Home / News / Retired Cubs starting pitcher Ryan Dempster lists Lakeview home for $2.5 million

Retired Cubs starting pitcher Ryan Dempster lists Lakeview home for $2.5 million


Retired Chicago Cubs starting pitcher and Marquee Sports Network analyst and talk show host Ryan Dempster put his six-bedroom, 5,650-square-foot Lakeview home on the market once again this week, this time for $2.45 million.

Dempster, 46, pitched for the Cubs from 2004 to 2012 and retired from baseball in 2014. He later took a job in the Cubs’ front office before signing on as an analyst with MLB Network and hosting a late-night talk show. Off the Mound” with Ryan Dempster on the Cubs’ Marquee Sports Network.

In Lakeview, Dempster bought his current new home in 2014 for $1.95 million. He listed it for sale as a pocket listing for $2.25 million before taking it off the market in 2021, and then relisted it as a pocket listing for $2.45 million on Thursday before putting it on the public market the next day.

The two-story home 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 custom office with a wall of built-in shelving and a large center island, butler’s pantry, and Sub -A kitchen with Zero, Wolf and Miele appliances. It also features a great room with custom built-ins and coffered ceilings, a master bedroom suite with an oversized steam shower and double vanity, and an oversized recreation room, wet bar, guest suite, exercise area, and a temperature-controlled wine cellar.

Outside of the extra-large property is a landscaped yard, a brick patio, an outdoor fireplace, a deck, and an oversized three-car garage with a full loft.

Listing agent Jeffrey Lowe of Compass told Elite Street that Dempster and his wife remain in Chicago and are just “changing footprints.”

“It’s a great house,” Lowe said. “They purchased new construction and did an incredible job developing it. Located on a large lot on a great street in Lakeview.

The home had a property tax bill of $36,382 in the 2022 tax year.

Previously, Dempster briefly owned a French Provincial-style home in Wilmette, which he bought in June 2021 for $2.12 million and sold six weeks later for $2.13 million. He previously sold a 5-bedroom, 5,300-square-foot home in Lakeview for $1.76 million in 2014, and as part of their 2014 divorce, he gave his ex-wife the deed to a larger Lakeview home they bought in 2008 for $2.69 million. Additionally, Dempster sold his Lakeview condominium for $525,000 in 2020. He had owned this apartment since 2009, when he bought it for $480,000.

Goldsborough is a freelance reporter.

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