$555,073Average Value$273Average Price per Sq Ft3Homes For Sale
Highwood is a diverse community with a lively downtown district
Named for its status as the tallest point between Chicago and Milwaukee, Highwood is a North Shore suburb known for its established downtown district. “It’s a community, with bars, restaurants and entertainment,” says Mike Del Monte, a broker with Coldwell Banker Commercial, who has more than 40 years of selling experience in Chicago’s North Shores. The suburb’s history has long centered around diversity, from the Irish and German immigrants working on the railroad during the 1800s, to the Northern Italian stonemasons and landscapers who sought work on nearby estates by the early 20th century. Generations of immigration formed a vibrant dining scene and a mix of cultures. "It's a small community with multifaceted residents," Del Monte says.
Highwood’s friendly character shines throughout with a welcoming community.
Highwood’s water tower stands as a familiar landmark near the downtown district.
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Waukegan Avenue and Green Bay Road are hubs for local dining
Dozens of eateries line Waukegan Avenue and Green Bay Road, where patrons fill outdoor dining spaces along the sidewalk or bars to enjoy live music. “There are a lot of locally owned old-school Italian places, like Maria’s Italian Bakery & Caffe,” Del Monte says. The homey spot sells classics like chicken vesuvio and cannoli. He also notes that the culinary scene has diversified beyond just Italian fare. “There’s Peruvian, Mexican and a very good French restaurant, Froggy’s French Café.” The latter has served the area since 1980. The community has several international grocers like Poeta’s Italian Food Mart and La Union Super Market. Sunset Foods offers a broader selection a couple of miles south. Target on Skokie Valley Road covers retail needs close to home, and Hawthorn Mall, 9 miles away, features over 120 stores.
Poeta’s Italian Food Mart provides international groceries in Highwood.
Target on Skokie Valley Road provides nearby retail options for Highwood.
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A mix of vintage cottages, midcentury styles and newer construction
The community has narrow streets flanked by mature maple and oak trees, providing shade for sidewalks and homes. These houses range from late 19th-century workers' cottages to recently built New Traditional styles. “Most of the housing stock was built during the mid-20th century,” Del Monte says. “It’s got that old-timey district feel to it, and it's more affordable than surrounding neighborhoods like Lake Forest Highland Park.” Highwood’s median sales price for single-family homes is $410,000, significantly lower than Highland Park's median of $780,000. Homes needing repair start at around $200,000, while larger, custom residences can sell for just under $2 million. Townhouses are also available and range in price from $625,000 to $890,000. Highwood supports a relatively even mix of renters and owners.
Vintage cottages remain common in Highwood’s residential areas.
New construction homes appear throughout evolving Highwood neighborhoods.
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Highland Park High School offers dual credit courses
Wayne Thomas Elementary receives an A from Niche, and Northwood Junior High has an A-minus. Highland Park High, rated A-plus, offers dual credit courses at Lake County High School Technology Campus in Grayslake. Students can take classes ranging from automotive services and culinary arts to cybersecurity.
One option for Highwood students is Wayne Thomas Elementary, rated A on Niche.
Highwood students grades sixth through eighth can attend the A‑minus rated Northwood Middle School.
Highwood students can take dual enrollment classes at Highland Park High School.
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Recreation includes local parks, a nearby preserve and more
Residents have access to several recreation areas in and around the community. Everts Park has open green space for picnics and a recently renovated playground. Del Monte says Sheridan Forest Preserve is a popular place to spend time outdoors. There are a series of walking trails that wind through the park and down to Lake Michigan’s sandy shoreline. Highwood Recreation Center hosts year-round programming, including youth sports and fitness classes like Zumba and yoga. Other nearby attractions include the Chicago Botanic Garden and Sunset Valley Golf Club, which has an 18-hole course open to the public.
Everts Park features green space and a playground near downtown Highwood.
Fort Sheridan Forest Preserve offers lakefront trails just east of Highwood.
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Community traditions thrive at Highwood Days and Everts Park
Though seasonal events bring neighbors together throughout the year, Highwood Days stands out as a community staple. The long-running annual tradition occurs downtown over four days in mid-July, featuring food vendors, carnival rides and more. Every Wednesday evening from early June through late August, Everts Park fills for Highwood Evening Gourmet Market, which serves up live music, drinks and features over 60 vendors selling fresh goods and handmade gifts.
