WINDERMERE, Fla. — The Orange County Jail is a far cry from J. Robert Ward’s seven-bedroom, nine-bathroom home in the exclusive gated community that is home to Tiger Woods and Shaquille O’Neill.

But the prominent developer charged with second-degree murder in his wife’s shooting death appeared perfectly at ease over the weekend in a videotaped jail visit with family members.

In a video released by the jail, the 61-year-old modeled his blue jail jumpsuit, danced and started to unbutton his shirt. He chatted about who would make a good character witness, whether he could buy anti-dandruff shampoo at the jail commissary and even where the family should celebrate Thanksgiving.

His daughter and sister-in-law giggled, belying the seriousness of the accusation against him. Police say he killed his wife in the master suite of their home on Sept. 21, then called 911 to say he had shot her. His attorney, Kirk Kirkconnell, has since raised questions about whether it was a homicide or a suicide. Kirkconnell did not return calls for comment Monday.

Diane Ward’s death is a disturbing turn in the life of her husband, a self-made millionaire who in recent years had suffered crushing financial troubles. J. Robert Ward hadn’t paid the $16,841 monthly mortgage on the estate in over a year, and had filed for bankruptcy after his business — developing vacation and resort home communities in five states — failed.

He may have had other demons as well. Dianne McClintock Callahan of Marietta, Ga., dated Ward some 25 years ago but kept in touch over the years. She said he was well-liked, kind and generous — until he drank.

“He was mean,” she said, describing their final night together, during which Ward allegedly pointed a gun at her and beat her with a bedpost he had ripped off her bed. Callahan recalls talking to police from a hospital, but doesn’t remember whether charges were filed.

“He was like the perfect man, other than that temper,” she said.

Ward was born in Daytona Beach, the son of a gas station owner. According to his profile on the LinkedIn Web site, he majored in business at both Florida State University and Georgia State University. While heading a mortgage company in Atlanta, he met Callahan, who worked in the office. They dated for five years.

“He’s always been successful,” she said. “He could turn a dime into a million dollars.”

Callahan said Ward enjoyed traveling, shopping and nice cars — when they dated, he owned two BMWs at the same time. But his temper drove her away.

A few years later, he married Diane Cardinale and they had two daughters. Ward continued to amass a real estate empire, becoming a member of the Atlanta Chamber of Commerce board and at least one civic group.

In mid-2005, court documents show, his Land Resources Group was developing 16 communities with 5,282 homesites. Ward had 250 employees and built high-end developments on properties that stretched from Cumberland Harbor in Georgia to the mountains of West Virginia.

But by 2006, people weren’t buying as many vacation homes. In 2007, Ward and his wife relocated to central Florida, saying that they wanted to be closer to the lucrative timeshare industry popular in Orlando.

The Wards bought their 8,708-square-foot home in the Isleworth development — the same home where Arnold Palmer once lived — for $4.3 million that same year.

They also bought cars — BMWs, Mercedes, Cadillacs and at least one Lexus, court records show.

A year later, Ward and Land Resources Group filed for bankruptcy. The company was down to 14 employees, $115 million in assets and $214 million in liabilities. The lavish home with a pool and formal gardens was put on the market with a $5.2 million price tag.