Notable Home Sales

Local developer pays $6.5M for historic Winter Park home, sells Oviedo estate

A view of the recently acquired 1920s-era home on N. Interlachen Avenue in Winter Park.

A veteran local developer and venture capitalist paid $6.5 million in January to buy one of downtown Winter Park's oldest homes, and this week sold his custom-built Oviedo estate for $2.6 million.

Located in the 300 block of N. Interlachen Avenue, the 2-acre property features elevated views of Lake Osceola with 300 feet of frontage, and a historic home from 1925 with 8,738 square feet across three stories, five bedrooms and five-and-a-half baths.


Amenities in the home include original wood floors, staircase and banister, chandeliers, crown molding, wood-burning fireplaces and french doors, a billiard room, office, music room, den/family room, screened lanai, pool and spa, cabana, summer kitchen, volleyball court and boat dock.

The buyers were Gregg and Stephanie Hill. Gregg is president of local  developer Hill/Gray Seven, senior managing director of technology-focused investment company H&S Capital Group, and founder of thoroughbred horse racing company Red Castle Farms.


"A couple years ago my wife said she loves our house, we built a custom home in Oviedo that's really amazing," Hill told GrowthSpotter. "But if she was ever going to move to Winter Park where our kids go to school, hands down that (Interlachen Avenue home) is the best location. I didn't think more of it because it seemed so expensive."

Fast forward to 2017, and luxury home sales agent Mick Night of Coldwell Banker Residential Real Estate was actively showing Hill properties in Winter Park, eyeing the market for home remodel options or new spec construction.

"Mick was really working on me to find something for the family, but we were happy in Oviedo, that house was one of a kind," Hill said. His custom-designed home there spanned 16,000 square feet of conditioned area across four buildings, including a barn, guest house, exercise building and main house.

Hill zeroed in on the 1925-era estate on Interlachen Avenue, which was not listed for sale. The home has had only four owners, with the most recent being Jeanne H. Atkinson, whose family paid $3.8 million in 2001.

"I had to come up with an offer that was pleasing enough for them to move," Hill said. "It wasn't just about the money, it was a way to allow transition and be considerate of the emotional tie to the home."

Hill brought the Interlachen home under contract in April 2017 and closed nine months later, in mid-January. That gave the seller time to find a new home, and Hill time to begin planning an extensive remodel.

"This home hasn't been remodeled in (93) years, so I'm doing a total renovation," he said. "We're starting in February, and it will take a full six months or longer depending on surprises that pop up. We'll add some space, taking total conditioned area to more than 9,000 square feet."

The Hills then closed on Jan. 31 with the sale of their Oviedo home for $2.6 million, made to an out-of-state buyer.


Mick Night and John Pinel of Coldwell Banker Residential Real Estate represented the buyer and seller in Winter Park.

Have a tip about Central Florida development? Contact me at, (407) 420-5685 or @bobmoser333. Follow GrowthSpotter on Facebook, Twitter and LinkedIn.