We believe money should serve your life — not control it. Our approach combines education and guidance, enabling you to build confidence, protect your family, and live with purpose.
We teach a system that’s simple, duplicatable, and deeply effective — focused on protecting income, growing wealth, and creating freedom that lasts generations.
You don’t need to have it all figured out — just the courage to start. We’re here to walk beside you, teach you, and celebrate every step forward. Because no family should be left behind.
Turn your property into a high-performing, beautifully managed short-term rental — without the overwhelm.
At Caldwell Heritage, we treat every home like it’s part of our own family legacy, handling everything from design to guest communication with care, precision, and purpose.
Once you add us as a co-host we jump right in and start your listing from scratch!
We use quality photographers to get your home in its best light.
Proactively and positively interact with all guests, verified or potential from start to finish.
We schedule all cleanings for immediate turnaround and ensure all supplies and linens are always available for guests.
Full trash bins are not very appealing, we make sure they are ready for pick up on their trash days.
The pricing software we use prices your listing competitively with the local market and similar listings every 24 hours.
Whether the yard needs weed removal, the air conditioner needs to be turned on, or the fence fell over, we will get it fixed as soon as possible!
Your home is special, and it has quirks, which guests need to know how to navigate. It is also important to share recommendations for the area with guests.
Email us for a complete list!
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It all began on a family road trip when Aaron suddenly blurted out,
“Honey! We’re going to start real estate!”
That spontaneous moment sparked a new chapter for our family. What started as a single fix-and-flip — a little house we transformed into an Airbnb called Sunny Sawmill — became the foundation of something much bigger.
Five years
It all began on a family road trip when Aaron suddenly blurted out,
“Honey! We’re going to start real estate!”
That spontaneous moment sparked a new chapter for our family. What started as a single fix-and-flip — a little house we transformed into an Airbnb called Sunny Sawmill — became the foundation of something much bigger.
Five years later, that spark has grown into Caldwell Heritage, a family-led business built on faith, freedom, and purpose. We’ve expanded from hosting beautiful homes to helping families design beautiful futures — through financial education, entrepreneurship, and leadership development.
Our mission is simple: to help others take ownership of their lives — to become their own boss, build lasting wealth, and create a legacy that outlives them.
Because freedom isn’t just about where you live — it’s about how you live, and who you become along the way.