Chesterton Homes with Detached Parking Features

Chesterton Homes with Detached Parking Features

Welcome to Chesterton, Indiana – a charming town that perfectly blends small-town warmth with modern conveniences. Nestled in Porter County, Chesterton is known for its picturesque landscapes, friendly community, and rich history. With its close proximity to the stunning Indiana Dunes National Park and the shimmering shores of Lake Michigan, residents enjoy a wealth of outdoor activities, from hiking and biking to beach outings and picnics.

Chesterton boasts a vibrant downtown area filled with unique shops, delightful eateries, and local events that foster a strong sense of community. The town is also home to top-rated schools and a variety of recreational facilities, making it an ideal place for families to thrive. With a commitment to preserving its historical charm while embracing growth, Chesterton is a community that welcomes newcomers with open arms.

When it comes to housing, Chesterton offers a diverse selection of homes, including those with detached parking features. These properties not only provide the convenience of ample parking but also add a touch of privacy and versatility to your living space. Imagine coming home to a beautiful residence with a spacious yard, where you can unwind after a long day, all while having the comfort of your own detached garage or carport.

Whether you’re a first-time homebuyer or looking to relocate, Chesterton’s real estate market has something for everyone. Explore the inviting homes with detached parking options, and discover the perfect blend of comfort and convenience in this delightful Indiana town. Come experience the charm of Chesterton, where your dream home awaits!

Newest Chesterton Homes with Detached Parking Features

4 Beds ⋅ 3 Baths

Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The entire home is freshly painted and welcoming. The highly functional kitchen boasts a center island, abundant cabinet space, and generous countertops. Just off the kitchen, the spacious dining room easily accommodates all your entertaining needs, while a versatile flex room makes a perfect home office or playroom. Cozy up in the expansive great room featuring a custom-built fireplace--ideal for cool winter nights. As an added perk, you'll find a cable-ready bonus room above the garage, offering the ultimate media room, teen hangout, or secluded retreat!

419 S 9th Street, Chesterton

3 Beds ⋅ 3 Baths

Bring your offer!!! Calling all buyers, contractors, and investors who see potential where others see projects. Some pictures are AI generated. See what the potential is when changing out the paint, carpet, laundry room flooring and stainless appliances. This 3-bed, 3-bath ranch home on a 0.77 acre lot in Chesterton is a rare chance to build instant equity in one of Northwest Indiana's most sought-after school districts. The roof is only 1 year old -- one of the biggest-ticket items already handled for you. Beneath the cosmetic wear is a home with genuinely good bones: a solid layout, real square footage (2232= 1st floor + 2232 =unfinished basement), and a floor plan worth restoring rather than replacing. Yes, it needs work -- this is NOT a move-in-ready listing, and it's priced accordingly. But for the right buyer, that's exactly the point. Bring your contractor, your vision, or your renovation loan, and turn this into serious equity in a market where finished homes are commanding a premium. In-ground pool, expansive decking, additional 2 car detached garage at the back of the property. Located minutes from downtown Chesterton, the South Shore Line, and the Indiana Dunes, with access to Duneland Schools -- this is a location buyers don't want to miss, at a price point that leaves room to make it your own.

1776 Indian Boundary Road, Chesterton

4 Beds ⋅ 4 Baths

Nestled on a private, wooded 4.5-acre lot in Chesterton's Jackson Township within the Duneland School District, this captivating multi-level home blends distinctive mid-century character with more than 4,300 square feet of versatile living space. Floor-to-ceiling windows, clean architectural lines, serene wooded and open views, and a year-round flowing creek create a peaceful setting that feels timeless and connected to nature. The main level offers a sunlit living room anchored by a dramatic Wisconsin Cascade stone fireplace, a formal dining room with updated lighting, and a fully equipped kitchen with new stainless steel appliances, updated fixtures, and a reverse osmosis water system. Upstairs, you'll find three bedrooms and two full baths--including a hall bath with radiant heated floors--plus a flexible office/flex space adjoined to the primary suite that can easily serve as a nursery, private sitting room, or expansive second walk-in closet. The main and lower levels provide additional living and entertaining space, featuring a fourth bedroom, half bath, family room with a second stone fireplace, and a spacious recreation room. Multiple bedrooms open to three private decks, while a screened porch overlooks the scenic grounds. A dedicated heated and cooled workshop with a private exterior entrance adds even more functionality. Recent improvements include a newer well pressure tank, Presby septic system, radon mitigation system, roof on the detached garage, kitchen reverse osmosis system, and an owned water softener. Outside, the property is a true retreat with parklike grounds, five garage bays, raised garden beds, fruit-bearing apple trees, mature woods, and picturesque outdoor spaces. All of this is located just minutes from downtown Chesterton, Indiana Dunes National Park, nearby beaches, and the South Shore Line with convenient access to Chicago.

