Highwood · Lake County · IL
Homes for sale in
Highwood.
- Active listings
- 4
- Median list
- $445K
- Avg time on market
- 30 days
- Sold · last year
- 0
Photo: Etombari / Wikimedia Commons (CC BY-SA 4.0)
Active listings
4 homes on the market
About the community
Living in Highwood.
Highwood is a compact, walkable North Shore city in Lake County, wedged between Highland Park to the south and Fort Sheridan and Lake Forest to the north. The city has a population of 5,074 (2020 Census) packed into a footprint of roughly one square mile, which gives the downtown core along Sheridan Road and Highwood Avenue an unusually dense, urban feel for the North Shore. A long-running Italian-American identity, rooted in late-1800s immigration from the Modena region of Emilia-Romagna, shows up in a restaurant strip that locals often call the Restaurant Capital of the North Shore, anchored by places like Buffo's, Del Rio, and Miramar Bistro. Commuters use the in-town Highwood station on Metra's Union Pacific North line, which terminates at Chicago Ogilvie Transportation Center. Elementary students attend Oak Terrace Elementary in North Shore School District 112, and high schoolers attend Highland Park High School in Township High School District 113.
At a glance
5,074 residents
2020 U.S. Census. Packed into a footprint of roughly one square mile, which makes Highwood one of the densest small cities on the North Shore.
Restaurant row
Dense downtown restaurant strip along Sheridan Road and Highwood Avenue, rooted in Italian-American heritage. Locally called the Restaurant Capital of the North Shore.
UP-N Metra in town
Highwood station at 317 Green Bay Road. Fare zone 4 on the Union Pacific North line to Chicago Ogilvie.
Fort Sheridan adjacent
Former U.S. Army post (1887 to 1993) immediately north. The bluff portion is now a 250-acre Lake County Forest Preserve.
NSSD 112 + Township HSD 113
Elementary at Oak Terrace in North Shore SD 112. High school at Highland Park High School in Township HSD 113.
Median income $107,875
Data USA 2024. About 1,937 households averaging two members each.
Combined sales tax 9.00%
Home-rule city. State 6.25 percent plus city 2.00 percent plus special 0.75 percent, effective July 1, 2025.
Property tax rate ~2.69%
Ownwell-reported effective rate. Median annual tax bill around $7,962.
What’s close
Highwood sits on the North Shore of Lake Michigan in southeast Lake County, roughly 28 miles north of downtown Chicago, immediately inland from the Fort Sheridan bluffs.
- Downtown restaurant row
- Concentrated along Sheridan Road and Highwood Avenue. Multi-generational Italian-American restaurants anchor the strip.
- Fort Sheridan Forest Preserve
- 250 acres of bluff, prairie, and a half mile of Lake Michigan shoreline at 117 Sheridan Road in adjacent Lake Forest.
- Highwood Metra station
- 317 Green Bay Road. Fare zone 4 on the UP-N line to Chicago Ogilvie Transportation Center.
- Everts Park
- 111 North Avenue. The city's central public park and festival grounds.
- Highwood Library and Community Center
- 102 Highwood Avenue. Renovated and reopened in December 2023 with bilingual programming.
- Lake Michigan beaches nearby
- Rosewood Beach in Highland Park and Forest Park Beach in Lake Forest are both within a short drive.
What it’s actually like to live here
Daily life in Highwood is shaped by the city's compact, roughly one-square-mile footprint and a downtown that residents can cover on foot. The grid of Sheridan Road, Green Bay Road, and Highwood Avenue concentrates restaurants, small retail, the public library, city hall, and the Metra station within a few blocks, which is unusual for the North Shore and gives Highwood a closer feel to an older streetcar suburb than to its larger neighbors. The Italian-American identity is still active and visible, from the multi-generational ownership of restaurants like Del Rio (a century-old family operation at 228 Green Bay Road) and Buffo's (opened 1977 at 431 Sheridan Road), to the Highwood Bocce Club and the city's annual festival calendar run by Celebrate Highwood.
Historically Highwood developed as the working-class neighbor to wealthier North Shore communities, originally housing soldiers, immigrant laborers, and the workers who staffed nearby estates. That history is reflected in a housing stock of bungalows, two-flats, frame cottages, and small apartment buildings that prices below comparable single-family product in Highland Park or Lake Forest, despite sharing the same Metra line, the same Highland Park High School, and the same access to the Fort Sheridan lakefront. Median household income is $107,875 and median age is 41, with about 1,937 households averaging two members each.
Neighborhoods
Detailed Highwood community pages coming soon.
Browse the listings above. Detailed neighborhood pages with market stats, school info, and lifestyle take-downs land here as we roll them out.
Schools
Districts serving Highwood.
Boundary lines do shift. Always confirm in writing for a specific address before writing an offer.
- D112Grades Pre-K to 8
North Shore School District 112
Schools serving the area
- Oak Terrace Elementary School
Highwood elementary students attend Oak Terrace Elementary at 240 Prairie Avenue in Highwood. Enrollment around 538. The school hosts the district-wide Dual Language program.
- D113Grades 9 to 12
Township High School District 113
Schools serving the area
- Highland Park High School
Highwood high schoolers attend Highland Park High School. District 113 also serves Highland Park, Deerfield, Bannockburn, and Riverwoods.
Around town
What there is to do in Highwood.
A handful of the places people who live here actually use. Not a directory.
- Food & Drink
Del Rio Restaurant
Fourth-generation Northern Italian restaurant at 228 Green Bay Road open since the 1920s.
