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.

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Newest Chesterton Homes and Condos for Sale

4 Beds ⋅ 3 Baths

Welcome to 964 Michael Drive in Chesterton, IN, BEST BUY IN DUNELAND COVE! This beautiful home offers a perfect blend of comfort and convenience. With 4 bedrooms and 2.5 bathrooms, plus a large finished basement offers plenty of room for everyone to spread out. The spacious living room with gas fireplace and large windows invites an abundance of natural light, creating a warm and welcoming atmosphere. The fully equipped kitchen boasts a cheerful eat-in area and large pantry. Enjoy quiet moments in the backyard with deck, perfect for summer barbecues and outdoor activities. The attached 2.5 -car garage and unfinished basement portion provide plenty of extra storage. Located in a desirable neighborhood, this home is close to schools, parks, shopping, and dining. 4 miles to the Indiana Dunes State Park and only a mile to I-94, making this home perfect for commuters. Don't miss out on this amazing opportunity to make 964 Michael Drive your new home!!

964 Michael Drive, Chesterton

3 Beds ⋅ 2 Baths

Absolutely charming! This 3 bedroom 2 bath home is situated on a pretty landscaped lot with mature trees, in Golfview Estates.A delightful covered front porch with railing welcomes you in to this sunlit, open concept, split ranch.Kitchen was remodeled in 2019 with new granite countertops, stove, refrigerator, & microwave, and new carpet was installed in living room and 3rd bedroom, which is currently used as an office with French doors.The master bedroom has an ensuite full bath. A full hall bath is shared. Laundry room includes washer & dryer. Concrete patio overlooks back yard. Spacious 2 car garage attached. HSA Home Warranty provided. All appliances included.

1484 Duffer Drive, Chesterton

GREAT INVESTMENT OPPORTUNITY In the Indiana Dunes National Park. Custom Built 3250sq.ft. Ranch style home/office. Building is like a duplex. Home on one side and Office on the other side.Seperate entrances. Possible related living. Office has 7 rooms with 1/2 Handicap restroom. Large parking lot with possible 10 cars. Professional Office is zoned C2. Also can be used for office space; insurance, attorney, or medical etc. Live on one side and work on the other. Home side has 4 bedrooms, 2 baths with 2000 sq. ft basement. Property borders the National Park. All is on 3.4 Acres of land with a pond. Also a 4 car garage. Very close to Beverly Shores Train Station, Lake Michigan Beaches, and minutes to expressways.

371 E US Highway 20, Chesterton

12 Beds ⋅ 8 Baths

2) 3 bedroom & 2) 2 bedrooms with den/office. 1 1/2 car garage each unit.

Chesterton

6 Beds ⋅ 4 Baths

Spacious Home in highly desirable Tamarack! This Two Story Home with Full Finished Basement, offers up to 6 Bedrooms! The Main Level with Beautiful Maple Floors host the Main Bedroom En-suite with newly Updated Bath. Light and Bright Kitchen leading into the inviting Living room with Soaring Ceilings and Fireplace. The Main Level is completed by a Private Den, Dining Room and Laundry/Mudroom. Upstairs you will find 3 bedrooms along with converted bonus space to make 4 total Bedrooms on the Upper Level. The Basement doesn't miss a beat with another Bedroom, Full Kitchen, Custom Built-ins and Steam Shower. This Home truly has room for everyone, in one of the most sought after neighborhoods in the Duneland School District!

1089 White Willow Lane, Chesterton

4 Beds ⋅ 3 Baths

Welcome to 411 Shamrock Dr. in Chesterton, IN! This stunning bi-level home offers a spacious and comfortable living environment, spanning 3000 sq ft. With 4 bedrooms and 3 full baths, this residence is perfect for those seeking ample living space. Upon entering, you'll immediately notice the fresh paint throughout, creating a bright and inviting atmosphere. The upstairs area boasts new carpeting, providing a cozy feel to the ample and spacious living room. Downstairs, the den and bedroom feature beautiful new vinyl flooring, adding a touch of modern elegance.The elevated deck, recently restored, offers a peaceful retreat where you can unwind and enjoy the surrounding views. The entire backyard is fenced in and a charming patio area provides a delightful setting for outdoor entertainment and relaxation.Situated on a corner lot in the heart of Chesterton, Indiana, this home offers the best of both worlds - a peaceful residential setting and close proximity to downtown.

411 Shamrock Drive, Chesterton

Located at 475 Sand Creek Dr, Chesterton, Indiana, this well-established breakfast and lunch restaurant is a fantastic investment opportunity. With nearly 20 years of successful operation, this turnkey business is ready for new owners to continue its legacy. The property boasts a spacious lot size of 41,580 square feet, providing ample parking space for customers. The building itself spans 3,126 square feet and offers a cozy dining area, well-equipped kitchen, and all necessary restaurant fixtures and equipment. Don't miss this exceptional opportunity to own a successful breakfast and lunch restaurant in Chesterton! Whether you are an experienced restaurateur looking to expand or a new entrepreneur seeking a turnkey business, this property offers both stability and growth potential. Contact us today to schedule a showing and explore this exciting investment!

475 Sand Creek Drive, Chesterton

4 Beds ⋅ 3 Baths

Beautiful Setting Property Borders Indiana Dunes National Park . Wooded with lots of nature on 3.4 acres of land w/pond. Custom Built 3250 sq.ft. Ranch Style all Brick and Stone home/office.4 bedrooms,2.5 baths with an additional 2000 sq.ft basement w/wood burn stove. Home has many possibilities for living expansion. Updated office side can convert to Related living, Vacation home, or Rental, Professional Office. Floor layout of Home/Office is like a Duplex. Separate entrance for both. Kitchen/Dining open concept. Granite with breakfast island. Large living rm. w/newer carpet and quartz stone Fireplace w/wood burner stove insert. Oak flooring thru out. Large main bedroom w/2 closets. Bath next to bedroom. Updated bath w/cultured granite. White cabinets. 4 car detached garage w/room for RV or Boat. Very close to Beverly Shores Train Station and Lake beaches. Minutes to Hwys and shopping.

