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Single Family Homes for Sale in Chesterton, IN

Welcome to your dedicated resource for single family homes for sale 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 single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Chesterton, IN

354 E 1300 N, Chesterton
$525,000
4 Beds ⋅ 2 Baths ⋅ 846693 MLS ⋅ 2,244 SqFt. ⋅ Krystal Bialata
Tucked away in Chesterton is a unique property where natural beauty, history, and opportunity come together! Spanning 11.52 acres across two separate parcels, this property features expansive open lawns, mature trees, wooded acreage, and the Calumet River winding through the back landscape. The first parcel consists of 2.35 acres and features a 4-bedroom, 1.75-bath bi-level home built in 1977. Inside, the spacious family room is highlighted by an impressive brick wood-burning fireplace with a wood stove insert and original wood accents. The kitchen offers abundant cabinetry, while the attached two-car garage provides convenience and additional storage. A backyard deck overlooks the expansive lawn framed by mature trees. The home remains largely in its original condition, offering the opportunity to update and make it your own. The second parcel consists of 9.17 acres and holds a unique piece of Chesterton history. Nestled among the trees is a 1,004-square-foot historic cottage featuring rustic wood interiors, exposed ceiling beams, and 2 fireplaces. Beyond the cottage, wooded acreage surrounds the Calumet River as it winds through the property, creating a beautiful natural setting. The cottage is in need of restoration, offering an opportunity for someone who appreciates its history and original character. From the open green spaces to the secluded wooded surroundings and historic cottage, this property offers something truly different. A rare opportunity to own 11.52 acres with a 2,244 sqft home and a 1,000 sqft 1900's cottage with a story waiting for its next chapter. There is an in-ground pool in between the house and the cottage, with a privacy fence around it. Condition unknown. Property and structures are being sold AS IS.

354 E 1300 N, Chesterton

Listing courtesy of Krystal Bialata from Blackrock Real Estate Services.

938 N 400 E, Chesterton
$320,000
3 Beds ⋅ 2 Baths ⋅ 846682 MLS ⋅ 1,812 SqFt. ⋅ Hannah Villani
Sellers offering a rate buy-down! Discover incredible land value and endless possibilities! Set far back from the road down a long driveway, this 3-bedroom, 2-bathroom bi-level is your private 2.58-acre oasis in the heart of Chesterton. This is the ultimate canvas for an investor looking to add to their portfolio, or a DIY homeowner looking for a live-in renovation with immediate equity potential. This home is a fantastic equity-building opportunity that is totally livable from day one. Move right in and take your time bringing your vision to life! The upper level features comfortable living spaces, open concept kitchen and dining area, 3 bedrooms, and a refreshed, newer bathroom. Downstairs, the lower level is far from just an unfinished basement; it's a bright, open canvas ready to be reimagined. Complete with a half bath and laundry area, this space could easily be transformed into a sprawling entertainment room, a dedicated home gym, a private guest suite, or a quiet home office.You'll also love the attached 2-car garage, offering plenty of extra room for storage or a workshop. Location is everything, and this property delivers. Enjoy the quiet privacy of acreage living while being just a short drive from Lake Michigan beaches, hiking at the Indiana Dunes State Park, and local downtown dining. Plus, quick access to major highways and the South Shore Line makes commuting a breeze. Bring your imagination, your tool belt, and make this Chesterton gem shine!

938 N 400 E, Chesterton

Listing courtesy of Hannah Villani from @properties/Christie's Intl RE.

2221 Easton Park Drive, Chesterton
$599,000
4 Beds ⋅ 3 Baths ⋅ 846593 MLS ⋅ 2,611 SqFt. ⋅ Madison Young
Welcome to the popular Melanie floor plan in Easton Park--FULLY LOADED with upgrades well beyond the standard features and MOVE IN READY! From custom cabinetry and elevated trim work to thoughtful built-ins and upgraded mechanicals, this home has been designed with the details already taken care of. You'll love the open-concept main floor with luxury viny plank and featuring a dedicated office with an elevated trim package, upgraded main-floor bath, pantry, and mudroom with BUILT-IN STORAGE. The living room is anchored by a beautiful FIREPLACE with custom built-ins, while the kitchen takes center stage with 42" cabinetry, soft-close features, interior cabinet organization, quartz countertops, a FULL QUARTZ BACKSPLASH, range hood, and a separate COFFEE BAR with open shelving and built-in beverage cooler. Upstairs, LVP flooring extends throughout the hallway and into the impressive primary suite featuring a TRAY CEILING, spacious ensuite with SOAKING TUB, and walk-in closet finished with CUSTOM CLOSET CABINETRY. The highly upgraded upstairs laundry room offers additional cabinetry and countertop space to make everyday tasks easier and more organized. The upgrades continue with a 3-CAR GARAGE, dual-zoned HVAC, tankless water heater, whole-house humidifier, additional soundproofing, and a FULLY FINISHED GARAGE. Outside, the home is be FULLY LANDSCAPED for a polished, move-in-ready finish. If you're looking for new construction with all the thoughtful touches done for you, this Melanie has the upgrades, finishes, and details already built in. Come see why Easton Park and why this move in ready Melanie floor plan should be at the top of your list!

