Chesterton Real Estate

Chesterton Real Estate

Welcome to Chesterton, a charming town nestled in Porter County, Indiana. Known for its small-town charm and friendly community, Chesterton offers a unique blend of modern amenities and natural beauty.

Located in the heart of the Midwest, Chesterton is a vibrant city with a rich history. The town boasts a thriving arts and culture scene, with numerous galleries, theaters, and music venues to explore. Outdoor enthusiasts will appreciate the town's proximity to the Indiana Dunes National Park, where they can enjoy hiking, biking, and birdwatching against the backdrop of stunning sand dunes and Lake Michigan.

Chesterton is also home to a variety of local shops, restaurants, and cafes, making it easy to support small businesses and enjoy delicious cuisine. The town hosts a range of community events throughout the year, including farmers markets, festivals, and concerts, providing plenty of opportunities to connect with neighbors and make lasting memories.

With its convenient location just a short drive from Chicago, Chesterton offers the perfect balance of small-town living and big-city amenities. Whether you're looking to settle down in a close-knit community or simply explore all that the Midwest has to offer, Chesterton is a wonderful place to call home.

Newest Listings in Chesterton

4 Beds ⋅ 4 Baths

Profitable duplex located less than 1 hour from Chicago, 10min to the South Shore Train, & 5min to I-94. Gross over 26,000 per year or live on one side & have your mortgage covered by passive income. You'll love this recently updated property with spacious rear yard, raised decks & 2 storage sheds. Loads of parking with an oversized driveway creating loads of space. Tenants pay utilities making for easy management & maximizing your bottom line. Management companies available as well. Weather you are starting your investment portfolio or looking to expand, this property will be a great asset to have.

429-431 Woodlawn Avenue, Chesterton

3 Beds ⋅ 2 Baths

Welcome HOME to this charming, classic all-brick 3-bedroom, 2-bath ranch offering comfortable MAIN level living! The home features beautiful picture-frame moulding, skylights that bring in an abundance of natural light, and a spacious layout ready for your personal vision. The larger hall bedroom was once two smaller bedrooms that could be converted back to add a 4th bedroom! The full basement provides exceptional additional space for storage, hobbies, a recreation area, or future finishing possibilities. Outside, enjoy a large yard with plenty of room for entertaining, gardening, play, or simply relaxing outdoors. Whether you're looking to add your own updates and finishes or create a home that reflects your personal style, this property offers a wonderful opportunity to build equity and bring your ideas to life. A solid brick ranch, great space, and tremendous potential--come see it today!!!

1250 Dogwood Drive, Chesterton

3 Beds ⋅ 2 Baths

Step into this nearly new Move-In ready 3- Bedroom, Maintenance-Free Ranch Duplex in Springdale! Open Concept layout with lots of natural light and beautiful Vinyl flooring. Enjoy a cozy night by the fireplace in the Great Room while making dinner or watching a movie. Kitchen has Maple cabinets, granite countertops and stainless steel appliances. The Master has an en suite with a double vanity and spacious walk-in closet. Sliding doors in the Kitchen lead to a covered patio. The neutral palette throughout this immaculate home will make moving in feel effortless!

2555 Springdale Street, Chesterton

2 Beds ⋅ 1 Baths

This charming two bedroom, one bath home is ready for its new owners. You'll love the refinished hardwood floors and wide trim that carry classic character throughout the home. Original solid wood doors with antique hardware add timeless appeal, while modern updates provide peace of mind. The home features newer windows, siding, furnace, and A/C, along with updated electrical. The kitchen and bathroom include built ins for added storage and style. Both bedrooms offer large walk in closets with lighting, a rare find in a home of this era. A perfect blend of vintage charm and thoughtful updates -- move in ready and full of personality. The attic space has the potential for future expansion and more living space. The large 2.5 car garage is truly a dream workspace. It's fully equipped with electric and even includes an A/C unit to keep you cool on hot days while tackling projects, hobbies, or storage needs. Plenty of room, plenty of comfort, and plenty of possibilities. Just minutes from major highways and next to the Duneland walking trail.

1708 Tower Street, Chesterton

5 Beds ⋅ 5 Baths

Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square feet of functional living space designed for a modern lifestyle. A massive kitchen, oversized island, dining area, living room with fireplace and 2 bedrooms on the main level. 2nd level offers oversized main bedroom suite with Full bathroom and walk-in closets and 3 additional bedrooms. 3rd level offers a bonus room (currently used as a bedroom). Enjoy a large 0.44-acre yard perfect for outdoor fun, an attached 3 car garage with ample storage nestled within a highly desired neighborhood, this home is a rare find. Priced Below Market value, carpet and painting needed. Call today for a private showing.

2941 Nautica Drive, Chesterton

3 Beds ⋅ 2 Baths

Historic Chesterton gem just steps from downtown! This solidly built 3-bedroom, 2-bath two-story home offers nearly 2900 sq. ft. of finished living space which includes a full basement. Beautiful original woodwork, doors, hardware and classic door knobs preserve the character of this special home, complemented by hardwood flooring. The bright, inviting kitchen features beautiful cabinetry and a convenient pantry. The updated main-level bathroom includes a charming clawfoot tub. Upstairs, the spacious primary bedroom offers a walk-in closet plus its own sitting area, filled with natural light. Situated on a desirable corner lot in Duneland School District and within walking distance to downtown Chesterton's shops, restaurants and amenities. Conveniently located near the beach and South Shore train station for those commuters. Historic charm, space, location and character--this is one you won't want to miss!

