The town of Olive has a blunt response to homeowners worried that the third reassessment in five years means higher taxes are coming this fall: It’s just wrong.
“These are never done with that intention,” Olive Town Assessor Diana Carchidi said in an interview. “It’s really about how it’s apportioned—making sure that everybody is paying their fair share rather than paying somebody else’s share.”
The grumbling started months ago, as chatter erupted on the social media site Nextdoor about a series of assessments that boosted valuations by as much as $300,000, even for properties that hadn’t been significantly improved. More than a dozen residents posted on the site to complain, and some speculated that the town was trying to push out longtime homeowners.
Take Theresa Widmann, who moved to Olive from Stone Ridge with her husband in 2016 and bought a home for about $300,000. Six years later, the home was assessed at $500,000. Now it’s valued at more than $800,000.
“It’s been a struggle,” she said. “In 2023, I had a child, and it wasn’t part of our plan to have to figure out how to get new income.”
Rising prices reflect a surge across the Hudson Valley, particularly after the pandemic sparked a frenzy of upstate purchases by New York City residents searching for open spaces and room to work from home. Ulster County home prices jumped almost 80% between 2019 and 2025—from $248,000 to $445,000—according to data from the county and from Rocket Companies, a fintech platform that operates a suite of major homeownership and personal finance brands.
In Olive, where homes sell for a median price of $480,000, residents have long been accustomed to low taxes, partly because New York City is the town’s single biggest taxpayer, reflecting the land it owns as a result of building the Ashokan Reservoir at the turn of the last century. Large parts of the town were flooded as part of the construction project, engulfing entire communities.
New York City paid almost $2 million in taxes to the town in 2023 and $8 million to the Onteora School District, which includes Olive, Woodstock and parts of Hurley and Marbletown.
A history of relatively low taxes may explain the online furor earlier this year as neighbors compared sizable increases in their valuations. It has a certain logic: People who own expensive homes, spend money on pricey renovations or replace modest homes with much bigger ones should naturally pay more in property taxes, and in-turn higher taxes fund more town spending on essential services.
Yet that isn’t how it plays out.
“That’s a very big misconception,” Carchidi said. “Let’s say you had a 20% increase in assessment. You are not going to have, necessarily, a 20% increase in taxes.”
In fact, towns and school districts each year settle on a budget funded by a tax levy. Those budgets do tend to increase over time, which will increase property taxes. Property assessments, meantime, aim to fairly distribute the existing tax burden on residents, regardless of the size of the budget.
If real estate values rise for the town as a whole while the total tax levy doesn’t change, only those whose assessments rise more than Olive’s average home price face higher property taxes. Others could expect a decrease.
“Everybody sees that and thinks that the percentage that their assessments are going up is how much their tax bill is going up,” Carchidi said. “That’s not the way that works.”
Residents do have the right to appeal their assessments. That’s how Widmann managed to knock her home’s valuation down by $100,000, using comparable valuations to persuade Carchidi that her home should carry a lower assessment.
Still, a strong housing market means homeowners stand to reap a profit should they choose to sell. Yet moving can be expensive and unsettling—and there’s always the reality that real estate prices rarely fall.
“Part of me is like, if it’s supposed to be worth so much, then let’s sell,” Widmann said. “But it’s hard to move.”
Kyle Bredberg is a contributing reporter. Send correspondence to reporting@theoverlooknews.com.
