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

2330 Legend Circle E, Chesterton
$459,000
3 Beds ⋅ 3 Baths
Welcome home to 2330 Legend Circle East in Chesterton! This inviting 3-bedroom, 3-bath home offers approximately 1,935 square feet filled with natural light and flexible living spaces. Choose your primary retreat upstairs or on the main level--both suites feature a private bath and walk-in closet, offering comfortable accommodations for extended family or guests. An additional bedroom at the front of the home enjoys abundant sunlight and could also serve as a home office. The basement not only has a designated crawl space for storage but also additional enclosed space and a recreation area that you can easily add your personal touches. Step outside to relax on the back deck, complete with a retractable awning for shade to enjoy all that nature has to offer. Speaking of nature just across the street is Coffee Creek Watershed Preserve that offers opportunities to enjoy scenic walks along the 5+ mile wetland boardwalk loops where you will see wildlife, seasonal leaf colors, bridges, a gathering space for and time outdoors. With versatile bedroom arrangements and inviting indoor and outdoor spaces, this home is ready for your next chapter. Schedule your private showing today!

2330 Legend Circle E, Chesterton
2524 Hilfiger Drive, Chesterton
$499,999
4 Beds ⋅ 4 Baths
Meticulously maintained and lovingly cared for by its original owner, this beautiful home is nestled in one of the area's most desirable neighborhoods. Offering four spacious bedrooms, four bathrooms, and a well-appointed kitchen, this home seamlessly blends comfort, style, and functionality. The thoughtfully designed floor plan provides inviting spaces for both everyday living and entertaining, while the fully finished basement offers exceptional additional living space with endless possibilities. The Ensuite Primary bedroom offers a beverage center, built-in window seat and a HUGE walk in closet. Pride of ownership is evident throughout, making this a wonderful opportunity to own a truly special home in a sought-after location. The big ticket items; roof, HVAC and HWH have all been replaced over the last 5 years

2524 Hilfiger Drive, Chesterton
350 Brown Court, Chesterton
$280,000
3 Beds ⋅ 2 Baths
Fall in love with the charm, convenience, and relaxed lifestyle this delightful 3-bedroom, 2-bathroom Pere Marquette cottage has to offer! Featuring a 2-car attached garage, a fully fenced backyard perfect for your four-legged family members, and a beautiful patio tucked away for added privacy among the arborvitae trees, this home is ready for its next chapter. Even better, everything stays! All appliances and personal property included in the sale make this an opportunity you won't want to miss. Please note that the property and included items are being sold AS IS. Craving a delicious gyro? George's Gyros is just down the street! Enjoy an unbeatable location close to the beautiful shores of Lake Michigan, Indiana Dunes State Park, the South Shore train, I-94, and the charming downtown Chesterton European Market. Whether you're looking for a cozy full-time residence, a weekend getaway, or a place to enjoy the best of Northwest Indiana living, this cottage is full of possibilities! No HOA! Enjoy the freedom to make this property your own without monthly association fees or HOA restrictions. Charming, convenient, and close to everything that makes this area special -- come discover the possibilities and make this Pere Marquette cottage your own!

350 Brown Court, Chesterton
1580 Eagle Street, Chesterton
$397,900
4 Beds ⋅ 3 Baths
Welcome to 1580 Eagle St in desirable Golfview Estates! This beautifully updated 4-bedroom, 3-full-bath home offers 2,364 sq ft of stylish and functional living space. Fresh interior paint and updated trim create a bright, move-in-ready feel. The open-concept kitchen, dining, and living area is perfect for everyday living and entertaining, featuring a large island, stainless steel appliances, and a mix of butcher block and granite countertops. The spacious lower-level primary suite offers a gorgeous ensuite bath and a private retreat. Bedroom 2 is located upstairs and also features its own ensuite. A separate family room provides additional living space with room for a home gym, playroom, or media area. Enjoy the large fenced backyard with a paver patio and two-level deck conveniently located off the kitchen. Surrounded by mature trees, Golfview Estates offers neighborhood charm with easy access to a nearby park and the Prairie Duneland Trail. Convenient access to Routes 49 and 94 makes commuting a breeze. Move-in ready and full of thoughtful updates--come see all this home has to offer!

