Chesterton Homes for Sale

Chesterton Homes for Sale

Welcome to Chesterton, a charming town nestled in Porter County, Indiana. Known for its small-town charm and friendly community, Chesterton offers a peaceful retreat while being conveniently located near the bustling city of Chicago.

If you are looking to make Chesterton your home, you will find a variety of homes for sale to suit your needs. Whether you are searching for a cozy bungalow, a spacious family home, or a modern townhouse, Chesterton has something for everyone. With a range of prices and styles, you are sure to find the perfect place to call your own in this lovely town.

Chesterton boasts a strong sense of community, with local events, farmers' markets, and outdoor activities that bring residents together. Enjoy exploring the nearby Indiana Dunes National Park, shopping in the quaint downtown area, or dining at one of the town's delicious restaurants.

With its excellent schools, parks, and amenities, Chesterton is a wonderful place to live and raise a family. Whether you are a first-time homebuyer or looking to downsize, Chesterton has the perfect home waiting for you. Come and discover all that this delightful town has to offer!

Newest Chesterton Homes for Sale

4 Beds ⋅ 3 Baths

Refined updates and timeless design come together in this exceptional Sand Creek residence, where light-filled interiors and thoughtfully curated finishes create an atmosphere of warmth and sophistication. At the heart of the home, the beautifully reimagined living space is anchored by a stunning new fireplace, complemented by modern LED recessed lighting that enhances the home's open, inviting feel. Three fully renovated bathrooms showcase quality craftsmanship and contemporary style, including an impressive primary en suite with a freestanding soaking tub, oversized tiled walk-in shower, dual-sink vanity, and skylight that creates a bright, spa-like atmosphere. The refreshed front entry and updated laundry room add both elegance and everyday functionality. The exterior is equally impressive, featuring premium James Hardie siding, new gutters, professionally designed landscaping, and tasteful exterior lighting that highlight the home's architectural character day and night. With over 3,000 square feet, four bedrooms, and three bathrooms, this residence offers generous spaces for both entertaining and quiet moments alike. Nestled within the prestigious Sand Creek community, enjoy a lifestyle surrounded by beautifully maintained streets, championship golf, scenic ponds, walking paths, and convenient access to Lake Michigan, the South Shore Line, and major expressways.

1650 Hogan Avenue, Chesterton

4 Beds ⋅ 3 Baths

Only 3 years young- this new construction build was completed by one of NWI's most prestigious builders in the desirable Preserve neighborhood known for its thick tree lines of protected land! A backyard oasis is already complete for you and makes this home the best value you could be looking for in Chesterton! It's not everyday you see a backyard like this - inground pool with automatic safety cover, putting green and large stamped concrete patio for backyard dinners. Beautiful mature landscaping and surrounded by trees on 2 sides. The home sits on a quiet cul de sac and is a show stopper with high end finishes. A 2 story foyer greets you and welcomes you into the 2 story great room with a gas fireplace at the heart. A bright kitchen overlooking your backyard oasis and featuring quartz countertops with a six drawer island, walk in pantry with built in shelving and including a mini fridge. Off kitchen dining for casual family dinners and a formal dining for entertaining. An office, half bath and bedroom finish the main level living with mudroom access from the garage to kitchen. Upstairs you will find a beutifully appointed primary en suite with wainscotting, walk in closet with custom built in organizers, walk in tiled shower with frameless glass doors, and double vanity. 2 other bedrooms complete the upstairs along with UPSTAIRS LAUNDRY for added convenience. And last but not least a full unfinished basement of additional 1300 potential living space with 9 ft ceilings for future expansion and includes egress window for future 5th bedroom and rough in plumbing for future 4th bathroom. This home has everything you are looking for and is 15 mins from train station for easy to commute to Chicago, 10 mins from Chesterton downtown with local restaurants, coffee shops and the famous European farmers market! Award winning Duneland School system with the high school and the popular Dogwood park only 4 minutes! Taxes will be lower with new owners homestead exemption!

18 Blue Grass Way, Chesterton

4 Beds ⋅ 3 Baths

Welcome to this 4-bedroom, 3-bathroom tri-level home located in the Porter Cove neighborhood of Chesterton. The upper level features three bedrooms, including the primary suite with its own private ensuite bathroom, while the lower level offers a fourth bedroom, an additional living room, and a newly finished third bathroom with a walk-in shower and glass doors, creating a flexible space for guests, related living, or a home office. New carpet adds a fresh update, and the attached garage provides everyday convenience. Step outside to a large patio overlooking the fenced backyard, complete with a storage shed for additional storage. Conveniently located near the Duneland Prairie Bike Trail, Indiana Dunes National Park, and the beaches of Lake Michigan, this home offers easy access to outdoor recreation year-round. Commuters will appreciate the close proximity to the South Shore Line, I-94, and the Indiana Toll Road, making travel to Chicago and surrounding communities simple and convenient. Offering a functional layout, recent updates, and a location close to both nature and commuter routes, this home is ready for its next owner.

1412 Essex Drive, Chesterton

4 Beds ⋅ 3 Baths

Introducing the Aspen on Lot 4 in 1100 Woods! PROPOSED CONSTRUCTION***** Located in the heart of Chesterton across from Dogwood Park and the Prairie Duneland Trail. The Aspen model is ideal for those looking for a primary ensuite on main level with walk in closet, a large kitchen island for extra seating to gather, and plenty of storage. Kitchen over looks your great room and dining for an open concept.

