Chesterton Real Estate

Chesterton Real Estate

Welcome to Chesterton, Indiana, a charming town nestled in the heart of Porter County. Known for its picturesque landscapes and vibrant community spirit, Chesterton is a delightful blend of small-town charm and modern convenience. With a population of around 13,000 residents, this welcoming community is perfectly situated just a short drive from the bustling city of Chicago, making it an ideal location for those seeking a peaceful retreat without sacrificing access to urban amenities.

One of the town's standout features is its proximity to the stunning Indiana Dunes National Park, where residents and visitors alike can enjoy miles of sandy beaches, scenic hiking trails, and breathtaking views of Lake Michigan. Chesterton also boasts a rich history, with a downtown area that showcases beautifully preserved architecture and a variety of local shops, restaurants, and cultural attractions. The Chesterton European Market, held every Saturday from May to October, is a must-visit, offering an array of fresh produce, artisanal goods, and handmade crafts that reflect the town's vibrant community spirit.

Families will appreciate the excellent schools and recreational facilities that Chesterton offers, including parks, sports leagues, and community events throughout the year. The town's friendly atmosphere and strong sense of community make it a wonderful place to call home.

Whether you're looking to settle down or simply explore, Chesterton, Indiana, is a hidden gem that promises a fulfilling lifestyle surrounded by natural beauty and a welcoming community. Discover the charm of Chesterton today!

Newest Listings in Chesterton

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

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

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

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

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

Turnkey opportunity in the heart of downtown Chesterton -- this fully renovated 1,744 SF, two-story restaurant building is ready for its next concept. The property features a full commercial kitchen with walk-in cooler, two levels of indoor dining, and a bathroom on each floor, plus a spacious courtyard and deck offering additional outdoor dining. Extensive top-to-bottom renovations include new HVAC, restored hardwood floors, new windows, gutters, soffit, fascia, siding, shutters, corbels, bathrooms, ceiling tiles, and lighting fixtures -- delivering a move-in-ready space with modern systems and timeless character. Situated in a highly walkable downtown corridor surrounded by shops and restaurants, the location offers excellent visibility and foot traffic, with the added draw of close proximity to Indiana Dunes National Park and convenient access to major highways. Call today to schedule your property tour.

321 Broadway Avenue, 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

4 Beds ⋅ 4 Baths

Unmatched curb appeal, custom craftsmanship, with 3.44 acres of privacy with 4 Bedroom and 4 Baths. This stunning Craftsman-style home offers an idyllic retreat within the coveted Duneland School District. From the moment you pull up to the expansive three-car garage. Featuring a generous 13 ft by 30 third bay perfect for a boat, workshop, or extra storage and see the gorgeous wrap-around front porch, you'll know you've found something special. Inside, the quality is undeniable 2x6 construction, solid wood doors, and wood trim throughout the main floor. Beautiful wood floors flow seamlessly through the entryway, dining room, kitchen, and hallway. Host gatherings in the elegant dining room, by solid wood columns and plantation shutters, or cook with ease in the spacious eat-in kitchen, complete with beautiful maple cabinets and an ample amount of counter and storage space. Step directly from the kitchen out to a charming screened-in porch, which opens to a durable Trex deck,ideal for outdoor dining and taking in views of your private acreage. Afterwards, relax in the impressive living room anchored by soaring vaulted ceilings and a warm gas fireplace. Main-floor primary sanctuary features direct access to the wrap-around porch and a spa-like ensuite bath complete with a double vanity, soaking tub, walk-in shower, private toilet closet, and a spacious walk-in closet. Down the hall, a secondary main-floor in-law suite with an adjacent 3/4 bath provides unmatched flexibility. As you head upstairs, you will notice the gorgeous wooden staircase. You'll find two generously sized bedrooms and a full bath with double sinks and along with an unfinished area above the garage offering incredible potential for future expansion. Downstairs in the partially finished basement adds even more versatile space, complete with daylight windows, a full bath, and direct interior stairs leading right up to the garage. For complete peace of mind, the home comes with Generac Generator

386 E 1050 N, Chesterton

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! This vacant lot backs directly to the golf course, offering beautiful views and a picturesque setting for your future custom home. Sand Creek Country Club features an outstanding array of membership amenities, including championship golf, swimming, tennis, fitness facilities, dining, social events, and year round recreational programs. Ideally located just minutes from the beautiful shores of Lake Michigan, this property also provides convenient access to the South Shore Line for an easy commute to downtown Chicago, approximately one hour away. Located within the highly regarded Duneland School Corporation, this homesite offers an outstanding combination of location, lifestyle, and accessibility. An adjoining golf course lot is also available for purchase under a separate MLS listing, providing the opportunity to expand your homesite or enhance your privacy. Buyer to verify lot dimensions, utilities, HOA information, building requirements, membership availability, and all intended uses.

1160 Monterey Drive, Chesterton

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