Formerly known as “Coffee Creek” when it was first settled, the charming town of Chesterton is home to an array of locally owned businesses and serene parks. “Chesterton is a small town community with a big town atmosphere. The whole downtown area is walkable, people often frequent the town square, and we have great amenities, restaurants, and events,” says Dave Woodson, a local resident and associate broker with Dream Team Agents Real Estate, who has ten years of experience in the industry. It’s no surprise that Chesterton is ranked as the No. 1 spot to buy a house in the Chicago suburbs on Niche, emulating the true definition of a small, bustling town.
Chesterton is quiet community situated within a natural setting in Northern Indiana.
Locally owned shops line the walkable streets of downtown Chesterton.
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Eateries along South Calumet Road
Chesterton’s downtown has a range of locally owned restaurants and shops like Chesterton Toys and Tethan’s Candy & Confections. From Octave Grill with savory burgers to Round the Clock Restaurant with American classics, residents can enjoy various casual and upscale dining options. “Another well-known restaurant and a personal favorite is Lucrezia Café,” Woodson says, serving authentic Italian cuisine. For a drink after work, patrons can frequent the popular Chesterton Brewery for craft beers and cocktails or opt for a glass of wine and charcuterie board at Running Vines Winery. Residents can pick up their groceries and other necessities at the nearby Strack & Van Til, Aldi or Jewel-Osco. Other major retailers include CVS and Hopkin’s Ace Hardware.
Locals shop for toys at Chesterton’s beloved toy store downtown.
Historic downtown Chesterton offers walkable shopping and dining.
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Events in the town square
The town of Chesterton is known for its seasonal Chesterton European Market. The Duneland Chamber of Commerce hosts the market every Saturday from May to October along Broadway and Third Street. Here, residents can support a range of local vendors from across the region while shopping for locally grown produce, baked goods, handmade décor, and more. “There’s also the annual Wine and Beer Fest held in the same market square,” Woodson says. “It brings the whole community together with local restaurants, vendors and residents.”
Single-family homes for every price range
A wide range of home prices and styles are found within Chesterton. Although the town consists primarily of single-family homes, a few condominium and townhouse communities are sprinkled in between. Residential streets showcase a mix of modest ranch-style homes, Split-Levels, Cape Cods, 21st-century Colonial Revivals, and modern traditional houses. On the east side of town, gated communities surround the Sand Creek Country Club, boasting massive properties on spacious lots. Prices can range from the mid $100,000s for quaint bungalows to $1.6 million for large, modern homes near the country club. New subdivisions are continuously popping up, causing the town to expand toward the surrounding farmlands and open fields.
Colonial Revival homes can be found scattered throughout Chesterton.
Distinctive homes with sunrooms appear throughout Chesterton.
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A-rated schools in Chesterton
The Duneland School Corporation serves the town of Chesterton, scoring outstanding ratings on Niche. Students here attend A-rated schools like Brummitt Elementary School for kindergarten through fourth grade and Westchester Intermediate School for fifth and sixth grade. Students then progress to Chesterton Middle School with an A-minus and to Chesterton Senior High School, scoring an A. Chesterton High is known for its wide selection of course offerings, from printmaking and digital design to robotics and carpentry.
Brummitt Elementary School serves Chesterton’s youngest students.
Westchester Intermediate School is home to 462 students grades 5-6 and has an A rating on Niche.
Chesterton Middle School is a top rated school in the area with 908 students.
Chesterton High School offers academics and after-school sports.
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Hiking, golfing and beaching around Lake Michigan
Between Morgan Lake and Billington Lake, Sand Creek Country Club has two beautifully maintained golf courses with 27 holes combined. Besides the golf course, locals can flock to Indiana Dunes National Park and the many sandy beaches along Lake Michigan’s shores. Sports lovers can often be found at one of the numerous sports fields at Dogwood Park, while other smaller parks, like Coffee Creek Park, are an excellent spot for an afternoon picnic. Traveling along South 11th Street leads to Westchester Migratory Bird Sanctuary. On land that was once the local dump, the natural wetland habitat has been restored to provide a haven for migratory shorebirds, or head further south to Coffee Creek Watershed Preserve for an afternoon hike.
The Marquette Trail offers miles of scenic pathways for hikers.
Golfers enjoy 27 holes at Sand Creek Country Club in Chestertoncourse.
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Commutes to Chicago
Nearby Interstates 94, 80, and 90 lead commuters to Chicago, about 45 miles away. Alternatively, locals can head to the South Shore Commuter Rail Line 3 miles away at Dune Park train station. Employees who work in the manufacturing industries along the shores of Lake Michigan are within easy commuting distance. For international travelers, Chicago Midway International Airport is 45 miles away, while the nearest hospital for emergencies and primary care is Northwest Health–Porter in neighboring Valparaiso.
Interstate 94 is the main travel vein running through West Chesterton.
Hop on the South Shore Line and beat the traffic to Chicago.
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Written By
Jeff Stapleton
Photography Contributed By
Jace Hirosky
Interested in learning more about homes in this area?
Reach out to
Brent Wright,
an experienced agent in this area.
On average, homes in Chesterton, IN sell after 60 days on the market compared to the national average of 53 days. The median sale price for homes in Chesterton, IN over the last 12 months is $340,000, consistent with the median home sale price over the previous 12 months.
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