The land that is now Longwood Hills was first purchased by John S. Young of Ohio, from the State of Florida. The 80-acre tract cost him just $60 (75 cents per acre) in 1873. Young sold the land to Richard H. Marks just three years later for $1,700. A year later it was sold to John F. Dunn for $2,000. In 1883 most of the property (60 acres) was purchased by John W. Park. The Park family defaulted on their mortgage in 1887 and the property was claimed by Agnes Wilson and Emma Andrews. However, the land was abandoned after the Great Freeze of 1893 and taxes went unpaid. So Orange County (since Seminole County did not yet exist) claimed the land for back taxes.
Horne & Overstreet Company purchased the land from the county in 1905 for pennies on the dollar. The company later became known as Overstreet Turpentine Company a few years later (and even later in the 1920s rechartered as Overstreet Investment Company). Its pine trees were harvested for turpentine between 1905 and 1925, in partnership with the Consolidated Naval Stores Company. By 1918 the land had been tapped of pine sap and the Overstreet Company wanted to sell the land, but found it unmarketable due to questions about the title. They filed suit to clear the title, which on some books still showed the descendants of John Park as the owner. The company advertised the challenge in the Sanford Herald for several weeks and after no one came forward to contest the claim, the judge granted the unencumbered title to Overstreet Investment Company.
The land was sold several times and ended up with the Entzminger family and their Seminole Lake Region Realty Company. The plat for the subdivision of Longwood Hills was submitted to Seminole County Commissioners by new owner Emmie Entzminger on April 5, 1927. Longwood Hills Road was surveyed and paved by the county in 1953, stretching from Old Dixie Highway (Old Orlando Road or now 427) to what was then called Longwood-Markham Road (now Rangeline and EE Williamson).
John C. and Irene Philpitt bought 20-acres of the Longwood Hills property, fronting the Old Dixie Highway (Old Orlando Road, 427) in 1954. John Philpitt died in 1964, but his wife Irene lived on the property to 96-years-old. She died in 2011. The Philpitt family owned the highway frontage until 2019 when it was sold the last two acres of the parcel to the developers that constructed the Circle K convenience store at the intersection, which opened in 2021.
Land Title and Abstract of Longwood Hills, donated by the Philpitt family: Scanned Images