Chesterton Real Estate

Welcome to Chesterton, Indiana – a charming town that beautifully blends small-town warmth with modern conveniences. Nestled in Porter County, Chesterton is a hidden gem located just a stone's throw away from the stunning shores of Lake Michigan. With its rich history, vibrant community, and an array of outdoor activities, it’s no wonder that Chesterton is a sought-after destination for families, young professionals, and retirees alike.

The heart of Chesterton is its picturesque downtown, where you’ll find an eclectic mix of boutique shops, cozy cafes, and delightful restaurants. Whether you’re in the mood for a leisurely stroll or a night out, the downtown area offers a welcoming atmosphere that makes every visit special. Don’t miss the Chesterton European Market, held weekly from May to October, where local vendors showcase fresh produce, artisanal goods, and handmade crafts.

Nature enthusiasts will revel in the town’s proximity to the Indiana Dunes National Park, where miles of sandy beaches and scenic trails await. Chesterton is also home to several parks and recreational facilities, making it easy to enjoy outdoor activities year-round.

For families, the town boasts top-rated schools and a strong sense of community, fostering an environment where children can thrive. With easy access to major highways and nearby cities like Valparaiso and Gary, Chesterton is perfectly positioned for commuters seeking a peaceful suburban lifestyle without sacrificing convenience.

Discover the charm of Chesterton, Indiana – where community spirit and natural beauty come together to create an idyllic place to call home!

Newest Listings in Chesterton

$130,000

2 Beds ⋅ 2 Baths ⋅ 846783 MLS ⋅ 789 SqFt. ⋅ Keri Nevarez

Discover the potential in this peaceful North Chesterton property, set on approximately 0.70 acres in a serene setting near Indiana Dunes National Park, beautiful Lake Michigan beaches, and the South Shore train station. Whether you're looking for your next investment opportunity, a property to make your own, or a quiet personal escape surrounded by nature, this property offers plenty of possibilities. The home could use a little TLC, making it an excellent opportunity for someone ready to bring their vision to life. Recent updates include a newer roof and a newer well pump head and bladder. The seller will pay for the septic system pump-out, offering added peace of mind. Outside, enjoy a tranquil setting with apple trees, blueberries, grapes, and beautiful multicolored lilies throughout the backyard, creating a garden-like atmosphere with abundant natural beauty and local wildlife. The property also features a two-car garage with a tool crib area and laundry, plus a finished room above the garage with a separate entrance, offering additional flexibility and potential. Enjoy the best of peaceful surroundings while staying close to the outdoor recreation, beaches, and attractions of the Indiana Dunes area. With its setting, acreage, and potential, this property is ready for its next chapter!

1720 Hale Avenue, Chesterton

Listing courtesy of Keri Nevarez from VIA Realty.

$280,000

3 Beds ⋅ 2 Baths ⋅ 846782 MLS ⋅ 1,368 SqFt. ⋅ Paul Boyter

Fall in love with the charm, convenience, and relaxed lifestyle this delightful 3-bedroom, 2-bathroom Pere Marquette cottage has to offer! Featuring a 2-car attached garage, a fully fenced backyard perfect for your four-legged family members, and a beautiful patio tucked away for added privacy among the arborvitae trees, this home is ready for its next chapter. Even better, everything stays! All appliances and personal property included in the sale make this an opportunity you won't want to miss. Please note that the property and included items are being sold AS IS. Craving a delicious gyro? George's Gyros is just down the street! Enjoy an unbeatable location close to the beautiful shores of Lake Michigan, Indiana Dunes State Park, the South Shore train, I-94, and the charming downtown Chesterton European Market. Whether you're looking for a cozy full-time residence, a weekend getaway, or a place to enjoy the best of Northwest Indiana living, this cottage is full of possibilities! No HOA! Enjoy the freedom to make this property your own without monthly association fees or HOA restrictions. Charming, convenient, and close to everything that makes this area special -- come discover the possibilities and make this Pere Marquette cottage your own!

