Homes for Sale in Chesterton, IN Between $350,000 to $400,000

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Welcome to your dedicated resource for Homes for Sale Between $350,000 to $400,000 in Chesterton, IN. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesterton, IN agent, Kimberly Sut Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $350,000 to $400,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Chesterton, IN Homes for Sale Between $350,000 to $400,000

$375,000

2 Beds ⋅ 2 Baths ⋅ 845231 MLS ⋅ 1,530 SqFt. ⋅ Nicole Szymanski

Welcome to this turn-key, single-story ranch home in Chesterton featuring 2 bedrooms and 2 full bathrooms. Meticulously maintained, immaculate, and completely move-in ready, this home offers effortless one-level living with stylish modern upgrades completed within the past year, including fresh paint throughout, a custom accent wall, custom blinds, updated lighting fixtures, and a custom organizer in the primary bedroom walk-in closet. The light-filled sunroom provides versatile additional living space that is perfect for a cozy morning coffee nook or a bright home office. Enjoy added value with all kitchen and laundry appliances as well as the main living room TV included with the sale, along with a fully enclosed backyard featuring a newly installed privacy fence for relaxation or outdoor gatherings. Conveniently located close to everything Chesterton has to offer, you are just minutes from local dining and shopping, the stunning Indiana Dunes National and State Parks, major highways, and the South Shore Line for an easy commute into Chicago or fun day trips.

1633 Gustafson Avenue, Chesterton

Listing courtesy of Nicole Szymanski from Better Homes and Gardens Real.

$359,900

3 Beds ⋅ 2 Baths ⋅ 845085 MLS ⋅ 1,400 SqFt. ⋅ Samantha Cheatham

Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, perfectly situated on an expansive .48-acre lot within the highly sought-after Duneland School Corporation. With approximately 1,400 square feet of comfortable living space, this home offers the ideal blend of modern updates, functionality, and peaceful outdoor space. The home was completely taken down to the studs and renovated approximately five years ago, providing an impressive list of major improvements including new windows, roof, siding, furnace, air conditioning, vinyl flooring, well, septic system, and a newly paved driveway. The thoughtful updates continue with new storm doors in 2025 and, in 2026, a new shower with warranty, new shed, owned water softener, and new sump pump with a battery backup system. The stainless-steel appliances are included, and the versatile mudroom adds even more functionality with the flexibility to serve as a home office, den, or additional everyday living space. Step outside and enjoy the beauty and privacy of nearly half an acre. The spacious, well-maintained yard provides plenty of room for entertaining, gardening, pets, play, or simply enjoying your own outdoor retreat. With extensive updates, major systems already addressed, a beautiful lot, and the advantage of Chesterton schools, this is a home that offers both comfort and peace of mind. A wonderful opportunity to enjoy a move-in-ready property with nothing left to do but make it your own!

1430 N Veden Road, Chesterton

Listing courtesy of Samantha Cheatham from Realty Executives Premier.

$389,000

4 Beds ⋅ 3 Baths ⋅ 844907 MLS ⋅ 2,270 SqFt. ⋅ Branden Luna

Welcome to this 4 bedroom, 3 bath, 2-story home located in desirable Villages of Sand Creek. Main level offers a Formal Living Room as well as a Formal Dining, spacious Eat-in Kitchen which is open to the Family Room, and the Laundry Room. Upstairs you will find all 4 bedrooms freshly painted with newer carpet. The Primary Suite has an attached full bath with separate shower and tub and large walk-in closet. This home is situated on a cul-de-sac with a lovely view of the pond located across the walking path. This neighborhood is only 3 miles from the Indiana Dunes & Lake Michigan, close to restaurants, shopping, golf courses, and is an easy commute to Chicago.

378 Ballenisle Court, Chesterton

Listing courtesy of Branden Luna from Coldwell Banker Real Estate Gr.

