Welcome to Caring Transitions of Berkshires & Hudson Valley

Pittsfield, MA

Transforming the way seniors and their families
transition through life's stages.

Join Our Team
Caring Transitions of Berkshires & Hudson Valley - Owner Bio Photo

We're Local and Ready to
Serve You and Your Family

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.

Schedule a no obligation, free consultation with us! Just fill out the form to get started.

Contact Us

Serving the following locations and surrounding areas

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.

A National Company with a Local Touch

We have experience with moving our clients from state to state.
  • 325+ Locations
  • 100,000+ Seniors Served
  • $100,000,000+ in Liquidations
  • 500,000+ Registered Bidders
We serve more than 325 locations across the U.S. and Canada
See All Locations

One Call Does It All.
We'll Match Our Services With Your Needs.

We're your total solution for senior relocation, downsizing, and liquidation needs. We give families peace of mind by creating a customized plan that manages all aspects of a transition.

See what some of our satisfied clients are saying about us

chair and end table

Every Home Has Treasures

Sell or shop on our auction site!

How to Get Started

We provide a total solution for your transition needs by developing a customized plan for your specific situation.

Our Process:

People looking at floor plan

Meet with us for a FREE consultation

We listen, we assess, we understand there are a lot of details to manage.

Two people discussing plans

Let's design the perfect plan together

We handle all the moving parts to meet your objective.

Caring Transitions branded packing tape and box

We do all the work, so you don't have to.

We manage the entire process with no work left for you.

Let's Talk

Schedule a free consultation with us.
Caring Transitions of Berkshires & Hudson Valley - Owner Bio Photo
Kendra MacLeod
Caring Transitions of Berkshires & Hudson Valley

Do you have questions or comments? Contact us by phone or email using the form on this page.

Pittsfield, MA 01201


We look forward to hearing from you!

The Caring Transitions Difference

Experience & Expertise

Over 100,000+ seniors served.

500,000+ registered auction bidders.

We have sold over $1,000,000 in household contents for our clients.

Certified & Trusted Specialists

Every franchise has a Certified Relocation Transition Specialist (CRTS) on staff.

Our employees are background checked, bonded, and insured.

We follow all state certification, licensing, and laws.

Time and Budget Management

You'll receive a timeline for your project.

We customize a plan that is built to meet your needs.

We provide an estimate for each service and the entire project.

Free Consultation - Tap Here! Free Consultation