Chesterton Homes for Sale

Chesterton Homes for Sale

Welcome to Chesterton, Indiana—a charming town where small-town warmth meets modern convenience! Nestled in Porter County, Chesterton is not just a place to live; it’s a community where families thrive, friendships flourish, and memories are made. Known for its picturesque landscapes and vibrant downtown area, Chesterton offers a delightful mix of history, culture, and natural beauty.

One of the highlights of Chesterton is its close proximity to the stunning Indiana Dunes National Park, where residents can enjoy miles of sandy beaches, hiking trails, and breathtaking views of Lake Michigan. The town is also home to several parks, offering ample opportunities for outdoor activities, picnics, and family gatherings. With a strong sense of community, Chesterton hosts various events throughout the year, including farmers' markets, festivals, and art shows, making it easy to connect with neighbors and celebrate local culture.

For those considering a move to this enchanting town, you’ll be pleased to discover a diverse array of homes for sale. From charming historic houses that reflect the town's rich heritage to modern family homes equipped with all the latest amenities, Chesterton has something for everyone. Whether you’re a first-time homebuyer or looking to settle into your forever home, the real estate market here is vibrant and full of potential.

Explore the possibilities and find your dream home in Chesterton, where a welcoming community and a beautiful setting await you! Let us help you embark on this exciting new chapter in your life.

Newest Chesterton Homes for Sale

1431 Maximilian Drive, Chesterton
$315,000
3 Beds ⋅ 2 Baths ⋅ 847317 MLS ⋅ ACTIVE Status
Move-In Ready 3 Bed, 2 Bath Ranch | New 2026 Roof, Carpet & Paint | Rose Hill Estates | Just unpack and enjoy. This 3-bedroom, 2-bath ranch in Rose Hill Estates offers 1,622 sq ft of one-level living, refreshed from top to bottom, with the big-ticket items already done for you. A brand-new roof installed in summer of 2026 tops the list, the furnace and A/C were both replaced in 2023, and the water heater was replaced in 2021, so the systems that matter most are handled. Inside, fresh paint throughout and brand-new carpet give every room a clean, bright feel. The open floor plan with cathedral ceilings keeps everything connected, while new kitchen flooring and a brand-new refrigerator make it ready for everyday cooking and entertaining. The water heater is just 5 years old, adding even more peace of mind. A new sliding glass door opens to a newly surfaced deck, the perfect spot for morning coffee, summer cookouts, or relaxing at the end of the day. The manageable 0.14-acre lot keeps yard work easy. Built in 2005 and located in Chesterton, this home is close to downtown shops and restaurants, Indiana Dunes National Park, the South Shore Railway, and major highways. It's served by the Duneland School District. Schedule your showing today!

1431 Maximilian Drive, Chesterton
2524 Hilfiger Drive, Chesterton
$499,999
4 Beds ⋅ 4 Baths ⋅ 847303 MLS ⋅ ACTIVE Status
Meticulously maintained and lovingly cared for by its original owner, this beautiful home is nestled in one of the area's most desirable neighborhoods. Offering four spacious bedrooms, four bathrooms, and a well-appointed kitchen, this home seamlessly blends comfort, style, and functionality. The thoughtfully designed floor plan provides inviting spaces for both everyday living and entertaining, while the fully finished basement offers exceptional additional living space with endless possibilities. The Ensuite Primary bedroom offers a beverage center, built-in window seat and a HUGE walk in closet. Pride of ownership is evident throughout, making this a wonderful opportunity to own a truly special home in a sought-after location. The big ticket items; roof, HVAC and HWH have all been replaced over the last 5 years

