It’s hard to imagine that parts of the Chicago metropolitan area were once viewed as “country.” The following multi-million dollar properties located on large acreage are far away from the hustle and bustle of Chicago, nodding back to that long-ago time. Some of the homes were used as farms or weekend retreats when they were originally built. One property’s original owner, Gaylord Donnelly, became a leading land conservationist through his foundation. Between a David Adler design or a home with an Ernest Hemingway connection, it’s hard to pick a favorite “country” house among the five listings currently for sale. If only money were not an option, I’d be delighted to call any of these places home. 

255 N Green Bay Rd, Lake Forest, $10,100,000

One of the most grand country houses designed by architect David Adler is Suffield House, a 15,000-square-foot neo-Georgian design originally built for Mrs. J. Ogden “Lolita” Armour in 1934. Located across from the entrance to the Onwentsia Club and near the heart of Lake Forest, the historic mansion with a hefty price tag is available for the first time in nearly 50 years. Many of its architectural features are perfectly preserved, from imported English paneling to vintage fireplaces and light fixtures. In addition to a swimming pool, pristine gardens, PGA-certified putting green, and four-car garage, the pricey property also comes with a staff apartment, passenger elevator, gift-wrapping and flower-arranging rooms. 

260 Otis Rd, Barrington, $1,695,000

On and off the market for the past five years, Valley View Farm sits on 10 pastoral acres of mature trees and sweeping vistas in Barrington Hills. Originally built in 1910 by Chicagoan John V. Walker as a “gentleman’s farm” and weekend retreat, today it’s an updated, sprawling Shingle-Style home of six bedrooms and eight bathrooms. Its second owner, Bill Horne, whose best friend was famed writer Ernest Hemingway, added the outdoor inground pool in the 1930s. It’s also perfect for car enthusiasts as the property comes with a six-car garage. 

31780 N Almond Rd, Libertyville, $3,995,000

The former home of Gaylord Donnelly, the president and chairman of R.R. Donnelley & Sons Company started by his grandfather in 1864, sold earlier this year to buyers who claimed they loved it. Known as Windblown Hill, the scenic property set between two forest preserves is now back on the market for almost $4 million. The main house is designed by the same architects behind Chicago’s Merchandise Mart. The property also features a caretaker’s residence, greenhouse, silos, and a seven-stall horse barn. Due to AG zoning, property taxes are low, just $22,000 for 70-plus acres.

​165/197 Schneider Rd, Elburn, $7,400,000

Here is a more unique example of a country estate: a gorgeous modern home located in Elburn and designed by Mark Zinni Architects. Influenced by Frank Lloyd Wright, the six-bedroom, 13-bathroom residence made of Fond du Lac stone was designated “Home of the Year” by Custom Builder magazine when it was completed in 1994. Spread over 6,500-square-feet of living space, this is definitely a party house with games, toys, a 12-seat screening room theater, and a wine tasting room. Did I mention the 151-acre gated property comes with its own helipad? There’s also a pool house, an expandable six-stable horse barn, and 7,000-square-foot indoor riding arena.

9210A Country Club Rd, Woodstock, $2,320,000

The village of Bull Valley has kept its low-density, rural character in favor of the suburban sprawl that’s taken over nearby Woodstock and Crystal Lake. On an estate of more than 60 acres with ponds and connections to equestrian riding trails, you’ll find two residences: a sprawling 1930s main house with indoor pool and a smaller building that’s currently used as an in-law apartment. Like some of the other listings, this historic property is on the market for the first time in 50 years. While it needs a lot of work, it has endless possibilities.