Population growth near Sandy Creek halted in the 1870s when the region's proprietor destroyed the granite landmark in retaliation to a local food theft.

In the late 1800s, local land developer Newburn H. Guinn attempted to change the town's name to Leesburg after his daughter Lee.

[8] In the 1800s, much of south Leesville was owned by Ezekiel Wimberly Cullen, a former Congressman and Supreme Court Justice of the Republic of Texas.

[10] In 1835, at Sandies Creek in what is now Leesville, 13 traders of Mexican and French origin traveling from Louisiana to Mexico were killed by Comanche Native Americans.

He later joined the Spanish Army and was compensated for his service with the title to 27,000 acres of Texas land in what is now Leesville, upon which he developed the original El Capote Ranch.

Virginia-born Michael Erskine (1794–1862) acquired the property from de la Baume's estate in 1840 and raised cattle there.

[citation needed] The Erskine family hosted several eminent visitors, including William Bollaert of the British Royal Geographical Society (1840), Ferdinand von Roemer (1845–1847), and Frederick Law Olmsted (1857).

After the Erskine family sold the ranch in the 1870s, part of the land was deeded to Edith Kermit Carow, the second wife of Theodore Roosevelt.

During the Spanish–American War, Roosevelt rode a horse from the ranch, named Seguin, at the 1898 Battle of San Juan Hill.

In 1880, the San Antonio Express newspaper rated the Capote Ranch as "the largest and most complete farm in Texas... if not in the south," giving examples of the diversity of livestock and crops that were raised at the scale of 75 workers over 20,000 acres.

[33] The ranch was acquired in 1897 by Judge Leroy Gilbert Denman (1855–1916), a justice of the Texas Supreme Court, and is currently owned by his descendants.

At present day, the property's remaining estate has generated significant caselaw in Texas in ConocoPhillips Co. v. Ramirez,[34] in which the rights to the minerals beneath the ranch's soil were contested.

The 190-mile line was proposed to reach San Antonio from Houston, stopping at Richmond, Garwood, Gonzales, Holmes' home of Leesville, Willow Springs and New Berlin.

[47] In late 2020, a porcelain sign weighing approximately 150 pounds was stolen from Leesville's Quien Sabe Ranch.

[21] Fitch Ratings remarked on this water company's inability to directly assign liabilities to either the City of Schertz or Seguin.

[60] In 1846, geologist Dr. Ferdinand von Roemer further described the area as composed of "fertile valleys" and "low hills... of gravel sand" with "farms every few miles.

"[61] In 1851, William Bollaert of the Royal Geographical Society became lost in the Leesville area, which he described as the "Big Hill prairies."

Near Guadalupe River, Bollaert found the land "fit for all agricultural purposes, although the surface soil is sandy," with chiltepin peppers "most abundant."

[62] In 1852, Frederick Law Olmsted, the then-future designer of New York City's Central Park, noted the area's principal species of trees as pecan, hickory, cypress, cotton wood, box elder, white oak and walnut.

He described the bottom land's "rich, black clay soil" as difficult to cultivate yet "producing high yields" of crops.

[64][65] During Tropical Depression Eight of 1981, several dwellings in and around Leesville suffered water damage after the O'Neill Creek reached its highest level since at least 1936.

[78] The local median cost of housing, as of 2018, ranged from $546 to $633 per month;[79][80] with the households of the city paying an aggregate $23,500 in annual property taxes.