2524 Hilfiger Drive, Chesterton
2227 W 1100 N, Chesterton
$899,900
6 Beds ⋅ 5 Baths ⋅ 847256 MLS ⋅ ACTIVE Status
SIGNIFICANT PRICE IMPROVEMENT! Now offered substantially below appraised value, this stunning NEW CONSTRUCTION home presents an opportunity to own one of Chesterton's most impressive luxury residences. Overlooking Dogwood Park and situated on nearly half an acre, this extraordinary 6-bedroom, 4.5-bath home offers over 5,000 square feet of thoughtfully designed living space. Luxury upgrades and designer finishes are showcased throughout. The main-level primary suite provides a private retreat featuring a soaking tub, custom tiled shower, dual vanity, walk-in closet, and dedicated laundry area. The open-concept great room boasts soaring 11-foot ceilings and flows seamlessly to a spacious 20' x 16' covered patio, perfect for entertaining or relaxing. The chef-inspired kitchen is truly the heart of the home, highlighted by an oversized island, Cafe matte white appliances, double ovens, high-efficiency double-drawer dishwasher, instant hot water dispenser, beverage center, ceiling-height backsplash, and an expansive walk-in pantry with built-in desk area. The main floor also features a dramatic two-story foyer, sun-filled den, generous dining area, convenient half bath, and a unique dog-washing station just inside the garage entry. Upstairs, you'll find a second private ensuite complete with dual vanity and laundry area, two additional bedrooms, a full hall bath, and a comfortable loft overlooking the park. The finished lower level offers 9-foot ceilings, a large recreation space, two additional bedrooms, a full bath, dedicated laundry room, and abundant unfinished storage space. Additional highlights include custom window treatments throughout, a 3-car garage with heated and cooled dog room, security system, and immediate availability. Ideally located directly across from Dogwood Park and within walking distance of Chesterton High School. Close to the Indiana Dunes National Park, expressways and less than an hour from downtown Chicago. Award-winning Duneland Schools.

2227 W 1100 N, Chesterton
620 S 18th Street, Chesterton
$349,900
3 Beds ⋅ 2 Baths ⋅ 847254 MLS ⋅ ACTIVE Status
Beautifully updated 3 bed, 2 bath ranch in the heart of charming Chesterton! This move-in ready home offers the perfect blend of modern updates and timeless character, situated on nearly a half-acre lot! The property offers a peaceful, country-like atmosphere while remaining just minutes from everything Chesterton has to offer. Inside, the stunning remodeled kitchen features custom maple cabinetry with soft-close doors and drawers, granite countertops, stainless steel appliances, updated lighting, and a spacious center island perfect for gathering with family and friends. Rich dark walnut hardwood floors flow throughout the main living areas. A charming fireplace highlights the dining room along with an abundance of natural light streaming in through the sliding glass door that opens onto the back covered porch. Step outside to enjoy the 12' x 20' concrete patio, perfect for entertaining or relaxing. A custom built shed featuring a SmartSide exterior, metal roof, and oversized double doors provide exceptional outdoor storage. Major improvements add both value and peace of mind, including a newer roof, insulated vinyl siding, soffits, gutters, windows, and sliding glass door. Both bathrooms have been tastefully updated, including a beautifully remodeled en suite bath with a tiled shower, updated lighting, and vanity. The partially finished basement expands the living space with recessed lighting, new windows, drywall, painted ceiling, and luxury vinyl plank flooring, making it ideal for a family room, home office, workout space, or recreation area. Conveniently located near award-winning Duneland Schools, Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, shopping, dining, and major highways for an easy Chicago commute, this exceptional property offers the best of both worlds: modern comfort with a spacious, country-feel setting in one of Northwest Indiana's most desirable communities!

620 S 18th Street, Chesterton
383 E 1050 N, Chesterton
$460,000
4 Beds ⋅ 3 Baths ⋅ 847099 MLS ⋅ ACTIVE Status
Looking for a country home just minutes away from town? This maybe be the one for you! This fully remodeled home boasts 4 bedrooms, 3 bathrooms and 2500 sq ft of living space on a full acre of land. The brand new kitchen offers granite countertops with all new appliances and soft close cabinets. All 3 bathrooms have been completely renovated with new bathtub/showers, and vanities. The large living room offers a massive picture window for plenty of natural light. Off the kitchen is a full dining room with a picturesque 4 seasons room with plenty of windows to view the natural surroundings. New laminate flooring flows through the entire upstairs for a clean and elegant appearance. There are 3 bedrooms on the main level with the primary bedroom having an en suite bathroom to escape for some privacy. Downstairs you will find a massive rec room that could be easily transformed into a game room, large media area, or anything else your heart could desire. With a full bathroom and separate bedroom with egress window, the lower level could even be converted into related living space. There is also a large flex area in the lower level that could be finished as a home office, gym, or used for large storage. Parking will never be an issue with a heated attached garage and a 20x24 ft detached 2 car garage. All the big ticket items in this house have been updated, windows, roof, kitchen, bathrooms, water heater, flooring, and more are all new! Don't miss your opportunity to buy in the very desirable Jackson Township area, schedule your showing today!

