Chesterton Homes under $300,000

Chesterton Homes under $300,000

Welcome to Chesterton, Indiana – a charming town nestled in the heart of Porter County, where small-town warmth meets vibrant community spirit! Known for its beautiful landscapes and proximity to the stunning Indiana Dunes National Park, Chesterton offers residents a unique blend of outdoor adventure and suburban comfort. With a rich history dating back to the late 1800s, this picturesque town boasts a quaint downtown area filled with local shops, delightful eateries, and a strong sense of community.

For those seeking affordable housing options, Chesterton is a hidden gem with homes available for under $300,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a variety of charming properties that fit your budget. From cozy bungalows to spacious single-family homes, Chesterton’s real estate market offers something for everyone. Many of these homes feature lovely yards, modern updates, and are conveniently located near local schools and parks.

In addition to its affordable housing, Chesterton is known for its excellent school system, making it an ideal place for families. Residents enjoy a wealth of recreational opportunities, from hiking and biking trails to community events and farmers' markets. With its friendly atmosphere and thriving local culture, Chesterton is not just a place to live; it’s a place to call home. Come explore the possibilities and discover why so many are choosing to make Chesterton their home sweet home!

Newest Chesterton Homes under $300,000

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
522 Park Avenue, Chesterton
$255,000
3 Beds ⋅ 1 Baths
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
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
$172,500
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
1708 Tower Street, Chesterton
$255,000
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
201 S 8th Street, Chesterton
$234,900
3 Beds ⋅ 2 Baths
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
1063 Frontage Road, Chesterton
$199,900
3 Beds ⋅ 2 Baths
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
656 S 4th Street, Chesterton
$259,000
4 Beds ⋅ 2 Baths
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
1913 David Drive, Chesterton
$186,500
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
515 S Park Drive, Chesterton
$259,900
2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton
769 S Calumet Road, Chesterton
$300,000
4 Beds ⋅ 2 Baths
Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 bedrooms plus an office, with character, space, and comfort throughout! The beautiful gourmet kitchen with cabinets galore is just waiting for you to host that special dinner party. The stunning formal dining room is perfect for entertaining, while the large living room with a spectacular fireplace creates the ideal place to cozy up on cool evenings. Now wait until you see the incredible upstairs retreat, a master suite to die for! Enjoy a walk-in closet that feels like an entire extra room along with your own private getaway featuring a grand 20x14 bathroom designed for relaxation and comfort. So much in this home is brand new! Beautiful arched doorways welcome you inside, while large windows flood the home with natural light. Gorgeous plank flooring flows throughout the home, complemented by new carpet in the bedrooms. Outside, you'll love the huge corner lot, fantastic location, fully fenced backyard, and gorgeous deck where you can sit and sip your favorite beverage while enjoying your own peaceful tranquility. ROOF AND GUTTERS are less than 7 months old! A fantastic 2.5-car detached garage adds even more convenience and storage space. There's even a welcoming front porch perfect for relaxing and watching the world go by. Step into tranquility with this beauty... priced under market value! and ready to welcome you home!

769 S Calumet Road, Chesterton
1717 Crocker Street, Chesterton
$249,000
3 Beds ⋅ 2 Baths
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
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