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$190,000
2 Beds ⋅ 2 Baths
Welcome Home! This 2 Bedroom 1.75 Bath main floor condo, has been meticulous updated and is ready for a new owner. Inside you will find newer flooring, kitchen cabinets, countertops, bathrooms, as well as newer stainless steel kitchen appliances. Main floor living at its finest! Outside you will find a patio that overlooks a large pond. This home is complete with a 1 car garage , with shelving for your storage needs. No need to worry about the exterior maintenance, grass cutting, snow removal, water and sewer bills. Those are all taken care for you through the Association. Just move right in!

1913 David Drive, Chesterton
$283,500
2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton
$579,900
4 Beds ⋅ 4 Baths
Unmatched curb appeal, custom craftsmanship, with 3.44 acres of privacy with 4 Bedroom and 4 Baths. This stunning Craftsman-style home offers an idyllic retreat within the coveted Duneland School District. From the moment you pull up to the expansive three-car garage. Featuring a generous 13 ft by 30 third bay perfect for a boat, workshop, or extra storage and see the gorgeous wrap-around front porch, you'll know you've found something special. Inside, the quality is undeniable 2x6 construction, solid wood doors, and wood trim throughout the main floor. Beautiful wood floors flow seamlessly through the entryway, dining room, kitchen, and hallway. Host gatherings in the elegant dining room, by solid wood columns and plantation shutters, or cook with ease in the spacious eat-in kitchen, complete with beautiful maple cabinets and an ample amount of counter and storage space. Step directly from the kitchen out to a charming screened-in porch, which opens to a durable Trex deck,ideal for outdoor dining and taking in views of your private acreage. Afterwards, relax in the impressive living room anchored by soaring vaulted ceilings and a warm gas fireplace. Main-floor primary sanctuary features direct access to the wrap-around porch and a spa-like ensuite bath complete with a double vanity, soaking tub, walk-in shower, private toilet closet, and a spacious walk-in closet. Down the hall, a secondary main-floor in-law suite with an adjacent 3/4 bath provides unmatched flexibility. As you head upstairs, you will notice the gorgeous wooden staircase. You'll find two generously sized bedrooms and a full bath with double sinks and along with an unfinished area above the garage offering incredible potential for future expansion. Downstairs in the partially finished basement adds even more versatile space, complete with daylight windows, a full bath, and direct interior stairs leading right up to the garage. For complete peace of mind, the home comes with Generac Generator

386 E 1050 N, Chesterton
$239,900
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
$625,000
4 Beds ⋅ 4 Baths
First Time on the Market! Proudly offered by its original owner, this exceptional property presents a rare opportunity to own a private retreat nestled on 5 picturesque acres. You will notice quality craftsmanship & attention to detail throughout the home. Surrounded by mature trees and abundant wildlife, the property features a cleared walking trail, a dedicated hunting area, a cozy fire pit, an apple tree, and a peaceful setting you'll enjoy year-round. Designed for both everyday living and entertaining, the home offers 4 bedrooms and 4 bathrooms with generous living spaces throughout. The spacious eat-in kitchen includes a pantry, built-in space saver and room for the whole family to gather for meals. The oversized living room is highlighted by a beautiful wood-burning fireplace and a large sliding glass door that showcases the serene backdrop. Step outside onto the expansive deck overlooking the private backyard--an ideal space for morning coffee, evening sunsets, or just relaxing with friends and family. The primary suite features an updated 3/4 bath and ample closet space. Throughout the home you'll find numerous custom built-in storage solutions and spacious closets designed with organization and storage in mind. The finished lower level expands your living space with a massive family room centered around a second wood-burning fireplace, complete with a convenient exterior-access wood storage cabinet for easy restocking. The lower level also offers a spacious fourth bedroom, w/ a bonus room connected & a half bath. A full bathroom, laundry room, and a dedicated tool/workshop room, provide endless possibilities for hobbies, guests, or multi-generational living. Additional highlights include oversized 2 car garage, a metal storage shed, a buoy/storage shed. If you've been searching for privacy, nature, and a home that has been lovingly maintained by one owner, you'll want to see this one! Survey & original blueprints attached for added peace of mind.

