Semi-annual Billing for Vehicular Personal Property FAQs

As of January 1, 2019 the City of Winchester now offers semi-annual billing for vehicle personal property taxes. This is part of a multi-year transition from the City’s unique billing methods to standard calendar year billing. In this first phase, vehicles newly added to the tax rolls will follow this cycle, but taxpayers may also transition an existing vehicle by request.

What is the new billing cycle?

Under the new process, the tax year corresponds to the calendar year (January to December) with semi-annual payments due April 5 and October 5. Taxpayers also have the option to pay the full bill at once. In considering due dates, the Common Council specifically chose dates which avoid holidays and other key tax payment dates.

How does this compare with the City’s traditional billing?

In the City’s traditional practice in each vehicles has been assigned a billing cycle (1 through 12) based upon the month the vehicle gains taxable status. Vehicles are assessed at the start of the cycle then billed for the full twelve months at the end of the cycle. While this unique anniversary method had merit when implemented, most of the original advantages are no longer relevant. Frequent taxpayer questions and complaints include:

  • Confusion in reading the bill: the vehicle is assessed as of one year ago and the billing period range is unclear
  • Inability to know when to expect a bill
  • Budget challenge in paying a full year’s bill at once
  • For owners of multiple vehicles, lack of a comprehensive listing
  • Annual payment during a challenging budget time, as almost one-third of the City’s annual vehicle tax bills fall during the winter holiday season

What are the advantages of the new billing cycle?

The primary advantages address our taxpayers' main concerns, above:

  • Logical billing cycle: the standard tax year begins January 1. Vehicles are assessed as of this date and taxes are prorated as of this date for any partial year bills
  • Standard billing due dates of April 5 and October 5, with bills mailed approximately 30 days in advance
  • Option to pay in semi-annual installments or in full with first half
  • Full listing of all vehicles for the account

Moreover, once we complete the transition to standard billing, the City will be able to take advantage of modern tax software offering the features our taxpayers expect and we at City Hall need. Because the traditional billing is unique specifically to Winchester, it is incompatible with modern tax software so we have been unable to move beyond the City’s old in-house computer programs.

What is the transition plan?

In this first phase, vehicles will be added to the tax rolls with current calendar year semi-annual billing as purchased or moved into the City. Vehicles which move out of the City or are sold will largely go off the anniversary billing. We will also transition vehicles by owner request.

Why not transition all vehicles at once?

An all-at-once transition would certainly be easier for the City but would be very challenging for our taxpayers for two reasons. First, although our anniversary billing is unusual, we recognize any sudden change is even more difficult when it involves taxes. Second, as the City is transitioning from billing in arrears to current year billing, a sudden switch would require extensive supplemental billing to bring all accounts to the current year. These “catch-up” bills would place an unexpected burden on taxpayers.

By contrast, a gradual transition allows taxpayers an extended period in which to choose when or if they wish to switch to semi-annual billing. In several years when the City completes the final transition to semi-annual billing, our taxpayers will have greater familiarity with the process. By that time the remaining vehicles on anniversary billing will have dropped significantly in both number and value, so the final “catch-up” billing will be greatly reduced.

I’m interested, but when is the best time to switch my vehicle?

Great! Please contact the Commissioner of the Revenue by any of the following:

  • Visit us at Creamery Building, 21 S. Kent Street, Ste. 100
  • Phone us at 540-667-1815, option 4
  • Email us at

We’ll be glad to conduct a review of your vehicle(s), including the billing cycles. If you’d like to switch to semi-annual billing now, we can estimate any catch-up bills along with your first semi-annual bill. For many taxpayers, it may be easiest to switch to semi-annual billing upon receipt of a traditional (anniversary cycle) bill. Upon payment of that bill, you’ll then start with a prorated semi-annual bill. In any case, we’ll be glad to explain the process and look forward to serving you.