Retired Chicago Cubs starting pitcher and Marquee Sports Network analyst and talk-show host Ryan Dempster placed his six-bedroom, 5,650-square-foot Lakeview house back on the market once again this week, this time for $2.45 million.
Dempster, 46, pitched for the Cubs from 2004 until 2012 and retired from baseball in 2014. He then took a job in the Cubs front office before signing on as an analyst for the MLB Network and hosting a late night-style talk show, “Off the Mound with Ryan Dempster,” on the Cubs’ Marquee Sports Network.
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In Lakeview, Dempster bought his current house new in 2014 for $1.95 million. He put it up for sale as a pocket listing in 2021 for $2.25 million before taking it off the market, and he then relisted it as a pocket listing on Thursday for $2.45 million before publicly placing it on the market the following day.
The two-story house has 6-1/2 bathrooms, four fireplaces, hardwood floors, high ceilings, custom millwork and cabinetry, a living room with moldings and a marble fireplace, a private office with a wall of built-in shelving, and a kitchen with a large center island, a butler’s pantry and Sub-Zero, Wolf and Miele appliances. It also has a great room with custom built-ins and coffered ceilings, a primary bedroom suite with an oversized steam shower and a dual vanity and a lower level with an oversized recreation room, a wet bar, a guest suite, an exercise space and a temperature-controlled wine cellar.
Outside on the extra-wide property are a landscaped yard, a brick patio, an outdoor fireplace, a deck and an oversized three-car garage with a full attic.
Listing agent Jeffrey Lowe of Compass told Elite Street that Dempster and his wife are staying in Chicago and simply “changing up their footprint.”
“It’s a wonderful home,” Lowe said. “They bought it new construction and they did an incredible job upgrading it. It’s on a wide lot on a wonderful street in Lakeview.”
The house had a $36,382 property tax bill in the 2022 tax year.
Previously, Dempster briefly owned a French Provincial-style house in Wilmette, which he purchased in June 2021 for $2.12 million and sold six weeks later for $2.13 million. Earlier, he sold a five-bedroom, 5,300-square-foot house in Lakeview for $1.76 million in 2014, and as part of a divorce in 2014 deeded to his ex-wife a larger Lakeview house that they bought in 2008 for $2.69 million. Also, Dempster in 2020 sold a Lakeview condominium for $525,000. He had owned that condo since buying it in 2009 for $480,000.
Goldsborough is a freelance reporter.
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