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

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

3 Beds ⋅ 2 Baths

Back on market at no fault of seller! Welcome to 252 S 21st St in Chesterton! This well-maintained home offers valuable updates, flexible living space, and outstanding garage/storage options, all tucked away at the end of a cul-de-sac. When you walk through the front door, you'll notice the vinyl flooring and open floor plan, with the floors flowing naturally into the kitchen and dining area. The renovated bathrooms provide a modern, updated feel alongside the main-floor bedrooms. Major improvements include a new roof, new air conditioner, new furnace, new gutters, and a newer sump pump, giving buyers added peace of mind. The home also features a partially finished basement with a family room, bedroom, and bathroom -- perfect for guests, hobbies, work-from-home needs, or additional living space. Out back, enjoy a deck overlooking the yard, ideal for relaxing, grilling, or entertaining. The property also stands out with two detached garages providing a total of four garage spaces, offering excellent room for vehicles, storage, tools, recreational equipment, or workshop potential. Conveniently located in Chesterton, this home combines practical updates, extra space, rare garage capacity, and a quiet cul-de-sac setting. Schedule your showing today!

252 S 21st Street, Chesterton

3 Beds ⋅ 1 Baths

ONLY 10 to 15 MINUTES to LAKE MICHIGAN'S SANDY BEACHES! 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-sized 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

9 Beds ⋅ 4 Baths

501 Wabash Ave is an extraordinary property located in the heart of Chesterton, Indiana. This versatile space offers numerous possibilities: Generational living? Absolutely. Income-producing potential? Yes. A stunning open-concept home with an apartment and guest suite for visiting family and friends? Definitely. Spanning 4,400 square feet, this property is as adaptable as it is distinctive. The main living area features beautiful hardwood floors, an expansive open layout perfect for entertaining and relaxation, four well-sized bedrooms, and a luxurious custom-built shower in the main bathroom. The kitchen, renovated in Spring 2026, is a chef's paradise, featuring new countertops, stainless steel appliances, a pot filler and plenty of cabinetry to accommodate all your cooking essentials. Additionally, there are two more bedrooms, a full bathroom, and another kitchen, dining and living room adjacent to the main area with brand new flooring. This area can function as space for multi-generational living or be easily separated to create two distinct spaces. But that's not all! Above the three-car garage, you will discover a three-bedroom, one-bathroom apartment with modern flooring, recessed lighting, its own entrance, and a private deck perfect for enjoying the outdoors. This hidden gem is situated within the award-winning Duneland School District, just a leisurely stroll from the Chesterton European Market, minutes from the beach and State & National Parks, and conveniently close to fantastic local amenities. Plus, it's just a short drive to Chicago. Don't wait or hesitate--schedule your showing today and make this versatile and delightful home yours!

501 Wabash Avenue, 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, updated home located in the highly sought-after Morgan Park neighborhood! This move-in-ready home features new carpet throughout, fresh interior paint, new bathroom floor 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 which is located on the main level 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 space and storage. Step outside to the beautifully landscaped backyard filled with mature greenery, flowers, and plants, 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

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

3 Beds ⋅ 2 Baths

Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning trails and beaches of Indiana Dunes National Park, this 1,977-square-foot haven offers 3 bedrooms, 2 bathrooms, and effortless access to Chicago commutes--blending small-town charm with big-city convenience in the highly rated Duneland School District. From the moment you arrive, the home's warm light yellow siding and inviting deck beckon you into a world of timeless elegance. Step inside to a light-filled living room with dramatic cathedral ceilings, creating an open, airy retreat perfect for family gatherings. The adjacent kitchen inspires gourmet meals and connects seamlessly to the versatile den--ideal as a home office or guest space. Enjoy a full main-floor bathroom, convenient laundry/mud room, and direct access to the expansive covered patio, with the sprawling backyard perfect for barbecues or serene views. Upstairs, unwind in the luxurious primary bedroom suite with a spa-like en-suite bathroom and generous closet. The adaptable loft offers endless possibilities, complemented by a spacious second bedroom. The full unfinished basement awaits your vision as a media room or workshop, alongside a dedicated office. Modern comforts include central air, natural gas heating, municipal utilities. This isn't just a house--it's a legacy of tranquility and adventure. With historic soul and unbeatable location, it's ready to welcome you home.

214 Woodlawn Avenue, Chesterton

Start Your Search

Updated . Information deemed reliable but not guaranteed.