If you love looking at beautiful old homes like I do, the affluent North Shore is a perfect place to walk, talk, and gawk — and pretend you have the money to afford these million-dollar-plus properties. Fortunately for me (and you!) there are some historically and architecturally significant homes available on the real estate market right now. I couldn’t help but include a classic country estate in Lake Forest as well as a stunner of a home in Evanston’s Lakeshore Historic District. Whether it’s the soaring ceilings and leaded glass windows of a private school’s sanctuary space or the water views from an army captain’s mansion, I know you’ll love the two adaptive reuse projects that are for sale. But the last listing is a sad reminder that many of these buildings are vulnerable to demolition and new development. So let’s appreciate them while they’re still here and take a look. 

539 N Mayflower Rd, Lake Forest, $1,599,000

Ferry Hall was an all-girl’s preparatory school originally founded in 1869. When it later merged into Lake Forest Academy, the campus was subdivided and the school’s former chapel, designed by architect Henry Ives Cobb in 1888, was adaptively reused as a three-bedroom, four-bathroom residence. Since it last sold over a decade ago, the owners made improvements to the original character of the building, adding wood floors and antique fireplace, preserving original windows, tuckpointing the brick exterior, and repairing the cedar roof. Keep in mind it is part of Mayflower Park Condominium Association, with $822 monthly HOA fees. 

214 Greenwood St, Evanston, $3,950,000

Just steps from the lakefront in Evanston is this historic landmark originally built in 1897. Not even 20 years later, architect George S. Kingsley remodeled the home to its present-day Tudor Revival appearance. The current owners restored this 8,000-square-foot, six-bedroom, six-bathroom residence, merging vintage architectural details with modern day comfort. Some of my favorite parts include the grand foyer, the gorgeous sunroom, and the rear stone patio. Another cool detail is found inside the renovated historic coach house/horse barn with its original “Tac” closet (now a repurposed powder room).

900 E Ringwood Rd N, Lake Forest, $4,995,000

Returning to East Lake Forest to share “House in the Woods,” a stunning four-acre estate originally built for Nettie Fowler McCormick, widow of Cyrus Hall McCormick (you know, the guy who invented the mechanical reaper). In 1916 Nettie and her daughter Anita hired the architectural firm of Perkins, Fellows & Hamilton to design a brown brick and stone Tudor-Prairie hybrid full of elegant and timeless details. On the market for the first time in 25 years, the seven-bedroom, 12-bathroom mansion is perfectly preserved but also comes with amenities that fit the hefty price tag like an elevator, wine cellar, basketball court, and in-ground pool.

23 Scott Loop, Highland Park, $2,199,000

When the U.S. Army established Fort Sheridan in 1887, Brigadier General Samuel Holabird gave his young son’s architectural firm (Holabird & Roche) the opportunity to design its buildings. The former military property officially closed nearly 30 years ago and the original structures were converted for private residential use. This standalone brick house has an off-center porch Captain’s Quarters, per military hierarchy. Located on a loop that dead-ends at the lakefront, the seven-bedroom, seven-bathroom residence has unobstructed water views from every single room, as well as the outdoor deck. Surrounded by a forest preserve, ravines, walking trail, and beach, it’s also close to the town of Highwood and the Robert McClory Bike Path.

976 Oak Ter, Glencoe, $3,450,000

Located just a few blocks from the lakefront in East Glencoe is an Arts & Crafts design by local architect Robert Seyfarth, known for his fashionable residences along the North Shore. Originally built between 1915-1920 for Allen A. Murray, a number of the home’s vintage details remain intact on the ground level, like classic ornamental trim on the walls and the blue-tiled floor in the sun room. There is a large modern kitchen and the second floor was completely renovated with new en-suite bathrooms. Although this is a great example of beautiful historic architecture, it’s still not surprising to see the listing state that the 1.25-acre property can be sold for its land value alone (it’s been on and off the market for the last three years).