1147 N 400 E, 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

This adorable 3 bedroom one bath home is ready for new owners. Kitchen has been updated. Quartz counter top with stainless steel sink and appliances. 1.5 car garage and storage shed as well. Yard is fenced. Duneland schools.

1025 W Porter Avenue, Chesterton

3 Beds ⋅ 1 Baths

ENJOY PEACE, QUIET, & SERENITY from your charming 3-bedroom ranch with a detached 1.5-car garage plus off-street parking! This lovely home is set back, away from the roadway. Enjoy soothing, natural views from your back yard & screened porch. Set on a spacious landscaped lot next to a private wooded area, this unique home boasts low-maintenance exterior, spacious open living room/dining room combo (great for entertaining! And the master bedroom will accommodate your king-size bed)! Newer lighting; freshly painted in soft neutrals to match any decor! All appliances stay. Two storage sheds. Close to everything: lakes, parks, trails, shopping, restaurants! This well-maintained property is being sold as is. Schedule your showing today. Welcome home!

704 S 22nd Street, Chesterton

4 Beds ⋅ 2 Baths

Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 bedrooms plus an office, with character, space, and comfort throughout! The beautiful gourmet kitchen with cabinets galore is just waiting for you to host that special dinner party. The stunning formal dining room is perfect for entertaining, while the large living room with a spectacular fireplace creates the ideal place to cozy up on cool evenings. Now wait until you see the incredible upstairs retreat, a master suite to die for! Enjoy a walk-in closet that feels like an entire extra room along with your own private getaway featuring a grand 20x14 bathroom designed for relaxation and comfort. So much in this home is brand new! Beautiful arched doorways welcome you inside, while large windows flood the home with natural light. Gorgeous plank flooring flows throughout the home, complemented by new carpet in the bedrooms. Outside, you'll love the huge corner lot, fantastic location, fully fenced backyard, and gorgeous deck where you can sit and sip your favorite beverage while enjoying your own peaceful tranquility. ROOF AND GUTTERS are less than 7 months old! A fantastic 2.5-car detached garage adds even more convenience and storage space. There's even a welcoming front porch perfect for relaxing and watching the world go by. Step into tranquility with this beauty... priced under market value! and ready to welcome you home!

769 S Calumet Road, 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

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

3 Beds ⋅ 3 Baths

Set on nearly an acre and within 5 minutes of the Indiana Dunes National Lakeshore, this well-maintained and spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort, flexibility, and convenience to parks, beaches and transportation. With its location and layout, it presents not only as a wonderful single family home but also an excellent investment opportunity as a vacation home or potential short-term rental. The expansive country kitchen is ideal for both everyday living and gathering with family and friends, while the large formal dining room provides an inviting space for entertaining and special occasions. Sliding doors off the kitchen open to a large deck overlooking the expansive backyard, perfect for outdoor gatherings or gardening and an abundance of space for outdoor entertainment. Two generously sized bedrooms and a full bath are conveniently located just off the expansive dining room. Beyond the kitchen, the large living space provides opportunity for relaxing, entertaining, or even creating a home office area. A nearby half bath leads to the impressive, extra-large, primary suite, complete with a private en-suite. Skylights and large windows bathe the home in abundant natural light. A detached tandem 3 car garage provides plenty of room for vehicles and more! Additional features include two separate unfinished basements offering exceptional storage potential, dual furnaces and central air units for enhanced efficiency, and separate electrical panels. Ideally located just minutes from Indiana Dunes National Park, Lake Michigan beaches, and the Dune Park South Shore train station, this property offers convenient access to major highways for easy commuting to Chicago or Southwest Michigan. Electric fireplace, washer and dryer do not stay. All measurements are deemed accurate but subject to buyer verification. Seller has selected Acuity Title Insurance Company to provide insurance underwriting for the Owner's Policy.

1395 Waverly Road, Chesterton

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