$399,900

4 Beds ⋅ 3 Baths ⋅ 844671 MLS ⋅ 2,372 SqFt. ⋅ Marco Trevino

Quality-built home that has been beautifully maintained and is truly move-in ready! This open-concept tri-level floor plan makes exceptional use of every square foot. The spacious primary suite features a vaulted ceiling, walk-in closet, and private full bath with a double vanity and a relaxing whirlpool tub. The new updated kitchen offers quartz counter tops, new dishwasher, abundant cabinetry, generous counter space, and a large pantry for added convenience. The huge lower-level rec room with a cozy gas fireplace provides the perfect space for entertaining or relaxing. The main level flooring has been updated with waterproof, scratch resistant, realistic wood grain LVP flooring, and outlets have been strategically installed higher on the walls in the bedrooms and rec room for easy TV mounting and setup. Enjoy the backyard with storage shed and plenty of room for outdoor activities. The exterior also features all season Govee lighting to really give your home that pop all year round. Frontier fiber optic cable has also been recently ran underground. A must-see home that combines quality craftsmanship, thoughtful updates, and functional living space.

1927 Cory Lane, Chesterton

Listing courtesy of Marco Trevino from Listing Leaders.

$399,500

3 Beds ⋅ 3 Baths ⋅ 844190 MLS ⋅ 2,332 SqFt. ⋅ Lisa Gaff

Bring your offer!!! Calling all buyers, contractors, and investors who see potential where others see projects. Some pictures are AI generated. See what the potential is when changing out the paint, carpet, laundry room flooring and stainless appliances. This 3-bed, 3-bath ranch home on a 0.77 acre lot in Chesterton is a rare chance to build instant equity in one of Northwest Indiana's most sought-after school districts. The roof is only 1 year old -- one of the biggest-ticket items already handled for you. Beneath the cosmetic wear is a home with genuinely good bones: a solid layout, real square footage (2232= 1st floor + 2232 =unfinished basement), and a floor plan worth restoring rather than replacing. Yes, it needs work -- this is NOT a move-in-ready listing, and it's priced accordingly. But for the right buyer, that's exactly the point. Bring your contractor, your vision, or your renovation loan, and turn this into serious equity in a market where finished homes are commanding a premium. In-ground pool, expansive decking, additional 2 car detached garage at the back of the property. Located minutes from downtown Chesterton, the South Shore Line, and the Indiana Dunes, with access to Duneland Schools -- this is a location buyers don't want to miss, at a price point that leaves room to make it your own.

1776 Indian Boundary Road, Chesterton

Listing courtesy of Lisa Gaff from White Hat Realty Group, LLC.

$359,900

4 Beds ⋅ 2 Baths ⋅ 843482 MLS ⋅ 1,828 SqFt. ⋅ Melissa Capellari

Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

2342 Westwood Lane, Chesterton

Listing courtesy of Melissa Capellari from Coldwell Banker Real Estate Gr.

$395,000

4 Beds ⋅ 4 Baths ⋅ 843317 MLS ⋅ Paul Boyter

Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining rental unit, now vacant, includes 2 bedrooms and 2 bathrooms, allowing you to choose the tenants and rents. The 455 side has a brand new air conditioner and new appliances last year. New windows were installed in 2025. Both units enjoy large, private backyards perfect for relaxing, entertaining, or gardening. Conveniently located just minutes from the beautiful beaches of Lake Michigan, charming downtown Chesterton, and the renowned European Market, this property also offers an easy commute with quick access to the South Shore Line and I-94, putting downtown Chicago within approximately 45 minutes. Whether you're looking to reduce your housing costs or expand your investment portfolio, this property offers the perfect combination of comfort, convenience, and income potential.

455 Woodlawn Avenue, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

$389,000

841312 MLS ⋅ Paul Boyter

This 1.44 acre lot is located close to the Indiana Toll Road, I-94, the South Shore train station, The Indiana Dunes State Park, and the Indiana Dunes National Park. Across Highway 49 you will find Culver's, AJ's Pizza, Popeye's, Dunkin Donuts, Hilton Garden Inn, Bob Evans, and multiple medical and office buildings.

