Five Oaks Sport Horses

03/02/2026

🎻 We’d like to introduce FO Calypso! This stunning 🥰 2020 16.2+ big bodied Holsteiner mare comes from a long list of winning jumpers. She is sired by Casall and like her lineage will jump the moon.

CC as we call her has shown in the 1M classes at WEC this winter and schooled 1.15M+ at home. She also has a bit of mileage showing in Europe. She is brave, smart and like most mares wants to please.

CC is a happy mare 😊 on no hormones, can travel alone and easy to work around, she happens to be the barn favorite! -

This young jumper was imported as GP prospect with the right program and time and has been given a great start 🏆.

🤳🏼Please reach out to come try CC located just minutes from WEC and HITS

02/10/2026

Young jumper FO Calypso having a great jump school today

02/09/2026

Offered proudly -

🐴 KT Chief Inspector aka Ollie. Ollie is a 2009 Gelding by Caretino who stands roughly 16.2+ with a big uphill build.

Ollie is a been there and done that type of guy with miles through 1.45/1.50M both in Europe and the USA w an amateur. Ollie is a true unicorn 🦄 looking to teach his text pupil the ropes of jumpers but, he can also dabble in dressage and be your next dance partner 🕺🏼 with his upper level movement! Ollie seeks a step down home and will be your winner in the 1.25 and under, surely able to school higher but, ready to have an easier show life. Ollie is a forward thinking ride so not for those who prefer to kick. His most ideal partner will have a good seat and foundation.

Ollie has an excellent full seller PPE open to all serious inquiries 🩺

Ollie may be tried in Ocala as the farm is just minutes from The World Equestrian Center and HITS shows.

Contact us to schedule a meeting with Ollie 🤳🏼

10/19/2025

https://www.theplaidhorse.com/2025/10/15/rethinking-the-hunter-ring-why-we-need-harder-courses/

Brought to you by The Plaidcast The hunter ring is known for its grace and polish, but veteran trainer Don Stewart believes it’s time to raise the bar—literally and figuratively. With decades of experience training top junior and amateur riders, Stewart has seen firsthand how course design impac...

03/12/2025

Misty sunrise at Five Oaks🥰

03/09/2025

Orlando’s Dream✨♥️

03/07/2025

Our new round pen at Five Oaks is almost ready for our young horses from Germany!! Thank you for the footing and for the fencing!!

02/26/2025

Five Oaks Orlando’s Dream
Our rising star with Josephine Decker!