Randy Winters Announces Candidacy for Board of Assessors

Randy and his daughters Harper (10), Gracie (9) and Elizabeth (4)

May 4, 2022 Submitted by Randall Winters

My name is Randy Winters and I am proud to announce my candidacy for the Board of Assessors.

For the past 15 years, I have worked extensively in the valuation and analysis of commercial and residential real estate. After completing an undergraduate degree in Finance and an MBA from Boston College, I began working for a commercial real estate law firm handling property tax appeals for commercial property owners and managers in Washington DC. I then transitioned to a startup real estate private lending firm managing a national portfolio of residential property valuations. A little over three years ago I started my own private lending company focusing on residential property values in Massachusetts.

Understanding that the majority of our town’s budget comes from our property taxes, I am ready to put my professional experience to work in this role to ensure that every property is assessed appropriately.

Given the dramatic changes in the real estate landscape over the past couple of years, we have to be sure we have the most qualified individuals on the Board to value our properties fairly and equitably. I believe my background will provide a positive infusion to the Board during this critical evaluation year.

Please note that the goal here is not high assessments or low assessments, but simply FAIR assessments.

I am a firm believer in leveling the playing field relative to property valuations throughout the town. We have to ensure the baseline of applying fair market values to the best of our ability is achieved.

We should all be aware of the significance role our property taxes play in revenue generation for the town. These tax funds support many great programs and resources that make this town great. Beyond the importance of setting the fair market value baseline, we need to do a better job of making our residents aware of the available exemptions. This is what will ultimately build greater diversity and opportunities within our town and allow us to flourish even further.

On May 14, I would be honored to earn your vote for the Board of Assessors.

1 thought on “Randy Winters Announces Candidacy for Board of Assessors”

  1. Great piece Randy. It is thoughtful, informative about your excellent qualifications and gives voters a sense of what your priorities are, and would be, if elected.
    Best of luck,
    Dan Quinn


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