Historic Southold Home That Belonged to Former Slaves Quickly Finds Buyer

Southold, historic house
Once only one room, the house at 150 Baywater Avenue now offers 2,100 square feet of living space. It was listed at $699,000 before a buyer came along.
Courtesy of Douglas Elliman

A Southold fixer-upper steeped in history has attracted multiple buyers shortly after being put on the market for $699,000.

The landmarked house at 150 Baywater Avenue was originally built in 1663 with a single room. In 1809, Daniel Goldsmith, a farmer, gifted the property to the Freeman family, who built a 30-acre farm around it.

The home was listed last month with Paul Loeb of Douglas Elliman, and pulled last week after finding a buyer. Though it is not officially in contract, an offer has been accepted and Behind The Hedges is told there are even several strong backup offers.

“The lot size of 1.05 acres, the nearby bay beach and winery, but mostly the charming style, antiquity and history of the house brought a steady stream of buyers ready to restore it back to its glory,” Loeb told Hedges.

It is also one of the 23 homes in the Town of Southold listed for under $700,000, according to a quick search on Zillow. The median home sales price in Southold, New Suffolk and Peconic has risen to $977,000, according to a recent market report, and $1.175 million in the hamlets further east.

Southold, historic house
An old photo attached to the Southold Towns Tax Accessor’s property cardCourtesy of Douglas Elliman

According to historical research, the Freeman family’s roots in Southold began with Kedar Derby and his wife Chloe who were enslaved and brought to the North Fork in 1780 by William Albertson of Hashamomuck.

Their son Maltby, who was born in 1777, was “‘sent to live’ (probably sold to) Zacheus Goldsmith at ‘a young age,'” wrote Amy Folk, the Town of Southold historian, in a history of the Freeman family.

Though the timing was not clear, Maltby was then sold to Goldsmith’s brother, Daniel Goldsmith. Eventually, Maltby, then 30 saved enough money to buy his freedom and Daniel manumitted him in 1807.

Folk said it was either Maltby or his son Jasper, born in 1809, who changed the family name from Derby to Freeman to reflect their status.

She believes Malby was given the house, on approximately an acre of land, “for his service along the edge of Daniel Godlsmith’s farm by South Harbor Road,” Folk wrote.

Though it had been a single room, it had been enlarged in the early 1800s.

“The Freeman family kept acquiring land until they eventually had a house and 30 acres,” she wrote. “The family made it into what we would consider the middle class.”

Jasper’s son, Albert, a seaman, inherited the farm, later selling it to Robert Overton by 1873. He moved to the Tuckahoe area in Southampton around 1913.

Southold, historic house
Another view of the homeCourtesy of Douglas Elliman

The house now offers 2,100 square feet of living space with three bedrooms and two-and-a-half baths. There are two fireplaces, wide-plank wood floors and plenty of natural light, but the house does need major work.

Though not in a historic district, the house has been landmarked by Southold Town because of its rich history. Any changes to the facade visible from the street falls under the purview of the Historic Preservation Commission.

“Each buyer that inquired was instructed in depth on the property’s current rough condition to prepare them for the showing and discourage those not ready for a project of this scale,” he explained.

Buyers were even encouraged to bring their contractors and architects.

Southold, historic house
A side view of the homeCourtesy of Douglas Elliman

“Each showing took about one hour and I was having five or six showings a day,” Loeb said. “It has been quite an experience and although I’m sure it will not be my largest sale for the year, I’m thankful I was able to be in the center of it and help usher this property to a new owner.”

With an acre of land, a lot can be done on the property. There is an existing shed and an older barn out back that even has a partial basement.

A bay beach is also a short distance away and because it is in the Southold Park District, there are special privileges at several nearby beaches.

It will be fun to watch what the new owners do with the place. We’ll keep you posted on the final sale price, as well.

Email tvecsey@danspapers.com with further comments, questions, or tips. Follow Behind The Hedges on TwitterInstagram and Facebook.