1580 Eagle Street, Chesterton
2519 Pradera Trail, Chesterton
$749,900
4 Beds ⋅ 3 Baths
We are proud to introduce the Ruby model in The 1100 Woods. This grand Craftsman-style new-construction two-story home offers four bedrooms, three bathrooms, and over 2,100 sq. ft. of open-concept living space. A covered front porch welcomes you into the foyer, which opens to a private study/office. Nine-foot ceilings on the main level create an elevated feel throughout. The expansive family room flows into the eat-in kitchen--the true heart of the home--featuring a center island, granite counters, quality cabinetry, stainless-steel appliances, and a walk-in pantry. Upstairs, the large owner's suite includes a spa-like bath with double vanities, a tiled shower, and a walk-in closet. Three additional generously sized bedrooms with ample closet space, a full bathroom, and a conveniently located laundry room complete the upper level. Situated on one of the last tree-lined lots in the neighborhood, the home features a composite deck overlooking a serene backyard. Additional highlights include a two-car garage with a 5-ft. bump-out, a full lookout basement, R-15 wall and R-38 ceiling insulation, a high-efficiency Carrier HVAC system, electrical metal conduit, and many other premium standard features. Homes of this caliber are uncommon. You'll have peace of mind knowing your home was built by an award-winning, multi-generational builder with decades of experience. The 1100 Woods sits just across the street from Dogwood Park and within walking distance of the Prairie Duneland Trail, with dining, shopping, and expressway access only minutes away. Start making this new-construction home yours today! Home is currently under construction. *Pricing is subject to change and should be confirmed with the builder upon inquiry*.

2519 Pradera Trail, Chesterton
1429 Calais Court, Chesterton
$649,500
3 Beds ⋅ 4 Baths
Welcome to 1429 Calais Court, a beautifully maintained paired home nestled in the CHATEAUX DU CHAMBORDE area in the sought-after Sand Creek community of Chesterton. Offering the perfect blend of comfort, convenience, and low-maintenance living, this home is ideal for anyone looking to enjoy a relaxed lifestyle in one of Northwest Indiana's premier neighborhoods. Step inside to find a bright, inviting floor plan with spacious living areas, abundant natural light, and a layout designed for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living spaces, creating a warm and welcoming atmosphere. The generous primary suite provides a private retreat, while additional living space offers flexibility for guests, a home office, or hobbies. Enjoy your morning coffee or unwind in the evening on your private patio while taking in the peaceful surroundings. Located within the prestigious Sand Creek community, you'll appreciate easy access to golf, walking paths, shopping, dining, top-rated Duneland schools, and the beautiful Indiana Dunes National Park and Lake Michigan shoreline. With convenient access to major highways and the South Shore Line, commuting to Chicago is also within easy reach.

1429 Calais Court, Chesterton
515 S Park Drive, Chesterton
$259,900
2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton
229 E Morgan Avenue, Chesterton
$875,000
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
1162 (lot 183) Putman Place, Chesterton
$440,000
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
830 E Sidewalk Road, Chesterton
$235,000
SELLER FINANCING OPTIONS AVAILABLE! 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
303 E Porter Avenue, Chesterton
$359,999
4 Beds ⋅ 3 Baths
Welcome to this charming and beautifully updated home in the highly sought-after Morgan Park neighborhood! Move-in ready and full of character, this spacious home offers over 2,200 square feet of living space, featuring four generously sized bedrooms with excellent closet space. The main-level primary suite offers a private full bathroom and a bright, inviting sunroom--perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious combined living and dining room provides a comfortable layout for entertaining guests and gathering with family. Recent updates include new carpet throughout, fresh interior paint, a new bathroom floor, and major improvements completed within the past 10 years, including the roof, furnace, air conditioning, and electrical system. One of the home's standout features is its enclosed front and back porches, offering additional year-round living space, storage, and plenty of charm. Outside, the beautifully landscaped backyard is filled with mature greenery, flowers, and established plants, creating a peaceful retreat on this large corner lot. The one-car garage provides convenient parking, additional storage, and protection from Indiana's changing weather. It is also equipped for electric vehicle charging. With its spacious layout, thoughtful updates, unique character, and desirable Morgan Park location, this home offers a wonderful opportunity to make it your own. Schedule your private showing today!

303 E Porter Avenue, Chesterton
700 Broadway Avenue, Chesterton
$1,339,000
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
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