Chesterton Homes with On Street Parking Features

Chesterton Homes with On Street Parking Features

Welcome to Chesterton, Indiana – a charming town nestled in Porter County that beautifully blends small-town warmth with a vibrant community spirit. Known for its picturesque landscapes and friendly atmosphere, Chesterton is the perfect place to call home. With easy access to the stunning Indiana Dunes National Park and the serene shores of Lake Michigan, outdoor enthusiasts will find endless opportunities for adventure right at their doorstep.

Chesterton boasts a rich history, which is reflected in its beautifully preserved downtown area. Here, you can explore quaint shops, delightful eateries, and local markets that create a sense of community and connection. The town hosts various events throughout the year, including the popular European Market, where you can find fresh produce, artisanal goods, and unique crafts that celebrate the local culture.

When it comes to housing, Chesterton offers a diverse selection of homes, many featuring convenient on-street parking. This is a significant advantage for residents, providing easy access to their homes without the hassle of searching for a spot. The neighborhoods are characterized by tree-lined streets and friendly neighbors, making it an inviting environment for families, young professionals, and retirees alike.

Whether you’re looking for a cozy starter home or a spacious family residence, Chesterton's real estate market has something for everyone. Discover the charm of Chesterton, where community, convenience, and character come together to create the perfect backdrop for your next chapter. Come explore today and find your dream home in this delightful Indiana gem!

Newest Chesterton Homes with On Street Parking Features

2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton

5 Beds ⋅ 5 Baths

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

229 E Morgan Avenue, Chesterton

3 Beds ⋅ 1 Baths

Welcome home to this beautifully renovated 3-bedroom, 1-bath home that's truly move-in ready! Completely updated from top to bottom, this home features all new mechanicals, giving you peace of mind for years to come. The bright and modern kitchen comes complete with brand-new stainless steel appliances that stay with the home. Outside, you'll find a detached 2-car garage, offering plenty of space for parking and additional storage. The backyard provides space for entertaining, or simply relaxing outdoors. Conveniently located close to shopping, restaurants, and everyday amenities, with quick access to major highways for an easy commute. Don't miss this incredible opportunity to own a beautifully updated home--schedule your showing today!

400 Woodlawn Avenue, Chesterton

4 Beds ⋅ 3 Baths

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 suite. The unfinished basement offers endless possibilities for future living space, storage, or recreation. Located in the Duneland School District and just minutes from the Indiana Dunes, South Shore train line, shopping, and an easy commute to Chicago. Don't miss your opportunity to own a home in this growing community!

1162 (lot 183) Putman Place, Chesterton

Beautiful office condo on second floor. Modern, stylish decor, move-in ready. Includes hard wood floors and recessed lighting. Bathroom also features a shower. Private entrance off street. Three spacious private offices overlooking Coffee Creek. Large administrative area. Open floor plan with plenty of natural light. Professionally managed by First American Property Management. Call to see today.

830 E Sidewalk Road, Chesterton

4 Beds ⋅ 3 Baths

Welcome to this charming, updated historic home located in the highly sought-after Morgan Park neighborhood! This move-in-ready home features new carpet throughout, fresh interior paint, and major updates completed within the last 10 years, including the roof, furnace, air conditioning, and electrical system. With over 2,200 square feet of living space, this home offers four spacious bedrooms, all with excellent closet space. The primary bedroom includes a private full bathroom and a bright sunroom, perfect for relaxing with your morning coffee or enjoying a quiet evening. The combined living and dining room provides an ideal layout for entertaining guests and hosting family gatherings. You'll also love the enclosed front and back porches, a rare feature that adds both charm and additional usable living space. Step outside to the beautifully landscaped backyard filled with mature greenery, flowers, and plantings, creating a peaceful retreat on the large corner lot. The one-car garage is perfect for extra storage or protection from Indiana's changing weather and is currently equipped for electric vehicle charging. This home is full of character, thoughtful updates, and endless possibilities. It's ready for you to make lasting memories--schedule your private showing today!

303 E Porter Avenue, Chesterton

FOR SALE - 20,528 SF Commercial Flex building on Broadway in Chesterton, IN. Unlock the possibilities with this expansive and adaptable 20,528 sq ft fully sprinkled commercial building, Zoned B-2. Ideally situated on Broadway, a high-visibility east -west corridor through the heart of Chesterton., Indiana. This versatile property is zoned B-2 and supports a broad range of potential commercial use including retail, office, flex, showroom and storage. The property includes 36 parking spaces, 24 on a private lot, and 12 on street. Two staircases, freight lift to 2nd floor, Netnitco fiber, cameras, over 95 percent LED lighting, with 400-amp 3 phase incoming power.

700 Broadway Avenue, Chesterton

Get your hands on the most ideal location in all of Chesterton. This building is full of history and charm right in the heart of downtown with frontage on Broadway and 2nd street. This is where the hustle and bustle of Chesterton happens, markets, parades, festivals, etc. Just a few miles from the National Park and major highways, Chesterton is now more than ever a huge draw!Prime Retail, Office and Residential spaces, many with long term tenancy. Current tenants include Chiropractic office, Art Gallery, Two residential apartments etc. Much of the original character is still intact! Cap rate is at 9 Do not let this opportunity pass you by!

119 Broadway Avenue, Chesterton

Opportunity to own the former Main Street Tap in the Heart of Chesterton. Three level bar restaurant has been completely renovated. Main floor features a huge bar and outdoor patio deck. Second floor features 2 private office spaces, large banquet facility or meeting area, and a second floor deck. Basement is walk out with space for dining or food preparation area. Existing three (3) way liquor license, trade fixtures, bar and tap equipment, A/V stage equipment, TVs, and Point of Sale system ALL INCLUDED!! Additionally, the Town of Chesterton just added a new parking lot in close proximity to the building making it convenient for customers to come and go. Call today to schedule your showing.

119 S Calumet Road, Chesterton

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