Florida’s Premier Acreage & Waterfront Real Estate Brokerage
Proudly rooted in North Central Florida heritage.
About
Osceola Properties
At Osceola Properties, we bring generations of Florida land knowledge to every transaction. Led by Seth Chester, Broker/Owner, we specialize in acreage, farms, and waterfront real estate across the region.
Our roots run deep in the region’s landscapes and waterways, giving us a unique perspective on property value, conservation, and opportunity. Whether you’re buying or selling, our goal is to connect you with land that fits your vision 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 Services: We offer a full suite of real estate services, including land, residential, farm, and commercial property sales. With the SFR® designation and extensive experience working alongside liquidators and court-appointed receivers to sell seized assets, we are equipped to handle complex transactions involving foreclosures, bankruptcies, probate proceedings, and other court-mandated sales.
Our expertise also extends to multi-family consulting, land-use evaluation, and providing professional Broker Price Opinions, giving you the insight and guidance necessary to make well-informed decisions.
Why Choose
Osceola Properties
With six generations of Florida land expertise, Osceola Properties offers unmatched insight into farms, acreage, and waterfront properties. Our deep local roots and strong connections ensure a smooth, trusted experience whether you’re buying or selling.
- Unparalleled Experience – Our team showcases niche knowledge gathered from years of experience in the construction and sales industry. We know what we are selling and know how to overcome common hurdles in transactions.
- Expert in Several Property Classes – Residential, waterfront, acreage, and commercial.
- Certified Appraiser Reviewed Valuations – All of our valuations completed in-house are reviewed by Certified Appraisers, while they may not be used as an appraisal they provide you with one of the most accurate BPO's in the industry.
Testimonials
"Seth made the selling process effortless. From the first conversation, he explained everything clearly and kept us updated at every step. His knowledge of Florida land is unmatched, and thanks to his connections, he found the right buyer for our property faster than we expected."
— Mark D.
"We had been searching for the right acreage for months with no luck. Once we connected with Osceola Properties, Seth really listened to what we wanted and guided us to the perfect spot. His expertise gave us confidence, and his professionalism made the entire experience enjoyable. Highly recommend!"
— Linda P.
"Professional, honest, and deeply connected to the local market — that’s how I would describe Seth. He worked tirelessly to help us secure our dream waterfront property and handled all the details we hadn’t even thought of. We couldn’t be happier with the outcome."
— James R.
"From start to finish, the Osceola Properties team made buying land smooth and stress-free. Seth walked us through every step, answered our questions with patience, and made sure everything was in order. We felt supported the whole way through and couldn’t have asked for better service."
— Emily S.
