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$849,900
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
$283,500
2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton
$579,900
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
$264,900
3 Beds ⋅ 2 Baths
Back on market at no fault of seller! Welcome to 252 S 21st St in Chesterton! This well-maintained home offers valuable updates, flexible living space, and outstanding garage/storage options, all tucked away at the end of a cul-de-sac. When you walk through the front door, you'll notice the vinyl flooring and open floor plan, with the floors flowing naturally into the kitchen and dining area. The renovated bathrooms provide a modern, updated feel alongside the main-floor bedrooms. Major improvements include a new roof, new air conditioner, new furnace, new gutters, and a newer sump pump, giving buyers added peace of mind. The home also features a partially finished basement with a family room, bedroom, and bathroom -- perfect for guests, hobbies, work-from-home needs, or additional living space. Out back, enjoy a deck overlooking the yard, ideal for relaxing, grilling, or entertaining. The property also stands out with two detached garages providing a total of four garage spaces, offering excellent room for vehicles, storage, tools, recreational equipment, or workshop potential. Conveniently located in Chesterton, this home combines practical updates, extra space, rare garage capacity, and a quiet cul-de-sac setting. Schedule your showing today!

252 S 21st Street, Chesterton
$185,000
3 Beds ⋅ 1 Baths
Welcome to this charming 1 1/2 story, 3 bedroom home ideally located in the heart of downtown Chesterton! Situated on a spacious .36 acre lot, this property offers an excellent location. The inviting great room features a vaulted ceiling, cozy, corner gas fireplace and sliding doors that lead out to the 24 x 8 deck overlooking the landscaped yard, which is filled with colorful perennial gardens that were planted with love and provide beautiful blooms throughout the seasons. Main floor also features a living/dining room, kitchen, 2 bedrooms and an updated bath with ceramic walk-in shower. The upper level features the 3rd bedroom. There is an attached garage, an additional detached garage, shed and extra parking, providing ample room for vehicles, hobbies or extra storage. Enjoy everything Chesterton has to offer just minutes from your doorstep, including restaurants, a winery and brewery, the seasonal European Market and a Farmer's Market, boutique and antique shopping, Lake Michigan beaches and recreational areas and year round community events. Bring your decorating ideas, this home has great bones and is ready for your personal updates and finishing touches. Don't miss this opportunity to own a home in one of Northwest Indiana's most desirable communities!

118 S 13th Street, Chesterton
$475,000
9 Beds ⋅ 4 Baths
501 Wabash Ave is an extraordinary property located in the heart of Chesterton, Indiana. This versatile space offers numerous possibilities: Generational living? Absolutely. Income-producing potential? Yes. A stunning open-concept home with an apartment and guest suite for visiting family and friends? Definitely. Spanning 4,400 square feet, this property is as adaptable as it is distinctive. The main living area features beautiful hardwood floors, an expansive open layout perfect for entertaining and relaxation, four well-sized bedrooms, and a luxurious custom-built shower in the main bathroom. The kitchen, renovated in Spring 2026, is a chef's paradise, featuring new countertops, stainless steel appliances, a pot filler and plenty of cabinetry to accommodate all your cooking essentials. Additionally, there are two more bedrooms, a full bathroom, and another kitchen, dining and living room adjacent to the main area with brand new flooring. This area can function as space for multi-generational living or be easily separated to create two distinct spaces. But that's not all! Above the three-car garage, you will discover a three-bedroom, one-bathroom apartment with modern flooring, recessed lighting, its own entrance, and a private deck perfect for enjoying the outdoors. This hidden gem is situated within the award-winning Duneland School District, just a leisurely stroll from the Chesterton European Market, minutes from the beach and State & National Parks, and conveniently close to fantastic local amenities. Plus, it's just a short drive to Chicago. Don't wait or hesitate--schedule your showing today and make this versatile and delightful home yours!

501 Wabash Avenue, Chesterton
$299,000
3 Beds ⋅ 2 Baths
Nice, solid all-brick ranch on a desirable corner lot directly across from the high school! This well-maintained home features a spacious eat-in kitchen with newer luxury vinyl hardwood flooring, a formal dining room, and all newer stainless steel appliances included. A built-in doggie door and sliders lead to a privacy-fenced backyard--perfect for pets and entertaining. Major updates include a new roof and sump pump in 2023, plus added washer and dryer hookups in the bathroom for extra convenience. Fantastic location close to schools, shopping, expressways and amenities!

1749 Green Meadow Lane, Chesterton
$1,500,000
Prime commercial opportunity with endless potential! Situated on just over an acre along a high-traffic roadway, this unique property features four buildings totaling nearly 6,500 square feet. Exceptional visibility and easy access make this an ideal location for a variety of business ventures, investment opportunities, retail, office space, storage, service industries, or mixed-use possibilities. The expansive lot offers ample parking, room for expansion, and flexibility to fit your vision. Whether you're looking to grow your business, start a new venture, or add to your investment portfolio, this property delivers location, exposure, and opportunity all in one package. Don't miss your chance to own a versatile commercial property in a prime location with unlimited potential!

