Chesterton Homes under $350,000

Chesterton Homes under $350,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Chesterton and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest Chesterton Homes under $350,000

1720 Hale Avenue, Chesterton
$130,000
2 Beds ⋅ 2 Baths
Discover the potential in this peaceful North Chesterton property, set on approximately 0.70 acres in a serene setting near Indiana Dunes National Park, beautiful Lake Michigan beaches, and the South Shore train station. Whether you're looking for your next investment opportunity, a property to make your own, or a quiet personal escape surrounded by nature, this property offers plenty of possibilities. The home could use a little TLC, making it an excellent opportunity for someone ready to bring their vision to life. Recent updates include a newer roof and a newer well pump head and bladder. The seller will pay for the septic system pump-out, offering added peace of mind. Outside, enjoy a tranquil setting with apple trees, blueberries, grapes, and beautiful multicolored lilies throughout the backyard, creating a garden-like atmosphere with abundant natural beauty and local wildlife. The property also features a two-car garage with a tool crib area and laundry, plus a finished room above the garage with a separate entrance, offering additional flexibility and potential. Enjoy the best of peaceful surroundings while staying close to the outdoor recreation, beaches, and attractions of the Indiana Dunes area. With its setting, acreage, and potential, this property is ready for its next chapter!

1720 Hale Avenue, 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
711 S 18th Street, Chesterton
$342,000
3 Beds ⋅ 3 Baths
Move-in ready, light and bright, and beautifully updated! Situated on a quiet, tree-lined street, just steps from downtown Chesterton, and in the Duneland School system. With 3-bedrooms and 3-baths, this home features an updated kitchen with green shaker cabinets, granite counters, tile backsplash and stainless appliances, including a gas range and French-door refrigerator. The light-filled entry level flows from kitchen to dining to living room under vaulted ceilings. One step down, the family room has a breakfast-bar partition and opens to the sunroom and back patio. A half bath and laundry are conveniently located at the far end of the main level. Upstairs are the primary suite with its own bath, two more bedrooms and a full bath. The partially finished basement adds a rec room and home office. Updated baths, new flooring and fresh, tasteful decor throughout. Located on a 0.21-acre lot with an adjacent platted, unbuilt right-of-way. Walk to the European Market and downtown shops, and minutes to Indiana Dunes parks and Lake Michigan beaches. South Shore Line service to Chicago from nearby Dune Park.

711 S 18th Street, Chesterton
231 E 1200 N, Chesterton
$249,900
4 Beds ⋅ 2 Baths
**BRING YOUR VISION AND UNLOCK THE POTENTIAL!** Opportunity awaits with this 4-bedroom, 1.5 -bath Cape Cod-style home offering approximately 2,000 square feet, an attached 2-car garage, and a little over an acre of land in Chesterton! Whether you're an investor searching for your next renovation project or a buyer ready to transform a house into your own masterpiece, this property is full of possibilities! The main level has been stripped down to a blank canvas, offering an open-concept layout ready for your creative ideas and personal touches. The basement provides additional possibilities, with what appears to have been a 3/4 bathroom, bonus room, spacious storage area, and laundry space. Property is serviced by well and septic. Enjoy the spacious setting while remaining conveniently located near downtown Chesterton's shopping, dining, and local attractions, along with Coffee Creek Preserve, nearby parks, and outdoor recreation. Bring your contractor, your imagination, and your plans to restore and reimagine this Cape Cod!

231 E 1200 N, Chesterton
938 N 400 E, Chesterton
$330,000
3 Beds ⋅ 2 Baths
Discover incredible land value and endless possibilities! Set far back from the road down a long driveway, this 3-bedroom, 2-bathroom bi-level is your private 2.58-acre oasis in the heart of Chesterton. This is the ultimate canvas for an investor looking to add to their portfolio, or a DIY homeowner looking for a live-in renovation with immediate equity potential. This home is a fantastic equity-building opportunity that is totally livable from day one. Move right in and take your time bringing your vision to life! The upper level features comfortable living spaces, open concept kitchen and dining area, 3 bedrooms, and a refreshed, newer bathroom. Downstairs, the lower level is far from just an unfinished basement; it's a bright, open canvas ready to be reimagined. Complete with a half bath and laundry area, this space could easily be transformed into a sprawling entertainment room, a dedicated home gym, a private guest suite, or a quiet home office.You'll also love the attached 2-car garage, offering plenty of extra room for storage or a workshop. Location is everything, and this property delivers. Enjoy the quiet privacy of acreage living while being just a short drive from Lake Michigan beaches, hiking at the Indiana Dunes State Park, and local downtown dining. Plus, quick access to major highways and the South Shore Line makes commuting a breeze. Bring your imagination, your tool belt, and make this Chesterton gem shine!

938 N 400 E, Chesterton
35 E 900 N, Chesterton
$325,000
4 Beds ⋅ 2 Baths
Rural residential property on 2.37 ACRES with POLE BARN! 4 bedroom/2 bath bi-level with attached garage. Spacious living room with fireplace, dining area & kitchen with all appliances included, attached 4-season room off the dining area with access to the private backyard, 3 bedroom and 1 full bath. Lower level has endless possibilities with bedroom, family room with wood burner, 3/4 bath, laundry with washer & dryer included and mechanical room. Enjoy the many things Chesterton has to offer: Lake Michigan beaches, Dunes State Park, Walking & Bike trails, Festivals, South Shore Train Station & Easy commute to Chicago! Home sold AS-IS.