2350 Pradera Trail, Chesterton

3 Beds ⋅ 2 Baths

Introducing The Chestnut - A Brand New Custom Ranch Floorplan on Lot 6! This thoughtfully designed ranch offers the perfect blend of style and function, featuring an open-concept layout with a spacious great room with optional fireplace, dining area, and kitchen complete with quartz countertops and upgrade options available. The primary ensuite provides a private retreat, while generous guest bedrooms offer comfort and versatility. Enjoy the flexibility of a partial unfinished basement--ideal for future living space or ample storage. Located in the heart of Chesterton, this home is being built by one of the area's most highly regarded custom builders. Now is the perfect opportunity to personalize your selections and bring your dream home to life!

2420 Pradera Trail, Chesterton

3 Beds ⋅ 2 Baths

Welcome home to The Prescott in 1100 Woods! PROPOSED CONSTRUCTION on lot 16- one of the last tree lined lots of the subdivision. Large 2000 sqft ranch with unfinished lookout basement with 3 car garage is the perfect blend of main level living with room to expand to almost 4000 sqft when finishing the basement. The view from your living room and deck is only of trees giving you a beautiful feeling of seclusion while being close to everything Chesterton has to offer! Across the street is the popular Dogwood Park and Prairie Duneland trail. If you are a waking, running or biking enthusiast this is the perfect location for you! Inside you will find a versatile floorplan that you can customize and select all finishes. Primary bedroom features spa like bathroom and walk in closet. 2nd and 3rd bedrooms are good sized and there is a bonus flex room perfect for an office or possible 4th bedrooms.

2431 Pradera Trail, Chesterton

3 Beds ⋅ 3 Baths

Welcome to this charming 3-bedroom, 2 1/2 bath ranch nestled in the established Chestnut Hill neighborhood! This inviting home offers comfortable one-level living with a spacious eat-in kitchen, providing plenty of room for everyday meals and entertaining. A 2-car garage offers convenient parking and additional storage space. The fenced-in backyard provides a wonderful space for outdoor enjoyment, pets, gardening, or relaxing with family and friends. With three bedrooms, two full bathrooms, and a desirable ranch layout, this home offers both convenience and functionality in a well-established neighborhood. Don't miss the opportunity to make this Chestnut Hill gem your new home!

610 Fox Point Drive, Chesterton

2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton

5 Beds ⋅ 5 Baths

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

229 E Morgan Avenue, Chesterton

3 Beds ⋅ 1 Baths

Welcome home to this beautifully renovated 3-bedroom, 1-bath home that's truly move-in ready! Completely updated from top to bottom, this home features all new mechanicals, giving you peace of mind for years to come. The bright and modern kitchen comes complete with brand-new stainless steel appliances that stay with the home. Outside, you'll find a detached 2-car garage, offering plenty of space for parking and additional storage. The backyard provides space for entertaining, or simply relaxing outdoors. Conveniently located close to shopping, restaurants, and everyday amenities, with quick access to major highways for an easy commute. Don't miss this incredible opportunity to own a beautifully updated home--schedule your showing today!

400 Woodlawn Avenue, Chesterton

4 Beds ⋅ 3 Baths

FORE! Welcome to this exquisite Cape Cod residence in the prestigious Estates of Sand Creek subdivision. Enjoy breathtaking views of the 4th hole of the Marsh Course at Sand Creek Country Club from the comfort of your own home, without being directly on the course. This spacious 4-bedroom, 2.5-bath home offers over 2,400 square feet of well-appointed living space. Open concept living with vaulted and cathedral ceilings allow for a plethora of natural light to shine throughout. The kitchen and bathrooms feature elegant quartz countertops, owner added a maintenance free gas fireplace with white fireglass, and a new roof that provides peace of mind. The unfinished full basement with 9-foot ceilings offers incredible potential for expansion, perfect for a family room, home gym, theater, or additional bedrooms. Outdoor living shines with a flagstone patio and permanent ceramic gas firepit, mesmerizing green fireglass, ideal for entertaining or quiet evenings. Residents enjoy resort-style amenities within the Sand Creek community, including access to championship 27-hole golf with 3 (9 hole )courses, a beautiful pool complex, fitness center, tennis courts, and fine dining at the clubhouse, all set among scenic ponds and rolling terrain. Conveniently located just minutes from the Indiana Dunes National Lakeshore, Lake Michigan's pristine beaches, the South Shore Train Station, and major highways. Top-rated Duneland School District completes this exceptional package. This is more than a home -- it's a lifestyle.

961 Monterey Drive, Chesterton

3 Beds ⋅ 3 Baths

Offered for the first time in nearly two decades, this exceptional custom ranch is a rare opportunity in the highly sought-after Sand Creek community. Perfectly positioned along the golf course, the home showcases breathtaking fairway views and the effortless main-level living today's buyers are searching for. Featuring three spacious bedrooms, a thoughtfully designed open floor plan, a custom gourmet kitchen with high-end appliances, and timeless craftsmanship throughout, every detail reflects quality and pride of ownership. Outside, the impeccably maintained grounds create a private setting that perfectly complements the home's picturesque surroundings. Meticulously cared for and rarely available, this is luxury golf course living at its finest.

1745 Nelson Drive, Chesterton

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