Chesterton Real Estate Search

Chesterton Homes for Sale

Chesterton Indiana is a small town of approximately 13,000 in Northwest Indiana with a ton of amenities. The town prides itself on offering a safe family-friendly environment to put down roots. An extensive parks and recreation program and good schools add to the Chesterton quality of life.

Chesterton borders Lake Michigan to the north, Portage to the west, Valparaiso to the south, and Michigan City and Westville to the east.

On this page you will find the latest listings for Chesterton. And we will be featuring specific neighborhoods in the coming months. If you have a neighborhood that you would like featured, please let us know.

We also have access to all of the foreclosures and short sales in Chesterton.

Our website features the best Chesterton real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Chesterton real estate market? Sign up for a Chesterton Real Estate Market Report to see what’s active, under contract, and sold!

Contact us today to find out how we can be of assistance to you!

Newest Chesterton Homes and Condos for Sale

3 Beds ⋅ 3 Baths

Check out the newest building in the maintenance-free community-now in construction! The open concept living spaces you'll find soaring cathedral ceilings, fireplace, wood floors underfoot, abundant soft-close cabinetry with 42'' uppers, elegant quartz countertops, stylish kitchen appliances, and triple sliding door overlooking the wooded views. In the master you'll find a stunning custom tile shower with glass enclosure paired with on-trend custom vanity. In the lower level there's a great family room with 9ft. ceilings and daylight windows, 3rd bedroom, and 3rd bathroom. Additional upgrades include custom lighting fixtures, composite deck, custom backsplash, soundproofing, tankless water heater, and more! Don't miss this home located just minutes from the IN Dunes, commuter expressways, and the vibrant downtown district! Hurry to make your own selections-complete December 2023! *Photos are of another home recently completed and are representative

1608 Melanie Lane, Chesterton

4 Beds ⋅ 3 Baths

Meticulous, thoughtful renovations are hallmarks of this handsome home with a rare combination of magnificent bordering woods and wide windows for an enchanting in-town setting. With emphasis on a spacious floorplan focused on considerate flow and circulation, living spaces are adaptable to the diverse must haves on every homebuyer list, from home office to playroom to an extra bedroom. Every surface and system have been replaced and refreshed in the past year and a half: 2 new furnaces, 2 new air conditioners, upgraded electric and LED lighting throughout, new luxury vinyl flooring and carpet, new stainless appliances, newly tiled master bath, new washer/dryer, newly finished deck and fencing, new landscape, drive and walkways, new garage door. Nothing left to do but move in.

1618 Beverly Drive, Chesterton

3 Beds ⋅ 3 Baths

Loaded with upgraded features, this maintenance-free condo is ready for your instant enjoyment! In the open concept living spaces you'll find soaring cathedral ceilings, fireplace, wood floors underfoot, abundant soft-close cabinetry with pantry, elegant quartz countertops, stylish appliances including range hood with micro-drawer, and triple sliding door overlooking the picturesque pond views. In the master suite you'll find a stunning custom shower with glass enclosure paired with on-trend custom vanity. In the lower level there's a great family room with wood floors, 3rd bedroom (great for guests!) and 3rd bathroom, all with daylight views and 9ft. ceilings. Additional upgrades include garage epoxy, full interior paint, custom lighting fixtures, composite deck, custom backsplash, tile showers in all bathrooms, and more! Don't miss this home located just minutes from the IN Dunes, commuter expressways, and the vibrant downtown district! Schedule your showing today!

1601 Melanie Lane, Chesterton

3 Beds ⋅ 2 Baths

Beautifully remodeled 3 bedroom 2 bath second story condo in desirable Westchester Village in Chesterton Indiana. Secluded community with many amenities including a community pool and tennis courts. Serene picturesque grounds surround the community with a beautiful pond and playground. The condo has just went through a complete remodel within the last two years. There is also a newer roof on the unit itself. HOA includes water,sewer,garbage pickup, lawn care and snow removal. The condo is close to the local bike trails, Dogwood park, Chesterton's down town and only minutes from I-94, the Indiana Dunes National Park and the beaches of Lake Michigan. The low taxes and central location makes this a great opportunity for the new owner. Schedule your viewing soon.

