Chesterton Homes under $250,000

Welcome to Chesterton, Indiana – a charming town nestled in Porter County that effortlessly combines small-town charm with modern conveniences. Known for its picturesque landscapes and friendly community, Chesterton is a hidden gem that offers a delightful place to call home. With its close proximity to the stunning Indiana Dunes National Park and the serene shores of Lake Michigan, residents enjoy an abundance of outdoor activities, from hiking and biking to swimming and picnicking.

Chesterton boasts a vibrant downtown area filled with unique shops, delicious eateries, and a bustling farmers' market that showcases local produce and artisanal goods. The town is also home to excellent schools, making it an ideal choice for families looking to settle down in a nurturing environment.

For those seeking affordable housing options, Chesterton has a variety of homes available for under $250,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a range of charming properties that suit your needs. From cozy bungalows to spacious single-family homes, Chesterton offers something for everyone.

The community spirit is palpable, with numerous events and festivals held throughout the year, fostering connections among residents. With its affordable housing, friendly atmosphere, and beautiful surroundings, Chesterton is not just a place to live – it’s a place to thrive. Discover your dream home in this enchanting town and experience all that Chesterton has to offer!

Newest Chesterton Homes under $250,000

$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.

$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.

$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.

$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.

$249,000

3 Beds ⋅ 2 Baths ⋅ 832918 MLS ⋅ 2,400 SqFt. ⋅ Paul Boyter

Move-in ready with built-in upside, this fully remodeled 11/2-story home offers three bedrooms and two full bathrooms. The basement bedroom and bathroom will be completed before closing. Recent improvements include new roof shingles, windows, doors, trim, abundant kitchen cabinets and countertops, whirlpool tub, waterproof vinyl plank flooring throughout, and central air conditioning. Enjoy outdoor living on the spacious new wraparound deck overlooking a large backyard, ideal for relaxing or entertaining. The home is adjacent to the Duneland Prairie Bike Trail, offering immediate access to miles of scenic recreation. The basement is fully framed and electrically roughed in for a private primary suite, including a large 17x20 bedroom, walk-in closet, full bath with double vanity, and laundry area. A new egress window is already in place, making this level bright, functional, and ready to finish with minimal additional investment. Ideally located in the award-winning Chesterton school district, near Hwy 149 and County Rd 1100, this home provides quick access to shopping, restaurants, Indiana Dunes on Lake Michigan, the South Shore Train, downtown Chesterton, and the popular European Market, with an easy 45-minute commute to Chicago. A rare opportunity for turnkey comfort with strong future value.

1717 Crocker Street, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

Start Your Search

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.