Hillsboro has historic homes, new development and lake access
Surrounded by greenery, open space and farmland, Hillsboro is a quiet, rural city serving as the county seat of Montgomery County. Century-old homes are scattered throughout the downtown area, where the Historic Courthouse Square often operates as a community gathering place. “Hillsboro has come a long way in the last couple of years, and we still have a lot of things we plan on doing,” says Melissa Smith, economic development and community planner for the City of Hillsboro, who also sells with MCR Realty Professionals. “There has been an increase of businesses that have come to the area, and a lot of development.”
Outside of the city center, Hillsboro offers many housing options with large lots.
Residents love to see travelers visiting their hometown of Hillsboro.
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Single-story homes spanning decades and centuries
Most homes in Hillsboro are found along tree-lined streets with grassy lawns and alleyway access. Traditional single-story homes and bungalows built between the 1900s and 1960s are common close to downtown. The area also has ranch-style homes from the 1960s to the 1980s. These smaller properties cost between $40,000 and $180,000, depending on age and condition. Multistory Victorian homes are also popular, sporting simple exteriors, a steep pointed roof and a front porch. Colonial homes are another option. Prices range from $100,000 to $220,000.
Outside the city limits are larger properties that sit on acreage. Midcentury, ranch-style homes and raised ranches go for $150,00 to $500,000. “We do have housing on the lakes. A lot of people from the Saint Louis area whose boats aren’t big enough for those lakes, they come here for their second homes because its close,” Smith says.
Unique two story homes offer bold housing choices in downtown Hillsboro.
Hillsboro offers a huge variety of homes, such as smaller white washed cottages.
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Staying active at city parks and lakes
Central Park is the city's primary recreational space. It has an all-inclusive playground, three pickleball courts, a basketball court and a field for baseball. Most of these facilities were recent additions from community fundraising in 2024. The Central Park Pool offers daily and seasonal passes. Across the street, Challacombe Park is the site of the historic Challacombe House, which was built by Hillsboro’s first mayor. The area also has a fenced-in dog park and walking paths.
Hillsboro’s proximity to two lakes is a huge draw for outdoor enthusiasts. Lake Hillsboro is about 2 miles northeast of the city and is referred to as “the old lake” by locals. A park area on its northern shoreline has picnic pavilions and a public boat launch. “There is a 10-miles-per-hour speed limit, so it’s more of a leisurely fishing lake,” Smith says. Nearby is the Sherwood Forest Campground, which has over 125 camping sites. The Hillsboro Country Club is also located along Lake Hillsboro and has a private 9-hole golf course. Farther north is Lake Glenn Shoals. Its North Access Area sits adjacent to the Meisenheimer Avenue Bridge, roughly 6 miles away, and is outfitted with two boat launches, a fishing dock and a kayak launch.
Have a picnic or enjoy the sun at Lake Glenn Shoals.
Residents love the all-inclusive playground at Central Park.
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Shopping and dining downtown and along Main Street
Downtown Hillsboro starts at the courthouse square and continues down Main Street. There are dozens of small businesses, gift shops and specialty stores – The Sweet Spot is a candy shop, and The Story Emporium sells books. Hillsboro Garden Family Restaurant is a casual eatery specializing in comfort food. More options are found farther south as Main turns into Vandalia Road. The Smokin Barrel is a newer restaurant serving barbeque. Capri Market is the area’s grocery store. Fast-food options include McDonald’s, Dairy Queen and Hardee’s.
The Hillsboro Farmers Market takes place on the second Saturday of every month during the summer, selling local produce, baked goods and handmade products.
The Sweet Spot in downtown Hillsboro has walls lined with candy and treats.
The Holiday Shop is one of many local retailers along Main Street in Hillsboro.
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Getting educated at Hillsboro public schools
The city is served by the Hillsboro Community School District. Beckemeyer Elementary School earns a B-minus grade from Niche and offers an afterschool program. From there, students attend the B-rated Hillsboro Junior High School. Hillsboro High School receives a B-minus and offers a teaching internship for students participating in the Child Care Career and Technical Education program. For higher education, Lincoln Land Community College has a satellite computer lab in Hillsboro, which is connected to the Litchfield outreach campus.
