Chesterton Real Estate

Chesterton Real Estate

Welcome to Chesterton, Indiana—a charming town that beautifully blends small-town warmth with vibrant community spirit. Nestled in Porter County, Chesterton is ideally situated just a stone's throw from the stunning shores of Lake Michigan, making it a perfect escape for those who appreciate both nature and a rich cultural tapestry.

Chesterton boasts a rich history, with its roots dating back to the 19th century. Today, the town is known for its picturesque downtown area, which features a delightful mix of local shops, cozy cafes, and inviting restaurants. Whether you’re indulging in a sweet treat from a local bakery or exploring unique boutiques, Chesterton’s downtown is a hub of activity that captures the essence of community life.

For outdoor enthusiasts, the town offers easy access to the breathtaking Indiana Dunes National Park, where you can hike, bike, or simply relax on the sandy beaches. The nearby Coffee Creek Watershed Preserve provides a tranquil setting for picnics and leisurely strolls, showcasing the natural beauty that Chesterton is known for.

Families will appreciate the highly-rated schools and a strong sense of community that makes Chesterton a wonderful place to raise children. With a variety of community events, including farmers' markets and seasonal festivals, there’s always something happening that brings residents together.

Whether you’re considering a move or just visiting, Chesterton, Indiana, offers a unique blend of history, natural beauty, and a welcoming atmosphere that makes it truly special. Come discover the charm of Chesterton—where every corner has a story to tell!

Newest Listings in Chesterton

4 Beds ⋅ 4 Baths ⋅ 843317 MLS ⋅ ACTIVE Status

Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining rental unit, currently generating 1,400 per month, includes 2 bedrooms and 2 bathrooms, making it an attractive income-producing asset. The 455 side has a brand new air conditioner and new appliances last year. New windows were installed in 2025. Both units enjoy large, private backyards perfect for relaxing, entertaining, or gardening. Conveniently located just minutes from the beautiful beaches of Lake Michigan, charming downtown Chesterton, and the renowned European Market, this property also offers an easy commute with quick access to the South Shore Line and I-94, putting downtown Chicago within approximately 45 minutes. Whether you're looking to reduce your housing costs or expand your investment portfolio, this property offers the perfect combination of comfort, convenience, and income potential.

455 Woodlawn Avenue, Chesterton

843301 MLS ⋅ ACTIVE Status

Imagine the possibilities! 52 acres ready for your dreams to be built here! There's even a 2 acre stocked pond! Approximately 880ft. of frontage on 1050N, and 2,500 ft. frontage on 150W. Zoned R-1 Residential. Property is currently farmed and is subject to crop rights. Located minutes from access to commuter expressways, South Shore train station, Lake Michigan and the Indiana Dunes National Lakeshore, award-winning schools, and the vibrant Chesterton downtown district for all of your shopping, entertainment, and recreation!

W 1050 N, Chesterton

4 Beds ⋅ 3 Baths ⋅ 842429 MLS ⋅ ACTIVE Status

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

843167 MLS ⋅ ACTIVE Status

Imagine your dream home nestled among the trees on this beautiful 1.36-acre corner lot at 369 Ridgeview Drive. Located in Woodridge Hills, a private Jackson Township community known for its spacious wooded homesites and impressive custom residences, this property offers the rare opportunity to create a home designed entirely around your lifestyle. The generous corner setting provides flexibility for a striking home design, welcoming driveway and outdoor living spaces while preserving the natural beauty and privacy of the surrounding woods. Building plans are subject to applicable covenants and approvals. Enjoy a peaceful, tucked-away setting without giving up convenience. Downtown Chesterton's locally owned restaurants, boutiques, art scene, festivals and popular European Market are just minutes away. Spend weekends hiking, biking and enjoying Lake Michigan's shoreline at Indiana Dunes National Park, which protects 15 miles of beaches along the southern shore of Lake Michigan. For commuters or Chicago day trips, nearby Dune Park Station provides access to the South Shore Line, connecting Northwest Indiana directly with Millennium Station in downtown Chicago. With convenient access to Route 49, major expressways, Chesterton and Valparaiso, this location brings together privacy, natural beauty and everyday convenience. Bring your vision and create something truly remarkable at 369 Ridgeview Drive.

369 Ridgeview Drive, Chesterton

4 Beds ⋅ 3 Baths ⋅ 843120 MLS ⋅ ACTIVE Status

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

2 Beds ⋅ 2 Baths ⋅ 843092 MLS ⋅ ACTIVE Status ⋅ Westchester Village Condo BLDG.

Welcome Home! This 2 Bedroom 1.75 Bath main floor condo, has been meticulous updated and is ready for a new owner. Inside you will find newer flooring, kitchen cabinets, countertops, bathrooms, as well as newer stainless steel kitchen appliances. Main floor living at its finest! Outside you will find a patio that overlooks a large pond. This home is complete with a 1 car garage , with shelving for your storage needs. No need to worry about the exterior maintenance, grass cutting, snow removal, water and sewer bills. Those are all taken care for you through the Association. Just move right in!

1913 David Drive, Chesterton

843068 MLS ⋅ ACTIVE Status

A unique opportunity awaits in the gated Sand Creek community, where very few vacant lots remain! Bring your own builder and create the home you've been dreaming of. Thanks to the lot's unique layout, it offers exciting design possibilities within one of Northwest Indiana's most sought-after neighborhoods. Ideally located just one hour from downtown Chicago, Sand Creek offers the perfect balance of luxury living and convenience. The South Shore Line commuter rail is just minutes away, making travel to and from Chicago effortless. Residents also enjoy being only minutes from the breathtaking shores of Lake Michigan, the nationally renowned Indiana Dunes National Park, miles of scenic hiking and biking trails, charming downtown Chesterton, and an abundance of local dining and shopping. Residents also have the opportunity to join the private Sand Creek Country Club, located just a golf cart ride away. Membership offers exceptional amenities, including championship golf, a golf simulator, swimming, tennis, fitness facilities, private dining, a pub, and a vibrant calendar of social events. Don't miss this rare opportunity to build your custom home in one of Northwest Indiana's premier gated communities with limited homesites remaining.

1800 Bramble Trace, Chesterton

4 Beds ⋅ 3 Baths ⋅ 843042 MLS ⋅ ACTIVE Status

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

843035 MLS ⋅ ACTIVE Status

Acreage in Liberty Township! Beautiful 4.12 Acre Lot in the sought out Duneland School District with just a 3 minute drive to Chestertion High School & 5 minutes to downtown Chesterton. No HOA, natural gas & electric have already been ran to the property, all other permits needed.

1065 N 50 W, Chesterton

4 Beds ⋅ 3 Baths ⋅ 842981 MLS ⋅ ACTIVE Status

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 ⋅ 842980 MLS ⋅ ACTIVE Status

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 ⋅ 842978 MLS ⋅ ACTIVE Status

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

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