$370,171Average Value$189Average Price per Sq Ft67Homes For Sale
Small town living with big town amenities
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
Richard Tokarz,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Chesterton, IN sell after 55 days on the market compared to the national average of 56 days. The median sale price for homes in Chesterton, IN over the last 12 months is $362,745, up 10% from the median home sale price over the previous 12 months.
Welcome home to this beautiful 4-bedroom, 2.5-bath two-story in the desirable Village of Burns Harbor community! This thoughtfully designed home features an open-concept layout filled with natural light, a spacious kitchen with quartz countertops and stainless steel appliances, and plenty of room for entertaining. Upstairs you'll find generously sized bedrooms including a comfortable primary
NOW OPEN! Introducing the stunning "Driftwood" model, a brand-new two-story home in the desirable Duneland school district. Boasting modern custom cabinetry, a full refrigerator and freezer, a coffee bar, and an expansive island, this move-in-ready property is perfect for those seeking sleek and convenient living. Featuring a main floor bedroom and two additional bedrooms upstairs, as well as a
The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offering just under 2,300 square feet of thoughtfully designed living space. Featuring 4 spacious bedrooms, 3 bathrooms and a spacious 2-car garage, this home perfectly blends comfort, quality and style. Step inside to an open-concept floor plan showcasing hardwood floors, custom cabinetry, a beautiful trim
Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning
Phase 3 is now open and ready for building. Lot 93 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
Move-in ready with built-in upside, this fully remodeled 11/2-story home offers three bedrooms and two full bathrooms. The basement bedroom and bathroom will be completed before closing. Recent improvements include new roof shingles, windows, doors, trim, abundant kitchen cabinets and countertops, whirlpool tub, waterproof vinyl plank flooring throughout, and central air conditioning. Enjoy
Phase 3 is now open and ready for building. Lot 70 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
Phase 3 is now open and ready for building. Lot 88 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
This 1.44 acre lot is located close to the Indiana Toll Road, I-94, the South Shore train station, The Indiana Dunes State Park, and the Indiana Dunes National Park. Across Highway 49 you will find Culver's, AJ's Pizza, Popeye's, Dunkin Donuts, Hilton Garden Inn, Bob Evans, and multiple medical and office buildings.
Phase 3 is now open and ready for building. Lot 71 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
This newly completed duplex was finished in 2024. This exceptional investment property features two spacious units--each offering 3 bedrooms, 3 bathrooms, and a convenient one-car garage. Both sides are currently leased, providing immediate rental income. The main level showcases durable LVP flooring, while the primary suite includes a generous walk-in closet. Quality finishes such as 6-panel oak
Imagine your dream home nestled among the trees on this beautiful 1.36-acre corner lot at 369 Ridgeview Drive. Located in Woodridge Hills, a private Jackson Township community known for its spacious wooded homesites and impressive custom residences, this property offers the rare opportunity to create a home designed entirely around your lifestyle. The generous corner setting provides flexibility
Now available in Sand Creek--currently the only townhouse on the market! Located in one of Northwest Indiana's premier golf course communities, Sand Creek offers beautifully maintained surroundings, mature trees, and an upscale lifestyle just minutes from downtown Chesterton and the Indiana Dunes. This beautifully updated three-bedroom home features a fully remodeled open concept main level and
Phase 3 is now open and ready for building. Lot 69 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
Phase 3 is now open and ready for building. Lot 86 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.
Inside beautiful Coffee Creek is a luxury community like no other. We are ideally situated and near all shopping, dining, and between I-80/90 Toll Rd and I-94. Appointed with numerous luxurious details, ease of living, privacy, and style.
Heat, water, garbage, sewer and cooking gas included with rent. Deer Run is conveniently located within the beautiful town of Chesterton, but is surrounded by woods. Residents enjoy the peace and quiet of nature, while still having the convenience of nearby shopping. Many residents take advantage of the quick access to I 94 and the South Shore Rail line to Chicago.This community features
Quiet location and minutes to South Shore Train, State Place Apartments feature a central location just west of the 49 Bypass, and close to Lake Michigan, shopping and bike trails. Move-in today and see what real hospitality feels like!
The Enclave is a luxurious apartment community nestled in Coffee Creek Center. Our rental properties include one bedroom and two bedroom floor plans. Select floor plans come with garages. Please view the floor plan page on ForRent.com to see what is offered. Experience outstanding amenities and remarkable features paired with all Coffee Creek Center's advantages. Welcome to a place where nature,
Comfortable house 1 half of duplex.2 bedrooms, 1 bathroom, laundry room, kitchen, living room, front porch, front yard and driveway, backyard, 1 shed.Air conditioner and hitting.
*Available 7/25/26 * This 3 Bedroom/2 Bath Ranch home is in a quiet neighborhood in the Duneland School community. This home features: 1.5 car garage, a four season room, a patio, hardwood floors, large fenced-in yard and a finished basement where 1 of the bedrooms and 1 bathroom are located. This home is on a 3/4 acre lot. Fireplaces are not to be used. NO PETS This rental is unfurnished
Welcome home to this beautifully renovated 3-bedroom, 1.5-bath duplex in Chesterton! Enjoy a modern kitchen with stainless steel appliances, brand-new cabinets, butcher block countertops, and cozy built-in booth seating. New LVP flooring runs throughout, and the updated bathroom features fresh tile finishes.Relax on the front deck, take advantage of in-unit washer/dryer, a heated garage, and
Move-in ready 2-bedroom, 1-bath apartment available now at Porter Ridge Apartments in Chesterton. This spacious unit features a private balcony, perfect for enjoying the outdoors. Rent includes water, sewer, and trash, plus a storage locker conveniently located in the laundry room with coin-operated washer/dryer access. Rent: 1,300/month Security Deposit: 1,300 Pets welcome with 25/month fee
Prospective tenants are NOT REQUIRED TO PAY 3rd Party Application fees. ALL applications MUST be submitted via the PMI NWI website. Applications submitted through 3RD PARTY websites/vendors WILL NOT BE ACCEPTED.PLEASE SUBMIT ANY QUESTIONS THROUGH THE "REQUEST A TOUR", "CHECK AVAILABILITY" or other contact options provided.Welcome home to this charming 3-bedroom, 1-bath home in the
- studio apartment- Approximately 682 sq ft- Monthly rent - $100 with water, sewer and trash included- 1-room, 1-bathroom suite with a waiting area- Kitchen area.- Stove and refrigerator.* Situated in the heart of Chesterton, Indiana* Close to major highways and local amenities* Walkable neighborhood with a Walk Score of 71Rental
Prospective tenants are NOT REQUIRED TO PAY 3rd Party Application fees. ALL applications MUST be submitted via the PMI NWI website. Applications submitted through 3RD PARTY websites/vendors WILL NOT BE ACCEPTED.PLEASE SUBMIT ANY QUESTIONS THROUGH THE "REQUEST A TOUR", "CHECK AVAILABILITY" or other contact options provided.Welcome to this inviting 3-bedroom, 2-bathroom home in
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