc., 516-330-2880

Built from a 1740s farmhouse

This historic home at 10 Old Homestead Way
(Credit: Coldwell Banker Residential Brokerage)

$1.789 million
LOCATION: 10 Old Homestead Way, Searingtown
LISTING HISTORY: On the market for two weeks
TAXES: $21,375
WHAT’S FOR SALE: This is a Dutch Colonial reconstructed in 1926 from timbers taken from an abandoned 1740s farmhouse in Queens. It has three bedrooms and 3.5 baths with a modern eat-in kitchen, formal dining room and a full, finished basement. Entry is through an antique Dutch door. The home has a great room, music room, living room, master bedroom, office and a walk-up attic. It has three large fireplaces, ceiling beams and wide-plank oak flooring. The basement has a family room with a summer kitchen that opens onto an in-ground heated pool in a parklike setting surrounded by a bamboo forest. It has a two-car detached garage and a front porch.
BIT OF HISTORY: The home was on 11 acres purchased in 1992, says owner Sally Magid. Her husband turned the surrounding land into a subdivision. Previously, the house was used by a doctor as a summer home. “I said to my husband, wouldn’t it be fun to move into the old house? And we did,” she says. A description from the Society for the Preservation of Long Island Antiquities in 1994 called the house one of the last remaining estate properties in North Hempstead that “retains the form and character as well as many period details in the interior of an early 18th century farmhouse.”
LISTING AGENT: Lenora Weiss with Coldwell Banker Residential Real Estate at 646-408-7733

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