Highwood: The North Shore's Best-Kept Secret — Authenticity, Value, and Remarkable Access

In a corridor defined by established wealth and centuries of residential character, Highwood occupies a genuinely different position. Small — fewer than 5,500 residents — and bounded by Highland Park to the north and south, it is a village that has always operated on its own terms. Where its neighbors project quiet affluence and manicured restraint, Highwood projects energy, authenticity, and something that the North Shore's more exclusive enclaves have largely lost: genuine walkability, a street-level dining culture of serious quality, and a community that actively mixes rather than self-sorts.

The Restaurant Scene: Disproportionately Excellent

Highwood has long been known across the North Shore and beyond for its restaurant concentration. The Green Bay Road corridor hosts an improbable number of acclaimed restaurants for a village its size — from Italian family institutions that have been feeding the North Shore for generations to newer chef-driven concepts that draw serious diners from Chicago. For residents, the dining scene functions as a daily amenity, not a destination drive.

The Market: North Shore Access, Exceptional Value

At a median home price of $485,000, Highwood offers the most compelling value proposition on the North Shore for buyers who want the lifestyle — access to Highland Park High School (District 113), proximity to the lakefront, and a Metra commute to downtown Chicago of under an hour — at a price point that is simply unavailable in any adjacent community. Days on market run just 28 — the fastest on the entire North Shore — because motivated buyers recognize the value and move decisively when inventory appears. Year-over-year appreciation of 4.2% has been steady and sustainable.

Fort Sheridan: History Transformed Into Residences

The former Fort Sheridan military reservation — decommissioned in 1993 and converted to mixed residential use — sits on Highwood's northern edge and spills into Highland Park. The conversion preserved the post's remarkable collection of late-19th century H.H. Richardson-influenced buildings, creating a historic district unlike anything else in the Chicago metropolitan area. Properties within Fort Sheridan offer architectural distinction, generous lot sizes, and a neighborhood character that feels genuinely singular.

Who Buys in Highwood

Highwood draws a particular buyer: sophisticated enough to see what the village offers that the North Shore's more expensive addresses don't, and pragmatic enough to value the combination of access and value. Young families entering the North Shore market, downsizers from larger Highland Park homes who want walkability and restaurant proximity, and buyers priced out of neighboring communities who refuse to leave the corridor — these are Highwood's buyers, and they tend to be enthusiastic advocates for the village once they arrive.

Considering Highwood? Patrick Milhaupt has deep knowledge of the Highwood market and can identify opportunities across every price tier, including pocket listings before they reach MLS.