$495,000
- 6 Beds
- 6 Baths
- 1,884 Sq Ft
106 Jeffrey St, Chesterton, IN 46304

Nick Scalise
Listing Leaders
(219) 300-6812
$495,000
106 Jeffrey St, Chesterton, IN 46304
Nick Scalise
Listing Leaders
(219) 300-6812
$375,000
200 Ivy St, Chesterton, IN 46304
Lisa Gaff
White Hat Realty Group, LLC
(219) 336-0887
$660,000
103-117 Jeffrey St, Chesterton, IN 46304
Nick Scalise
Listing Leaders
(219) 327-8192
Chesterton, Indiana, formerly known as "Coffee Creek," is a small town with a vibrant atmosphere, offering a blend of local businesses and serene parks. The downtown area is walkable, featuring a variety of locally owned restaurants and shops such as Chesterton Toys and Tethan’s Candy & Confections. Dining options range from savory burgers at Octave Grill to authentic Italian cuisine at Lucrezia Café. For beverages, Chesterton Brewery and Running Vines Winery are popular spots. The town hosts the seasonal Chesterton European Market from May to October, where residents can shop for local produce and handmade goods. Chesterton's housing market includes a mix of single-family homes, condominiums, and townhouses, with styles ranging from modest ranches to modern Colonials. The Duneland School Corporation serves the area, with highly rated schools like Brummitt Elementary and Chesterton Senior High School. Outdoor activities abound with the Sand Creek Country Club's golf courses, Indiana Dunes National Park, and numerous parks such as Dogwood Park and Coffee Creek Park. For commuters, Interstates 94, 80, and 90 provide access to Chicago, 45 miles away, and the South Shore Commuter Rail Line is just 3 miles away. Chicago Midway International Airport is also 45 miles from Chesterton, and Northwest Health–Porter in Valparaiso is the nearest hospital for healthcare needs.
On average, homes in Chesterton, IN sell after 87 days on the market compared to the national average of 70 days. The median sale price for homes in Chesterton, IN over the last 12 months is $375,000, down 18% from the median home sale price over the previous 12 months.
In Chesterton, there are currently 3 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes priced between $375,000 to $660,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Chesterton is $419,900, while the average sale price is $461,719, offering insights into the local housing market. On average, multi-family homes spend 87 days listed before being sold. Multi-family homes include a variety of property types, from duplexes, triplexes, and fourplexes, to apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're considering a duplex for a beginner investment or an apartment complex for a more substantial venture, there are investment properties available to meet your requirements. Explore the range of multi-family homes for sale in Chesterton, IN.