For residents of Sleepy Hollow in South Haven, Michigan, it’s as though the clocks stopped in the 1930s. Rounded, Art Moderne cottages line a stone path leading to Lake Michigan, and undulating metal umbrellas straight out of a vintage Hollywood flick shade an outdoor eating area. “It’s like going back in time,” says Debby Gershbein, who’s lived here since 1999. “You can relax and enjoy life like you’re supposed to.”
Basking in the sun outside her quirky, streamlined house, Debby waves a neighbor over to visit. Their conversation quickly turns to the restoration of this vintage resort community.
In 1997, the condo association crafted a plan to demolish Sleepy Hollow’s 70-year-old cottages—which lacked modern amenities and were in dire need of an overhaul—and rebuild them. Residents chose to replicate the old cottages’ exteriors, patterned after buildings at the 1933 Chicago World’s Fair. Though the project would prove costly, owners backed the plan. Demolition began in 2000, and reconstruction continued for more than two years. Today within the 30-acre gated community, there are 61 individually owned units built to contemporary standards. The original office/restaurant building stands as a reminder of the past.
“I am very happy with our decision,” says lakeview cottage owner Stuart Levin. “It was a big undertaking and it wasn’t done to make a profit.” Stuart estimates the rebuilding process cost owners up to six times more than what they paid for their units. But, he says, the memories created here make Sleepy Hollow priceless to generations of families. “I know my kids and my grandkids will always take care of this place,” he says. “We love it so much.”
This slice of retro paradise is also available to newcomers. Renters occupy about 50 percent of the buildings here, and weekly rates for a one-bedroom cottage can run as much as $2,300. Despite the cost, units go fast. Visitors love Sleepy Hollow’s hip style—and the 1,000 feet of private shoreline.
Tonight, as the sun descends into Lake Michigan, torching the sky orange, red, and pink, Debby greets a visitor who vacationed here as a child. His family sold during reconstruction because they feared the community wouldn’t look the same. “Not a single unit is for sale,” Debby says, reading his mind. With a rental request in hand, the man vows to return—if he can get a reservation.
For more, visit sleepyhollowbeach.com.
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