Chesterton, IN Real Estate Search

Chesterton, IN Homes for Sale

Overview of Chesterton, IN

Chesterton is a charming small town located in northwestern Indiana, just a short distance from the southern shores of Lake Michigan. Known for its peaceful atmosphere and friendly community, Chesterton offers a unique blend of suburban living and easy access to natural beauty. The town boasts excellent schools, numerous parks, and a vibrant downtown area with a variety of shops and restaurants.

The Real Estate Market in Chesterton, IN

The real estate market in Chesterton, IN, is highly desirable for both homebuyers and investors. The town offers a wide range of properties, including single-family homes, townhouses, and condos. The median home price in Chesterton is affordable compared to neighboring cities, making it an attractive option for first-time homebuyers. Additionally, there are many new housing developments in the area, providing modern housing options for those seeking a more contemporary style.

Attractions and Amenities

Chesterton, IN, offers a multitude of attractions and amenities for residents to enjoy. One of the highlights of the town is the Indiana Dunes National Park, a stunning natural area located along the southern shores of Lake Michigan. Here, visitors can explore miles of sandy beaches, hiking trails, and picturesque dunes. The town also features several golf courses, allowing avid golfers to indulge in their favorite pastime.

Quality Education and Community

Chesterton prioritizes education, and the town is served by a highly regarded school system. The Duneland School Corporation includes multiple public schools that consistently achieve high academic ratings. These schools provide students with quality educational opportunities, emphasizing strong academic programs and extracurricular activities for well-rounded development.

Conclusion

Chesterton, IN, is a wonderful place to consider investing in real estate or finding your perfect home. With its friendly community, excellent schools, and abundance of recreational opportunities, Chesterton offers a high quality of life in a picturesque setting. Whether you are looking for a cozy suburban residence or a modern housing option, you are sure to find a great selection of properties within the town's diverse real estate market.

Our website features the best Chesterton, IN real estate search for homes available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Chesterton, IN Homes for Sale

Avg. No of Beds
Avg. No of Baths
Avg. Living Ft2
Avg. Listing Price
Cost per ft2
Days on Market
Chesterton, IN Popular Searches
Chesterton, IN Homes by Price
Chesterton, IN Homes by # of Bedroom(s)
Chesterton, IN Homes by # of Bathroom(s)

Curious about what’s happening in the Chesterton, IN real estate market? Sign up for a  Chesterton, IN Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Chesterton, IN Homes for Sale

1240 Ryder Road, Chesterton
$1,199,900
5 Beds ⋅ 6 Baths
Perfectly positioned along the fairway in the gated Sand Creek community, this impressive custom residence blends grand scale living with thoughtful design and exceptional versatility. From the moment you enter, a dramatic two-story foyer sets the tone, opening to inviting living spaces and a sweeping catwalk overlooking the heart of the home. The two-story great room is anchored by a striking stone fireplace and windows framing picturesque golf course views. Designed for gathering, the kitchen offers premium appliances, a center island, walk-in pantry, and butler's pantry, all seamlessly connected to casual dining and living areas. Dual staircases provide both functionality and architectural interest throughout the home. The main-level primary suite offers a private retreat complete with a spa-inspired bath, steam shower, soaking tub and dual vanities. A home office or study with French doors is also located on the main. Upstairs, 3 spacious bedrooms each feature access to full baths, while a large bonus room offers endless possibilities as an additional bedroom, playroom, media lounge, creative studio, home office, fitness area, or hobby space -- truly adaptable to fit your lifestyle. Outdoor living shines with a 900-sq ft deck overlooking the large backyard and sweeping fairway views, creating the perfect setting for entertaining or quiet evenings at home. The finished daylight basement is designed with entertainment in mind, featuring a large recreation area, custom bar, theatre room, and hidden rooms cleverly tucked behind built-in shelving for a unique and memorable experience. The basement easily functions as a guest retreat or extended living quarters. Additional highlights include a heated 3-car garage, abundant storage throughout, NEW Furnace, AC and water heaters! Experience elevated living-where grand entertaining, everyday comfort, and breathtaking views create a truly unforgettable home.

1240 Ryder Road, Chesterton
Tbd Union Avenue, Chesterton
$55,000
Rare 1-Acre Wooded Lot in a Desirable Established Area! Conveniently located near schools, shopping, dining, and major commuter routes. The seller has obtained a land-clearing quote of approximately 10k, with costs varying based on how much of the lot the buyer chooses to clear. Enjoy the privacy, flexibility, and space to build your dream home. Large lots like this are hard to find - the seller is motivated and welcomes all offers!

