Some of these historic properties outside of Brooklyn might already be off the market, but you can still drool over period details and soak in some history with tales of a grand estate, a religious retreat, and a Gothic charmer.

The five most popular Upstate listing stories in 2024 featured properties in Ulster, Rockland, and Dutchess counties. Click through to read the full list.

kingston - second empire house painted yellow surrounded by a lawn
Photo via BHHS Hudson Valley Properties

5. Father Divine’s Piece of Heaven in Ulster County, Yours for $1.5 Million

It offered a bit of heavenly living for the followers of the charismatic Father Divine in the 1930s, and this Kingston property still offers a bucolic bit of acreage with a substantial Second Empire brick manse. There is room for plenty with an additional carriage house, playhouse, and 20th century garage.

At 67 Chapel Street in the Wilbur neighborhood of Kingston, New York, the house on the market was built circa 1870, well before the 1936 purchase by Father Divine’s followers, but it is perhaps that slice of history in the long chain of ownership that is the most attention grabbing.

dining room with mantel and wainscoting painted green
Photo via Houlihan Lawrence

4. Condemned Kingston Cottage Turned Picturesque Charmer, Yours for $475K

For an old house lover with more admiration than patience for renovation, this Kingston cottage looks picture perfect inside and out after a 10-year project to rescue the previously condemned structure. Some remaining details were salvaged amidst a full house overhaul by Kingston designer, blogger, and old-house rehabber Daniel Kanter, resulting in a petite dwelling with an abundance of charm.

Located at 110 Clinton Avenue, the gable-front house on the market is given a date of 1895 in the county records, but historic maps indicate it might be an earlier structure that was once part of the adjacent property at 114 Clinton Avenue.

rockland county - gothic stone cottage exterior
Photo via Corcoran Baer & McIntosh

3. A Fetching Rockland County Gothic Cottage, Yours for $2.495 Million

Even without a stone handily carved with a construction date, the design details of this stone cottage make its era of construction fairly clear. The Gothic-inspired cottage dates to 1865 when villas and cottages with picturesque style were made popular by the work of a group of architects promoting their vision of the American home, including Andrew Jackson Downing, Alexander Jackson Davis, Calvert Vaux, and Frederick Clarke Withers.

There is plenty of picturesque style to admire here with a rough-faced stone exterior, Gothic arched windows ornamented with panels of quatrefoils, bargeboard, quoining, a jerkin-head gable, and decorative chimneys with decorative detailing. The property, which is currently on the market, is in the hamlet of Sparkill at 65 Rockland Road and also includes a gatehouse and barn.

exterior showing one story wing with a tower
Photo via Douglas Elliman

2. Live in Grand Style in Sally Jessy Raphael’s Dutchess County Mansion, Yours for $6.5 Million

Transformed in the early 20th century from a modest country home to a grand Tudor Revival pile, this Dutchess County estate has been home to former talk show host Sally Jessy Raphael since the 1990s. Packed with intricate woodwork and an abundance of rooms, the house is just one of the architecturally intriguing structures on the 25-acre property known as Elmwood Farm.

The estate on the market at 618 Quaker Hill Road in Pawling is, as the road name implies, in the historic settlement of Quaker Hill. The first Quaker meeting house was constructed on the ridge of land around 1764 and still stands. A prosperous community developed, including the Akin family, whose descendants lived on this property until 1997.

sunken living room with wood walls and ceiling and a brick fireplace
Photo via Ellis Sotheby’s International

1. Rockland County Mid-Century Modern House With Atrium, Sunken Living Room, Yours for $625K

You can embrace some woodland style, inside and out, with this mid-century house that is a bit of a time capsule with much of its original character intact. That includes an indoor garden complete with a tree, a sunken living room, and wood-covered walls and ceilings.

The Rockland County house on the market for the first time since 1968 is located at 49 Pomona Road in Suffern, New York, a hamlet of Ramapo. It is nestled in a subdivision developed in the mid 1960s originally known as Pomona Park II.

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