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

3 Beds ⋅ 3 Baths ⋅ 844916 MLS ⋅ ACTIVE Status

Completely 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

4 Beds ⋅ 3 Baths ⋅ 844907 MLS ⋅ ACTIVE Status

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

3 Beds ⋅ 3 Baths ⋅ 844902 MLS ⋅ ACTIVE Status

Charming 2-Story in Chesterton -- Priced to Sell! Welcome home to this adorable two-story gem, where soaring cathedral ceilings create an airy, light-filled feel from the moment you walk in. The heart of the home is a brand-new kitchen outfitted with all-new appliances -- move-in ready and waiting for your first meal. Don't miss the sunroom, featuring its own vaulted ceilings -- the perfect spot for morning coffee or curling up with a good book. Many major updates have already been done for you: new flooring in kitchen and living room, a new hot water heater, and a new furnace, so you can settle in worry-free. Outside, you'll fall in love with the picture-perfect lot -- mature trees, a fully fenced yard, and that classic Chesterton charm on a quiet, welcoming street. Homes like this don't last. Schedule your showing today!

801 S 19th Street, Chesterton

3 Beds ⋅ 3 Baths ⋅ 844895 MLS ⋅ ACTIVE Status

Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly 3,000 sq. ft. of finished living space has been thoughtfully updated from top to bottom, offering the charm of an established home with the finishes, comfort, and peace of mind of something new. Major upgrades include a **NEW ROOF, NEW FURNACE, NEW CENTRAL A/C, and a WHOLE-HOME GENERATOR**--making this home truly move-in ready. Inside, you'll find 3 spacious bedrooms, 2.5 beautifully updated baths, TWO separate living areas, an eat-in kitchen with stone countertops and stainless steel appliances, high ceilings, recessed lighting, a main-level primary bedroom, and convenient main-level laundry. The upper level offers two generously sized bedrooms plus a large loft, providing plenty of flexibility for an office, playroom, additional lounge, or guest space. Outside, enjoy a private, landscaped **0.54-acre lot**, rear deck, storage shed, and attached 2-car garage with NO HOA. With virtually everything already upgraded, all that's left to do is move in and enjoy this stunning Chesterton home!

2332 Dakota Street, Chesterton

3 Beds ⋅ 2 Baths ⋅ 844885 MLS ⋅ ACTIVE Status

This sweet villa home has everything you need--without the worry of exterior maintenance! Conveniently located on the near east side of Chesterton, you'll enjoy easy access to shopping, expressways, the train station, and one of the area's greatest attractions, Indiana Dunes National Park. More than cute and gently lived in, this charming three-bedroom, two-bath, 1,700-square-foot ranch is sure to impress. The open floor plan is perfect for entertaining, with a cozy fireplace to warm you in the winter and a large patio with a retractable sunshade to enjoy during the summer. Luxury vinyl flooring runs throughout the home, with tile flooring in the bathrooms. The primary bedroom is privately situated on one side of the home, while the other two bedrooms are located on the opposite side. The primary bath features a tiled shower with a frameless glass door, double sinks, a walk-in closet with organizers, and a linen closet. The kitchen features a large island that provides additional seating, along with a beverage refrigerator, newer stainless steel appliances, and a pantry. The laundry/mudroom offers a convenient place to sit and remove your shoes, along with space for coats and keys, a storage closet, plenty of cabinetry, a washer and dryer, and a laundry sink. The slightly oversized two-car garage provides plenty of additional storage along both sides. The home's mechanicals are conveniently housed in a large garage closet, and pull-down attic stairs provide access to even more floored storage above the garage. The maintenance package makes life easy and includes lawn mowing, snow removal up to your door and driveway, trimming, fertilizing, and spring and fall sprinkler-system maintenance. Comfortable, convenient, and easy to maintain--come see this one soon! .

472 Cypress Lane, Chesterton

4 Beds ⋅ 3 Baths ⋅ 844730 MLS ⋅ ACTIVE Status

Built in 2025 and practically brand new, this beautiful 4-bedroom, 2.5-bath home offers modern finishes, a functional layout, and plenty of room to grow! The open-concept main level is designed for both everyday living and entertaining, featuring a spacious kitchen with quartz countertops, abundant counter and cabinet space, and a large center island. The kitchen flows seamlessly into the inviting living room and out to the deck, creating a great space for gatherings or relaxing outdoors. A private office and convenient half bath complete the main level. Upstairs, you'll find all four bedrooms, including a spacious primary suite with a private ensuite bath and an impressively large walk-in closet. The unfinished daylight basement provides excellent potential for additional living space, a recreation room, home gym, or whatever fits your needs. Outside, enjoy the convenience of an irrigation system and a newer home without the wait of new construction. Ideally located near downtown Chesterton with easy access to local restaurants, shops, parks, and highly regarded schools. Move right in and enjoy everything this nearly new home has to offer!

29 Karner Blue Court, Chesterton

4 Beds ⋅ 3 Baths ⋅ 844671 MLS ⋅ ACTIVE Status

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

4 Beds ⋅ 3 Baths ⋅ 844631 MLS ⋅ ACTIVE Status

Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The entire home is freshly painted and welcoming. The highly functional kitchen boasts a center island, abundant cabinet space, and generous countertops. Just off the kitchen, the spacious dining room easily accommodates all your entertaining needs, while a versatile flex room makes a perfect home office or playroom. Cozy up in the expansive great room featuring a custom-built fireplace--ideal for cool winter nights. As an added perk, you'll find a cable-ready bonus room above the garage, offering the ultimate media room, teen hangout, or secluded retreat!