- Food & Drink
Buffo's
Downtown Italian-American spot at 431 Sheridan Road known for the Double Decker pizza.
- Food & Drink
Miramar Bistro
Gabriel Viti's French-Cuban bistro on Sheridan Road in the heart of downtown Highwood.
- Parks
Fort Sheridan Forest Preserve
250 acres of bluff and prairie with a 1.7-mile Birding Trail Loop along the Lake Michigan bluff.
- Family
Great Highwood Pumpkin Fest
October festival staged at City Hall, Everts Park, and the Metra station lot.
- Culture
Highwood Library and Community Center
Bilingual programming and community events at 102 Highwood Avenue.
Getting around
Commute + transit from Highwood.
MetraUP-N line
- Stations: Highwood
- Terminal: Chicago Ogilvie (OTC)
- Distance: 28 miles to downtown Chicago
DriveBy car
- Routes: US 41 (Skokie Highway) · Sheridan Road · Green Bay Road · IL 22 (Half Day Road, nearby) · I-94 (Tri-State Tollway, west)
- O'Hare Airport: ~29 min
- Chicago Loop: ~43 min
By the numbers
Highwood taxes + market stats.
Property tax rates vary by exact township and assessor district. Confirm per address before pricing a purchase.
Property tax rate
2.69%
effective avg
Sales tax
9.00%
combined
Median sold price
$420,000
MRED · last 12 mo (30 sales)
Median household income
$107,875
ACS
How Highwood got here
A bit of history.
Highwood was platted in the 1860s, briefly carried the name Duluth, and was incorporated in 1887. In July 1888 the village trustees voted to rename the community Fort Sheridan to capitalize on the new U.S. Army post being built immediately north, but postal confusion and resident frustration led to the name being changed back to Highwood in 1894. Construction of the fort and work on the Chicago and North Western Railway drew labor to town, and the population jumped from 451 in 1890 to 1,575 by 1900. Italian immigrants, predominantly from the mountainous Modena area of Emilia-Romagna, settled in Highwood beginning in the late 1800s, with a second wave arriving in the 1920s, many by way of the Bureau County coal-mining town of Dalzell.
By the mid-1950s, Italian-American families owned and operated most of the shops along Highwood's main streets, and the community's Italian cultural footprint, including bocce, festivals, and a deep bench of restaurants, has remained a defining feature. Fort Sheridan operated as a U.S. Army post from 1887 until its formal closure on May 3, 1993, under the Base Realignment and Closure program. The fort's land was subsequently redeveloped, with the 250-acre bluff portion preserved as Fort Sheridan Forest Preserve under the Lake County Forest Preserves, and historic officers' housing converted into a residential historic district.
The questions buyers actually ask
Highwood FAQ
The questions I get most from buyers shopping Highwood. If yours isn't here, text 815-355-0582, same-day reply.
- Where is Highwood, Illinois?
- Highwood is a North Shore city in southeast Lake County, Illinois, located between Highland Park to the south and Fort Sheridan and Lake Forest to the north, about 28 miles north of downtown Chicago.
- How big is Highwood?
- The 2020 U.S. Census recorded a population of 5,074 residents in a city footprint of roughly one square mile, which makes Highwood one of the densest small cities on the North Shore.
- Why is Highwood known for restaurants?
- Italian immigrants from the Modena region of Emilia-Romagna began settling Highwood in the late 1800s, and by the mid-1950s Italian-American families owned and managed most of the businesses in the downtown commercial strip. The restaurant concentration along Sheridan Road and Highwood Avenue, including long-running places like Del Rio and Buffo's, grew out of that heritage.
- What schools serve Highwood?
- Elementary students attend Oak Terrace Elementary in North Shore School District 112, and high schoolers attend Highland Park High School in Township High School District 113.
- Does Highwood have a Metra station?
- Yes. The Highwood station at 317 Green Bay Road sits on Metra's Union Pacific North (UP-N) line in fare zone 4, with trains running to Chicago Ogilvie Transportation Center.
- What happened to Fort Sheridan?
- The U.S. Army post operated from 1887 until it was closed on May 3, 1993, under the Base Realignment and Closure program. The bluff portion was preserved as the 250-acre Fort Sheridan Forest Preserve, and the historic officers' housing was converted into a residential historic district.
- How does Highwood housing compare to Highland Park or Lake Forest?
- Highwood's housing stock leans toward bungalows, two-flats, and smaller frame homes, and typically prices below comparable single-family product in Highland Park or Lake Forest, despite sharing the same Metra line, the same Highland Park High School, and the same Lake Michigan access at Fort Sheridan Forest Preserve.
- What are taxes like in Highwood?
- Highwood is a home-rule municipality with a combined sales tax rate of 9.00 percent as of 2026 (6.25 percent state, 2.00 percent city, 0.75 percent special). The effective property tax rate is about 2.69 percent per Ownwell, with a median annual tax bill of $7,962.
Nearby
Towns next to Highwood.
If you’re cross-shopping the area, these are the places that border Highwood.
Your local agent
Joe knows Highwood
Most agents will list anything. I focus on the communities I actually know, and the details that determine resale value here aren't in the MLS write-up: which lots back to open space, which streets carry the most consistent demand, which floor plans buyers ask for by name, and what each HOA actually covers.
When you're ready to tour or list, you want someone who's walked the streets, talked to the residents, and read the last 50 closed comps in this market specifically. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Lives in McHenry County
- Local specialist
- Highwood specialist
- Honest local market take
- Brokerocity
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
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