2114 Dogwood Lane, Chesterton

3 Beds ⋅ 4 Baths

FRESHLY REMODELED MAINTANCE FREE SAND CREEK TOWNHOUSE!! From top to bottom this Sand Creek townhouse has been upgraded. New kitchen counters and appliances, new flooring, all new primary bathroom, the list of details are endless. Sand Creek is one of Northwest Indiana's premier gated communities featuring 27-hole championship golf course, just steps from every amenity the country club has to offer. The Sand Creek lifestyle awaits you. Schedule your private tour today!

1066 Mission Hills Court, Chesterton

4 Beds ⋅ 2 Baths

Totally new top to bottom split level in the heart of Chesterton in a quiet subdivison is ready for your finishing touches. This home was completely renovated with all new plumbing, electrical, drywall, siding, windows, driveway, and even a freshly seeded yard. Upon entering you will find custom tile and beautiful open concept greets you. Upstairs the home offers a large living room with all new flooring that flows into a completely new kitchen. Down the hall this home has three large bedrooms with all new carpet, also upstairs there is an all tile bathroom with subway tile surround. Downstairs has a large great room with tons of space for entertaining, also another additional bedroom, a possible office, and another bathroom with brand new shower. Outside the home offers a brand new deck, all new grey siding, brand new windows, a fresh driveway, and a freshly seeded yard! This home just needs your finishing touches and its ready to be called home!

719 S Jackson Boulevard, Chesterton

4 Beds ⋅ 3 Baths

Construction beginning December 2023-hurry and you can still make all of your own selections! The new Sandra May floor plan offers all of the space you have been looking for! 4 bedrooms, 2.5 baths, full basement, 3-car garage, and there's even a sunroom! The kitchen offers an abundance of soft-close cabinetry, 42 uppers, island, and walk in pantry. Surrounded by windows, the sunroom is sure to be your favorite room in the house! In the master suite you'll find a fantastic walk in closet and private bath with dual vanities. Thoughtful features such as tankless water heater, dual-zoned HVAC, soundproofing, finished garage, full kitchen appliance package, custom lighting allowance, premium Delta hardware, raised ADA accessible toilets, and more are all included! Located minutes from IN Dunes, commuter expressways, award-winning schools, and more. Schedule your showing today! *Photos are of another home recently completed and are representative.

570 Sequoia Court, Chesterton

2 Beds ⋅ 1 Baths

JUST LIKE NEW! This maintenance free condo is perfect for the first time home buyer or for downsizing. This open concept unit offers a remodeled kitchen with new electrical wiring and plumbing, new cabinets, new flooring, a pantry plus new stainless appliances. Enjoy views from the dining room and living room which features a fireplace, new flooring and a door leads to balcony for relaxing. The main bedroom is connected to the bathroom which has been completely renovated including new electrical and plumbing. Laundry room includes a washer and dryer. This upstairs unit has been freshly painted throughout. The convenient garage is attached and provides security. HOA fees includes water, sewer, trash, lawn mowing, snow removal and exterior maintenance. The building has a new roof. This condo is conveniently located to the South Shore train, Indiana Dunes State Park, Dogwood Park, and Interstates. There is nothing to do except just Move In! There is no homestead filed for taxes.

2123 Tupelo Lane, Chesterton

4 Beds ⋅ 4 Baths

This uniquely charming home welcomes with a bright entryway leading to a sunken living room featuring a gas fireplace and a captivating backyard view. The kitchen, adorned with a stylish light-tiled backsplash, quartz countertops, stainless appliances, and a central island for added functionality. A discreet main-level bedroom with a bookshelf entry is adjacent to a full bathroom. Upstairs, three spacious bedrooms, including a master with backyard views, two large closets, and a master bath with a double vanity sink, Jacuzzi tub, and stand-up shower. The upper level hosts another full bathroom and a convenient laundry room. The finished basement offers versatility with an office or potential fifth bedroom. The quiet backyard, embraced by a privacy fence, features a storage shed, beautiful deck, and flagstone fire pit area. Throughout, the home exudes charm, character, and functional elegance. Taxes only $4,099 a year & a perfect location for commuting w/ easy access to I-94 & I-90.