371 E US Highway 20, 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

4 Beds ⋅ 4 Baths

This two story home with incredible wrap around porch in sought-after Abercrombie Woods has it all- hardwood floors, storage pantry, stainless appliances, custom blinds, granite countertops, upgraded cabinets, main level bedroom, main level bathrooms, main level laundry/mud room, walk-in closets, finished basement(with bar, rec room, bathroom, & exercise area), balcony off of the upstairs bedroom, fenced yard, patio off of the porch, cathedral ceilings, Border Magic landscaping, and irrigation system. Plenty of storage throughout home. Easy access to Indiana Dunes State Park, I-94, Indiana Toll Road, South Shore Train, and the beaches of Lake Michigan.

4221 Abercrombie Drive, Chesterton

4 Beds ⋅ 3 Baths

*SELLER WILLING TO BUY RATE DOWN*Welcome to your private Oasis. Stunning custom- built Ranch with 4 bedrooms, 3 baths, 3 car garage (gas line hook up), recreation room, dry bar, heated chicken coop & a whole house generator! The home offers 11 foot ceilings, master bedroom with a recessed ceiling, walk-in closet, walk-in shower, double vanity and a private door to the deck/ backyard.With its open concept design, the living room presents large casement windows and luxury hand-scraped bamboo flooring leading you to the kitchen with a HUGE walk-in pantry, quartz countertops, maple cabinets, and stainless-steel appliances that include a double oven. Beautifully landscaped with a fire pit, brick patio, and shed, that are all surrounded with native flower.Plenty of storage space including an attic (with electricity), shed, and basement. Fantastic location: few minutes from Dogwood park, Lake Michigan Beach & the South Shore train.

1103 S 23rd Street, Chesterton

5 Beds ⋅ 6 Baths

Highly desirable Sand Creek property! Presenting this sprawling over 4,700 square foot, 5 bedroom, 5.5 bath custom built home. Gourmet functional kitchen with custom pantry, granite countertops and wood floors throughout, all baths have heated floors, Master Bedroom w/custom walk-in closets. Additionally, a second kitchen provides prep options for large gatherings or related living. The master ensuite includes a separate sitting room with fireplace and the list goes on. Enjoy relaxing under the 18' x 16' covered patio. EV charging system is available in the garage. Sand Creek is one of Northwest Indiana's premier gated communities featuring a clubhouse that can be utilized for hosting events, aquatic center, tennis courts, and a 27 hole golf course. All of this just minutes from every modern day convenience, only 50 minutes from Chicago's West Loop and 30 minutes from Michigan. This property truly has it all. Schedule a tour today!

1830 Bramble Trace, Chesterton

5 Beds ⋅ 3 Baths

Prepare to be impressed by this BEAUTIFUL NEW 2-story Home in the The Preserve Community! The elegant Gardner Plan boasts a flex space and a guest suite with a walk-in closet on the main floor. The Kitchen features gorgeous cabinets, granite countertops, and stainless-steel appliances (Including Range, microwave, and Dishwasher). All other bedrooms are on the 2nd floor. The oversized primary suite has a private bath, dual vanity sinks, and a walk-in closet. This desirable plan also comes complete with a 2-car garage.

1019 Preserve Lane, Chesterton

5 Beds ⋅ 4 Baths

Welcome to this idyllic 2 story with a modern farmhouse motif nestled in the heart of Coffee Creek Preserve. This architectural gem seamlessly blends contemporary design with rustic charm, creating a harmonious and inviting abode. The exterior features reverse board and batten siding, stone and wood accents, large windows, and 8 ft exterior doors that offer an abundance of natural sunlight. Inside, an open-concept layout awaits, boasting a spacious living area adorned with a striking fireplace. The farmhouse kitchen is a chef's dream, equipped with custom cabinetry, sleek countertops, and top-of-the-line appliances. The related living space provides a separate suite, complete with a comfortable living room, a private bedroom with a balcony, and a luxurious bathroom. Upstairs, the primary suite offers a serene retreat with a massive closet, second laundry, and the closet of your dreams! The lower level is complete with a full living space for extras! Located minutes to everything!

2315 Dickinson Road, Chesterton

3 Beds ⋅ 3 Baths

LOCATION!! LOCATION!! Over 3,000 sq. ft. home with FIRST FLOOR MAIN SUITE plus large unfinished basement. Open floor plan with hardwood floors. Beautiful living room boasts of a vaulted ceiling and fireplace. Eat-in kitchen with plenty of cabinet storage plus quartz counters and stainless appliances. Cozy gathering room/dining room with awesome vaulted ceiling overlooks private, tree-line backyard. Backyard has huge deck for relaxing and entertaining, plus a fire pit, vegetable planter boxes, and secluded storage shed. Primary bedroom has an attached en-suite with soaking tub, shower and walk-in closet. There is also a main floor mud room with laundry. An extra wide staircase leads upstairs to two spacious bedrooms + full bathroom and extra large bonus room (office or playroom.) Home has tons of storage options plus full basement for expansion. Very peaceful and walkable neighborhood on a No Outlet Street. Walk to downtown, European Market, WIS, Chesterton H.S. and Bailey Elementary.

1111 Olivia Court, Chesterton

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