Most Popular Upstate Listings of 2023: An 18th Century Stone House, a Cobblestone Church

While some of these historic properties outside of Brooklyn are already off the market, you can still soak in some history with tales of cobblestone buildings, a Black-owned guesthouse, and a secret passageway.

The most popular Upstate listing story in 2023 featured a house in Westchester County, while other popular stories focused on properties scattered across the state in Orange, Greene, Ulster, and Ontario counties. Click through to read the full list.

5. An 18th Century Kingston Stone House With a Secret Passageway, Yours for $975K

Filled with enough visual delights to captivate any old house lover, this lovingly restored stone house in Kingston has centuries worth of history within its walls. Built in the 18th century, it was enlarged in the 19th century, and got some mid 20th century updates. The more recent renovation restored original details while adding a dash of additional character, like a secret doorway, along with modern amenities with sympathetic period flair.

The house at 88 Maiden Lane is set between the city’s Stockade and Fair Street Historic Districts and known locally as the Elmendorf Tavern. The original portion of the structure reportedly predates the Revolutionary War by more than a few decades, with local accounts dating it to the 1720s. Its local renown comes from hosting a meeting of the Council of Safety in October of 1777, right before the British burned Kingston, then the capitol of New York State.

4. A Dry Good Merchant’s Second Empire-Style Newburgh Townhouse, Yours for $578K

This Newburgh residence was involved in an interesting court tussle in the 1930s, but before that the Second Empire-style dwelling was the home of a 19th century dry goods merchant and his family. The house has had some more recent renovations, but there is still room for a new owner to wrap up some projects and make some major design decisions, including finding some period-appropriate mantels.

The brick dwelling at 272 Liberty Street is within the architecturally rich East End Historic District. A historic district inventory dates the three bay-wide house to 1870 and a map of that year seems to show the dwelling in place and labelled as owned by S. C. Mills.

3. Former Black-Owned Catskill Guest House in Need of Rescue, Yours for $99K

It requires looking past some caution tape, but for those not daunted by old-house challenges, this Catskill cottage offers the opportunity to bring some life back to a dwelling that spent decades as a Black-owned guest house. In the early 20th century two women made this quirky cottage a welcoming place of respite for Black travelers looking to enjoy the natural beauty of the area.

Operated as the English House from about 1907 to 1938, the house at 145 North Street in Catskill offered boarding year-round with a promise of mountain views and light and airy rooms. The house itself dates to the previous century and its architectural details, which suggest a 19th century builder was gleefully experimenting with craft, add another layer of appealing character to the history-rich house.

2. Rare Cobblestone Church on Market Highlights Unusual Upstate Building Style

Texturally delightful, with rows of cobblestones rippling across the facade, this former church in Ontario County is an intriguing bit of New York architectural history. Between the 1820s and the mid 1860s, builders in the area used what was plentiful — small, rounded stones — to build houses, churches, schools, and other structures.

Completed in 1835 as the Second Baptist Church and turned into a residence in the 1950s, this house at 1070 County Road 27 in Clifton Springs needs more than a bit of TLC on the interior. However, its unusual qualities make it quite the alluring project for the right old-building lover.

1. A Classical Westchester County Manse With a Farming Heritage, Yours for $1.3 Million

It is an impressive sight, with its bold portico and a setting amidst a spacious lawn, but while it has some hints of Greek Revival about it this Westchester County dwelling got an early 20th century renovation that shaped its look and a 1970s restoration that rescued it from decay. Perhaps not surprisingly it also has a fair bit of mythology to go along with some of the recorded history.

In the small hamlet of Goldens Bridge in the town of Lewisboro, the house and just over five acres at 175 Waccabuc Road were once the center of a massive cattle and dairy farm owned by the Brady family. The first Brady, Simeon, settled in the area in the 18th century according to local histories, and it was his son, another Simeon, who built the current house not far away from his father’s original one.

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