1147 N Salt Creek Road, Chesterton
$450,000
3 Beds ⋅ 3 Baths
This property offers the ideal combination of location, lot, and lifestyle. Located in Duneland Cove, this nearly 3,000-square-foot home features 3 bedrooms, 3 bathrooms, and a 3-car garage, all just minutes from shopping, healthcare, major highways, rail access, and the shoreline beaches of Lake Michigan. The main level's circular floor plan connects the living room, dining room, kitchen, and family room, with beautiful backyard views from inside the home and from the deck. A centrally located half bath sits next to the den. Upstairs, you'll find three spacious bedrooms and a full hall bathroom shared by Bedrooms 2 and 3. The primary suite includes a three-quarter bath and an adjacent loft that can serve as an office or flexible living space. The daylight basement adds more finished living area, including recreation space and a double-door walkout to a brick patio and garden path. This two-story home also features a welcoming covered front porch, a split HVAC system for garage comfort, a functional layout, and a convenient location. Home is being sold "As Is".

947 Sandpiper Drive, Chesterton
$329,900
4 Beds ⋅ 2 Baths
Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 bedrooms plus an office, with character, space, and comfort throughout! The beautiful gourmet kitchen with cabinets galore is just waiting for you to host that special dinner party. The stunning formal dining room is perfect for entertaining, while the large living room with a spectacular fireplace creates the ideal place to cozy up on cool evenings. Now wait until you see the incredible upstairs retreat, a master suite to die for! Enjoy a walk-in closet that feels like an entire extra room along with your own private getaway featuring a grand 20x14 bathroom designed for relaxation and comfort. So much in this home is brand new! Beautiful arched doorways welcome you inside, while large windows flood the home with natural light. Gorgeous plank flooring flows throughout the home, complemented by new carpet in the bedrooms. Outside, you'll love the huge corner lot, fantastic location, fully fenced backyard, and gorgeous deck where you can sit and sip your favorite beverage while enjoying your own peaceful tranquility. ROOF AND GUTTERS are less than 7 months old! A fantastic 2.5-car detached garage adds even more convenience and storage space. There's even a welcoming front porch perfect for relaxing and watching the world go by. Step into tranquility with this beauty... priced under market value! and ready to welcome you home!

769 S Calumet Road, Chesterton
$599,900
4 Beds ⋅ 3 Baths
The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offering just under 2,300 square feet of thoughtfully designed living space. Featuring 4 spacious bedrooms, 3 bathrooms and a spacious 2-car garage, this home perfectly blends comfort, quality and style. Step inside to an open-concept floor plan showcasing hardwood floors, custom cabinetry, a beautiful trim package throughout, solid core doors and soft-close cabinets. The gourmet kitchen is complete with stainless steel appliances, quartz countertops, a large island and an abundance of workspace, making it perfect for entertaining or everyday living. Gather around the custom fireplace, thoughtfully placed to create a warm and inviting living space. The luxurious primary suite offers a peaceful retreat with a double vanity, alcove tub, custom tiled shower with seamless glass enclosures and a large walk-in closet. 3 additional bedrooms, 1 w/walk-in closet and a beautiful full bath complete the upper level. Additional highlights include energy-smart features, zoned efficient HVAC, humidifier, fresh air intake, R-20 insulation in exterior walls, tankless hot water heater, generous electrical lighting package, irrigation system and a beautiful composite deck perfect for outdoor enjoyment. The unfinished basement includes roughed-in plumbing and an egress window, providing endless possibilities for a future bedroom, bathroom, recreation space, or additional living area. Situated on a desirable corner lot in the highly sought-after Easton Park subdivision, this exceptional home is just minutes from the Indiana Dunes National Park, the South Shore Line, major expressways and award-winning schools! Call for your showing today!

2230 Redwood Lane, Chesterton
$248,000
3 Beds ⋅ 1 Baths
Welcome to 270 Woodlawn Ave in Chesterton. This beautifully remodeled 3-bedroom home offers soaring ceilings, bright open living spaces, and updates throughout. Newer mechanicals provide added peace of mind, making this home truly move-in ready. Located just minutes from downtown, parks, and the Indiana Dunes, this home combines charm, comfort, and exceptional value in a highly desirable area. Schedule your showing today.

270 Woodlawn Avenue, Chesterton
$420,000
3 Beds ⋅ 2 Baths
Looking for a place in Chesterton where you can actually breathe? This peaceful 2.2-acre country retreat offers the perfect balance of wide-open green space and a home designed for everyone to have their own corner. The main house features airy vaulted ceilings, a large country kitchen with stainless steel appliances, and oversized bedrooms with deep closets, plus extra attic storage in both garages. A standout feature is the clever "related living" setup: just close the French doors to create a fully private apartment complete with its own kitchen, laundry, and appliances. You can soak up the views year-round from the heated sunroom, which overlooks an above-ground pool with a wrap-around sun deck, or choose between the large party-sized fire pit and the smaller, cozy one for quieter nights. To top it all off, the property includes a massive 40' x 60' fully insulated pole barn with concrete floors, electric, and even a built-in bedroom and bathroom. With double barn doors and a drive-through exit for easy rear parking, this is the ultimate setup for hobbies, guests, or just enjoying the quiet life. Located in the award-winning Chesterton/Duneland School District, convenient to all major highways, don't wait - schedule your showing today!