1022 N Old State Rd 49, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

$359,900

4 Beds ⋅ 2 Baths ⋅ 840771 MLS ⋅ 1,975 SqFt. ⋅ Geremy Rinker

Welcome to 3624 Fairway Drive in Chesterton's desirable Golfview Estates! Offering nearly 2,000 square feet of living space, this 4-bedroom, 2-bath quad-level home provides the room and flexibility today's buyers are looking for. The home's multi-level design creates distinct spaces for gathering, relaxing, entertaining, working from home, or simply spreading out. Step inside to vaulted ceilings, warm bamboo hardwood flooring, a welcoming fireplace, and multiple living areas filled with possibilities. Outside, the generously sized corner lot and expansive two-tier deck create an inviting setting for summer cookouts, entertaining friends and family, or enjoying a quiet evening at home. Beyond the property itself, you'll love everything this location has to offer. Golfview Estates features neighborhood walking opportunities, a playground and park, while nearby trails, the Indiana Dunes National Park, South Shore Line, shopping, dining, and major highways put recreation and everyday conveniences within easy reach. Commuters will also appreciate convenient access toward Chicago and the surrounding Northwest Indiana communities. Located within the Duneland School Corporation, 3624 Fairway Drive offers a wonderful combination of space, location, and versatility in an established Chesterton neighborhood. Come see the possibilities and imagine making this home your own!

3624 Fairway Drive, Chesterton

Listing courtesy of Geremy Rinker from @properties/Christie's Intl RE.

$364,999

3 Beds ⋅ 3 Baths ⋅ 840573 MLS ⋅ 2,109 SqFt. ⋅ Daniel Meyer

Welcome to this beautifully maintained ranch home in the desirable community of Chesterton, now featuring a brand-new roof! This spacious residence offers 3 bedrooms, 3 bathrooms, and 3 inviting fireplaces, creating the perfect blend of comfort, warmth, and timeless charm. The thoughtfully designed floor plan provides generous living spaces ideal for both everyday living and entertaining guests. Enjoy the convenience of true single-level living while relaxing by one of the cozy fireplaces on cool Indiana evenings, and enjoy a nice hot soak in the new hot tub! Ideally situated just minutes from downtown Chesterton, parks, top-rated schools, shopping, restaurants, the South Shore Line, and major highways, this home offers exceptional accessibility for commuters and anyone looking to experience the best of Northwest Indiana. Don't miss your chance to own this wonderful home--schedule your private showing today!

117 Washington Avenue, Chesterton

Listing courtesy of Daniel Meyer from Listing Leaders.

$367,999

4 Beds ⋅ 3 Baths ⋅ 837425 MLS ⋅ 2,282 SqFt. ⋅ Lacey Lafata

Welcome to this charming and beautifully updated home in the highly sought-after Morgan Park neighborhood! Move-in ready and full of character, this spacious home offers over 2,200 square feet of living space, featuring four generously sized bedrooms with excellent closet space. The main-level primary suite offers a private full bathroom and a bright, inviting sunroom--perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious combined living and dining room provides a comfortable layout for entertaining guests and gathering with family. Recent updates include new carpet throughout, fresh interior paint, a new bathroom floor, and major improvements completed within the past 10 years, including the roof, furnace, air conditioning, and electrical system. One of the home's standout features is its enclosed front and back porches, offering additional year-round living space, storage, and plenty of charm. Outside, the beautifully landscaped backyard is filled with mature greenery, flowers, and established plants, creating a peaceful retreat on this large corner lot. The one-car garage provides convenient parking, additional storage, and protection from Indiana's changing weather. It is also equipped for electric vehicle charging. With its spacious layout, thoughtful updates, unique character, and desirable Morgan Park location, this home offers a wonderful opportunity to make it your own. Schedule your private showing today!

303 E Porter Avenue, Chesterton

Listing courtesy of Lacey Lafata from McColly Real Estate.

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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.