$547,998Average Value$285Average Price per Sq Ft4Homes 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
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On average, homes in Highwood, IL sell after 15 days on the market compared to the national average of 57 days. The median sale price for homes in Highwood, IL over the last 12 months is $410,000, down 18% from the median home sale price over the previous 12 months.
Exceptional investment opportunity in the heart of downtown ! Perfectly situated on a quiet one-way street within the city's vibrant business district, this beautifully maintained and newly remodeled three-flat has been thoughtfully updated from top to bottom. Each unit showcases stylish new kitchens and baths with modern cabinetry, quartz countertops, updated lighting and fixtures, new tile,
Discover an incredible opportunity in the heart of downtown Highwood! This 3-bedroom, 2-bath home offers unbeatable location and flexibility, perfect for both investors and owner-occupants. The second floor features 3 spacious bedrooms and a full bath, providing a comfortable and functional living space, while the main level offers great potential to customize or enhance to your vision.
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
TOTALLY UPDATED in 2025 and MOVE IN READY RANCH with a finished basement and two full bathrooms! The main level features an open kitchen with space for a breakfast or dining table and home office desk, a comfortable living room, and two bedrooms served by a full bath with a walk-in shower. The finished lower level offers an additional full bath with tub, laundry area, and a bedroom with an
Beautifully updated historic 4-bedroom home in sought-after Fort Sheridan, offering the perfect blend of charm and thoughtful updates. Step into an expansive foyer that opens to a spacious great room featuring a gas fireplace and stunning hardwood floors. The eat-in kitchen opens to a lovely patio-ideal for morning coffee while enjoying the scenic surroundings Fort Sheridan is known for. The
Susan Brown Burklin@properties Christie's International Real Estate
Fully rehabbed brick 3-flat on an oversized double lot in the heart of Highwood-an exceptional, turn-key investment opportunity with strong, stable income already in place. This property features two expansive 3-bedroom, 1-bath units (Unit 1 rented at $2,950 and Unit 2 at $2,755) plus a 1-bedroom, 1-bath unit (Unit 3 rented at $1,450), all leased through March 2027 for immediate cash flow and
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
This fully renovated ranch in Highwood blends clean design with thoughtful upgrades throughout, including a newly finished basement and major 2024-2025 improvements. A bright four-season front porch sets the tone on entry, offering flexible space for a sitting room, office, or mudroom. Inside, the open living and dining area flows naturally into a crisp white kitchen with quartz countertops,
Situated on a tranquil cul-de-sac just off the shores of Lake Michigan, in Highland Park's prestigious and historically rich Fort Sheridan neighborhood, this architectural masterpiece by renowned architect Samuel G. Footlik seamlessly blends timeless craftsmanship with sophisticated modern updates-just steps from the lakefront, scenic trails, and pristine beaches. A grand foyer with a sweeping
Welcome to 2648 Western Ave, an exceptional opportunity in one of Highland Park's most desirable locations. Set on a beautiful half-acre lot, this classic brick ranch with a walk-out lower level offers the perfect canvas to create your ideal home or a compelling value-add investment. With 5 bedrooms and 3.1 bathrooms, the home features a functional, flexible layout with strong bones and abundant
Aaron Walsh@properties Christie's International Real Estate
Discover the perfect blend of vintage charm and modern comfort in this spacious Colonial, just blocks to the shores of Lake Michigan. Warm hardwood floors guide you through living spaces, including a sun-drenched dining room featuring classic dentil crown molding and French doors that lead to a serene sunroom. The living room has a wood burning fireplace and there is an office/playroom off the
Welcome to Highpoint Highwood Station 440 modern 1, 2 & 3-bedroom apartments for rent in Highwood, IL. Enjoy updated kitchens, in-unit laundry, and walkable access to downtown Highwood, Green Bay Road, and Fort Sheridan. Our pet-friendly community offers convenient living near Highland Park, boutique dining, and local shops. Schedule your tour today.
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.
Welcome to this beautifully situated apartment home nestled on a quiet, tree-lined street in one of Highland Park's most desirable neighborhoods. This spacious property offers a bright, comfortable layout with generous living areas, abundant natural light, and timeless character throughout.The location can't be beat just minutes from downtown Highland Park, 1/2 mile to Metra & Lake
Discover luxury living at 425 Bloom St Townhomes, a beautiful community of spacious 3 bedroom, 2.5 bathroom townhomes totaling 2,000 sqft. Each home offers a bonus office/flex space, perfect for remote work or extra living area. Enjoy the convenience of a private entrance and an attached 2-car garage. Nestled within a charming courtyard setting, this pet-friendly community is located in the
Property Id: 2434416Renovated 4BR Brick Home in Heart of HighwoodThis solid brick 4-bedroom, 2-bathroom home has been updated and is move-in ready. Located just steps from Highwood’s restaurants, the Metra, and the lake, it offers a great balance of neighborhood charm and modern reliability.The SpaceThe house features a functional layout with a bright living room,
Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-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
Beautiful unfurnished 3 bedroom (or 2 bedroom + office) apartment in Highwood. 1st floor of 2 unit building. Walk to town and train. Laundry + storage in basement. 1 garage spot + 1 parking spot. Yard and patio. Tenant pays electric and cable. Available June 15th. $1950 per month. $1950 security deposit + 1 month rent required at lease signing. No pets.
Lovely rehabbed 3 bedroom apartment ideally located close to all the action in the vibrant village of Highwood. This inviting home features a modern kitchen with granite countertops, gas cooking, and ample storage. Both bedrooms are generously sized and offer flexibility for a variety of needs, while the bonus space is perfect for a dedicated home office.The beautifully updated bathroom features
Charming 1st Floor 2-Bedroom, 1-Bath Apartment Available June 1st. This Sun-Filled, Well-Maintained Unit Offers Spacious Rooms With A Bright & Welcoming Atmosphere. New Refrigerator, Stove, Exhaust Fan, Dishwasher + New Paint Thru (2025). The Large Kitchen Boasts Abundant Cabinet Space & A Walk-In Pantry/Mudroom For Added Convenience. The Full Bath Features A Tub/Shower Combo & Dual Sinks.
Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-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 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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