Former Major League Baseball All-Star Matt Holliday and his family have listed their extensive estate in Stillwater, Oklahoma, for sale as they transition to a new chapter of life in Arizona. The property, spanning 136 acres and featuring numerous custom amenities, represents a rare combination of luxury and sports-centric design tailored to the Hollidays’ athletic lifestyle.
Holliday, a seven-time All-Star, purchased the Oklahoma land in 2018 for $3 million and began construction on the home in 2020, moving in two years later. The property includes a full baseball diamond, batting cages, a custom $2 million pool designed by HGTV personality Kelly Caviness, a pickleball court, jogging, and ATV trails. Originally listed at $12 million in February, the home is currently offered for $8.95 million, covering 20 acres that encompass the primary residence and outdoor amenities. The remaining land is slated for separate sale, potentially to developers if not purchased in conjunction with the main parcel.
Holliday and his wife, Leslee, have embraced a nomadic lifestyle dictated by the professional demands of baseball. Their two sons, Jackson and Ethan, both professional baseball players themselves, have left the family home, with Jackson completing his third major league season and Ethan projected as a top draft pick for the Colorado Rockies in 2025. The couple relocated to Arizona in February, drawn by the region’s more consistent climate and outdoor recreational opportunities.
A native of Stillwater, Holliday spent a substantial portion of his career with the St. Louis Cardinals after debuting with the Colorado Rockies in 2004. He retired in 2018 after stints with the New York Yankees and a return to Colorado. Throughout his career, Holliday was known not only for his on-field achievements, including four Silver Slugger awards and a National League Championship Series MVP honor in 2007, but also for maintaining close family ties despite frequent relocations.
The Oklahoma estate reflects this connection to home and family. His brother, Josh Holliday, has served as Oklahoma State University’s baseball coach since 2013, and both Holliday’s and his wife’s parents reside nearby. The property’s barn was converted to house a pickleball court and batting cage, where Holliday would occasionally practice with his sons.
The sale comes amid a market challenge given Oklahoma’s median net worth ranking and limited pool of high-net-worth buyers. According to the estate’s agent, Wyatt Poindexter, interest is driven by the property’s unique combination of luxury features and Holliday’s high-profile name. While professional athletes and coaches are among the potential buyers, the primary market tends to be successful oil executives in the region.
Despite the property’s specialized amenities, Holliday expressed confidence that its baseball-related features would not deter prospective buyers, as spaces like the baseball field could be subdivided if necessary. Reflecting on the sale, Holliday emphasized that while the family cherishes the memories created at the estate, home is ultimately about being together rather than the physical property.
“We’re a baseball family,” he said. “Every house has a lot of great memories... but it served its purpose.”