On the Market: 4 Hot Chicago and North Shore Properties With Stunning Outdoor Spaces

If there were ever a time to invest in your dream home, it’s during a pandemic. Despite the easing of some restrictions this summer, most of us are still spending an unprecedented amount of time at home. With limitations on beaches, public pools, and even trips to the lake if you’re headed over the border to Wisconsin, plus an increasing number of Chicago-area schools announcing full remote learning, it’s never been more important to prioritize the space you call home.

Top Chicagoland realtors are calling Covid-19 merely a “blip” for a strong real estate market. And, just last week, Winnetka saw the sale of a second home for more than $8 million after no Winnetka homes sold for more than $5 million last year. “It’s an exciting time on the North Shore,” says realtor Kelly Rynes, who notes that demand is driving some home prices up right now.

Whether you’re looking for a suburban property with room to roam or a city abode that puts an urban spin on outdoor access, these five Chicago and North Shore hot properties combine top-tier interior amenities with breathtaking outdoor spaces.

887 Private Road, Winnetka


887 Private Road, Winnetka. Photos by Belen Aquino; design by Yoanna Kulas.

We can’t stop gushing over this breathtaking Belgian-style farmhouse, and we’re not the only ones. The American Institute of Architects named this tranquil, modern home the number-one residential design in Illinois and Sub Zero named the De Giulio-designed kitchen the number-two kitchen in the world. Tucked down a private lane in Winnetka, an outdoor patio takes the comforts of the indoors outside while a first floor suite has its own private garden. A meditation space, exercise room, massage treatment room, and infrared sauna, a rec room with a bar, and a media room all ensure plenty to of space to stay centered and engaged at home.

1521 N. State Pkwy, Chicago


Photo courtesy of Ames Group Chicago, Engel & Völkers Chicago

This 1894 Gold Coast home, designed by architect George Maher, boasts 9,700 square feet of sophisticated details like plaster moldings, ornate paneling, and stylish herringbone floors. A Beaux-Art–style white limestone facade draws the attention of passersby, while a terraced penthouse roof deck, landscaped and featuring a built-in grill and outdoor fireplace, provides a private outdoor escape right in the heart of the Gold Coast. Inside, six bedrooms and eight bathrooms include a master suite with a fireplace, marble bath and custom dressing room.

203 Sheridan Road, Winnetka


VHT Studios

With 100 feet of private sand beach right outside your door, who needs a vacation? This one-acre property on Winnetka’s gorgeous lakefront features sprawling front and back lawns, plus balconies and terraces offering breathtaking views of Lake Michigan. The 5-bedroom, 4.5-bath home is perfect for a family looking for an escape right in their own backyard.

2414 West Erie Street, Chicago


This spacious custom home in West Town features a whopping five outdoor spaces, including a rooftop kitchen and lounge area. Five bedrooms, three baths, a gym, and a fully finished basement provide plenty of places to spread out inside too.

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Editor in Chief of Better, Brooke Geiger McDonald is a Chicago native who has worked for O, The Oprah Magazine and Shape magazine in New York and in book publishing in London. Back home in Chicago, she’s outnumbered by her husband and two sons, and the four of them are certifiable Disney and Star Wars fanatics, always counting down the days to their next Disney vacation. Her favorite nonprofits to support include The Walt Disney Birthplace in Chicago and organizations focused on environmental conservation and combatting climate change, such as the Environmental Defense Fund and Shedd Aquarium. Follow her on Instagram: @brookegmcdonald and Twitter.

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