Top 10 Most Expensive Home Sales of 2018 in Upstate New York

There’s always something that grabs people’s attention when it comes to top 10 lists, especially when it’s about people paying exorbitant prices for luxury real estate in interesting locations.

As 2018 came to a close, we thought about rounding up the top 10 most expensive residential sales in Upstate New York. The sale prices in this ranking range from $6 million and $33 million, with high-profile buyers and sellers that include the late David Rockefeller, Bill Gates and Rolling Stone magazine co-founder, Jann Wenner.

8 of the 10 properties that made the list are in Westchester County, with the remaining 2 in Dutchess County. We considered every county north of New York City Upstate NY, including Westchester and Rockland.

So, without any further ado, let’s jump straight into the rundown and see what were the most expensive Upstate NY homes of 2018.

Rockefeller Estate Goes for $33M and Becomes #1 Priciest Upstate NY Sale in 2018

The priciest home to change hands last year was an 11,000-square-foot residence in Westchester County, that traded for $33 million. Apart from the mansion, the property also encompasses 75 acres of land. The manor was owned by late David Rockefeller and was sold by Mastrosimone Salvatore on behalf of him to Hudson Pines Land LLC in February 28, 2018. The initial listing price of the estate was $22 million but went on to sell for 50% above its price.

The property is located at 180 Bedford Road in Mount Pleasant, NY, in Pocantico Hills. The Georgian-style main residence was completed in 1938 and boasts a rolling staircase, a large living room and dining room, a library and many more luxurious amenities.

Other structures on the 75-acre property include stables, cattle barns, a carriage house, greenhouses as well as staff quarters.

Trust with Ties to Bill Gates Acquires 124 Acres in Westchester County

Robert Buote, as trustee of Wellington Trust, purchased a $15.8 million home in North Salem, NY on behalf of billionaire Bill Gates. The property, located at 371 – 397 Mills Road, sits on 124 acres. The 3,560-square-foot home was built in 1930 and has 4 bedrooms and 4 bathrooms.

The deal was closed on the 5th of January, making it the second most expensive transaction in Upstate New York in 2018.

Financer Steven Rattner Sells Waterfront Oasis for $12.8M

Beth and Steven Rattner sold their 10,000-square-foot property in July to Grace Church St LLC for $12.8 million. The waterfront property is a 6-bedroom, 6-bathroom home with stunning views of Long Island, featuring both indoor and outdoor pools as well as 1,000 feet of shoreline.

The property is located in Rye in Westchester County, at 408 Grace Church Street. It was the third most expensive sale of last year.

A Property Owned by Rolling Stone Magazine Co-Founder Lands at #5

The Dutchess County mansion previously owned by media mogul Jann Wenner changed hands last year in November for just under $11 million. Wenner, as Teviot Property LLC, sold his Tivoli, NY, mansion to Eversleight LLC.

The 7,979-square-foot 5-bedroom, 4-bathroom mansion was built in 1994.

Take a look at the full top 10 list below:


In order to determine which were the most expensive homes sold in Upstate New York, we looked at all residential transactions closed in 2018, taking into account condo, single- and the two-family homes. All package deals were excluded.

We defined Upstate New York as all areas of New York State, excluding Bronx, Kings, Queens, Richmond, New York, Nassau, and Suffolk counties.

If we were to exclude Westchester and Rockland counties, the ranking would’ve been very different, with Dutchess County dominating the top.

Robert Demeter

Robert Demeter

Robert is a copywriter at CommercialCafe and brings 3+ years of experience in commercial real estate. He previously worked as a copywriter at PropertyShark, as a senior associate editor at Commercial Property Executive and Multi-Housing News, and also wrote monthly market reports at Yardi Matrix.