Hillsboro Junior High School is home to 327 students in grades 6-8.
Hillsboro High School prepares students for their journey to college and beyond.
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Celebrating Hillsboro’s annual community events
Multiple events are celebrated in Hillsboro. The Annual Harvest Market is a festival held at Hillsboro’s Historic Courthouse Square in October, featuring handmade and homegrown products. The event also has live entertainment and a cornhole tournament. Hillsboro’s annual Small Town Christmas sets up a holiday-themed vendor market, petting zoo and carriage rides. “They’ll close downtown off and do a block party, and they’ll have fake snow,” Smith says. There are also contests for cookie decorating and gingerbread house building.
Driving in and around Hillsboro
Hillsboro’s rural landscape requires a vehicle to navigate. Illinois state Route 127 is the city’s main thoroughfare, traveling north and south. The road merges with Illinois state Route 16 in the city, which commuters can use to reach Litchfield to the west and Vandalia in the southeast. Hillsboro Health is the area’s general hospital, located along Tremont Street. The Abraham Lincoln Capital Airport is roughly 54 miles away in Springfield.
Written By
Brittany Bell
Photography Contributed By
Ethan Babor
Video By
Colleen Carey
Interested in learning more about homes in this area?
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On average, homes in Hillsboro, IL sell after 77 days on the market compared to the national average of 55 days. The median sale price for homes in Hillsboro, IL over the last 12 months is $99,900, down 15% from the median home sale price over the previous 12 months.
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Looking to build your own personal lake resort or divide the property for multiple home sites? Look no further than this one of a kind nearly 8 acre, waterfront property, just 1hr from St. Louis. Everything is ready to begin your dream lakefront home on this 1,200 acre lake. Enter your own security gate to your private oasis drive, lined with beautiful oak trees & vista views of Lake Glen Shoals.
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8.76 acres located approximately 2 miles from Glenn Shoals beautiful boating and fishing Lake. Also this property is close to the boat marina and bridge. Deer and turkey roam freely. A 30x12 cabin and 30x26 pole barn are also part of the package! Cabin and pole barn need TLC. (There is a tank for hauling water to the cabin, but is not installed. No septic. 2 large overhead doors on the pole
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Beautiful Lake House with Boat and Jet /Ski docks for sale in Hillsboro, Illinois. Ultra private and offered for sale for the first time in 30 years, this home sits on 2.1 acres located at the end of a private street and adjacent to a peninsula with an additional 5 acres of undeveloped land. Hillsboro Illinois is approximately one hour from downtown Saint Louis and three hours and forty five
Welcome to this charming and inviting 1.5-story home, situated directly across from the junior high and high school and walking distance of Beckemeyer Elementary and downtown attractions. This well-maintained home offers a comfortable and functional layout with plenty of space for everyday living.The main level features a spacious primary bedroom with a walk-in closet and private full
Cattle farm with 68 acres of wonderful pastures for any animals you wish to have. There are several creeks on the property that have never ran dry. Multiple builds that have been used for Cattle, horses, sheep, goats and chickens. Big red barn was built with solid oak and has plenty of room. Smaller barn near the house was built with solid oak as well and has a tackle room for horses. The back of
Welcome to the Bungalow on Main! Step outside your front door and take in the beautiful view of Hillsboro, looking down "Major Hill". This charming 2-bedroom, 1-bath home offers comfortable, easy living and is the perfect choice for a first-time homebuyer, someone looking to downsize, or anyone wanting the convenience of having everything on one level.The home features a newer metal roof,
Dreams do come true! Imagine waking up every day in your beautiful log home, surrounded by nature and all these luxurious amenities! Whether you're playing a round of golf on your private 6-hole course with putting green, taking a refreshing dip in the pool, or enjoying time with your horses, this place has it all! The spacious layout has 4 bedrooms, 4.5 baths, open concept eat-in kitchen/living
This charming 2 bedroom, 1 bathroom home is situated on a spacious 0.47-acre corner lot, offering plenty of outdoor space and room to spread out. Conveniently located just moments from the grade school, it’s an ideal spot for easy daily routines. Inside, you'll find a versatile heated and cooled bonus room that can easily adapt to your needs—perfect for a home office, playroom, or hobby space.
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