About Us

A Family-Run Team Built on Relationships, Not Transactions

Flip Flop Real Estate Management & Sales is a family-owned company founded by Casey, Julie, and Aurora Caldwell — proudly serving property owners and residents in Clermont, Lake County, Orlando, and surrounding Central and Northern Florida communities.

The Flip Flop Real Estate team — Casey, Julie, and Aurora Caldwell
The Caldwell family — Casey, Julie, and Aurora

After years of working in real estate, property management, and customer service, Casey, Julie, and Aurora Caldwell saw an opportunity to create something different — a company where relationships matter more than transactions and where every client is treated with honesty, respect, and genuine care.

As a family, the Caldwells understand that a home is much more than a piece of real estate. It's where families grow, memories are made, and futures are built. For property owners, it's also a significant investment that deserves to be protected by people who care about it as much as they do.

That philosophy is the foundation of Flip Flop. Every decision is guided by integrity, open communication, and a commitment to doing what's right. Whether helping a first-time landlord lease a home, managing an expanding investment portfolio, or assisting residents throughout their tenancy, the goal is always the same — to provide exceptional service while building relationships that last.

Being locally owned and family operated means every phone call, every maintenance request, every showing, and every owner conversation matters. There are no call centers, no passing clients from one department to another, and no treating people like account numbers. When you work with Flip Flop, you're working with a family that is invested in your success and committed to earning your trust every single day.

At Flip Flop Real Estate Management & Sales, property management isn't just a business — it's a promise. A promise to communicate openly, act with integrity, protect every investment, and provide the kind of service that gives owners and residents confidence and peace of mind.

Service So Good It Will Knock Your Socks Off® isn't just our slogan — it's the standard we hold ourselves to every day.

Our Promise

What we commit to, every day

Hands-on, not hands-off

Our family personally tours properties, meets residents, and stays close to every home we manage. You won't be a file number here.

Neighbors first

We live and work in the same communities we manage. That changes how quickly we respond and how much we care about the result.

Straight answers

Transparent pricing, honest reporting, and no inflated repair markups. If something costs more than expected, you'll hear it from us first.

Brokerage Information

Flip Flop Real Estate Management & Sales, LLC is a Florida licensed real estate brokerage.

Brokerage License No. BK3565891

Casey Rhea Caldwell — Florida Licensed Real Estate Broker

Go Local. Choose Flip Flop.

Go Local. Choose Flip Flop.

We'd love to hear about your property and show you what hands-on, family-run management actually looks like.

Service So Good It Will Knock Your Socks Off®