383 E 1050 N, Chesterton
408 S 11th Street, Chesterton
$274,900
3 Beds ⋅ 1 Baths ⋅ 846797 MLS ⋅ ACTIVE Status
Did you know that the average buyer for this home here can get a monthly payment savings of approx three hundred per month. Ask me how while you view this Beautifully Updated Ranch in a Highly Desirable Chesterton Neighborhood! This exceptionally clean, 3-bedroom, 1-bath home offers the perfect combination of charm, modern updates, and a fantastic location within a sought-after school district! Step inside to an inviting sunroom, perfect for the morning coffee and a good book. The open-concept floor plan features updated flooring, accent wall with an electric fireplace and just a welcoming living space. The beautifully updated eat-in kitchen offers an abundance of cabinetry, quartz countertops, stainless steel appliances, and a spacious peninsula. All the updates were done within the last 5 yrs. The unfinished basement provides generous storage and possibilities .Located in an established, desirable neighborhood just minutes from Chesterton's shopping, dining, parks, and everyday conveniences. A wonderful opportunity to own a move-in-ready, beautifully cared-for home in a location that's hard to beat! Schedule your private viewing today!

408 S 11th Street, Chesterton
1909 Catkin Circle, Chesterton
$750,000
3 Beds ⋅ 4 Baths ⋅ 846887 MLS ⋅ ACTIVE Status
Timeless Elegance Meets Exceptional Craftsmanship! Welcome to this stunning 3-bedroom, 3.5-bath, two-story residence, where sophisticated design, beautiful architectural details, and serene pond views create an extraordinary living experience. From the moment you enter the grand foyer, you're greeted by a beautiful beveled-glass entry door, natural light from overhead skylights, and an inviting sense of elegance. The formal dining room showcases a striking illuminated tray ceiling, while the spacious living room impresses with its dramatic double tray ceiling and refined finishes. The beautifully appointed kitchen features rich wood cabinetry, elegant granite countertops, and ambient above-cabinet lighting. An adjoining breakfast area offers a charming bow window framing picturesque pond views. Designed for both entertaining and everyday comfort, the inviting family room features a cozy fireplace and French doors opening to a covered wraparound porch and patio, creating a seamless connection between indoor and outdoor living. Enjoy peaceful mornings and breathtaking waterfront views from your own private retreat. Upstairs the luxurious primary suite offers a cathedral ceiling, recessed lighting, and a generous walk-in closet. A stunning two-sided fireplace connects the bedroom to the spa-inspired ensuite, complete with a whirlpool soaking tub and separate shower. Two additional spacious bedrooms feature walk-in closets, while an elegant upper level sitting area with cathedral ceilings provides the perfect space to relax. The fully finished basement offers exceptional additional living and entertaining space, complemented by beautiful wood flooring. Additional highlights include convenient main-level laundry, a 2.5-car garage, and a one-year home warranty for added peace of mind. A remarkable combination of timeless sophistication, thoughtful design, and scenic waterfront living. This exceptional home is truly one you won't want to miss!

1909 Catkin Circle, Chesterton
1720 Hale Avenue, Chesterton
$130,000
2 Beds ⋅ 2 Baths ⋅ 846783 MLS ⋅ ACTIVE Status
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
350 Brown Court, Chesterton
$280,000
3 Beds ⋅ 2 Baths ⋅ 846782 MLS ⋅ ACTIVE Status
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
493 Magnolia Lane, Chesterton
$524,900
3 Beds ⋅ 2 Baths ⋅ 846741 MLS ⋅ ACTIVE Status
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
354 E 1300 N, Chesterton
$525,000
4 Beds ⋅ 2 Baths ⋅ 846693 MLS ⋅ ACTIVE Status
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
231 E 1200 N, Chesterton
$249,900
4 Beds ⋅ 2 Baths ⋅ 846683 MLS ⋅ ACTIVE Status
**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
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