141 W 900 N, Chesterton
$1,479,999
4 Beds ⋅ 5 Baths
Welcome to your private Northwest Indiana retreat in desirable Jackson Township--where space, luxury, and nature come together on just over 15 stunning acres. This all-brick estate offers the perfect blend of elegance and outdoor adventure, featuring 4 bedrooms and 5 bathrooms, thoughtfully designed for both everyday living and unforgettable entertaining. Inside, you'll find a generously sized kitchen with granite counters and stainless appliances, including a 6-burner cooktop with a griddle. 4 bedrooms include a spacious primary suite that serves as a true sanctuary, complete with a large en suite bath and plenty of room to unwind. Two additional bedrooms also feature private en-suite bathrooms, providing comfort and privacy for family or guests. The home offers many living spaces filled with natural light, including a beautiful sunroom with a hot tub--the perfect place to relax year-round. Conveniently located nearby is a dedicated bathroom designed to service the pool area. Step outside and experience a property that truly feels like a personal resort. Enjoy summers by the in-ground pool, host gatherings on the expansive deck, or explore your own private walking trails and mature woods. The stocked pond adds to the peaceful setting and creates the perfect spot for fishing, quiet reflection, or simply taking in the scenery. The unfinished basement provides incredible opportunity for future expansion--whether you envision a home theater, gym, additional living space, or guest quarters. Located in the highly sought-after Duneland School District, this property offers the perfect balance of privacy and convenience. Just minutes away, you'll find the breathtaking beaches and trails of the Indiana Dunes National Lakeshore, while the South Shore Railway provides an easy commute to downtown Chicago.

1137 N 475 E, Chesterton
$594,900
3 Beds ⋅ 2 Baths
This newly constructed ranch-style home presents an exceptional opportunity for buyers seeking quality craftsmanship and thoughtful design within the highly regarded Easton Park community. Encompassing approximately 1,892 square feet of well-appointed living space, the residence offers a refined single-story floor plan that balances elegance with everyday functionality. Upon entering, vaulted ceilings create an immediate sense of openness and architectural interest, establishing a welcoming atmosphere throughout the main living areas. The centerpiece of the home is a generously proportioned gourmet eat-in kitchen, complete with an oversized island that provides ample space for meal preparation, casual dining, and entertaining. The residence features three well-sized bedrooms and two tastefully finished bathrooms, each designed with attention to proportion and detail. The primary bedroom serves as a private retreat, complemented by a spa-like ensuite bathroom that incorporates premium fixtures and finishes designed to elevate daily routines into moments of genuine comfort and relaxation. As a new construction property, every element of this home remains in pristine condition. Prospective owners will benefit from modern building standards, updated systems, and contemporary finishes throughout -- with no prior wear or deferred maintenance to address. Each surface and system stands ready for its first owner. Properties of this quality in Easton Park are uncommon. Interested parties are encouraged to schedule a private showing at their earliest convenience.

840 Idlewild Lane, Chesterton
$290,000
3 Beds ⋅ 2 Baths
Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning trails and beaches of Indiana Dunes National Park, this 1,977-square-foot haven offers 3 bedrooms, 2 bathrooms, and effortless access to Chicago commutes--blending small-town charm with big-city convenience in the highly rated Duneland School District. From the moment you arrive, the home's warm light yellow siding and inviting deck beckon you into a world of timeless elegance. Step inside to a light-filled living room with dramatic cathedral ceilings, creating an open, airy retreat perfect for family gatherings. The adjacent kitchen inspires gourmet meals and connects seamlessly to the versatile den--ideal as a home office or guest space. Enjoy a full main-floor bathroom, convenient laundry/mud room, and direct access to the expansive covered patio, with the sprawling backyard perfect for barbecues or serene views. Upstairs, unwind in the luxurious primary bedroom suite with a spa-like en-suite bathroom and generous closet. The adaptable loft offers endless possibilities, complemented by a spacious second bedroom. The full unfinished basement awaits your vision as a media room or workshop, alongside a dedicated office. Modern comforts include central air, natural gas heating, municipal utilities. This isn't just a house--it's a legacy of tranquility and adventure. With historic soul and unbeatable location, it's ready to welcome you home.

214 Woodlawn Avenue, Chesterton
$999,000
Opportunity to own the former Main Street Tap in the Heart of Chesterton. Three level bar restaurant has been completely renovated. Main floor features a huge bar and outdoor patio deck. Second floor features 2 private office spaces, large banquet facility or meeting area, and a second floor deck. Basement is walk out with space for dining or food preparation area. Existing three (3) way liquor license, trade fixtures, bar and tap equipment, A/V stage equipment, TVs, and Point of Sale system ALL INCLUDED!! Additionally, the Town of Chesterton just added a new parking lot in close proximity to the building making it convenient for customers to come and go. Call today to schedule your showing.

119 S Calumet Road, Chesterton

Updated . Information deemed reliable but not guaranteed.