Your Trusted Land Selling Partner
Rooted in generations of Florida land knowledge, Osceola Properties is proud to serve our region with honesty, expertise, and dedication. Led by Broker/Owner Seth Chester, our mission is to connect people with land that reflects their goals while honoring the natural beauty and heritage of the region.
About
Seth Chester — Broker/Owner
A sixth-generation Floridian, Seth offers deep-rooted insight into the state’s land and waterways. Specializing in farms, large tracts, and waterfront properties, he has guided countless clients through buying and selling with confidence. His portfolio includes multi-million-dollar transactions, with properties spanning more than 400± acres, showcasing his ability to handle deals of any scale. With a multitude of strong community connections across Florida and Georgia, Seth closes just as many off-market transactions as he does on the open market each year, earning the trust of landowners and buyers alike.
- Experience: Seth Chester is a highly accomplished real estate broker and investor, licensed in both Florida and Georgia, with a proven track record of selling large acreage, waterfront, and income-producing properties. A sixth-generation Floridian, he has been immersed in the land and aquatic management industry since childhood, gaining lifelong, hands-on experience with Florida’s diverse terrain and natural resources. Over the years, Seth has worked closely with contractors, engineers, foresters, and municipal agencies—expertise that has sharpened his understanding of land use, infrastructure, and development. Beyond brokerage, he actively owns and manages rental units, participates in residential and land flips, and brings firsthand investment knowledge to every transaction. His credibility and professionalism are further underscored by being entrusted by forensic liquidators and the Federal Trade Commission to oversee the liquidation of seized real estate assets, a responsibility that reflects his reputation in complex, high-stakes matters.
- Quote from Seth: Land isn’t just property — it’s legacy, opportunity, and future.
Our mission
Who We Are
We’re more than a real estate brokerage — at Osceola Properties, we understand the stories, traditions, and opportunities tied to the land we sell. Our mission is to connect people with the right land while preserving the heritage and natural beauty of our region. We are dedicated to presenting your land in the most prized way possible, and we proudly donate a portion of proceeds each year to nonprofit organizations such as the NWTF, CCA, and other conservation and community partners.
Our mission: We’re more than a real estate brokerage — at Osceola Properties, we understand the stories, traditions, and opportunities tied to the land we sell. Our mission is to connect people with the right land while preserving the heritage and natural beauty of our region. We are dedicated to presenting your land in the most prized way possible, and we proudly donate a portion of proceeds each year to nonprofit organizations such as the NWTF, CCA, and other conservation and community partners.
Testimonials
"Seth knocked it out of the park for my husband and myself. He was always available, very knowledgeable, and walked us through every step of the way in our selling process. If we had any questions he would answer them promptly in a way that we understood and he made the selling process super easy for us. We could not be happier with how smoothly everything went through the selling process. We definitely recommend Seth to friends and family who are looking to buy or sell, whether it’s land, a farm, or a home."
— Brenda L.
"I could not be more impressed with Seth as a real estate agent. He is incredibly knowledgeable about the area, respectful to clients and he goes above and beyond to complete the deal to the satisfaction of all parties. He is a pleasure to work with and I hope to work with him again in the future!"
— Jennifer B.
"Seth is such a conscientious realtor. He knows the area from life experience which makes your house shopping a treat. He goes above and beyond to lead you to the best decision on homes and land."
— Sheila H.
"Seth provided an excellent experience in the purchase of our home. He is very knowledgeable and professional. He was also very proactive throughout the entire process and answered any questions that came about. I would highly recommend him to anyone looking to buy or sell."
— Garrett R.