Highland, N.Y.: A Small Neighborhood With a ‘Really feel-Good’ Spirit

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Highland, N.Y.: A Small Community With a ‘Feel-Good’ Spirit

Mr. Smykowski was living in Kingston before he and Ms. Henneberry married, but “Highland is small,” he said, “and it’s easier to get to know the community.”

He is in contract to buy a pair of commercial buildings that he plans to lease. His agent, Elizabeth Decker, who owns Hello Dolly Real Estate, said she has “been doing this for over 40 years in this same area” and has “never seen such demand or such a rise in prices.”

That’s true not just for commercial real estate in Highland: As in other areas outside New York City, residential inventory has been low since the pandemic, and competition for homes fierce.

“The problem is no one wants to leave Highland,” said Dawn Passante, an associate broker with Coldwell Banker Village Green Realty, who moved to Highland from Queens with her parents when she was 12. “There is a saying among the locals that once you live in Highland, you stay in Highland. When Covid hit, houses were selling virtually, without the buyers physically seeing them, and most offers were cash and for above asking price.”

Ms. Passante, who said she sold 30 homes in Highland in 2020 and 2021 combined, compared with 18 in 2018 and 2019, noted that proximity to the Metro-North Railroad in Poughkeepsie and the New York State Thruway has been a strong selling point, although many buyers are still working remotely. Recently, she has been seeing local buyers lose out to buyers from the city with cash.

It’s a far cry from the situation in 1998, when Jessica Stirberg and her wife bought a 2,000-square-foot antique farmhouse for less than $200,000. “We were more interested in New Paltz, but we fell in love with this house,” said Ms. Stirberg, 52, the assistant director for a child-care center. “It’s on the border between New Paltz and Highland, and the town and school taxes are more affordable.”

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