Notable Home Sales

Scion of Orange auto dealership family pays $3.6+M for Winter Park, lake-front home

The executive manager of one of Orange County's oldest family-owned auto dealerships paid just over $3.6 million for a lakefront estate in Winter Park, according to a deed signed Monday.

The single-story, 5,994-square-foot house on Summerland Avenue boasts 180 feet of Lake Maitland frontage on the Winter Park Chain of Lakes. Built in 2001 for Charlie Bradshaw, a car enthusiast, the custom home sports a six-car garage with three separate double-space bays. A circular drive adorned with Olde Winter Park brick, greets visitors in the front.


The four-bedroom, six-bath home has a split plan with a central kitchen connecting the two wings. The house was designed to take full advantage of lakefront views with floor-to-ceiling windows spanning the back wall. The exterior features include a 350-year-old oak tree and a two-bay boathouse snuggled along the cypress tree-lined lake. The interior has walnut hardwood floors, detailed volume ceilings, custom millwork, crown moldings and wainscoting.

Jack Starling, executive manager of Starling Automotive Group, and his wife, Meghan Starling, an artist,  were the buyers. The family-owned automotive business was founded by Jack's grandfather, Carroll Starling, who moved from Ocala to Kissimmee in the 1950s and opened Sterling Chevrolet.


The group now owns four Florida dealerships: Starling Chevrolet, now in Orlando; Starling Chevrolet Cadillac in Deland; Starling Chevrolet Buick GMC in St. Cloud; and the former Kunz Buick GMC dealership in Venice, which Starling acquired in October 2017. The family added a fifth dealership in Mount Pleasant, South Carolina, this year.

The sellers were John L. Steinbrun and his wife, Lisa Ann Hughes-Steinbrun. The couple bought the home for $2.85 million in August 2014.

John Steinbrun is CEO of Colonial Management Group, owner of the New Season group of opioid addiction treatment clinics. Lisa Hughes-Steinbrun is co-founder of  Steinbrun Hughes and Associates executive recruiting and placement firm.

Alison Mosley of Premier Sotheby's International Realty represented the sellers.

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