Matt Holliday Listed His Stillwater Estate
The former major leaguer has listed his 20-acre Oklahoma property for $8.95 million.
Updated on Oct. 14, 2026 in Residential
Live Poll
Is now a good time for you to invest in luxury properties with niche, custom amenities?
Matt Holliday has listed his Stillwater, Oklahoma, estate for $8.95 million. The property, which spans 20 acres, features custom amenities including a full baseball diamond and batting cages.
Why it matters
The sale follows the Holliday family move to Arizona in February 2026 to seek consistent weather. The decision comes after the family's sons finished their baseball seasons or were drafted, marking a transition away from the property.
The property was purchased in 2018 for $3 million, with house construction beginning in 2020 and finishing in 2022. The estate includes a $2 million custom pool and has received 270,000 online listing views.
The players
Matt Holliday
He is a former professional baseball player who purchased the Stillwater property in 2018.
Wyatt Poindexter
He is the realtor currently managing the sale of the Stillwater estate.
Kelly Caviness
He is the builder responsible for the construction of the estate's custom pool.
Leslee Holliday
She resides in Arizona with Matt Holliday and relocated there in February 2026.
The details
Realtor Wyatt Poindexter is managing the sale of the residence, which also includes a pickleball court and running trails. If the buyer of the 20-acre estate does not purchase the remaining land, those portions will be offered to developers.
Timeline
Matt Holliday purchased the property in 2018.
Construction of the home began in 2020.
The house was completed in 2022.
The property was first listed for $12 million in February 2026.
Matt Holliday discussed the sale in October 2026.
Culture Shift
The listing highlights the significant disparity between luxury athletic real estate valuations and the local Oklahoma median net worth of $78,510. This sale reflects a broader trend of high-profile athletes divesting from custom-built estates once their primary career phases conclude.
Potential buyers interested in the property must consider the maintenance requirements of the custom baseball diamond and running trails on the 20-acre lot. If the remaining land is sold to developers, it may lead to new construction activity in the Stillwater area.
The takeaway
Large-scale luxury properties often require significant ongoing maintenance, which prospective buyers should evaluate alongside the property's unique athletic amenities. Moving to new regions can be an effective way to reset a lifestyle after major career milestones.
Further reading
For more information on the local market, see Residential.
Source note: This article includes information reported by The New York Times.
Live Poll
Is now a good time for you to invest in luxury properties with niche, custom amenities?
