5 Long Island houses from the 1700s and earlier

The land of the free, and the home of the highest bidder.

From grand restorations to storybook backyard gardens, there are several historical homes on Long Island's East End that are currently on the market, awaiting their next chapter.

Four of these properties were constructed the same century as the founding of the United States, which turns 249 years old on Friday. One of these homes precedes the era. Read on to learn about their storied pasts and original features.

Southampton, 1740

In 1740, a farmhouse was built on the East End of Long Island. In 1944, building inventory records show it was moved from North Main Street to its current location on Post Lane in Southampton.

Now, it's been lovingly maintained and converted into a home, on the market for nearly $7 million. The house is listed by Harald Grant, of Sotheby's International Realty. Sitting on a 0.41-acre lot, the property is in the Southampton Union Free School District.

"I've gone to great lengths to try to keep as much character as possible," said Patricia Ross, the current owner.

For example, Ross, a landscape designer, discovered some of the plantings around the house had caused the shingles to darken in color, so she figured out a way to revitalize them.

"I did not want to do any kind of power washing," she said, "because I wanted to keep the shingles intact, along with the old nails. So we had the house hand-bleached, and it was lovely because we were able to get all the mold and mildew off the house and bring the shingles back to a nice gray, without damaging anything."

Ross has lived here for two years, and the owners before her had been there for 40 years, she said. The house contains four bedrooms and three bathrooms, totaling 3,000 square feet. There is a barn (which can be used as a living space) with a second-story loft, along with a cabana by the in-ground pool.

Inside, original beams and plaster have been maintained, and there are new additions, such as a revamped kitchen and primary suite.

The "sense of history" is what first attracted Ross to this area. She once lived in Chappaqua, in a home that used to be an old schoolhouse on a big estate.

"I'm drawn to older houses," she said.

1790s, Sag Harbor

Located in the Sag Harbor Historic District on Main Street, this vintage gem is on the market for nearly $18 million. The taxes are $51,000.

Known as The Hannibal French House, it was built in the 1790s and remodeled around 1860. During that time, the house was transformed into the Italianate architectural style seen today, according to documents from the National Register of Historic Places. This design is attributed to Minard Lafever, who also built churches throughout the early 19th century.

The house boasts seven bedrooms and six bathrooms, spanning 6,500 square feet. It sits on a 0.59-acre lot.

"It's been restored," said Susan Breitenbach, of The Corcoran Group. She is co-listing the property with Cutter Koster. "This was not a gut renovation by any means."

Much of the intricate detailing baked into the interior is original, she said.

"The moldings are beautiful, the woodworking is incredible," Breitenbach said. "It's just a blast from the past, which is really special."

Notable features include a heated gunite pool, several sparkling chandeliers and 10 wood-burning fireplaces, with one in almost every bedroom. The property is in the Sag Harbor Union Free School District.

The home is "a merge of grandeur and modern comforts," the agent said.

"The architecture and the bones of it are just amazing," Breitenbach said. "I sell a lot of real estate and I've been doing this for a very long time, and it's just very exciting to have a house like this."

1783, Southold

This Southold home was built in 1783, with an extension added in 2007, said listing agent Eugene Rindfuss, of Coldwell Banker Reliable Real Estate.

"They kept the same flow as the original house," he said. "They did the same type of wood floors, and made it really nice."

The three-bedroom, three-bathroom Colonial is on the market for $895,000. The taxes are $6,656. The house is located on Route 25, which was first known as King's Highway, said Rindfuss.

Additions to the property include an ensuite bedroom, another living area, a dining room and an outdoor porch. This section also has central air conditioning and cathedral ceilings, Rindfuss said.

This is one of Southold's oldest homes — building inventory records show it was in the family of Richard and Thomas Terry. The brothers first settled in Southold after sailing there from England in 1635, and their descendants later lived throughout the area, along with Cutchogue and Orient, per historical records.

The 2,100-square-foot house on a ½-acre lot was deemed a landmark in the town. The property is in the Southold Union Free School District.

"For historical homes, it's a special type of person you're targeting," Rindfuss said. "Usually artsy, or really into history. It's a harder audience to get."

