Welcome to Caring Transitions of Berkshires & Hudson Valley

I’m Kendra MacLeod and I launched Caring Transitions Berkshires and Hudson Valley because I wanted to help seniors and their families bridge the gap between where they are and where they need to be – whether that’s downsizing, moving in with family or into assisted living, or maximizing the value of an estate.
I built my career on helping people. Prior to opening Caring Transitions, I owned a Sylvan Learning Center for almost 20 years. During that time, my staff and I helped more than 10,000 families overcome a wide variety of educational hurdles. Although I was ready to move on, I wasn’t quite ready to retire. That’s when I decided to open Caring Transitions of Berkshires and Hudson Valley. I wanted the opportunity to help people proceed gracefully through what can be a very complicated set of challenges to a simpler, happier living arrangement.
I live right here in Lenox and I understand what you’re going through. I have helped my 96 year-old mother downsize twice. Like me, I’m sure you want to support your parents and make things as comfortable as possible for them, but, there just never seems to be enough time. Caring Transitions is here to take that weight off your shoulders!
In addition to my experience working with families to create solutions for unique challenges, my first career was banking and my last assignment was running a private banking team, so I am very familiar with the financial aspects of retirement and can often refer you to qualified local specialists in those fields. I’m a Certified Relocation and Transitions Specialist and an active volunteer with many local organizations such as St. Paul Episcopal Church in Stockbridge, the Lenox Garden Club, and Berkshire Botanical Garden.