TX REALTOR® #776486
Jonathan is a local Wimberley resident that has his pulse on the hill country real estate market. Having personally purchased multiple short-term rental properties in the hill country exp, his experience affords him the education of knowing what it takes to land that unique property that many envision. Whether finding that 2nd home, primary home, or investment property, he can guide you through the entire process. Buying or selling can be confusing and overwhelming on your own. Jonathan prides himself in making your experience as smooth and enjoyable as possible.
Jonathan lives in Wimberley, Texas with his wife Brittany Bailey (Realtor). They have 3 kids (Carson, Caroline, and Claire) along with their 2 dogs, Baxter and Cici. Jonathan also operates 2 short-term rental properties in Wimberley. He enjoys hiking at blue hole, swimming/fishing/kayaking at their Blanco river front property. They love any outdoor activities and utilize their off time to take advantage of the hill country and all that Wimberley has to offer.
Testimonials
Working with Jonathan Bailey at Hills of Texas Sky Realty has been one of the best experiences we’ve ever had. From day one, Jonathan showed an unmatched level of punctuality, knowledge, and genuine care for us as clients. He wasn’t just trying to sell us a piece of property—he took the time to understand exactly what we were looking for and guided us through every step with honesty and patience.
His attention to detail and understanding of the market made the entire process feel seamless and stress-free. What really stood out was how he treated us like family, always putting our best interests first. It’s rare to find someone so passionate about their work and so committed to their clients’ happiness.
If you’re looking for a Realtor who will truly go the extra mile, who will be in your corner from start to finish, Jonathan is the one you want on your side. We are beyond grateful for everything he did for us and can’t recommend him highly enough.
– Evan S.
I am pleased to write this character reference for Jonathan. I’ve known Jonathan for over 10 years, and in that time I was able to watch him grow into a confident, polite, and outgoing individual. He’s demonstrated a high level of dedication and enthusiasm on various occasions, both in terms of integrity and work ethic. Jonathan is also an extremely goal driven person, who has always shown an ability to meet deadlines promptly, submitting work that frequently exceeds expectations. Therefore, I am confident that he will be able to show the same level of commitment and professionalism in his work.
– DeAnthony R.
I am writing this letter to recommend Jonathan Bailey. Jonathan was a key sales rep at our company for more than two years, and in that short timespan he had perhaps the best sales record of anyone on the team. He has demonstrated integrity and dedication beyond expectation. He was able to forge some excellent customer relationships and facilitate sales that other of our salesman simply couldn’t. Jonathan was one of the hardest workers, doing whatever it took to get the best, and he almost always accomplished it.
Sales requires a natural skill in dealing with people and knowing the right thing to say, and this was perhaps where Jonathan set himself apart the most. Customers simply loved him and he was able to connect with them in a meaningful way earning their trust and loyalty. His skills, and the results he achieved, make sure that he comes with the highest recommendation.
– Wade B.
I have had the pleasure of knowing Jonathan for the last decade. Jonathan has been volunteering as assistant baseball coach for the past two years. He is excellent with the young players. He navigates their development, both in terms of practical skills and in terms of character, with the maturity of someone twice his age. He is fair, but also has high standards. He is the first to commend one of the boys for a job well done, and also the first to reprimand poor behavior. Teasing among our players has stopped since they have had Jonathan as a role model and leader.
Working with youth sports has also given Jonathan the opportunity to develop customer service skills. He has truly excelled. One parent arrived on the field scathing over his child being sat on the bench for the majority of the game, and left ten minutes later apologizing. Jonathan has a way with people and this shines through in all that he does.
Jonathan is an asset to any company and to any team. I highly recommend Jonathan for any help with real estate or any professional help you may require.
– Glen R.
