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

2 Beds ⋅ 1 Baths ⋅ 845440 MLS ⋅ ACTIVE Status

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 ⋅ 845429 MLS ⋅ ACTIVE Status

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 ⋅ 845277 MLS ⋅ ACTIVE Status

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 ⋅ 845256 MLS ⋅ ACTIVE Status ⋅ Villages/Sand Crk Ph 2 BLDG.

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

2 Beds ⋅ 2 Baths ⋅ 845231 MLS ⋅ ACTIVE Status

Welcome to this turn-key, single-story ranch home in Chesterton featuring 2 bedrooms and 2 full bathrooms. Meticulously maintained, immaculate, and completely move-in ready, this home offers effortless one-level living with stylish modern upgrades completed within the past year, including fresh paint throughout, a custom accent wall, custom blinds, updated lighting fixtures, and a custom organizer in the primary bedroom walk-in closet. The light-filled sunroom provides versatile additional living space that is perfect for a cozy morning coffee nook or a bright home office. Enjoy added value with all kitchen and laundry appliances as well as the main living room TV included with the sale, along with a fully enclosed backyard featuring a newly installed privacy fence for relaxation or outdoor gatherings. Conveniently located close to everything Chesterton has to offer, you are just minutes from local dining and shopping, the stunning Indiana Dunes National and State Parks, major highways, and the South Shore Line for an easy commute into Chicago or fun day trips.

1633 Gustafson Avenue, Chesterton

3 Beds ⋅ 2 Baths ⋅ 845153 MLS ⋅ ACTIVE Status

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 ⋅ 845085 MLS ⋅ ACTIVE Status

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 ⋅ 845039 MLS ⋅ ACTIVE Status ⋅ Providence Community Assn Inc BLDG.

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

845034 MLS ⋅ ACTIVE Status

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 ⋅ 844916 MLS ⋅ ACTIVE Status

Completely 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

4 Beds ⋅ 3 Baths ⋅ 844907 MLS ⋅ ACTIVE Status

Welcome to this 4 bedroom, 3 bath, 2-story home located in desirable Villages of Sand Creek. Main level offers a Formal Living Room as well as a Formal Dining, spacious Eat-in Kitchen which is open to the Family Room, and the Laundry Room. Upstairs you will find all 4 bedrooms freshly painted with newer carpet. The Primary Suite has an attached full bath with separate shower and tub and large walk-in closet. This home is situated on a cul-de-sac with a lovely view of the pond located across the walking path. This neighborhood is only 3 miles from the Indiana Dunes & Lake Michigan, close to restaurants, shopping, golf courses, and is an easy commute to Chicago.

378 Ballenisle Court, Chesterton

3 Beds ⋅ 3 Baths ⋅ 844895 MLS ⋅ ACTIVE Status

Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly 3,000 sq. ft. of finished living space has been thoughtfully updated from top to bottom, offering the charm of an established home with the finishes, comfort, and peace of mind of something new. Major upgrades include a **NEW ROOF, NEW FURNACE, NEW CENTRAL A/C, and a WHOLE-HOME GENERATOR**--making this home truly move-in ready. Inside, you'll find 3 spacious bedrooms, 2.5 beautifully updated baths, TWO separate living areas, an eat-in kitchen with stone countertops and stainless steel appliances, high ceilings, recessed lighting, a main-level primary bedroom, and convenient main-level laundry. The upper level offers two generously sized bedrooms plus a large loft, providing plenty of flexibility for an office, playroom, additional lounge, or guest space. Outside, enjoy a private, landscaped **0.54-acre lot**, rear deck, storage shed, and attached 2-car garage with NO HOA. With virtually everything already upgraded, all that's left to do is move in and enjoy this stunning Chesterton home!

2332 Dakota Street, Chesterton

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