Caring Transitions of Winter Park

185 Drennen Rd #333

Orlando, FL 32806

407-543-2273

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Senior Relocation, Estate Sales

5.0 (5 reviews)
Welcome to Caring Transitions of Winter Park Orlando, FL Transforming the way seniors and their families transition through life's stages. We're Local and Ready to Serve You and Your Family As John Lennon once said, “We can’t turn back time”, but We, Carly and Erik Olson can find you a caring solution to any of your moving and relocating needs. We are the local owners of Caring Transitions of Winter Park. Together we have over 30 years of experience in healthcare and in helping people. Our team can handle every detail of your move, including sorting, organizing, decluttering, clean out, move management, estate sale options including an online auction platform called CTBIDS and resettling into your new home. All of our services are customizable, so you and your family can choose the solution that best fits your needs. Caring Transitions can work with anyone facing a transition, but we are trained in specific areas to work with seniors and their families. Our journey to Caring Transition

Ratings & Reviews

Mat K.

Jul 25, 2025

5.00

"Caring Transition did a great job and at a very reasonable price. Moving team was quick, professional and pleasant to work with. Highly recommend."

lianna f.

Mar 29, 2025

5.00

"I’ve working with Caring Transitions for years and have brought them as a partner to every senior living community I have worked in. I cannot recommend their services enough! Always on time, professional and in their consultations really go out of their way to understand the needs of the client, their family and the community on every job they do. I recommend them to every incoming resident!"

Sheilla S.

Mar 24, 2025

5.00

"Carly and her team came to my rescue. My aunt needed to move immediately into an assisted living community. Not only did Carly help me with finding the perfect home, her team packed, moved and resettled her. The team was a delight. We are definitely going to talk to Caring Transitions of Winter park about doing our estate sale. Thanks Guys!"

Laura L.

Mar 12, 2025

5.00

"What an awesome team! They made the move so much easier, as my mother was moving from independent living to assisted living within the same facility. The room size changed, reducing some square footage. Carly and Eric worked together to help us best place the furniture in the new unit. Their efficiency, knowledge and expertise made this a much easier move than I dreamed possible. I did not have to pack anything, Carly, Erik and their team handled everything! Truly a 5 Star team! Thank you Caring transitions!"

LI R.

Mar 8, 2025

5.00

"Caring Transitions – A Company That Truly Cares The name "Caring Transitions" beautifully reflects the exceptional service this company provides. I was searching for a reliable and compassionate team to help transition my 91-year-old mother to a senior living community. After reaching out to several companies, I was fortunate to find Caring Transitions. From the moment I met Erik and Carly, I felt confident I was in the right hands. They offered exactly what we needed—packing, moving, and resettling services. My mother felt at ease placing her trust in this company, and their professionalism and kindness reassured her throughout the entire process. On the morning of the move, a team of energetic and meticulous individuals arrived, ready to work. Their attention to detail and thoughtful care gave my mother confidence that her belongings were safe and well-handled. Within just two days, everything was packed, moved, and unpacked, with every item carefully placed in its new home. The transition was seamless, and the team’s dedication truly lived up to the company’s name. What could have been an incredibly stressful time turned into a smooth, positive experience, thanks to their thoughtful approach. Thank you to the entire Caring Transitions team for your outstanding support and care. You made a significant difference during this important time for my mother and me, her daughter. With heartfelt appreciation, Linda"