Chesterton Homes for Sale

Chesterton Homes for Sale

### Discover the Charm of Chesterton, Indiana

Nestled in the heart of Porter County, Chesterton, Indiana, is a delightful town that perfectly blends small-town charm with modern conveniences. Known for its friendly community and rich history, Chesterton offers a welcoming atmosphere for families, professionals, and retirees alike. Just a stone’s throw from the stunning shores of Lake Michigan, residents enjoy easy access to beautiful beaches, scenic parks, and outdoor recreational activities.

Chesterton boasts a vibrant downtown area, where quaint shops, cozy cafes, and local eateries invite you to explore and unwind. The town is also home to a variety of annual events and festivals, fostering a sense of community and tradition that residents cherish. With highly-rated schools and a strong commitment to public safety, Chesterton is an ideal place to raise a family or settle down.

For those looking to make Chesterton their home, the real estate market is thriving. A diverse array of homes for sale caters to various tastes and budgets, from charming historic properties to modern new builds. Whether you’re searching for a spacious family home with a backyard oasis or a cozy bungalow close to downtown, Chesterton has something for everyone.

With its picturesque landscapes, excellent amenities, and a close-knit community, Chesterton, Indiana, is not just a place to live; it’s a place to call home. Explore the available homes for sale today and discover the perfect property to start your next chapter in this enchanting town!

Newest Chesterton Homes for Sale

2 Beds ⋅ 1 Baths

This charming two bedroom, one bath home is ready for its new owners. You'll love the refinished hardwood floors and wide trim that carry classic character throughout the home. Original solid wood doors with antique hardware add timeless appeal, while modern updates provide peace of mind. The home features newer windows, siding, furnace, and A/C, along with updated electrical. The kitchen and bathroom include built ins for added storage and style. Both bedrooms offer large walk in closets with lighting, a rare find in a home of this era. A perfect blend of vintage charm and thoughtful updates -- move in ready and full of personality. The attic space has the potential for future expansion and more living space. The large 2.5 car garage is truly a dream workspace. It's fully equipped with electric and even includes an A/C unit to keep you cool on hot days while tackling projects, hobbies, or storage needs. Plenty of room, plenty of comfort, and plenty of possibilities. Just minutes from major highways and next to the Duneland walking trail.

1708 Tower Street, Chesterton

5 Beds ⋅ 5 Baths

Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square feet of functional living space designed for a modern lifestyle. A massive kitchen, oversized island, dining area, living room with fireplace and 2 bedrooms on the main level. 2nd level offers oversized main bedroom suite with Full bathroom and walk-in closets and 3 additional bedrooms. 3rd level offers a bonus room (currently used as a bedroom). Enjoy a large 0.44-acre yard perfect for outdoor fun, an attached 3 car garage with ample storage nestled within a highly desired neighborhood, this home is a rare find. Priced Below Market value, carpet and painting needed. Call today for a private showing.

2941 Nautica Drive, Chesterton

3 Beds ⋅ 2 Baths

Historic Chesterton gem just steps from downtown! This solidly built 3-bedroom, 2-bath two-story home offers nearly 2900 sq. ft. of finished living space which includes a full basement. Beautiful original woodwork, doors, hardware and classic door knobs preserve the character of this special home, complemented by hardwood flooring. The bright, inviting kitchen features beautiful cabinetry and a convenient pantry. The updated main-level bathroom includes a charming clawfoot tub. Upstairs, the spacious primary bedroom offers a walk-in closet plus its own sitting area, filled with natural light. Situated on a desirable corner lot in Duneland School District and within walking distance to downtown Chesterton's shops, restaurants and amenities. Conveniently located near the beach and South Shore train station for those commuters. Historic charm, space, location and character--this is one you won't want to miss!

201 S 8th Street, Chesterton

2 Beds ⋅ 2 Baths

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

3 Beds ⋅ 2 Baths

Welcome to your new warm and cozy home! You'll enjoy the fireplaces, solid hardwood floors and privacy from your back yard. The home is situated on over 4 acres and is adjacent to protected wetlands. It is also close to shopping, expressways and the Indiana Dunes. The windows, furnace, air conditioner and hot water heater are newer. Come take a look!

1063 Frontage Road, Chesterton

3 Beds ⋅ 2 Baths

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

4 Beds ⋅ 2 Baths

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

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

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

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

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

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

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