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About Caring Transitions of Berkshires & Hudson Valley

Caring Transitions of Berkshires & Hudson Valley is the Professional Solution for relocation services including downsizing, decluttering, & estate sales for both full and partial liquidations.

Moving is always stressful, and when you combine family politics, a senior who may not be at their best and a sometimes unwelcome relocation, it can be overwhelming. 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 – who lives more than 12 hours away in Canada – 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.

We serve families in Berkshire County, Columbia County, Northwestern Litchfield, Duchess County and the greater Albany area. Contact me today and let’s talk about how Caring Transitions can make your life easier.

Create a Customized Transition Plan That Fits Your Needs!

  • Inventory, Sort, De-clutter, Downsize
  • Estate Move Management – Coordinate Movers, Pack/Unpack
  • Sell Items – Estate Sales, On-line Auction Services
  • Disperse, Donate, Recycle, Discard Items
  • Liquidate Business Assets
  • Floor Planning for New Residence
  • Repair, Paint, Clean, Stage Home for Resale
  • Assist Executors, Attorneys, Trustees, Realtors
  • Decluttering and Organizing
  • Fund Raisers
  • Other Special Projects

Call Us Today to Schedule your FREE In-Home Consultation.

Transition Specialists

Caring Transitions of Berkshires & Hudson Valley employees are held to the highest standards, and maintain ongoing security and education requirements. All of our employees are bonded, insured and thoroughly screened, and each of our offices participates in the comprehensive Certified Relocation Transition Specialist (CRTS) Program. The CRTS credential is a professional mark of ethics and excellence in the field of move management.

Certified Relocation Transition Specialist (CRTS)

Areas Served

Berkshire County, Hudson Valley, Litchfield County, Duchess County, Columbia County, Lenox, Stockbridge, Great Barrington, Lakeville, Salisbury, Kent, Rhinebeck, Millbrook, Glenmont, Delmar, Slingerlands, Colonie, Clifton Park and surrounding areas.

Adapting to a New Lifestyle

As life changes, it may become necessary to leave a familiar home and part with personal belongings in order to downsize and relocate to a smaller home or retirement community. At Caring Transitions of Berkshires & Hudson Valley, we help our clients understand the process, evaluate their options and make informed decisions that suit their best interests. We are committed to making each client’s experience positive by minimizing stress and maximizing results.