419 S 9th Street, Chesterton

4 Beds ⋅ 3 Baths ⋅ 844618 MLS ⋅ ACTIVE Status

Construction Complete - July! MOVE IN READY! The Preserve in the Duneland School Corp. This 2,735 square foot home makes an unforgettable impression. Off the foyer, a private den with French doors offers a quiet, refined space for a home office or study, while a discreetly placed powder room at the front of the home adds convenience without interrupting the flow. The heart of the home unfolds into a spacious great room filled with natural light and inviting views of the backyard. A dedicated dining nook bridges the great room and kitchen, with sliding glass doors that extend gatherings outdoors. The kitchen is both expansive and elegant, anchored by a striking 72-inch island with pendant lighting and an extended edge for barstool seating. Quartz countertops, a tile backsplash, and stainless steel range, dishwasher, and microwave complement the modern, open layout, while a large pantry adds impressive built-in storage. The mudroom connects seamlessly to the attached garage and includes a built-in bench and oversized walk-in closet, creating an organized landing zone for everyday living. Upstairs, four bedrooms each feature their own walk-in closet, offering exceptional storage and personal space, along with a well-appointed full bath that serves the secondary bedrooms with comfort and convenience. A conveniently located laundry room on this level adds everyday ease right where it's needed most. The primary suite stands out as a true retreat, complete with a private bath and an oversized walk-in closet designed to impress. Blending dramatic architectural elements with thoughtful functionality, this home delivers the kind of space, style, and presence that leaves a lasting impact. RESNET energy smart construction will save an estimated 1,699 annually. Actual savings may vary; see HERSA(r) Rating Certificate and Energy Smart Flyer for details. Home includes a 10-year structural warranty, offering lasting peace of mind. Contact our team to schedule your private tour today!

40 Karner Blue Court, Chesterton

4 Beds ⋅ 3 Baths ⋅ 844236 MLS ⋅ ACTIVE Status

Stunning, updated 2-story home nestled on a private, wooded 0.56-acre in-town lot in Chesterton! A grand 2-story entry welcomes you with luxury vinyl plank flooring extending throughout the main level, featuring a formal dining room. French doors from a den/office and flow into the family room, highlighted by a gas-start fireplace and a wall of windows showcasing the woods. The open-concept layout effortlessly connects the family room, eating area, and peninsula counter kitchen, which boasts painted oak cabinets, solid surface countertops, and recessed lighting. The rear hallway leads to the laundry room, a 3-car garage, and a vaulted ceiling screen porch with skylights. Step outside to a private, professionally designed outdoor oasis featuring a paver patio, a granite gas grill island with bar seating, a 55" outdoor TV in a storm box, a wood-burning fireplace, and a 4-person hot tub. Upstairs, the primary suite offers vaulted ceilings, a walk-in closet, a double vanity, a soaking tub, and separate shower, alongside three additional bedrooms and a full bath. The garage features a walk-up attic stairwell for easy storage or potential expansion with access through the 4th bedroom too. Complete with zoned 2010 Lennox HVAC and city utilities, this property offers quick access to Highways 49, I-90, and I-94 and near the Indiana Dunes National Park.

131 Beverly Drive, Chesterton

3 Beds ⋅ 4 Baths ⋅ 844410 MLS ⋅ ACTIVE Status

Welcome to 1909 Catkin Circle, an impressive fully updated Modern Farmhouse located in the highly desirable Tamarack Subdivision of Chesterton. Situated on nearly half an acre with beautiful pond views, this 4,284 sq. ft. home offers exceptional indoor and outdoor living with mature landscaping surrounding the property and an expansive wraparound porch. Inside, you'll find 3 bedrooms and 3.5 bathrooms with a thoughtfully designed layout featuring an enlarged, vaulted primary suite, a spacious butler's pantry, and inviting living and entertaining spaces throughout. Three fireplaces add warmth and character, while a whole-house entertainment speaker system makes the home ideal for both everyday living and hosting. The Modern Farmhouse design carries throughout the home, combining updated finishes with comfortable, functional spaces. Step outside to enjoy the wraparound porch, professionally landscaped grounds, and peaceful pond setting that make this property stand out within Tamarack. With 4,284 square feet of living space, a premium pond-side lot, extensive updates, and a combination of luxury, privacy, and character, 1909 Catkin Circle offers a rare opportunity in one of Chesterton's desirable residential communities.

1909 Catkin Circle, Chesterton

4 Beds ⋅ 3 Baths ⋅ 844343 MLS ⋅ ACTIVE Status

This meticulously updated four-bedroom, three-bathroom residence is situated in a prime Chesterton location. The interior features a thoughtfully redesigned kitchen equipped with custom hickory cabinetry, granite countertops, and premium stainless-steel appliances. Abundant natural light fills the living room through a newly installed expansive window, flowing seamlessly into a spacious dining area and a comfortable sunroom - perfect for morning coffee and evening relaxing. The home offers four generously proportioned bedrooms, including two en-suite bathrooms located on the upper and lower levels respectively, all complemented by new modern vanities and fixtures. Fresh interior paint, new lighting, and a combination of new carpeting and new luxury vinyl plank flooring complete the refined interior. Additional versatility is provided by lower-level bonus spaces suitable for a recreation room, home gym, or multi-generational living arrangements. The attached garage features all-new shelving and a new insulated overhead door with new quiet, side-mount opener. Exterior improvements include a new roof installed in 2025, upgraded gutters, fascia, soffit, exterior doors, and a newly constructed composite front porch. Conveniently positioned on a dead-end, cul-de-sac street, the property offers exceptional proximity to schools, parks, shopping, commuter transit, major interstates, and the Indiana Dunes National Park. Schedule your showing today!

762 Dunewood Drive, Chesterton

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