Highwood Real Estate

Highwood Real Estate Market

Highwood is the North Shore's best-kept secret. Nestled between Highland Park and Fort Sheridan on the shores of Lake Michigan, Highwood is a small, culturally rich city with a genuine character all its own — and a real estate market that represents some of the best value on the entire North Shore. For buyers priced out of Highland Park or looking for more home for their budget in a lakefront community, Highwood is a compelling answer.

Home prices in Highwood range from approximately $350,000 for smaller single-family homes and condos to approach $900,000 for larger, updated properties. The median sale price typically falls between $400,000 and $600,000, making Highwood the most accessible lakefront community Lyn Wise Group serves — and one that is increasingly attracting buyers who recognize the value it represents.

About the Highwood Real Estate Market

Highwood's market is driven by its unique combination of affordability, location, and lifestyle. Buyers here include first-time homeowners stepping onto the North Shore for the first time, investors attracted by the rental market, and buyers who want walkable access to one of the best restaurant scenes in the suburbs without paying Highland Park prices. The market moves at a moderate pace, giving buyers time to evaluate while rewarding sellers who present well and price strategically.

Highwood Neighborhoods

Highwood's compact footprint means most neighborhoods are within easy walking distance of the downtown area along Sheridan Road and Green Bay Road — home to a remarkable concentration of restaurants that have made Highwood a dining destination for the entire North Shore. The areas closest to the Fort Sheridan border include some of Highwood's newer and larger homes, while the historic downtown core features a mix of older bungalows, two-flats, and converted properties. Lake Michigan is minutes away, with access through Highland Park's lakefront parks and beaches.

Schools in Highwood

Highwood elementary and middle school students are served by North Shore School District 112 — the same district as Highland Park — and high school students attend Highland Park High School in Township High School District 113. Shared school districts with Highland Park is a significant value driver for Highwood buyers who want top-rated public schools at a lower entry price.

Why Lyn Wise Group for Highwood Real Estate

Lyn and Bob Wise are based right next door in Highland Park and have deep familiarity with the Highwood market — including the nuances of school district boundaries, the neighborhoods that are appreciating fastest, and how to help buyers navigate a community that is genuinely undervalued relative to its surroundings. If you're curious about what Highwood has to offer, we'd love to show you.

Contact Lyn Wise Group for a Highwood real estate consultation: (847) 624-6143

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Contact Lyn Wise Group for Highwood real estate consultation.

Work With Us

Lyn Wise Group represents buyers and sellers in Chicago, Highland Park, Highwood, Deerfield, Northbrook, Glencoe, Lake Forest, Glenview, Buffalo Grove, Winnetka, Wilmette and other surrounding suburbs with data-driven North Shore and North Suburban real estate expertise. We specialize in hyper-local expertise, and personalized client service. We have exceptional relationships with local agents and often hear about properties before they come on the market.