Chesterton Homes under $400,000

Welcome to Chesterton, Indiana – a charming town nestled in Porter County that seamlessly blends small-town warmth with modern conveniences. Known for its rich history and vibrant community spirit, Chesterton is a hidden gem that offers a delightful lifestyle for families, retirees, and everyone in between.

One of the town’s standout features is its proximity to the stunning Indiana Dunes National Park, where residents can enjoy miles of sandy beaches, scenic hiking trails, and breathtaking views of Lake Michigan. Chesterton is also home to a thriving downtown area filled with unique shops, cozy cafes, and local eateries, making it easy to support local businesses while enjoying the friendly atmosphere.

For those seeking a home in Chesterton, the market is brimming with opportunities, especially for properties under $400,000. This price range allows for a diverse selection of charming single-family homes, modern townhouses, and inviting condominiums, all set within picturesque neighborhoods. Whether you’re looking for a quaint starter home or a spacious residence for a growing family, Chesterton has something to fit every need and budget.

Families will appreciate the highly-rated schools and community programs, while outdoor enthusiasts will find plenty of recreational activities to enjoy year-round. With its welcoming community, beautiful landscapes, and affordable housing options, Chesterton is not just a place to live; it’s a place to thrive. Come discover the magic of Chesterton, where your dream home awaits!

Newest Chesterton Homes under $400,000

$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) new YMCA Healthy Living Campus. Enjoy the convenience of having so many of Chesterton's favorite amenities just minutes from your front door. Inside, the ranch-style layout offers comfortable single-level living, plus a basement that provides additional space and plenty of possibilities. Outside, the fenced-in backyard is ready for summer gatherings, pets, play, gardening, or simply relaxing at home. Whether you're looking for your first home, downsizing, or searching for a property in a convenient in-town location, this home offers a great opportunity to enjoy everything Chesterton has to offer!

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.

$399,900

3 Beds ⋅ 2 Baths ⋅ 846066 MLS ⋅ 2,716 SqFt. ⋅ Tiffany Wallen

Welcome to this beautifully remodeled 3 bedroom, 2 bath home situated on 1.5 acres in Chesterton. Offering approximately 2,200 square feet of living space, this home blends stylish updates, generous indoor and outdoor space, and a peaceful setting with a convenient Duneland location. Inside you'll find 3 comfortable bedrooms, 2 beautifully updated bathrooms, and thoughtfully renovated living spaces throughout. The finished basement and dedicated office add even more flexibility, providing plenty of room for working from home, hobbies, recreation, storage, or additional living space. A tankless water heater adds to the home's modern conveniences. Outside the beautiful front porch creates a welcoming first impression, while the spacious 1.5 acre lot offers plenty of room to relax, entertain, and enjoy the peaceful surroundings. A new 16' x 16' deck and 8' x 10' brick patio are scheduled for completion in October, creating even more outdoor living and entertaining space. The tall garage offers additional functionality and features durable epoxy flooring. Enjoy the peace and privacy while remaining close to everything Chesterton has to offer, including shopping, dining, schools, and recreation. Indiana Dunes National Park, Lake Michigan beaches, hiking trails, and countless outdoor activities are just minutes away. Schedule your showing today! Beautifully remodeled, move-in ready, and situated on 1.5 acres, this home offers an incredible combination of space, privacy, modern updates, and location.

904 Mar Mar, Chesterton

Listing courtesy of Tiffany Wallen from Listing Leaders Stately, LLC.

$359,000

5 Beds ⋅ 2 Baths ⋅ 845984 MLS ⋅ 1,728 SqFt. ⋅ Lana Conroy

Welcome to this classic two-story home nestled in an established neighborhood surrounded by mature trees. This spacious home offers five bedrooms, beautiful hardwood floors, and an inviting eat in kitchen with new stainless appliances. This home has been owned and cared for by the same family since it was built, and pride of ownership is evident throughout. Seller has just had brand new mini split system installed, roof and gutters replaced in 2021 as well. Newer Pella windows, trim and doors too. Driveway was seal coated this summer. The basement is finished and would be great as additional living space, office or play-room.

1247 Dogwood Drive, Chesterton

Listing courtesy of Lana Conroy from Coldwell Banker Realty.

$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.

$399,999

4 Beds ⋅ 3 Baths ⋅ 845780 MLS ⋅ 2,406 SqFt. ⋅ Alexis Metcalf

Spacious Bi Level home in the Perfect Chesterton Location! Westchester South offers quiet streets lined with mature trees, close to all Chesterton has to offer. This tastefully updated 4 Bedroom, 3 Bath home offers Real Hardwood floors, Updated Kitchen with Island and Pantry, Updated Bathrooms throughout, Primary Ensuite, Inviting Living room with Gas Fireplace.Outback enjoy a sweet deck looking over the fenced yard. Furnace, A/C and sump pump new in 2026! Roof new in 2019, windows 2022!

301 Primrose Circle, Chesterton

Listing courtesy of Alexis Metcalf from Seramur Properties, LLC.

$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.

$255,000

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.

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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.