350 Brown Court, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

$342,000

3 Beds ⋅ 3 Baths ⋅ 846644 MLS ⋅ 2,326 SqFt. ⋅ Bonnie Hawksworth

Move-in ready, light and bright, and beautifully updated! Situated on a quiet, tree-lined street, just steps from downtown Chesterton, and in the Duneland School system. With 3-bedrooms and 3-baths, this home features an updated kitchen with green shaker cabinets, granite counters, tile backsplash and stainless appliances, including a gas range and French-door refrigerator. The light-filled entry level flows from kitchen to dining to living room under vaulted ceilings. One step down, the family room has a breakfast-bar partition and opens to the sunroom and back patio. A half bath and laundry are conveniently located at the far end of the main level. Upstairs are the primary suite with its own bath, two more bedrooms and a full bath. The partially finished basement adds a rec room and home office. Updated baths, new flooring and fresh, tasteful decor throughout. Located on a 0.21-acre lot with an adjacent platted, unbuilt right-of-way. Walk to the European Market and downtown shops, and minutes to Indiana Dunes parks and Lake Michigan beaches. South Shore Line service to Chicago from nearby Dune Park.

711 S 18th Street, Chesterton

Listing courtesy of Bonnie Hawksworth from @properties/Christie's Intl RE.

$524,900

3 Beds ⋅ 2 Baths ⋅ 846741 MLS ⋅ 2,146 SqFt. ⋅ Madison Young

LAST MAINTENANCE-FREE LOT IN EASTON PARK! Welcome to the popular Charlie floorplan, our LARGEST ranch design, offering spacious main-level living with thoughtful details throughout! Step inside to discover an impressive open-concept kitchen and great room featuring vaulted ceilings, an electric fireplace, and an abundance of natural light. Just beyond, the 12x12 sunroom with cathedral ceilings provides the perfect space to relax and unwind! The oversized primary suite is privately tucked away from the main living areas and features a spa-inspired bathroom complete with a soaking tub, walk-in shower, double vanity, and spacious walk-in closet. Two additional bedrooms share a full bathroom, offering comfort and privacy for family or guests. A conveniently located main-level laundry room adds to the ease of everyday living. Quality finishes and upgrades include luxury vinyl plank flooring throughout the main living areas, custom cabinetry with 42" uppers, soft-close doors and drawers, soundproofed bathrooms, a tankless water heater, whole-home humidifier, and a fully finished garage with a quiet belt-drive MyQ opener. NEED MORE SPACE? The full unfinished basement with 8-foot ceilings offers incredible potential for future expansion, with the opportunity to nearly DOUBLE your finished living space! Enjoy the convenience of maintenance-free living in Chesterton's beautiful Easton Park neighborhood! Ideally located just minutes from Indiana Dunes State Park, the South Shore train line for easy Chicago commuting, and downtown Chesterton's charming shops and restaurants. Don't miss your final opportunity to build maintenance-free in Easton Park! Hurry to be able to choose your own finishes! Photos are from previous build and are representative only.

493 Magnolia Lane, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$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.

$249,900

4 Beds ⋅ 2 Baths ⋅ 846683 MLS ⋅ 970 SqFt. ⋅ Melissa Yanez

**BRING YOUR VISION AND UNLOCK THE POTENTIAL!** Opportunity awaits with this 4-bedroom, 1.5 -bath Cape Cod-style home offering approximately 2,000 square feet, an attached 2-car garage, and a little over an acre of land in Chesterton! Whether you're an investor searching for your next renovation project or a buyer ready to transform a house into your own masterpiece, this property is full of possibilities! The main level has been stripped down to a blank canvas, offering an open-concept layout ready for your creative ideas and personal touches. The basement provides additional possibilities, with what appears to have been a 3/4 bathroom, bonus room, spacious storage area, and laundry space. Property is serviced by well and septic. Enjoy the spacious setting while remaining conveniently located near downtown Chesterton's shopping, dining, and local attractions, along with Coffee Creek Preserve, nearby parks, and outdoor recreation. Bring your contractor, your imagination, and your plans to restore and reimagine this Cape Cod!