1089 N 200 W, Chesterton
$350,000
3 Beds ⋅ 3 Baths
Trade traffic for trailheads and design a home that completely reflects your soul. Tucked away on an expansive 2.03-acre wooded lot in Chesterton, this solid tri-level property is a dream canvas for the visionary buyer ready to bring a high-contrast, moody aesthetic to life. With 2,531 square feet, three bedrooms, and three bathrooms, plus a bonus room, the spacious layout features great architectural bones that practically beg for rich textures, deep color palettes, and a custom modern remodel. Location Highlights Outdoor Adventure: The Heron Rookery Trail and Dale B. Engquist Nature Preserve are practically at your doorstep. Spend your weekends exploring the Indiana Dunes State Park Nature Center or Coffee Creek Preserve. Top-Tier Education: Located within the highly desirable Duneland School Corporation boundaries. Easy Commuting: Enjoy the perfect balance of a secluded, peaceful retreat that is still highly connected--the Beverly Shores train station or by car is just a short drive away for effortless city trips. (approx. 40 minutes to the city). Outside, the massive yard is surrounded by trees, offering ultimate privacy for a stunning outdoor living area, a native garden, or quiet mornings listening to birdsong. Ample parking and a 2.5-car garage mean there's plenty of room for your weekend toys and guests. Opportunities that blend acreage, top schools, immediate trail access, and true renovation potential don't last long. Schedule your tour today. Home is being sold AS-IS.

397 E 1300 N, Chesterton
$475,000
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
$450,000
3 Beds ⋅ 3 Baths
This property offers the ideal combination of location, lot, and lifestyle. Located in Duneland Cove, this nearly 3,000-square-foot home features 3 bedrooms, 3 bathrooms, and a 3-car garage, all just minutes from shopping, healthcare, major highways, rail access, and the shoreline beaches of Lake Michigan. The main level's circular floor plan connects the living room, dining room, kitchen, and family room, with beautiful backyard views from inside the home and from the deck. A centrally located half bath sits next to the den. Upstairs, you'll find three spacious bedrooms and a full hall bathroom shared by Bedrooms 2 and 3. The primary suite includes a three-quarter bath and an adjacent loft that can serve as an office or flexible living space. The daylight basement adds more finished living area, including recreation space and a double-door walkout to a brick patio and garden path. This two-story home also features a welcoming covered front porch, a split HVAC system for garage comfort, a functional layout, and a convenient location. Home is being sold "As Is".

947 Sandpiper Drive, Chesterton
$420,000
3 Beds ⋅ 2 Baths
Looking for a place in Chesterton where you can actually breathe? This peaceful 2.2-acre country retreat offers the perfect balance of wide-open green space and a home designed for everyone to have their own corner. The main house features airy vaulted ceilings, a large country kitchen with stainless steel appliances, and oversized bedrooms with deep closets, plus extra attic storage in both garages. A standout feature is the clever "related living" setup: just close the French doors to create a fully private apartment complete with its own kitchen, laundry, and appliances. You can soak up the views year-round from the heated sunroom, which overlooks an above-ground pool with a wrap-around sun deck, or choose between the large party-sized fire pit and the smaller, cozy one for quieter nights. To top it all off, the property includes a massive 40' x 60' fully insulated pole barn with concrete floors, electric, and even a built-in bedroom and bathroom. With double barn doors and a drive-through exit for easy rear parking, this is the ultimate setup for hobbies, guests, or just enjoying the quiet life. Located in the award-winning Chesterton/Duneland School District, convenient to all major highways, don't wait - schedule your showing today!

141 W 900 N, Chesterton
$345,000
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
$290,000
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

Updated . Information deemed reliable but not guaranteed.