35 E 900 N, Chesterton
601 Long Bridge Drive, Chesterton
$295,000
4 Beds ⋅ 2 Baths
Welcome home to this charming and spacious 4-bedroom, 1.75-bathroom tri-level property perfectly situated in the heart of Chesterton, Indiana. Designed with a highly functional layout, this classic tri-level architecture maximizes living space, giving your family plenty of room to spread out, entertain, and grow. Key Features You'll Love: Versatile Tri-Level Living: Enjoy a seamless flow between the distinct levels. The bright and inviting main level serves as the central hub, ideal for daily gatherings and home-cooked meals. 4 Comfortable Bedrooms: Three well-appointed bedrooms are tucked away on the upper level, while a versatile fourth bedroom sits on the lower level. This separate space is perfect for a quiet home office, guest suite, or related living setup. 1.75 Bathrooms: Features a full guest bathroom alongside a convenient three-quarter bath, making busy mornings a breeze. The Perfect Location: Nestled in a peaceful Chesterton neighborhood, you are just minutes away from top-rated Duneland schools, local parks, and the beautiful Indiana Dunes National Park. Plus, commuting is a breeze with easy access to major highways and the South Shore Line. Whether you're looking for a cozy retreat or a home with room to entertain, this tri-level gem delivers the perfect blend of comfort and convenience. Schedule your private showing today and see why so many love calling Chesterton home!

601 Long Bridge Drive, Chesterton
224 S Calumet Road, Chesterton
$275,000
3 Beds ⋅ 2 Baths
Welcome to this charming and beautifully updated 3-bedroom, 2-bath home in the heart of Chesterton just a short walking distance to town, where the character of a 1900s home meets the comfort of today's improvements! From the moment you step inside, you'll appreciate the inviting layout, beautiful flooring, original built-ins, and thoughtful updates that have brought new life to this classic home. The updated kitchen features granite countertops, plenty of cabinetry, and a fresh, functional design, while the main level bathroom includes an added shower. The upper level provides a full bathroom with a soaking tub. This home provides a detached 2 car garage and it sits on just under a quarter of an acre with a fire pit and partially fenced backyard. Even better, many of the major improvements have already been taken care of, including a new sewer in 2021, updated upstairs plumbing in 2021, updated basement/main-level plumbing in 2023, upstairs electrical updates in 2025, and a new central A/C, and whole-house ductwork in 2025. The home also features a newer roof. And then there's the location! Enjoy everything that makes Chesterton such a special place to call home. Spend Saturday mornings browsing Chesterton's European Market in historic downtown, explore local shops and restaurants, or head to the Indiana Dunes and Lake Michigan just minutes away. The European Market is held downtown from May through October, and Chesterton offers an impressive mix of dining, shopping, community events, and outdoor recreation. Chesterton has convenient access to I-94, the Indiana Toll Road, and State Road 49 which also makes getting around Northwest Indiana and beyond easy. Schedule your showing today!

224 S Calumet Road, Chesterton
1954 David Drive, Chesterton
$168,000
1 Beds ⋅ 1 Baths
This charming 1-bedroom, 1-bath condo offers comfortable, maintenance-free living in a convenient location. Enjoy home ownership without the hassle of exterior maintenance, giving you more time to enjoy your home and everything the area has to offer. The inviting layout provides a comfortable space to relax and entertain, making this an excellent option for a first-time buyer, downsizer, or anyone looking for a low-maintenance lifestyle. Conveniently located near shopping, dining, parks, and major transportation routes, this condo combines comfort and convenience. HOA includes trash pick up, water, sewer, snow removal, landscaping, and building maintenance! Don't miss this opportunity! Schedule your showing today!

1954 David Drive, Chesterton
429-431 Woodlawn Avenue, Chesterton
$347,900
4 Beds ⋅ 4 Baths
Profitable duplex located less than 1 hour from Chicago, 10min to the South Shore Train, & 5min to I-94. Gross over 26,000 per year or live on one side & have your mortgage covered by passive income. You'll love this recently updated property with spacious rear yard, raised decks & 2 storage sheds. Loads of parking with an oversized driveway creating loads of space. Tenants pay utilities making for easy management & maximizing your bottom line. Management companies available as well. Weather you are starting your investment portfolio or looking to expand, this property will be a great asset to have.

429-431 Woodlawn Avenue, Chesterton
2555 Springdale Street, Chesterton
$329,900
3 Beds ⋅ 2 Baths
Step into this nearly new Move-In ready 3- Bedroom, Maintenance-Free Ranch Duplex in Springdale! Open Concept layout with lots of natural light and beautiful Vinyl flooring. Enjoy a cozy night by the fireplace in the Great Room while making dinner or watching a movie. Kitchen has Maple cabinets, granite countertops and stainless steel appliances. The Master has an en suite with a double vanity and spacious walk-in closet. Sliding doors in the Kitchen lead to a covered patio. The neutral palette throughout this immaculate home will make moving in feel effortless!

2555 Springdale Street, Chesterton
1708 Tower Street, Chesterton
$249,000
2 Beds ⋅ 1 Baths
This charming two bedroom, one bath home is ready for its new owners. You'll love the refinished hardwood floors and wide trim that carry classic character throughout the home. Original solid wood doors with antique hardware add timeless appeal, while modern updates provide peace of mind. The home features newer windows, siding, furnace, and A/C, along with updated electrical. The kitchen and bathroom include built ins for added storage and style. Both bedrooms offer large walk in closets with lighting, a rare find in a home of this era. A perfect blend of vintage charm and thoughtful updates -- move in ready and full of personality. The attic space has the potential for future expansion and more living space. The large 2.5 car garage is truly a dream workspace. It's fully equipped with electric and even includes an A/C unit to keep you cool on hot days while tackling projects, hobbies, or storage needs. Plenty of room, plenty of comfort, and plenty of possibilities. Just minutes from major highways and next to the Duneland walking trail.

1708 Tower Street, Chesterton
Start Your Search

Updated . Information deemed reliable but not guaranteed.