Highwood Overview

The city of Highwood is a unique and vibrant community on the shores of Lake Michigan, about 30 miles north of Chicago. Sitting atop the Skokie ravine, Highwood is located at the highest point between Chicago and Milwaukee. Nearby Metra lines connect Highwood with the city and the southern parts of Wisconsin, making the area an ideal place for commuters to both Chicago and Kenosha. Highwood also provides easy access to Milwaukee via US-41.

10 Highwood Homes For Sale

Showing 1 - 10 of

Listed 2 days ago

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$289,900 - 2 bed/2 bath

430 Lake View, Highwood IL, 60040 #2B

Suburban Condo

Listed 6 days ago

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$1,200,000 - 5 bed/4.2 bath

46 Holabird, Highwood IL, 60040

Suburban Home

Listed 20 days ago

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$399,000 - 2 bed/2 bath

25 Ronan, Highwood IL, 60040 #104

Suburban Condo

Listed 21 days ago

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$750,000 - 4 bed/2.1 bath

44 WESTOVER, Highwood IL, 60040

Suburban Home

Listed 31 days ago

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$358,000 - 4 bed/2 bath

416 N Central, Highwood IL, 60040

Suburban Two to Four Units

Listed 61 days ago

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$275,000 - 2 bed/2 bath

500 Lake View, Highwood IL, 60040 #2A

Suburban Condo

Listed 195 days ago

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$325,000

27 Prairie, Highwood IL, 60040

Suburban Land

Listed 224 days ago

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$350,000 - 4 bed/2 bath

226 Evolution, Highwood IL, 60040

Suburban Two to Four Units

Listed 266 days ago

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$725,000 - 11 bed/4 bath

235 North, Highwood IL, 60040

Suburban Two to Four Units

Listed 888 days ago

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$599,000

105 Prairie, Highwood IL, 60040

Suburban Land

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Highwood real estate includes several type of properties. Highwood homes are high-end and mid-century modern single family homes, in-town bungalows, apartments, townhomes, luxury condominium developments, and many other types

Highwood History

The Highwood suburb is a unique, vibrant, growing community on the shores of Lake Michigan, about 30 miles north of Chicago. It was founded in 1887 in conjunction with the establishment of Fort Sheridan and gradually grew around the fort. For several years at the beginning of the 20th century, the Highwood suburb was defined by its highly utilized Chicago North Shore and Milwaukee Railroad and its population of Italian immigrants—while the railroad is no longer active, today the community still boasts some of the area’s best purveyors of Italian cuisine. Highwood doubled in size in 1993 after the active duty section of Fort Sheridan was closed and some of its property annexed by the town.

Dream Town Knows Highwood

As suburban experts, Dream Town has successfully sold properties in Highwood. Dream Town holds a well-earned reputation for its impressive sales volume and dedication to personal, attentive service. Benefit from the Dream Town advantage when selling your Highwood home. Utilizing state-of-the-art technology, Dream Town drives more sales than any other Chicago brokerage.

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