The house boasts three fireplaces, two of which are original. The newer fireplace features a hand-carved mantle that came from a Victorian mansion in the Hudson Valley, Rindfuss said. The soaking tub upstairs is also likely an original feature.

The seller has owned the home for 25 years and has restored it over that time, making sure to maintain its charm.

"She had the wood floors reinforced, and she reinforced the locust posts that support the house with metal posts," Rindfuss said. "She's done a lot of work that you can't see."

Additionally, there is a 400-square-foot cottage on site that needs some TLC, but "it is very cute," Rindfuss said. It has a small bathroom with a shower, kitchen, dining area, one bedroom and a living room, along with a private backyard.

As for the main house, "it's really got a lot of character just the way it is," the agent said.

1653, Southold

This is known as the Richard Terry House — yes, the same Terry family with another house for sale, on the same street in Southold. The home is listed for $799,000, with taxes of $7,681. It was built in 1653.

Plenty of additions have been made through the years, including the porches and the dormer, according to building inventory records. These records also state that Richard Terry was a lieutenant and the second town recorder of Southold during its early settlement.

The house features two bedrooms and two bathrooms, sitting on a ¼-acre lot. The property is in the Southold Union Free School District.

"The previous owner, not the current owner, was an architect," said listing agent Mariah Mills, of Daniel Gale Sotheby's International Realty. "And he was the one who really restored the home and made it what it is now."

One of the major touches done by that owner was a spacious covered deck surrounded by tall beams, providing a "huge ceiling height," Mills said. "That's another jaw-dropping moment for buyers when they come in."

Some original features include a two-sided wood-burning fireplace (it faces both the dining room and living room), a kitchen door and the ceilings.

"The ceiling itself is all the original wood," Mills said. "You can even see the nails kind of popping through the ceiling, which are the old, original nails, which are really cool to see."

This part of Southold is known for its antique collection of homes, and as time went on, neighborhoods were formed around this area, Mills said.

"This is the main road on the North Fork," she said. "So you will find a lot of older, 1600s homes along this strip."

There is also a guest house and a meditation tower on site, both of which are not original to the property.

"The meditation tower is essentially a shed down below, and you climb up an exterior staircase and go into a room to meditate if you wish, or drink coffee," Mills said.

The backyard includes a "storybook" garden with winding pathways throughout, she said.

"You just feel like it has so many stories inside," Mills said. "It's a true North Fork classic home."

1760, Remsenburg

Built around 1760, this house had a past life as a barn, said listing agent Ashley Farrell, of The Corcoran Group. It was part of another property on South Country Road and moved to the lot behind it, which is its current location on Pheasant Lane, Farrell said.

The house that the converted barn used to belong to is "arguably the oldest house in Remsenburg," she noted.

Her listing was refashioned into a residence in the 1970s, she said. Now, it is a four-bedroom, three-bathroom home, on the market for nearly $2.2 million. The taxes are $8,538.

Totaling 2,525 square feet, the house sits on a 0.92-acre lot. The property is in the Remsenburg-Speonk Union Free School District.

A builder restored the home around 2019, Farrell said, and during that time he redid the exterior with cedar shingle siding.

"He kept the footprint, he kept a lot of the original integrity, but he did change things that needed to be changed, whether for modernization or just things that weren't salvageable," she said.

For example, the front entrance porch was added and several exterior doors were removed.

"When you think about a barn, you have a lot of places where animals and livestock are going in," Farrell said. "So he made it much more of a home than a barn."

There is also a second-level deck that used to have two wooden beams as the railing, Farrell said, and that has since been updated and secured.

The house and barn belonged to the Phillips-Dayton family, according to the Southampton town website, and was in their family for 200 years, Farrell added. Some of its modern amenities include central air conditioning, radiant heat flooring, an in-ground pool, hot tub, outdoor shower and fire pit. "You can feel both eras," Farrell said.

And the one-of-a-kind features don't stop with the 1700s detailing: The pool house in the backyard is a converted shipping container with a roll-up garage door.

"This one, you really have to see in person to see how special it is," Farrell said.