We’re all familiar with the proverbial saying that a person’s home is their castle, but these five properties take the idea a bit more literally: from courtyards to wrought-iron gates, custom stained glass and expansive square footage, these elevated estates evoke Old World romanticism wrapped in updated, modern luxury.
86 Prospect Ave, Highland Park, $6,500,000
This 7-bedroom estate is just off the shores of Lake Michigan, nestled on a quiet cul-de-sac. It doesn’t take a leap of imagination to see the medieval influences throughout the home, starting with the wrought-iron gate leading to a courtyard that is actually a five-car split garage. The 12,000-square-foot residence is custom built with painstaking attention to detail and time-worn finishes like hand-troweled plaster, arched doorways, aged slate roofing, barreled ceilings, limestone entry, copper accents, reclaimed and hand-scraped wood flooring, prominent base and crown moldings and soaring ceilings.
4 High Terrace Ln, Bannockburn, $3,399,000
While a castle was often fortified by moats and drawbridges, this contemporary 6-bedroom boasts a wraparound terrace, generous sundeck and large pool. Sitting on nearly four private acres of professionally-maintained grounds, the sprawling construction was designed by renowned architect Edward Raap and built by John Teschky, and features a wall of windows offering water views of its own stocked pond from nearly every room.
25 Meadowood Ln, Northfield, $3,999,000
On a private lane with over an acre of land adjacent to a forest preserve, this 6-bedroom home features a Chalet-designed rose garden with gazebo and fountains, and an enormous terrace with outdoor kitchen for elevated entertaining. Interior finishes range from timeless marble and wood to unique hand-painted walls and ceiling reliefs, along with imported French and English fireplaces and an oversized stained-glass dome in the foyer.
1091 Johnson Dr, Naperville, $3,750,000
This 6-bedroom estate has been lovingly renovated by the owners to create a luxury home with memorable and enchanting details. The grand roundabout leads to a 4-car garage and porte cochere with a new concrete driveway. The wine room leads directly into the private garden, and the lush grounds can be viewed from almost every room. Five ensuite bedrooms each have a unique feature, like bookcases that lead into a hidden room, and closets that connect behind the walls.
104 Longmeadow Rd, Winnetka, $5,500,000
This striking stone estate sits on a circular paver driveway, with an elegant manor style that recalls the towers and turrets of medieval structures. An open floor plan creates airy spaciousness in the 6-bedroom home, with detailed millwork and cozy fireplaces to ground it in warmth and comfort. The third-floor private library, safe room, and full bath also has two flexible rooms and is accessible by a wood-paneled elevator. There is a Rome-inspired wine cellar with a tasting room in the lower level, and a private island with a fire pit and canoe launch on Lake Longmeadow, features that would make any homeowner feel like a king.
How to Help:
Consider giving to a local housing nonprofit. The below are all previous Make It Better Foundation Philanthropy Award Winners:
- A Safe Haven Foundation provides food, shelter, treatment, medical care, education, job training and job placement to people in crisis and helps them transition from homelessness to self-sufficiency.
- Mercy Housing Lakefront is a nonprofit developer of program-enriched, affordable housing for people in need.
- The Night Ministry provides housing, health care, outreach, spiritual care and social services to adults and youth who struggle with homelessness, poverty and loneliness.
- Housing Opportunities and Maintenance for the Elderly (H.O.M.E) helps seniors remain independent and active in their community by offering intergenerational living opportunities and a variety of citywide support services.
If you’re interested in helping more people have access to design services, you can support the nonprofit Designs for Dignity, which transforms nonprofit environments through pro bono design services and in-kind donations.
If you have the opportunity to join a local housewalk tour of private homes, many partner with nonprofits and local museums, like the Wilmette Historical Museum or Evanston History Center.
More from Better:
- A Double-Height Ceiling Steals the Show in This Chicago Home in North Center
- An Adventurous Designer Breathed New Life into a Greystone Row House in Old Town
- You Said It: How Home Design and Decor Can Support Mental Well-Being
Stephanie Fallon is a freelance writer who has spent her professional career in non-profit adult education, first in adult English literacy at Blue Ridge Literacy and then overseeing interpretation and public programming for the Taubman Museum of Art. She lives in Roanoke, Virginia and writes about visual culture, design, motherhood, and work.
