ABOUT US — PERSONAL, MEANINGFUL, AND SERVICE-FOCUSED
At Caring Transitions of Chesapeake and Virginia Beach West, our purpose is simple: serve the community that helped raise my family, and be a force for good — especially for seniors and the families who love them.
I started this company because I saw too many businesses taking advantage of people during vulnerable moments.
Seniors deserve better.
Families deserve honesty, compassion, and real support.
This company exists to make sure they receive it.
Meet Todd Osborne
Owner, Caring Transitions of Chesapeake & Virginia Beach West
After serving in the military and leading large teams in high-pressure environments, Todd built this business on the same principles that guided him throughout his life:
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Service
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Integrity
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Fairness
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Respect
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Compassion
Why I Started This Company
“I wanted to give back to the community that helped raise my family.
This region has given us so much, and I wanted to bring something positive — something protective — to the people here, especially seniors.”
Todd saw the reality: many companies prey on seniors, rushing them, overcharging them, or treating them as transactions instead of people.
He knew he could do better.
He knew he could build a company that stood up for them.
A company families could trust.
Our Customer Service Promise
We lead with heart — always.
Great customer service isn’t something we “offer.”
It’s who we are.
- We put seniors and families first
- Your best interests always guide our decisions.
- We communicate clearly and kindly
- You’ll always know what’s happening, what’s next, and what your options are.
- We create calm in overwhelming situations
- Whether it’s a large estate or a small decluttering project, we help you breathe easier.
- We deliver honesty — every time
- No hidden fees.
- No pressure.
- No judgment.
- Just real support.
- We treat every project with care — big or small
We gladly take on:
Every family deserves help, not just the “big jobs.”
How We Treat Our Employees
Todd built this company with a simple belief:
Happy team = better customer experience.
We provide:
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A safe, respectful workplace
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A fun environment where people enjoy helping others
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Fair compensation
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Training and support to build skills
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A team culture built on empathy and integrity
Our employees take pride in what they do — and that pride shows in how they treat your home, your items, and your family.
Why Families Trust Us
Families choose us because:
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We protect seniors from being taken advantage of
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We believe in doing the right thing
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We offer truth, not sales pressure
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We take care of belongings like they’re our own
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We understand the emotional weight of transitions
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We serve with compassion — not judgment
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We earn trust through actions, not promises
When you work with us, you’re not hiring a company.
You’re partnering with people who care.
Our Commitment to This Community
We are proud to serve:
This community raised our children, supported our growth, and shaped who we are.
We’re here to give that back — one family at a time.
Let’s Talk About Your Needs
Every transition has a story.
Every story deserves respect.
We offer free consultations because understanding your needs is the first step to helping you.
757-320-2918
Contact Us
For a full list of areas that we serve, click here
For a full list of services, click here