$369,215Average Value$192Average Price per Sq Ft64Homes 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
David Speckman,
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 $360,000, up 10% from the median home sale price over the previous 12 months.
*Updated Interior pictures coming soon* Move-in ready and thoughtfully updated, this all brick 3 bed/1 and 3/4 bath Chesterton home offers flexible living space and a clean, well-maintained feel throughout. The main level features a bright and inviting layout with updated finishes. The finished lower level provides additional living space. An egress window adds flexibility for guest space, home
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
Welcome to this brand new construction home in the Duneland School District! The main level features an open kitchen and living area, flowing into a dining room with high ceilings, recessed lighting, and durable luxury vinyl plank and luxury vinyl tile flooring throughout, along with a main floor laundry room and convenient powder room. Upstairs offers three bedrooms and two full bathrooms. A
Freshly updated Split-level located just outside Chicago & minutes from Lake Michigan. Set in the desirable Porter Cove community you'll instantly love this open concept home complete with brand new carpet, just painted, & updated bathrooms making it turn-key. 3 bedroom & 2 baths on upper level with main level offering living room, dining/flex room, & large eat-in kitchen leading out to the
Your Dream Home Awaits on a Quiet Cul-de-Sac! This stunning two-story with full basement offers everything today's buyers crave-- brand new carpet, cathedral ceilings, skylights, a cozy fireplace, and a master suite built for relaxation. Step out onto your oversized deck with pond views and enjoy the peace and privacy you deserve. 4 spacious bedrooms | 2.5 baths | 2.5-car garage- with a home
Located in the desirable Sand Creek community, this stunning 4-bedroom, 3-bath home seamlessly blends luxury, comfort, and modern updates. The home features LED lighting throughout, hardwood floors, crown molding, and a stone fireplace just five years old. The main floor and upper level both include convenient laundry areas, while the huge primary suite offers a tray ceiling, brand-new carpet,
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
Discover the possibilities with this beautiful 3.38-acre parcel. Located in the highly desirable Jackson Township and within the award-winning Duneland School Corporation, this property offers the perfect opportunity to build the home of your dreams. Enjoy the space, privacy, and peaceful surroundings while still being just minutes from major highways and the amenities of Chesterton. With endless
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.
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
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
Welcome to the undeveloped phase of the desirable Hunters Glen Subdivision in Porter, Indiana--an excellent opportunity for builders or investors. This offering includes 8 spacious, wooded lots plus 2 additional parcels designated for roads and drainage infrastructure. Nestled in a peaceful, natural setting, this subdivision combines privacy with convenience. With easy access to I-94 and the
Discover the possibilities with this beautiful 3.38-acre parcel. Located in the highly desirable Jackson Township and within the award-winning Duneland School Corporation, this property offers the perfect opportunity to build the home of your dreams. Enjoy the space, privacy, and peaceful surroundings while still being just minutes from major highways and the amenities of Chesterton. With endless
HOME SWEET HOME! This Exceptional 2011 Built Open Concept 3 Bed, 3 Bath 2-Story Home with a FINISHED BASEMENT, 2.5 Car Garage, and Situated on Just Over an Acre is a MUST SEE! From the moment you enter, you'll appreciate the 9' ceilings, expansive feel, and thoughtfully designed layout that seamlessly blends everyday comfort with elevated living. The formal living room offers a refined space for
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.
Maintenance free 3 bedroom/2.5 bath townhome for rent near the Indiana Dunes. All new paint and carpeting throughout. Over 1700 sq ft of living space. Primary suite has private bath and walk-in-closet. 2 car garage, new driveway, and corner lot overlooking neighborhood park. Enjoy the convenience and comfort of maintenance free living with provided lawn care and snow removal. Just minutes to
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
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
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,
This maintenance free, 2-story condo unit with its 2+ bedrooms has over 1600 sqft of living space. Main floor primary bdrm has attached 3/4 bath with views of the front fenced courtyard. Center hall shared bath with main floor 2nd bedroom also is within steps away from the main level laundry room and open vaulted living room with adjacent dine-in kitchen. The upper level loft space can also be
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!
Property Id: 2501544Welcome to this newly updated 3 bedroom, 3 bathroom condo in Chesterton, Indiana! This 1,500 Square foot 2-Story condo has a private entrance, new carpet, updated bathrooms, new washer & dryer and a private 1 car garage. It is located in the award winning Duneland school district, very close to Dogwood Park and to the charming and historic downtown with great
Charming Updated Duplex in Chesterton Schools | 2BR/1.5BA | Recently RenovatedWelcome to 122 Jeffrey St, a beautifully updated bi-level duplex unit in a quiet Chesterton neighborhood. This 2-bedroom, 1.5-bathroom home boasts a full interior refresh, perfect for modern living.Key Features & Recent Updates: Modern Kitchen: Equipped with brand-new stainless-steel appliances,
** Half off your first months rent! Move-in by May 1st to qualify!**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
Welcome to Abbey Lane Apartments, located in the charming town of Chesterton, IN. Our community offers a range of amenities that will enhance your lifestyle. Dive into relaxation at our sparkling pool, perfect for those hot summer days. Stay active and fit in our state-of-the-art gym, equipped with everything you need for a great workout. With covered parking, you can protect your vehicle from
Welcome to Abbey Lane Apartments, located in the charming town of Chesterton, IN. Our community offers a range of amenities that will enhance your lifestyle. Dive into relaxation at our sparkling pool, perfect for those hot summer days. Stay active and fit in our state-of-the-art gym, equipped with everything you need for a great workout. With covered parking, you can protect your vehicle from
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