Retired media mogul sells Isleworth mansion for $7M+ to local auto dealer

GrowthSpotter contributor

One of the country’s major media moguls sold his Isleworth estate for more than $7.189 million on June 20 to the top executive of a leading Orlando automobile sales company.

The sale ranks as the highest value single-family home sold in Orange County so far this year, topping the $6.5 million purchase in January by local real estate developer Gregg Hill in Winter Park.

Located on Isleworth Country Club Drive, the home is tucked in a private cul-de-sac and spans three lots, totaling 1.89 acres. Comprised of a main house, guesthouse and a caretaker’s cottage, the property overlooks Lake Butler and the fairways of the Isleworth golf course’s 14th hole. 

The 13,519-square-foot home’s exterior was inspired by the architecture of Bermuda. The house boasts seven bedrooms, nine full baths and one half bath.

The seller was Ramsay (Rance) E. Crain, former president, editorial director and a member of the board of directors at Crain Communications, a Detroit-based media company his father founded in 1916.

Among the trade newspapers Crain publishes are Advertising Age, Crain’s Chicago Business and Crain’s New York Business. In 2017 he stepped down, selling a 50 percent stake in the company to his brother Keith Crain.

Crain originally bought the Isleworth land in 1995 for $575,000 and built the house in 1998.

Elegantly appointed, the formal living room and dining room feature fireplaces and chandeliers. The master suite has oculus windows and hand-tufted carpeting; its adjacent bath has a shower with two rain showerheads and a basin bathtub. 

Designed to accommodate two chefs, the kitchen features three islands, two Jenn-Air ranges with gas cooktops, and three Sub-Zero 700 series refrigerators. Outdoor living space includes a heated pool, grotto-style spa, waterfall and private boat dock.

The buyer of the Isleworth estate is Joseph A. Siviglia, chairman of Vineland Motor Sales, which includes Toyota of Orlando and Toyota of Clermont.

Monica Lochmandy of Isleworth Realty, who represented the seller, told GrowthSpotter that despite the house being listed at $15 million both the buyer and seller were satisfied with the sale price of the 20-year-old home, which was in good condition.

“It was a good price for the square footage when you look at the square footage sales in the area. This wasn’t a fire sale. They came to an agreement and both walked away happy,” Lochmandy said. “The seller, who plans to remain in the area, wanted to downsize." 

The home is also located in the same section of Isleworth as that of retired NBA superstar Shaquille O’Neal, which is currently on the market for $28 million.

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