201 S 8th Street, Chesterton

4 Beds ⋅ 2 Baths

Welcome to this Charming Townhome in the sought out Villages of Sand Creek! This home has great curb appeal with perennials galore and is a bird and butterfly paradise. This townhome checks all the boxes: 4 bedrooms, 2 full baths, full basement & a 2 car garage. This home has MAIN FLOOR LIVING with laundry and primary bedroom, full bathroom with double sinks, a shower and jetted tub on the main floor. The living room boasts a vaulted ceiling and fireplace, leading to the kitchen and dining room area with all stainless appliances, pantry and a nice sliding glass door that leads to the back patio. The upper level has a full bathroom and 3 large bedrooms with huge walk-in closets and there is an additional walk-in storage closet. The basement offers an additional 1,272 sq ft of space that is ready to be finished. This home is minutes from 80/94, 80/90, Coffee Creek, the Indiana Dunes State Park, downtown Chesterton shopping, restaurants, farmers markets, parks and so much more!

376 Cherry Hills Drive, Chesterton

3 Beds ⋅ 2 Baths

Welcome to your new warm and cozy home! You'll enjoy the fireplaces, solid hardwood floors and privacy from your back yard. The home is situated on over 4 acres and is adjacent to protected wetlands. It is also close to shopping, expressways and the Indiana Dunes. The windows, furnace, air conditioner and hot water heater are newer. Come take a look!

1063 Frontage Road, Chesterton

3 Beds ⋅ 2 Baths

Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, perfectly situated on an expansive .48-acre lot within the highly sought-after Duneland School Corporation. With approximately 1,400 square feet of comfortable living space, this home offers the ideal blend of modern updates, functionality, and peaceful outdoor space. The home was completely taken down to the studs and renovated approximately five years ago, providing an impressive list of major improvements including new windows, roof, siding, furnace, air conditioning, vinyl flooring, well, septic system, and a newly paved driveway. The thoughtful updates continue with new storm doors in 2025 and, in 2026, a new shower with warranty, new shed, owned water softener, and new sump pump with a battery backup system. The stainless-steel appliances are included, and the versatile mudroom adds even more functionality with the flexibility to serve as a home office, den, or additional everyday living space. Step outside and enjoy the beauty and privacy of nearly half an acre. The spacious, well-maintained yard provides plenty of room for entertaining, gardening, pets, play, or simply enjoying your own outdoor retreat. With extensive updates, major systems already addressed, a beautiful lot, and the advantage of Chesterton schools, this is a home that offers both comfort and peace of mind. A wonderful opportunity to enjoy a move-in-ready property with nothing left to do but make it your own!

1430 N Veden Road, Chesterton

2 Beds ⋅ 1 Baths

Move-in ready 2-bedroom, 1-bath MAIN LEVEL Condo offering easy, low maintenance living! Beautifully updated throughout with all new flooring, updated lighting, and a stylish updated kitchen featuring quartz countertops and stainless steel appliances. The fully renovated bathroom offers a fresh, modern feel. Enjoy the convenience of an attached garage, private side entrance, and patio area perfect for relaxing outdoors. A new roof is scheduled to be installed within the next few weeks! Two HOA associations provide extensive coverage, including lawn care, shrub rimming, siding, roof, snow removal, trash, and water-- taking care of many of the costly exterior maintenance items for you. With everything on one level and so much already updated, this condo is truly move-in ready!

1972 Laura Lane, Chesterton

Six-unit multifamily property in Chesterton, built in 1999 and masonry-framed over two stories: four two-bedroom, one-bath units and two one-bedroom, one-bath units across 4,952 SF, averaging 825 SF per unit on a 0.27-acre parcel with 16 off-street parking spaces. Address range 1217 to 1227 W Porter Ave. Unit finish is unusually strong for the price point. Every unit carries its own forced-air furnace, central air conditioning and water heater, and the county record card values in-unit fireplaces at 30,200 dollars. Tenants pay their own gas, electric and in-unit water, leaving ownership responsible only for common-area electric, water and sewer, trash and grounds. That structure holds the current expense load to 36.8 percent of collected income and produces in-place NOI of 52,281 dollars, a going-in cap rate of 6.02 percent at the offering price. The value-add case is the rent roll. In-place rents average 1,158 dollars per unit against ownership pro forma of 1,528, roughly 32 percent of embedded upside, with two units already on month-to-month terms and a third rolling in January 2027. Marked to those levels the property produces pro forma NOI of 69,515 dollars, a cap rate of 8.00 percent at the offering price, with no change to the physical plant. Chesterton sits inside the Duneland School Corporation, minutes from I-94, US-20 and the Dune Park South Shore station, and adjacent to Indiana Dunes National Park.

1227 W Porter Avenue Unit #1217, Chesterton

4 Beds ⋅ 2 Baths

Motivated seller! Bring an offer! Remodeled home in a highly desired location! Location is one of the key features of this home located 5 minutes from Hwy 49, the Dunes, and approximately 45 minutes from Chicago. The up and coming downtown Chesterton, YMCA, Chesterton Park, and splash pad are only 3 minutes away. Bailey Elementary & Montessori School are only a few blocks away. Featuring a spacious updated living room with a beautiful fireplace. The formal dining room is a wonderful addition to the home. The modern kitchen includes new flooring, cabinets, countertops, and bar overhang for barstools. A full bathroom was added downstairs. There is a small office and bedroom with bathroom on the main level. Upstairs you will find 2 spacious updated bedrooms. The backyard space has been transformed into a private oasis with edible grapes on the fence. The storage shed is perfect for storing outdoor equipment. The home sits on a nice size lot with additional yard space to the right of the carport. Enjoy lower taxes and a quiet neighborhood.

656 S 4th Street, Chesterton

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