When Bailey Spasovski and her husband asked realtor Kelly Drost if she and her husband Chris might consider selling their 1925 Maine Colony neighborhood home to them when the time came, Drost said "yes"—and eventually delivered on that promise. 

“Chris and Kelly knew we weren’t going to mess with their home. It’s a great-sized lot for a tear-down, and it’s been a bummer watching old homes here get bulldozed over the years,” Spasovski says.

The couples' shared love for Old Florida-style homes kicked off more than a real estate transaction. “Now Chris and Kelly are some of our best friends,” Spasovski says.

“The kids,” as Drost calls Spasovski and her husband—even though they're only about 10 years younger than she is—bought the 1925 home at 2736 Ashton Road in 2021 for $198,000 after Drost and her husband Chris Kurvin spent the previous eight years nurturing the wood frame home and flipping its shabby charm into a vintage treasure box.

Indeed, both Drost and Spasovski had in common a call for picking up rocks and finding the gem within. They both saw the value in the two-bedroom, one-bathroom home at 2736 Ashton Road and knew that its 888 square feet could shine with some patience and attention.

“It used to be a cut-through when I worked at the Paddywagon [a former nearby pub]," says Drost. "I loved this little historic district even though it was a little transient at the time. The old houses looked like these little gems no one had found. One day I saw a 'for sale' sign. We're suckers for old Florida Cracker houses. We loved the front porch and the windows.”

Before selling to the Spasovskis, Drost and Kurvin remodeled the kitchen and single bathroom to complement its Old Florida aesthetic. They also upgraded it with its first central air conditioning system, jacked up the front two corners of the home and reinforced sagging pilings.

The Spasovskis picked up where Drost and Kurvin left off.

The backyard is huge—the property occupies a little over a quarter acre—and “it had an old two-car garage house in the back that would have probably been condemned if the county saw the massive lean on it,” Spasovski, 36, who owns the witty wholesale stationery company Cheek & Pen Paper Co., says. So they removed some walls and rewired it for electricity, and turned it into a pergola while also maintaining its 100-year-old cedar roof.

The backyard is large enough for a potential pool, additional dwelling unit or workshop. The Spasovskis added a new roof on the main home, and all the electrical and plumbing have been updated too, making this almost century-old home a turnkey affair.

The couple also rebuilt the front porch, which “felt like a bounce house at the time,” Spasovski adds. 

Inside, she finished it off with personal touches—but what you see in the photos is just for staging purposes and isn't included in the sale. Although letting go of the home after just a couple of years is bittersweet, it's part of Spasovski's family's transition to the North Carolina mountains. However, they still split their time in Sarasota.

What they’ll miss most about the home are the neighborhood and its people.

“During the pandemic, we were all home and walking, and the tennis courts were open and we’d sneak into Riverview High School's soccer courts and track," she says. "At night you can hear the band practice and it’s so sweet. I love a horn and drum line carrying through the night. That never got old.”

During her time in the historic neighborhood, Spasovski also made quick friends with community leaders Jeffrey Frank and Anja Palombo, who’ve spearheaded bringing the neighborhood’s almost 100-year-old Philippi Crest Clubhouse back to life with regular gatherings, live concerts, art and kids' activities, and more. 

“They needed someone to fill out the paperwork on the Six to Save–a local initiative that highlights older, beloved Sarasota structures and their significance. "We worked together on that," Bailey says.

There are no formal HOA fees to live in the historic Maine Colony neighborhood, but there is a voluntary community association that subsists on volunteer time and donations. And although the neighborhood is on the National Register of Historic Places, many of the houses themselves don't have the designation, so if a buyer wanted to demolish the house on Ashton Road, they could. But Spasovski hopes they don't.

“It's the swampy Florida vibes you want. Everyone is just chill in that neighborhood and there are no mega-homes. There's no amount of money that could dry my tears if it was destroyed," she says.

So far, Drost says the home is attracting investors looking for a beachy short-term vacation rental and single young people looking for something affordable.

“It's crazy to call a $345,000 home affordable, but that's the first-time home buyer price range now,” Drost says. With a Sarasota County median single-family home price of $460,000, she’s right. A retired snowbird couple could also make a winter getaway out of the home, she notes.

“It's weird and quirky and smaller. I hope it doesn't get replaced with a concrete box. That's not what the neighborhood needs," Spasovski says.

Interested? Contact Kelly Drost of Fine Properties at (941) 822-6926.