68 Round Hill Road in Greenwich, CT: Judge Judy’s Mansion

Judge Judy, one of television’s most recognized and successful legal figures, has built an empire both in the courtroom and in real estate. Among her impressive properties is a stunning estate in Greenwich, CT, worth an estimated $26 million, with annual property taxes exceeding $240,000.

Before the grand mansion that stands today, the property was home to a historic manor designed by 20th-century architect Harrie Lindeberg. The original estate featured an 11,000-square-foot country manor built in Lindeberg’s signature grand style, with a brick-and-hand-cut stone structure, a slate roof, and stained-glass windows.

In 2007, Judge Judy and her husband, Jerry Sheindlin, purchased the estate for $13.2 million. Rather than restoring the existing mansion, they opted to demolish it and create a new, grander residence. The result? A breathtaking 17,000-square-foot mansion.

The newly built home includes 10 bedrooms and 11 bathrooms, a private gated driveway for enhanced security, a guardhouse, a four-car garage, a swimming pool, a pool house, a guest house, and meticulously landscaped gardens spanning over 12 acres.

Brooklyn-born Judy Sheindlin presided over Judge Judy, which ran for 25 seasons, drawing more than 10 million viewers daily before its final episode in 2021. Beyond her Greenwich estate, Judge Judy has owned multiple properties across the U.S., including a penthouse in New York City, a waterfront mansion in Newport, Rhode Island, a home in Naples, Florida, and a residence in Beverly Hills, California.