Tbd Union Avenue, Chesterton
no property photo
$89,900
Only an hour from Chicago sits a picturesque neighborhood behind private gates. Sand Creek offers upscale living in an exclusive neighborhood. Unique estate homes line the streets of this sought-after subdivision. This is one of the last lots available before this community is completely sold out. If you have been dreaming about building a home, this is the time and place to do it.

1915 Toms Court, Chesterton
1717 Crocker Street, Chesterton
$249,000
3 Beds ⋅ 2 Baths
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 outdoor living on the spacious new wraparound deck overlooking a large backyard, ideal for relaxing or entertaining. The home is adjacent to the Duneland Prairie Bike Trail, offering immediate access to miles of scenic recreation. The basement is fully framed and electrically roughed in for a private primary suite, including a large 17x20 bedroom, walk-in closet, full bath with double vanity, and laundry area. A new egress window is already in place, making this level bright, functional, and ready to finish with minimal additional investment. Ideally located in the award-winning Chesterton school district, near Hwy 149 and County Rd 1100, this home provides quick access to shopping, restaurants, Indiana Dunes on Lake Michigan, the South Shore Train, downtown Chesterton, and the popular European Market, with an easy 45-minute commute to Chicago. A rare opportunity for turnkey comfort with strong future value.

1717 Crocker Street, Chesterton
150-152 N 16th Street, Chesterton
$499,900
6 Beds ⋅ 6 Baths
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 interior doors add warmth and character throughout. Ideally located near downtown Chesterton and Porter, the South Shore Train Station, and the breathtaking Indiana Dunes State Park, this property combines modern comfort with unbeatable access to Northwest Indiana's top amenities.

150-152 N 16th Street, Chesterton
27 Karner Blue Court, Chesterton
$58,000
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.

27 Karner Blue Court, Chesterton
47 Karner Blue Court, Chesterton
$58,000
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.

47 Karner Blue Court, Chesterton
23 Karner Blue Court, Chesterton
$58,000
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.

23 Karner Blue Court, Chesterton
25 Karner Blue Court, Chesterton
$58,000
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.

25 Karner Blue Court, Chesterton
43 Karner Blue Court, Chesterton
$54,000
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.

43 Karner Blue Court, Chesterton
1005 Preserve Lane, Chesterton
$54,000
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.

1005 Preserve Lane, Chesterton
Village Point, Chesterton
$199,999
Unique lot in Coffee Creek. Many possibilities. Subject to approvals. The lot is 100x100 and is on a hill overlooking the pond and fountain.

Village Point, Chesterton
395 Eagle Nest Drive, Chesterton
$49,900
Beautiful building site in the desirable Villages of Sand Creek! Chesterton Schools! The neighborhood features sidewalks, a park, ponds and walking trails. Close to all the shopping, major expressways, Indiana Dunes, South Shore train and biking trails! Come view this wonderful neighborhood! This cul-de-sac lot is located between house No. 407 and 379 Eagle Nest. Proposed construction plans can be obtained.

395 Eagle Nest Drive, Chesterton
Michael Dr. Lot 133, Chesterton
$97,000
Create the possible! These, in town, Duneland Cove lots have municipal water and sewer, gas and electric available. Convenient easy transit to highways, rails, shopping, schools, parks, playgrounds and within minutes to our beautiful Lake Michigan shoreline beaches, parks and trails. All permits required, No HOA, covenants and restrictions apply.

Michael Dr. Lot 133, Chesterton
108 Indian Boundary Road, Chesterton
$95,000
High traffic commercial lots. Two adjoining commercial properties totaling almost 2 acres on Indian Boundary Road. The property is zoned Business 2 which enables most retail applications, medical uses, and office functions. Property is in a TIF district.

108 Indian Boundary Road, Chesterton
1032-Lot 26 Preserve Lane, Chesterton
$61,500
Lot 26 is for sale located in the Preserve Subdivision in Chesterton. This beautiful lot is bordered by the nature preserve on two sides and is ready for you to bring your builder and build your new home. Located near Chesterton High School, close to Lake Michigan's Indiana Dunes State Park, the South Shore Train and Indiana Toll Road. Lake Michigan water. All soil tests have been completed!

1032-Lot 26 Preserve Lane, Chesterton
Michael Dr. Lot 135, Chesterton
$101,000
Create the possible! These in town, Duneland Cove lots, have municipal water & sewer, gas and electric available. Convenient easy transit to highways, rails, shopping, schools, parks, playgrounds and within minutes to our beautiful Lake Michigan shoreline beaches, parks and trails. All permits required, No HOA, covenants and restrictions apply.

Michael Dr. Lot 135, Chesterton
Start Your Search

Updated . Information deemed reliable but not guaranteed.

How much is your home worth?

Get instant property value now!