231 E 1200 N, Chesterton

Listing courtesy of Melissa Yanez from Favela Real Estate, LLC.

$330,000

3 Beds ⋅ 2 Baths ⋅ 846682 MLS ⋅ 1,812 SqFt. ⋅ Hannah Villani

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.

$249,000

846609 MLS ⋅ 1,400 SqFt. ⋅ Ryan Peters

This commercial space is located within a modern retail condominium development in Chesterton. Zoned PUD and features 1,400 SF with four private rooms, one bathroom, and an 840 SF open retail/showroom floor. Interior finishes include luxury vinyl, carpet, and tile. Large south-facing windows flood the front space with natural light, creating an inviting and professional atmosphere. The Property Owners Association (POA) manages all exterior maintenance, including landscaping, snow removal, and trash services, offering a hands-off ownership experience. POA dues are 1,671.38 per quarter. Whether you're an investor seeking low-maintenance income or a business owner planning a future relocation, this location offers strong long-term potential in a growing community.

850 Sidewalk Road Unit #101, Chesterton

Listing courtesy of Ryan Peters from StreetFront, LLC.

$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.

$369,000

4 Beds ⋅ 3 Baths ⋅ 846592 MLS ⋅ 2,165 SqFt. ⋅ Braedan Gallas

Welcome to Olde Towne, where space, comfort, and a convenient Chesterton location come together in a home designed for everyday living. Located within the highly regarded Duneland School District, this inviting two-story offers a flexible layout with room to grow. Step inside to a dramatic foyer and living room with soaring ceilings, warm updated flooring throughout, and an elegant gas fireplace that anchors the space. The kitchen is equally functional, offering generous cabinetry and countertop space, a convenient breakfast bar, and an adjoining dining area perfect for casual meals or entertaining. The main-level primary suite creates a private retreat with a tray ceiling, walk-in closet, and en suite bath featuring a whirlpool tub and bidet. Upstairs, a spacious loft offers the perfect setting for a home office, playroom, reading area, or additional lounge space. Two more bedrooms, a full bath, and a versatile bonus room, ideal as a fourth bedroom, guest room, or hobby space to complete the upper level. Outside you will find a back patio, garden bed, and flagstone fire pit area. The unfinished basement also provides even more opportunity, whether you envision a future recreation room, home gym, workshop, or additional storage and laundry. With a spacious floor plan, multiple flexible living areas, and a desirable setting in Olde Towne, this home offers the kind of space that adapts with you through every season of life. Come see why this could be the one you've been waiting to call home to create memories built to last.

817 Olde Towne Square, Chesterton

Listing courtesy of Braedan Gallas from @properties/Christie's Intl RE.

$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.

$397,900

4 Beds ⋅ 3 Baths ⋅ 846510 MLS ⋅ 2,364 SqFt. ⋅ Jennifer Gregg

Welcome to 1580 Eagle St in desirable Golfview Estates! This beautifully updated 4-bedroom, 3-full-bath home offers 2,364 sq ft of stylish and functional living space. Fresh interior paint and updated trim create a bright, move-in-ready feel. The open-concept kitchen, dining, and living area is perfect for everyday living and entertaining, featuring a large island, stainless steel appliances, and a mix of butcher block and granite countertops. The spacious lower-level primary suite offers a gorgeous ensuite bath and a private retreat. Bedroom 2 is located upstairs and also features its own ensuite. A separate family room provides additional living space with room for a home gym, playroom, or media area. Enjoy the large fenced backyard with a paver patio and two-level deck conveniently located off the kitchen. Surrounded by mature trees, Golfview Estates offers neighborhood charm with easy access to a nearby park and the Prairie Duneland Trail. Convenient access to Routes 49 and 94 makes commuting a breeze. Move-in ready and full of thoughtful updates--come see all this home has to offer!

1580 Eagle Street, Chesterton

Listing courtesy of Jennifer Gregg from @properties/Christie's Intl RE.

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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.