Chesterton Homes under $350,000

Welcome to Chesterton, Indiana—a charming town nestled in Porter County that beautifully blends small-town charm with modern conveniences. Known for its picturesque landscapes and vibrant community spirit, Chesterton is a hidden gem just a stone's throw away from the stunning shores of Lake Michigan. With its rich history, friendly atmosphere, and an array of local shops and eateries, this town offers an inviting environment for families, professionals, and retirees alike.

One of the most appealing aspects of Chesterton is its accessibility to affordable housing. For those seeking a home under $350,000, the options are plentiful. From cozy single-family homes to modern townhouses, Chesterton provides a variety of properties that cater to diverse lifestyles and budgets. Imagine settling into a quaint neighborhood where tree-lined streets and well-maintained parks create a serene backdrop for everyday living. Many of these homes boast spacious yards, perfect for outdoor gatherings or quiet evenings under the stars.

Chesterton is not just about affordability; it’s also about community and connection. Residents enjoy easy access to top-rated schools, local farmers' markets, and annual festivals that celebrate the town’s rich culture. Plus, with the nearby Indiana Dunes National Park, outdoor enthusiasts can explore beautiful trails, sandy beaches, and breathtaking views.

In Chesterton, you’ll find not just a house, but a place to call home. Discover the charm of this delightful town and see how it can fit your lifestyle—without breaking the bank!

Newest Chesterton Homes under $350,000

$295,000

4 Beds ⋅ 2 Baths ⋅ 846319 MLS ⋅ 1,945 SqFt. ⋅ Neil Csonka

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

Listing courtesy of Neil Csonka from Listing Leaders MVPs.

$255,000

3 Beds ⋅ 1 Baths ⋅ 846149 MLS ⋅ 1,056 SqFt. ⋅ Elizabeth Garcia

Location, convenience, and small-town charm come together in this 3-bedroom, 1-bath ranch in the heart of Chesterton! Centrally located in town, this home puts you within easy walking distance of parks, splash pads, the European Market, and the future YMCA Healthy Living Campus. Enjoy having so many of Chesterton's favorite amenities just minutes from your front door! Inside, the functional ranch-style layout offers comfortable single-level living, while the basement provides additional space and plenty of possibilities. An especially valuable feature is the well-maintained whole-house Generac generator, offering added peace of mind and convenience during power outages--an increasingly appealing benefit with the storms our area has experienced. Step outside to a fenced-in backyard with plenty of room for summer gatherings, pets, play, gardening, or simply relaxing at home. Whether you're a first-time buyer, looking to downsize, or searching for a home in a convenient in-town location, this property offers a wonderful opportunity to enjoy all that Chesterton has to offer, with the added reassurance of whole-house backup power!

522 Park Avenue, Chesterton

Listing courtesy of Elizabeth Garcia from Blackrock Real Estate Services.

$275,000

3 Beds ⋅ 2 Baths ⋅ 846148 MLS ⋅ 1,324 SqFt. ⋅ Heather Alexander

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

Listing courtesy of Heather Alexander from @properties/Christie's Intl RE.

$172,500

1 Beds ⋅ 1 Baths ⋅ 845895 MLS ⋅ 780 SqFt. ⋅ Providence Community Assn Inc BLDG. ⋅ Sarah Eenigenburg

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

Listing courtesy of Sarah Eenigenburg from Better Homes and Gardens Real.

$349,900

4 Beds ⋅ 4 Baths ⋅ 845634 MLS ⋅ Nicholas Scalise

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

Listing courtesy of Nicholas Scalise from Listing Leaders.

$329,900

3 Beds ⋅ 2 Baths ⋅ 845617 MLS ⋅ 1,512 SqFt. ⋅ Springdale Ph 3 BLDG. ⋅ Tiffany Razo

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

Listing courtesy of Tiffany Razo from New Chapter Real Estate.

$249,000

2 Beds ⋅ 1 Baths ⋅ 845440 MLS ⋅ 1,250 SqFt. ⋅ Marcy Norman

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

Listing courtesy of Marcy Norman from Trendsetters Realty, LLC.