2221 Easton Park Drive, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

1137 N 475 E, Chesterton
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 846577 MLS ⋅ 5,809 SqFt. ⋅ Lisa Gaff
15.67 Private Acres | 4 Bed, 5 Bath All-Brick Estate | Pool, Pond & Sunroom | Duneland Schools *THE INTERIOR IS BEING PAINTED A BEAUTIFUL CREAMY WHITE* NEW PICS COMING! Tucked away on 15.67 sprawling acres in Jackson Township, this all-brick estate feels less like a home and more like a private escape -- where luxury, space, and nature meet in perfect balance. With 4 bedrooms and 5 bathrooms across a layout built for both quiet evenings and unforgettable gatherings, every room here earns its place. The kitchen is the heart of the show: granite counters, stainless appliances, and a 6-burner cooktop with griddle ready for anything from Sunday brunch to a full holiday spread. Just off the kitchen, a huge, light-filled family room offers the flexibility to suit however you live -- set it up as a game room for movie nights and gatherings, or dress it up as a formal dining space for holiday entertaining; the choice is yours. The primary suite is a true retreat, with a spacious en suite bath designed for unwinding, while two more bedrooms come with their own private en-suite baths -- comfort and privacy for family or guests alike. A sunroom with a built-in hot tub turns any season into relaxation season, and a dedicated bathroom just steps from the pool keeps pool days effortless. Outside, the estate transforms into a personal resort: dive into the in-ground pool, host under the stars on the expansive deck, or wander private walking trails through mature woods. The stocked pond rounds things out -- perfect for a lazy afternoon of fishing or simply soaking in the scenery. Downstairs, an unfinished basement is a blank canvas waiting for a home theater, gym, extra living space, or guest suite. Zoned for Duneland School Corporation and just minutes from the beaches of Indiana Dunes National Lakeshore, with the South Shore Railway offering an easy ride into Chicago, this is countryside living without giving up the convenience of the city. Schedule your private tour today!

1137 N 475 E, Chesterton

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

601 Long Bridge Drive, Chesterton
$289,000
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.

363 Ridgeview Drive, Chesterton
$974,900
3 Beds ⋅ 4 Baths ⋅ 846121 MLS ⋅ 2,775 SqFt. ⋅ Alexander Nickla
This stunning custom RANCH home sits on a private 1.18 wooded acre lot in the beautiful subdivision of Woodridge Hills featuring 3 bedrooms all with EN-SUITE BATHROOMS, 3.5 total bathrooms, full unfinished WALKOUT BASEMENT, THREE CAR side-loaded garage, three fireplaces, and nearly 2800 ft. of quality construction. This home features a well designed split bedroom floor plan with multiple living spaces. The main living area features vaulted ceilings, an OPEN CONCEPT living space, a beautiful stone fireplace, and tons of windows for natural light and views of the backyard. The kitchen features gorgeous, high-end cabinetry with crown molding, granite countertops, and a secret walk-in pantry with tons of storage and an additional refrigerator. Next to the kitchen is a spacious dining area with a sliding glass door to the backyard. Off of the living room is a sliding glass door that leads to the massive covered back patio with vaulted ceilings and beautiful wood beams. The master suite features a custom double-Trey ceiling, fireplace, walk-in closet, and private bathroom. The master bathroom features quality cabinetry, freestanding tub, and custom tiled full walk-through shower. The other side of the home offers a second living room with a beautiful fireplace, two spacious bedrooms with private en-suite bathrooms, a finished laundry room, and a beautiful staircase leading to the full unfinished WALKOUT BASEMENT, providing the opportunity for somebody to double their square footage! Other features of this home include a main Floor office, powder room, 2x6 exterior walls, Anderson windows, 16" on-center framing, covered back patio, additional fire pit patio space, lots of trees for privacy, and conveniently located for commuting to the city, Lake Michigan beaches, and all of NWI's amenities!

363 Ridgeview Drive, Chesterton

Listing courtesy of Alexander Nickla from Realty Executives Premier.

2350 Pradera Trail, Chesterton
$569,900
4 Beds ⋅ 3 Baths ⋅ 846100 MLS ⋅ 1,820 SqFt. ⋅ Nickolas Witvoet
Proposed Construction: We are excited to showcase THE ASPEN! This new construction, two-story craftsman style home encompasses four bedrooms, three bathrooms, and 1820 sq. ft of open-concept living. A covered front porch greets you upon arrival and welcomes you inside where you will discover an open foyer area that leads to the cozy den/office. Nine foot ceilings guide you throughout the first floor and into the kitchen and great room area. The kitchen showcases luxury cabinetry, granite counters, island, and stainless steel appliances. The great room provides lots of room to relax and entertain, plus you can add a fireplace to serve as the focal point for the room (an optional upgrade). The FIRST-FLOOR primary bedroom is vast in size and has a walk-in closet and a lavish ensuite with tiled shower! The main level also has a conveniently positioned laundry room and half bath. Upstairs you will find three additional bedrooms, all spacious with plenty of closet space, and a quaint computer or reading area. Outside you have a concrete patio in the backyard providing views of the pond. Because this home is still in the pre-construction phase, you can make modifications and personalized selections that suit your taste and lifestyle--giving you the opportunity to customize and upgrade the way you want. Additional highlights include a two-car garage, a full basement, R-15 wall and R-38 ceiling insulation, a high-efficiency Carrier HVAC system, electrical metal conduit, and many other premium standard features. You'll have peace of mind knowing your home was built by an award-winning, multi-generational builder with decades of experience. The 1100 Woods sits just across the street from Dogwood Park and within walking distance of the Prairie Duneland Trail, with dining, shopping, and expressway access only minutes away. Start making this new-construction home yours today! *Pricing is subject to change and should be confirmed with the builder upon inquiry*.

2350 Pradera Trail, Chesterton

Listing courtesy of Nickolas Witvoet from Listing Leaders Northwest.

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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.


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