220 Sandpiper Drive, Chesterton

3 Beds ⋅ 1 Baths

HURRY FOR THE HOLIDAYS! This Beautifully Updated Cozy OPEN CONCEPT 3 Bed 1 Bath Ranch home with a basement is a MUST SEE! From the Moment you walk in you will love all the finishes from new flooring throughout, accent wall, updated kitchen, and bath, and so much more. The living room offers an electric wall fireplace, an accent wall and plenty of space. The kitchen has been completely updated with New Cabinets, Quartz Counters, Stainless-steel appliances (which stay), peninsula and so much more. If you like to entertain, you will love this space! There is also an unfinished basement which offers nothing but possibilities. The Master Bedroom is a good size and offers a lot of closet space. The bathroom has been completely updated with new floors, 3D tiled walls and more. The backyard is also fenced-in, which is a great perk. This home is located close to all Chesterton has to offer and is PRICED TO SELL so SCHEDULE YOUR SHOWINGS TODAY!

408 S 11th Street, Chesterton

This is an accessible, free-standing building on a corner lot in downtown Chesterton with convenient parking. B-2 zoning has many permitted uses. Some examples are offices, multiple kinds of retail opportunities, coin laundry, dry cleaning, bakeries, convenience stores, farmers markets, restaurants, bank/credit unions, funeral homes, vet clinics, barbershops, childcare centers, tanning salons, bar/ night club, billiards, and a dance studio, plus much more.The building's current use is as a medical office. It has seven exam rooms, each approximately 9 x 14, a lobby, a reception area, and an office area. There is one bathroom and a basement for plenty of storage.The building is well-maintained, and the rubber roof is about 15 years old. Central Air and Gas Furnace. City Water and Sewers.

621 Broadway, Chesterton

3 Beds ⋅ 3 Baths

Step into timeless elegance with this meticulously crafted ranch-style home.Surpassing initial impressions, this residence unfolds with an expansive 3600 sq ft of living space, showcasing a 2+ car garage,open-concept layout with 9-foot ceilings, ample storage, and a generously sized finished basement featuring a FULL KITCHEN and an egress window.Designed for both comfort and convenience, the residence offers 3 bedrooms, complemented by two additional non-conforming bedrooms in the basement, 3 bathrooms, and extra-wide hallways and doors.Perfectly suited for entertaining or creating a versatile living space, this home seamlessly blends style and functionality.The 2 bonus rooms in the basement would be great for hobbies!The outdoors has a fenced-in yard, mature trees, and a patio featuring an adjustable pergola, providing an ideal setting for outdoor gatherings.Escape to the nearby Dunes National Lakeshore, offering breathtaking beaches, sand dunes, and a plethora of outdoor activities.

2470 Westwood Lane S, Chesterton

Only an hour from Chicago sits a picturesque neighborhood behind private gates. Sand Creek offers upscale living in an exclusive neighborhood. Unique estate homes line the streets of this sought-after subdivision. This is one of the last lots available before this community is completely sold out. If you have been dreaming about building a home, this is the time and place to do it.

1915 Toms Court, Chesterton

Build your dream within the gates of Sand Creek! This established invites you to not settle for an existing home. Get exactly what you want just minutes from Lake Michigan, Dunes National Park and two major highways. This lot is perfectly situated in the award winning Duneland Schools

1840 Bramble Trace, Chesterton

4 Beds ⋅ 4 Baths

A rare jewel. This elegant property in Sand Creek provides the ultimate in location, space, and luxury. This spacious property offers 4 bedrooms, and 4 baths. MAIN FLOOR PRIMARY BEDROOM with Spa like Bath. Open Floor plan with Gourmet Kitchen featuring Sub-Zero and Wolf Appliances. Two-Story Great Room with fireplace, custom bookcases and floor to ceiling windows. Entertain with ease in the fully finished lower level featuring custom club style bar, kitchenette, work out room, and a home office dream workspace. Enjoy sitting fireside at your very spacious custom patio complete with grilling center. If you are looking for Luxury Maintenance Free Living within the gates of Sand Creek look no further than this fabulous lock and leave property. Sand Creek features 27- Hole Championship Golf Course, fine dining, and so much more. The Country Club lifestyle awaits you!

1437 Calais Court, Chesterton

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Updated . Information deemed reliable but not guaranteed.