He bought 10 acres south of Largo in Pinellas County for $50 down plus one horse and one cow. In 1927 his friend Dave Cunningham became his partner and over time the two men grew the ranch to more than 650 acres. The property became known as Ulmerton Ranch.
As the Great Depression waned, it became evident to Starkey and Cunningham that rising land prices and encroaching development would hinder opportunities to expand in Pinellas, so they looked farther north for opportunities. In 1937, they drove their 300-head herd to the grassy expanses of southwest Pasco County and turned the cattle loose on 16,000 acres of unfenced pasture and forest cut by the Pithlachascotee and Anclote rivers.
Jay Starkey, Dave Cunningham, and Dave’s brothers Howard and Ernest formed a partnership to buy the land, creating the CS Ranch. They got much of the property cheap, in some cases from tax sales on land abandoned by logging companies. The ranch remained open rangeland until 1940, when Starkey and his partners painstakingly barb-wired the perimeter. They raised purebred Brahma cattle, and had timber and citrus operations. By 1956, Jay Starkey was the sole owner of what by then was known as the Anclote River Ranch, having survived all three Cunningham brothers.
In 1965, he sold the cattle on the ranch to his son, Jay B, Jr. The elder Starkey retained a 75-acre orange grove and the timber operation. Having seen development in Florida consume so much land, Starkey set out to preserve much of the Ranch as wilderness, so that future generations would be able to see what the land looked like when he was young. He sold a vast tract of the Ranch to the Southwest Florida Water Management District (SWFWMD) to ensure that it would not be developed. This was the start of the Jay B Starkey Wilderness Preserve, which is a Pasco County park. After his death in 1989, his heirs sold more land to the State to expand the Preserve.
Jay B Starkey, Jr., his wife Marsha and their children continued to live and work on the Ranch. Their collective goal was to ensure that the development that would happen on the remainder of the Ranch didn’t follow the sprawl patterns of tract housing and strip shopping centers. Starting in the late 1990s, they developed several hundred acres on the western edge of the Ranch into Longleaf, a neighborhood with traditional development patterns, walkable streets, homes with front porches, and a small town center.
The cattle herd was sold in 2003 to a rancher who leased back pasture on the ranch. Jay B, Jr., then devoted his time to running an ecotourism venture on the Ranch.
In early 2013, Wheelock Communities announced the purchase of the remaining 2,500 acres of Starkey Ranch from the family, with plans to create a vibrant master-planned community with 800 acres of parks and open space and more than 20 miles of trails connecting the community with the adjacent Jay B Starkey Wilderness Park.
Outside the former Starkey family ranch house, northwest of State Road 54 and Gunn Highway, stood a large wooden plaque made of weathered gray boards, erected by Jay Starkey as a tribute to his friends. He listed their names, names such as Odis Cowart, Whitfield Bryan, and Ham Beckett. "In appreciation of my former partners and old friends who, in the early days of the ranch, camped, rode and hunted here and whose friendship I will always cherish," the plaque read.
Many of the names on the boards have found a place in the new Starkey Ranch community—as street names, park names and neighborhood names. Their legacy will live on as new generations put down roots on this storied land.