When Caitlin and Ameesh Kapoor bought their Lawrenceville home in 2012, prices in the trendy Pittsburgh neighborhood were still fairly affordable. 

“We are not wealthy,” says Caitlin, “but we are fortunate to have a house in a neighborhood that blew up.”  

When they moved north of Pittsburgh to be closer to family, they were able to keep that first home as a rental property. 

Now, after more than a decade of both long-term tenants and Airbnb guests, the Kapoors are contemplating investing in a property in a nearby vacation destination.

“For the record, it feels like a pipe dream — but maybe not?” Caitlin says.  

AERIAL VIEW OF DEEP CREEK LAKE/PHOTO COURTESY OF SHUTTERSTOCK

The couple has set their eyes on Deep Creek Lake in Maryland, where they envision spending weekends at a lake house with their two children, and then renting out the home when they are not using it as a way to cover the mortgage and other costs. 

“We love weekend getaways and the idea of escaping city life for a lake and the woods,” says Caitlin. “A place two hours away is the dream.”

The Kapoors are among a group of Pittsburghers who, driven by the flexibility of remote work and a rise in popularity of homeshare platforms such as Airbnb and VRBO, are considering vacation properties in areas that are within a two-hour drive of Pittsburgh. Popular destinations are Deep Creek Lake, the Laurel Highlands or the shores of Lake Erie.

“As a realtor, I have definitely seen a rising interest in the Laurel Highlands from Pittsburghers looking for a second home or investment property,” says Adam Cannon of Piatt Sotheby’s Cannon Group. “The proximity is ideal. You’re only in the car for an hour, but you still feel like you’re getting away from it all. Plus, the prices are very reasonable when compared to other resort areas.” 

During the pandemic, Cannon’s own family purchased a home in the Laurel Highlands, where, depending on the season, they enjoy skiing, hiking and kayaking. 

415 GARDNER ROAD IN HIDDEN VALLEY QUICKLY WENT UNDER CONTRACT/PHOTO COURTESY ADAM CANNON

Cannon currently has 415 Gardner Road, in the Hidden Valley Resort, co-listed with his colleague Kathe Barge. The three-bedroom, three-bathroom log cabin is listed for $620,000 and features cathedral ceilings, a stone fireplace and a massive deck surrounded by peaceful woods. Ski lockers and a sauna are available for the next owners — and their weekend tenants — once the snow begins to fall again. 

“We went under contract after a single day of showings, so it’s clear the Laurel Highlands market remains hot, despite [interest] rates being higher than they were in the last few years,” says Cannon. 

Although those higher interest rates have slowed the purchase of second homes since the market boomed in 2020, sales remain steady and are currently consistent with pre-pandemic levels. With the ability to borrow against retirement savings, or their primary residence’s rising value, some home buyers are banking on a quiet retreat that pays off — eventually. 

For Jennie Rose Denton, a second home in the Laurel Highlands was not on her radar, but when a quaint cabin in the woods became available close to her extended family near Ligonier, she and her husband decided to take a chance. 

“We love spending time there and plan to retire there,” she says. “Remote work and Airbnb are what make it possible to do this now.” 

The Dentons say they love being able to enjoy their time in Pittsburgh while also escaping to the peace and quiet of the woods on the weekends. 

“Having both homes allows us to have the best of both city and country life, and spend time with both sides of our family,” says Jennie. 

A CABIN FOR RENT VIA HIGHLANDS RESORT REALTY

At Highlands Resort Realty, Realtor John Tierney says he understands the draw of the recreation and outdoor spaces in the Allegheny Mountains — over half of his clients are from Western Pennsylvania, with the bulk being from the Pittsburgh metro region. 

Tierney adds advances in technology have also made managing an investment property easier. 

“The platforms of Airbnb and VRBO have increased the ease of renting these properties,” he says. “That, in combination with local property managers, have made the process relatively easy for the remote property owners.” 

Ann Nemanic, executive director of GO Laurel Highlands, says a property in the region is likely to return a good investment for owners, adding that “vacation rentals” is one of the top search terms on their site. 

“As a four-season destination, a vacation rental in the Laurel Highlands is a wise investment for those wishing to venture into the tourism market,” she says. 

Vail Resort Inc.’s purchase of Seven Springs and Hidden Valley near the end of 2021 has also drawn new visitors to the region who are eager to use their Epic passes at Vail-owned resorts; this has made the vacation rental market even stronger. 

THIS CONDO ON SWISS MOUNTAIN DRIVE IS LISTED FOR SALE THROUGH HIGHLANDS RESORT REALTY

Keep in mind, while real estate has always been a solid investment, a second home can still feel like a big leap for some home buyers. Home sharing platforms allow most owners to cover their costs, though many don’t turn a profit beyond that for many years. 

Luxury cabins are also eye-catching, but the truth is small hunting cabins and modest getaways have been a popular indulgence for Pittsburghers for generations — and can be just as popular for weekend rentals.

 In fact, many of those second homes have been passed down through generations themselves. Tierney says for him, that’s what it’s really all about.  

“I have been known to say that I don’t sell real estate, I sell memories,” he says.