Highwood Evening Gourmet Market features live music and delicacies from local restaurants each summer.
The Great Highwood Pumpkin Festival brings fall activities to downtown each October.
28 Mile Distilling Company often anchors festive events in downtown Highwood, like the Elf Invasion Pub Crawl.
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Getting around on U.S. Route 41 and Interstate 94
U.S. Route 41 is the area’s main north-south highway. Residents can use the route to access I-94, which leads to Chicago, 30 miles south. Metra’s Union Pacific North Line passes through Highwood Station, offering 50-minute rides into downtown. Pace buses service stops along main roads. The nearest commercial flights take off from Chicago O’Hare International Airport, 20 miles south. Endeavor Health Highland Park Hospital is closer to home on Park Avenue.
Endeavor Health Highland Park Hospital offers nearby medical care for Highwood.
Air travel for Highwood is available at Chicago O’Hare International Airport 20 miles south.
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Written By
Matthew Simmons
Photography Contributed By
Michael Carey
Video By
Vladislav Sedykh
Interested in learning more about homes in this area?
Reach out to
Nancy Karp,
an experienced agent in this area.
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On average, homes in Highwood, IL sell after 17 days on the market compared to the national average of 53 days. The median sale price for homes in Highwood, IL over the last 12 months is $410,000, down 17% from the median home sale price over the previous 12 months.
Detached single family with over 2,400 square ft with a once in a lifetime layout. 45 foot backyard that lays out directly from the kitchen. 4 bedrooms or an office. Open layout. Pre-construction pricing. Pictures are architectural renderings of possibilities and potential options to be decided with builder. - $15,000 of free options if under contract by 2/15/2026
Charming Home Steps from Downtown Highwood! Welcome to this inviting 3-bedroom, 1-bath home located just steps from vibrant downtown Highwood. Featuring a large kitchen with an attached dining room, this home offers the perfect blend of comfort and convenience. The partially finished basement provides additional living space or room to grow, while the 2-car garage adds valuable storage and
Builder's Dream Opportunity! Seize this prime Highland Park lot - a 7,900 sq. ft. blank canvas ready for a stunning 3,085 sq. ft. home! Perfectly located near Highland Park and Highwood's vibrant festivals, top-rated restaurants, and thriving businesses, this property offers the best location. With utilities already in place from a previous home, you can hit the ground running on your next
Melissa Newman@properties Christie's International Real Estate
Proposed custom home well below market value for a limited time. First floor owners suites and ranch plans now available. Won't last long. Act now and receive up to an additional $15,000 of free upgrades.
BUILD YOUR DREAM HOME ON THIS GREAT LOT IN SOUTHEAST HIGHWOOD! LOT HAS A WATER LINE INSTALLED AND AN EASEMENT FOR OTHER UTILITIES. GREAT LOCATION, WALK TO EVERYTHING IN BOOMING HIGHWOOD! ZONED R2 (residential). BUILD UP TO A 2,864 SQUARE FOOT SINGLE FAMILY HOME ON THIS LOT.
Cory Albiani@properties Christie's International Real Estate
Beautiful expansive lot with mature foliage located on the charming Hill Street cul-de-sac. Four levels of living spaces. Stellar location moments to parks, metra and north shore entertainment. The home is ready for updating allowing the buyer to create perfection at this gorgeous location. Room sizes are approximate. Bank Owned. Hold harmless and release of liability document must be signed
Harold Blum@properties Christie's International Real Estate
Nestled between affluent Lake Forest and Highland Park, Arrive North Shore® is located in vibrant downtown Highwood and offers a unique opportunity to live on Chicago's scenic North Shore, just minutes away from Downtown Highwood shops and restaurants and Fort Sheridan Metra Stations. Our newly restyled apartment homes are equipped with deluxe kitchens, generous living spaces, and private patios.
This two-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine
Welcome to Bloom Street Townhomes at 425 Bloom St — luxury, new-construction townhomes in east Highland Park. Each home spans over 2,000 sq ft and features 3 bedrooms plus office/flex space, 2.5 baths, private entrance, and an attached 2-car garage. Interiors showcase designer finishes, vaulted ceilings, large windows, smart Nest thermostats, and in-unit laundry. The community includes a
Luxury Living in the Heart of Highwood! This stunning 2-bedroom, 2-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully
This three-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine
This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
This two-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,
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