$234,900

3 Beds ⋅ 2 Baths ⋅ 845277 MLS ⋅ 2,348 SqFt. ⋅ Wendy Hammonds

Historic Chesterton gem just steps from downtown! This solidly built 3-bedroom, 2-bath two-story home offers nearly 2900 sq. ft. of finished living space which includes a full basement. Beautiful original woodwork, doors, hardware and classic door knobs preserve the character of this special home, complemented by hardwood flooring. The bright, inviting kitchen features beautiful cabinetry and a convenient pantry. The updated main-level bathroom includes a charming clawfoot tub. Upstairs, the spacious primary bedroom offers a walk-in closet plus its own sitting area, filled with natural light. Situated on a desirable corner lot in Duneland School District and within walking distance to downtown Chesterton's shops, restaurants and amenities. Conveniently located near the beach and South Shore train station for those commuters. Historic charm, space, location and character--this is one you won't want to miss!

201 S 8th Street, Chesterton

Listing courtesy of Wendy Hammonds from Key Realty Indiana, LLC.

$349,000

4 Beds ⋅ 2 Baths ⋅ 845256 MLS ⋅ 2,535 SqFt. ⋅ Villages/Sand Crk Ph 2 BLDG. ⋅ Marina Klein

Welcome to this Charming Townhome in the sought out Villages of Sand Creek! This home has great curb appeal with perennials galore and is a bird and butterfly paradise. This townhome checks all the boxes: 4 bedrooms, 2 full baths, full basement & a 2 car garage. This home has MAIN FLOOR LIVING with laundry and primary bedroom, full bathroom with double sinks, a shower and jetted tub on the main floor. The living room boasts a vaulted ceiling and fireplace, leading to the kitchen and dining room area with all stainless appliances, pantry and a nice sliding glass door that leads to the back patio. The upper level has a full bathroom and 3 large bedrooms with huge walk-in closets and there is an additional walk-in storage closet. The basement offers an additional 1,272 sq ft of space that is ready to be finished. This home is minutes from 80/94, 80/90, Coffee Creek, the Indiana Dunes State Park, downtown Chesterton shopping, restaurants, farmers markets, parks and so much more!

376 Cherry Hills Drive, Chesterton

Listing courtesy of Marina Klein from Blackrock Real Estate Services.

$199,900

3 Beds ⋅ 2 Baths ⋅ 845153 MLS ⋅ 1,764 SqFt. ⋅ Jared Gomez

Welcome to your new warm and cozy home! You'll enjoy the fireplaces, solid hardwood floors and privacy from your back yard. The home is situated on over 4 acres and is adjacent to protected wetlands. It is also close to shopping, expressways and the Indiana Dunes. The windows, furnace, air conditioner and hot water heater are newer. Come take a look!

1063 Frontage Road, Chesterton

Listing courtesy of Jared Gomez from Listing Leaders.

$259,000

4 Beds ⋅ 2 Baths ⋅ 844916 MLS ⋅ 1,542 SqFt. ⋅ Jasmine Gonzalez

Price Improvement from this motivated seller! Bring an offer! Remodeled home in a highly desired location! Location is one of the key features of this home located 5 minutes from Hwy 49, the Dunes, and approximately 45 minutes from Chicago. The up and coming downtown Chesterton, YMCA, Chesterton Park, and splash pad are only 3 minutes away. Bailey Elementary & Montessori School are only a few blocks away. Featuring a spacious updated living room with a beautiful fireplace. The formal dining room is a wonderful addition to the home. The modern kitchen includes new flooring, cabinets, countertops, and bar overhang for barstools. A full bathroom was added downstairs. There is a small office and bedroom with bathroom on the main level. Upstairs you will find 2 spacious updated bedrooms. The backyard space has been transformed into a private oasis with edible grapes on the fence. The storage shed is perfect for storing outdoor equipment. The home sits on a nice size lot with additional yard space to the right of the carport. Enjoy lower taxes and a quiet neighborhood.

656 S 4th Street, Chesterton

Listing courtesy of Jasmine Gonzalez from Coldwell Banker Realty.

$186,500

2 Beds ⋅ 2 Baths ⋅ 843092 MLS ⋅ 1,165 SqFt. ⋅ Westchester Village Condo BLDG. ⋅ Edwin Negron

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

Listing courtesy of Edwin Negron from BluKey Realty.

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Updated . Information deemed reliable but not guaranteed.

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.