Chicago North Shore Real Estate and Neighborhoods: A Glimpse of Highwood

Highwood is a cool and interesting community on the North Shore. It is located between Highland Park and Lake Forest. Ft. Sheridan and Lake Michigan are located to the east. It is known as the “Entertainment District of the North Shore”. It has easy accessibility to Rt. 41 and the Tri-State Tollway, off Rt. 22 (Half Day Rd.). There are two commuter train stations, Highwood and Ft. Sheridan. There is a vibrant downtown with a number of independent boutiques, restaurants, and nightclubs/lounges. Highwood, to me, has always been about the bars and the restaurants! It has many entertainment events, including Garlic Fest, Bloody Mary Fest, Pumpkin Fest, Farmer’s Market and Highwood Days.

It is rumored that Tony Bennett always goes to one restaurant in Highwood when he is performing at Ravinia. Some of the best Italian food in the metropolitan area can be found here, from old school (grandmas Italian red sauce), a new Italian restaurant (Disotto) to French (Froggy’s), contemporary bistros, Miramar, several Mexican restaurants and more. There are small music venues, and neighborhood taverns with affordable cocktails. I also have it on very good authority that there is a new brewery opening soon. Eve and I will be at the grand opening. Can’t wait for the IPA and Stout. I will do my best investigating and let everyone know how it is. Highwood is also home to Skokie Valley Laundry and Dry Cleaners. You can see their trucks from the far south suburbs to the Wisconsin border. They are the premier hand laundry and dry cleaner in the metropolitan area. They are 70 years young and still going strong.

I was a youth football coach in Highwood for 3 years. We resurrected the Highwood Indians youth football team with great success. I really enjoyed working with Evon at the youth center, which provides an outlet for the local kids and community events.

Highwood real estate has a distinct architectural character. Many of the houses are 1920’s bungalows and turn-of-the-century 1.5 story and two-story properties. Highwood has good quality, affordable houses in relation to other North Shore areas. Ft. Sheridan is east of Highwood. It was the former Army training base. It has been converted to upscale condominiums, townhomes, and newer residence. There are still some old officer’s quarters for sale near the lake. During the conversion my father-in-law was looking for a new condominium. We asked if he was interested in looking in the Fort. He politely declined as he was in basic training there before WWII.

When thinking of Highwood, I think of Bocce. One of the few Bocce clubs in the area is located in Highwood. It hosted the international Bocce tournament a few years ago. My father came in from Cleveland to attend the tournament. He had such a great time and still talks about it.

Let me take you on a tour of Highwood to find your dream home,or if you want to know what to know the sale’s price of your neighbors’ homes, contact me.  For over 33 years, we have been the Realtor of choice from Chicagoland to Dairyland! 847-409-0850 or delmonte@delmontehomes.com

Ciao! Ciao!

Mike