Most Popular Upstate Listings of 2025

Most Popular Upstate Listings of 2025

The five most popular Upstate listing stories in 2025 include properties in Columbia, Orange and Westchester counties.

While some of these historic properties may no longer be on the market outside Brooklyn, you can still look at the period details and delve into historical stories about a Greek Revival charmer, a mansion designed by Frederick Clarke Withers, and a Shingle Style home that was home to a presidential candidate.

The five most popular Upstate listing stories in 2025 include properties in Columbia, Orange and Westchester counties.

exterior with stone wall, brick facade
Photo via Four Seasons Sotheby’s

5. Columbia County Federal with charming interior, barn asking $1.9 million

In Columbia County, a sprawling 27-acre landscape stretches from secluded woods to rolling lawns and includes a 19th-century brick main house filled with lovingly cared for period details and enough outbuildings to accommodate guests and a host of hobbies.

With an address at 3 Pratt Road, the house on the market is located in the small hamlet of Malden Bridge, near Kinderhook Creek. Although there were some houses in the area before the 1840s, including this one, the town grew with the establishment of a paper mill. Even with the increase in industry, it was still a modest community in 1860. At that time, New York Gazetteer reported a population of 193 with one church, a sawmill and tannery next to the paper mill.

shingle style house exterior, with tower and wraparound porch
Photo via Houlihan Lawrence

4. George Palliser-designed shingle-style Larchmont Cottage asks $2.695 million

This Shingle-style home dates to the 1890s and was designed by an architect best known for his numerous 19th-century pattern books. In Larchmont, New York, it still retains much of its original character on the outside – and there are some nice historic details on the inside.

At 71 Beach Avenue, the Westchester County market house was built on land purchased from the Larchmont Manor Company. The company was founded in 1872 and divided a former estate into hundreds of pieces building plots that extended to the water’s edge. While cottage construction began in the 1870s, it continued over the next several decades as larger homes were built in the popular architectural styles of the time.

Philmont - Greek Revival House
Photo via Four Seasons Sotheby’s International

3. A picture book-worthy Greek revival in Columbia County, yours for $735,000

The sleek symmetry of the Greek Revival is matched by a warm interior filled with wide, weathered floorboards, rich colors and charming details in this Columbia County home. In Philmont, New York, the house is also not as small as it seems on the facade; The early 19th century house has a spacious space.

At Hoofdstraat 169, the house on the market is located just east of the small village center. Located in the town of Claverack, Philmont is a short distance from some of the region’s natural beauties.

exterior view of the brick house with bargeboard
Photo via Julia B. Fee Sotheby’s International Realty

2. Mansion near Newburgh with architectural pedigree, river views asking $2.275 million

While 19th-century home design volumes urged the adoption of picturesque architectural styles, not every home they inspired is a tiny house. This spacious brick mansion was designed around 1857 by architect Frederick Clarke Withers and although it has been updated over the centuries, it still retains some of its picturesque details.

The house on the market at 560 Grand Avenue is located in Balmville, a hamlet bordering the northern edge of Newburgh. Located along the Hudson River, the property offers water views and views of the Newburgh-Beacon Bridge.

entrance, hall with wooden stairs, stained glass, fireplace
Photo via Redfin

1. A shingle-style home in Yonkers’ historic Park Hill neighborhood, yours for $949,000

It’s not as sprawling as some of the more lavish homes in Yonkers’ Park Hill neighborhood, but this Edwardian home has a quirky charm, well-preserved interior details, and an unexpectedly intriguing social history.

The house on the market at 230 Van Cortlandt Park Avenue was built in the early 20th century as part of the planned suburb.

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