Chesterton Homes for Sale

Chesterton Homes for Sale

Welcome to Chesterton, Indiana – a hidden gem nestled in Porter County that perfectly blends small-town charm with modern conveniences. Known for its picturesque landscapes and friendly community, Chesterton is the ideal place for families, retirees, and anyone looking to enjoy a tranquil lifestyle without sacrificing access to urban amenities.

Chesterton boasts a rich history, with roots dating back to the late 1800s. Today, it offers a vibrant downtown area filled with unique shops, delightful eateries, and local events that foster a strong sense of community. The town is also home to the renowned Indiana Dunes National Park, where outdoor enthusiasts can explore miles of sandy beaches, hiking trails, and stunning natural beauty along the shores of Lake Michigan.

For those considering a move, Chesterton presents a diverse selection of homes for sale. Whether you’re looking for a cozy bungalow, a spacious family home, or a modern townhouse, the real estate market here has something to suit every taste and budget. Many properties feature beautiful yards, contemporary designs, and easy access to local parks and schools, making it an excellent choice for families and professionals alike.

With its prime location just a short drive from Chicago, Chesterton offers the perfect balance of peaceful living and city accessibility. Experience the warmth of this charming community and discover your dream home in Chesterton today! Let us guide you through the available listings and help you find the perfect place to call home in this delightful Indiana town.

Newest Chesterton Homes for Sale

$849,900
5 Beds ⋅ 4 Baths
One of the most RARE and incredible properties you will find in all of NWI, this gorgeous Cabin Style Home has ALL of the features and amenities that are desirable about new homes, but with so much more charm and character. With this home, you don't have to settle for desirable features in order to have a cabin style home, because this property has it all. Sitting on 1.63 PRIVATE/WOODED acres of land this home features over 4100 finished square feet, a 30x45' FINISHED GARAGE with HEATED FLOORS and LOFT STORAGE SPACE, additional attached 2.5 car garage, finished WALKOUT BASEMENT with FULL RELATED LIVING, 4 bedrooms (plus an office), 3.5 bathrooms, MAIN FLOOR MASTER SUITE, beautiful pool, home gym space, and so much more. The MAIN LEVEL features an incredible main living space with vaulted ceilings, stone fireplace, wet bar area, OPEN CONCEPT, and natural wood finishes throughout. The kitchen features HIGH-END finishes with granite countertops, custom backsplash, high-end appliances, and gorgeous custom wood cabinetry. There is a spacious dining area that leads to the HUGE exterior back deck. The back deck is perfect for indoor & outdoor entertaining, leading to the beautifully private pool! The MAIN FLOOR MASTER SUITE is HUGE and offers an updated en-suite bathroom featuring a custom/tiled shower, large soaking tub, and double vanity sinks. The main floor also features a large mudroom space with wood cabinetry for storage, powder bathroom, and custom made doggie shower. The FINISHED WALKOUT BASEMENT offers full RELATED LIVING with a large living room (with a fireplace), tons of natural lighting with the glass walkout doors, 4th bedroom with direct access to the 3/4 bathroom, FULL KITCHEN, basement home gym/office, and a MASSIVE laundry room! The upper level offers a large landing with views of the main floor living room/vaulted ceilings, 2 large bedrooms, an additional offer (no closet), and full upper level bathroom with double vanity sinks.

1003 Country Creek Lane, Chesterton
$559,900
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
$519,900
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
$569,900
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
$295,000
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
$283,500
2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton
$900,000
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
$240,000
3 Beds ⋅ 1 Baths
Welcome home to this inviting 3 bedroom, 1 bath residence located in the desirable community of Porter. Perfect for first-time homebuyers, those looking to downsize or anyone seeking a comfortable place to call home. This property offers a blend of charm, functionality and convenience. Conveniently located near local parks, schools and major highways. Also its just a short drive tin Indiana Dunes and Lake Michigan beaches.

107 Francis Street, Chesterton
$239,900
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
$539,900
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
$1,100,000
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
$575,000
3 Beds ⋅ 3 Baths
PROPOSED CONSTRUCTION-Welcome to the Sonoma in Easton Park! This stunning custom-built, 1.5-story home offers over 2,100 square feet of luxury living with 3 bedrooms, 2.5 baths and a 3-car garage, all situated on a desirable corner lot. Step inside to a spacious foyer featuring a private office and convenient half bath before entering the impressive open-concept living space. The great room showcases beautiful hardwood floors, a custom fireplace, solid-core doors, an upgraded trim package and quality craftsmanship throughout. The kitchen is designed for both everyday living and entertaining, featuring quartz countertops, custom cabinetry, stainless steel appliances and a large walk-in pantry. The main-level primary suite offers a relaxing retreat with double sinks, a soaking tub and a spacious walk-in closet. Upstairs, you'll find two additional bedrooms...each with its own walk-in closet...a full bath, and a huge loft offering flexible space for a second living area, playroom, or entertainment space. Additional highlights include energy-smart features, zoned high-efficiency HVAC, a whole-home humidifier, fresh air intake, R-20 basement insulation, an egress window for a possible future bedroom and rough-in plumbing for a future bathroom. Located in the desirable Easton Park neighborhood, this home offers convenient access to Indiana Dunes National Park, the South Shore Line, major expressways, shopping, dining, and award-winning schools. Experience luxury, quality craftsmanship and thoughtful design in the Sonoma!

801 Ashwood Lane, Chesterton
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Updated . Information deemed reliable but not guaranteed.