Chester voters to decide on preservation tax

News. Highway superintendent selection process also subject to vote this November.

| 05 Aug 2026 | 08:05

Chester voters will decide on two referendums on the ballot this November.

One is whether to approve a 0.75 percent real estate transfer tax to fund a plan to preserve open space. The other is to change the highway superintendent position from an elected to an appointed position.

During its July 22 meeting, the Chester Town Board approved local laws establishing these referendums, which Chester residents will have the opportunity to vote on during the Nov. 3 election.

Public expresses support for transfer tax

Susannah Devine spoke at the public hearing on the transfer tax. She said it is a “rare and historic opportunity.” She urged the board to vote yes and residents to vote yes in November. She said contrary to fears it would impede the real estate market, the fund actually increases home values in the aggregate.

Ryan Senning expressed his support for transfer tax. He suggested the exemption on the transfer tax increase from $100,000 to $200,000. That number, however, is already in the state law that permitted the town to pursue the transfer tax.

Former planning board chairman Don Serotta noted that the tax adds $3,000 to the average $500,000 home purchase. If the buyer is paying 10 percent down payment he or she likely will pay over $20,000 in costs and fees on top of the $50,000 payment.

The law passed the board 4-0 with Bob Courtenay absent. Councilman Tom Becker voted for the bill, in spite of previously voting against moving the law along because he feels the tax is onerous.

In regular business the town board passed a local law outlining Chester’s preservation plan that names properties to be considered for preservation by the preservation fund, which is funded by the 0.75 percent real estate transfer tax.

The board appointed Aaron Lefkowitz, William Greene, James Donovan, Susannah Devine and Martine DiPasquale to the Conservation Advisory Council.

Chester debates highway superintendent appointment process

The highway superintendent position garnered mixed opinions from the audience. A 28-year veteran of the DPW said he supported the change because it gives the public more oversight of the position through the town board. “It’s a real good move,” he said.

Brian Ross said he researched the past 50 years and did not find any issues or controversies with the position until the 2025 arrest of John Reilly for shooting a Door Dash driver. “When it is up for appointment, the voters are left out,” he said. “The town voters have done a great job.”

Supervisor Brandon Holdridge noted that the election for highway superintendent is rarely a competitive one. He said a special election is being held this year to fill the final year of Reilly’s term and that in 2027, depending on what voters decide, there will either be a new superintendent appointed or elected. The first term of the supervisor elected in 2027 would be three years, because of even year voting rules. If appointed, the term would be two years.

Councilman Giuseppe Cassara said, “The position should always stay elected. The board should strengthen relationship with the superintendent.”

Becker noted that as an elected position it is only a part-time job and as an appointed position it would be 40 hours per week.

The board passed the law to go to referendum 3-1 with Cassara voting against it.

Praise for Knapp’s View maintenance

During public comments Elizabeth Zahn praised the board for the town’s maintenance of Knapp’s View. “The space is being enjoyed by people and wildlife.” She said Audubon hosted a bird viewing at Knapp’s View that was attended by 16 bird watchers. She also said the Sugar Loaf Community Foundation has published a newsletter that will go out four times per year.

Other business

The board voted to move $310,000 that had been earmarked for a single axle truck for the highway department. They moved the money to a reserve account for the future purchase of a tandem dump truck. They will need another $60,000 to buy the dump truck, presumably coming in next year’s budget.

The board voted to approve assessor services with Orange County for 2027-29. The fees for the contract are $250,800, $262,000 and $275,900 for each year.

The board accepted a $15,926 bid from Sealcoat USA for line striping 20.1 miles of road. This was the lowest of three bids.

The board had to decide whether to spend $14,000 or endure a two-day boil water notice for half of the Sugar Loaf water district. They voted to spend the $14,000 on a TAM insertion valve and spare the community the aggravation of a boil water notice. Wood Road would still be subject to a boil water notice, however.