Chesterton, IN Homes for Sale

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  /56

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 2,494 Sq Ft

  450 E Greening Rd, Chesterton, IN 46304

  Escape to your own private paradise on this stunning 14+ acre property, where a tree-lined driveway winds gracefully through mature hardwoods, welcoming you home the moment you arrive. This is more than a home -- it's a lifestyle.The charming main farmhouse offers 4 spacious bedrooms and 2.5 baths, with an open and inviting floor plan centered around a gorgeous brand-new stone fireplace with

  Kalahni Krygier New Chapter Real Estate

  450 E Greening Rd, Chesterton, IN 46304
• Explore Chesterton

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  /18

  $210,000

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft

  1949 David Dr, Chesterton, IN 46304

  Welcome to Westchester Village, a sought-after condo community in Chesterton, just 7 minutes south of Lake Michigan's shoreline and the Indiana Dunes. This beautifully updated 3-bedroom, 2.5-bath condo offers 1,480 finished square feet of comfortable, low-maintenance living with serene pond views. Step inside to an inviting main level featuring hardwood flooring, a bright living area, and a

  Katie Phillips McColly Real Estate

  1949 David Dr, Chesterton, IN 46304
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  /13

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,860 Sq Ft

  1198 N Babcock Rd, Chesterton, IN 46304

  Escape to your own 1.7-acre private retreat just minutes from Lake Michigan and the Indiana Dunes! This classic Cape Cod-style home blends cozy charm with incredible potential. Step inside to find two comfortable bedrooms plus a spacious open loft that's perfect for a home office, playroom, or easy conversion to a third bedroom. The flowing layout and natural light create a warm, inviting

  Brian Manning Listing Leaders

  1198 N Babcock Rd, Chesterton, IN 46304
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  /16

  $499,900

  • 6 Beds
  • 6 Baths
  • 2,896 Sq Ft

  150 16th St, Chesterton, IN 46304

  This newly completed duplex was finished in 2024. This exceptional investment property features two spacious units--each offering 3 bedrooms, 3 bathrooms, and a convenient one-car garage. Both sides are currently leased, providing immediate rental income. The main level showcases durable LVP flooring, while the primary suite includes a generous walk-in closet. Quality finishes such as 6-panel oak

  

  Paul Boyter

  McColly Real Estate

  (219) 946-4328

  150 16th St, Chesterton, IN 46304
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  /17

  $525,000

  • 6 Beds
  • 6 Baths
  • 2,920 Sq Ft

  140 N Jackson Blvd, Chesterton, IN 46304

  This newly completed duplex was finished in 2024. This exceptional investment property features two spacious units--each offering 3 bedrooms, 3 bathrooms, and a convenient one-car garage. Both sides are currently leased, providing immediate rental income. The main level showcases durable LVP flooring, while the primary suite includes a generous walk-in closet. Quality finishes such as 6-panel oak

  

  Paul Boyter

  McColly Real Estate

  (219) 402-3372

  140 N Jackson Blvd, Chesterton, IN 46304
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  /2

  $529,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  2350 Pradera Trail, Chesterton, IN 46304

  New Spec home to begin construction! Still time to choose your finishes! Introducing the Aspen on Lot 9 in 1100 Woods! This is proposed construction with a 2026 building completion date. Located in the heart of Chesterton across from Dogwood Park and the Prairie Duneland Trail. The Aspen model is ideal for those looking for a primary ensuite on main level with walk in closet, a large kitchen

  Madison Young Brokerworks Group

  2350 Pradera Trail, Chesterton, IN 46304
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  /34

  $449,900

  • 3 Beds
  • 3 Baths
  • 2,636 Sq Ft

  1034 N 350 E, Chesterton, IN 46304

  Welcome to this beautifully updated bi-level home on a private 1-acre lot in Jackson Township! This property offers 3 spacious bedrooms and 3 baths, including a primary suite with walk-in closet and remodeled ensuite. Enjoy the open-concept floor plan featuring a modern kitchen (renovated in 2016) with sleek finishes, flowing into the dining and living areas--perfect for entertaining and family

  Jana Caudill eXp Realty, LLC

  1034 N 350 E, Chesterton, IN 46304
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  /27

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  696 Admiral Dr, Chesterton, IN 46304

  Welcome home to 696 Admiral Drive! This well-maintained and tastefully updated home in Porter Cove features three bedrooms, 2.5 baths, a whole home generator and an over-sized 2.5 car attached garage. The home is situated conveniently on a corner lot with a 6 foot vinyl privacy fence. The stylish kitchen offers plenty of cabinet space, granite countertops and a sleek tile backsplash that

  Jennifer Sanders Blue Ridge Realty Group

  696 Admiral Dr, Chesterton, IN 46304
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  /22

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  2034 Texas St, Chesterton, IN 46304

  This immaculate half duplex features threetwo bedrooms and 2 baths, offering 1,623 finished square feet on a crawl space. Enjoy beautiful wood and partial pond views from the back deck. As you enter, you'll find a spacious 7 x 17 ft ceramic-tiled foyer that opens up to a vaulted great room, complete with large nine-foot sliding glass doors leading out to the rear deck. The home features a

  Tami Bianco @properties/Christie's Intl RE

  2034 Texas St, Chesterton, IN 46304
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  /2

  $300,000

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  1807 W Porter Ave, Chesterton, IN 46304

  **Professional photos coming soon!!** Don't miss this one!! Welcome to your dream home in the heart of Chesterton, Indiana! This beautiful residence offers the perfect blend of charm and modern convenience. With three spacious bedrooms and two full baths, this home has been tastefully updated to meet the needs of today's discerning buyer. Step inside and admire the finishes, including a kitchen

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 306-8062

  1807 W Porter Ave, Chesterton, IN 46304
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  /21

  $399,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  30 Karner Blue Ct, Chesterton, IN 46304

  New construction home in The Preserve, located in Duneland School Corp. RESNET energy smart construction will save owner over 1000 yearly plus home has 10-year structural warranty! With over 2,200 sq ft of living space this floorplan is sure to please with its convenience & style! The main floor welcomes into the foyer, with a convenient powder bath tucked away, and past a den that serves as a

  Allen Edwin Homes Builder

  30 Karner Blue Ct, Chesterton, IN 46304
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  /53

  $559,900

  • 4 Beds
  • 3 Baths
  • 2,872 Sq Ft

  1329 N 375 E, Chesterton, IN 46304

  Nestled on 5 private acres, this spacious ranch offers four bedrooms (potentially five) plus a dedicated office and three bathrooms, with the convenience of an attached three-car garage and a detached two-car garage for hobbies, storage, or a workshop. The bright, open living spaces flow effortlessly to a well-appointed kitchen, while the split-bedroom layout provides privacy and comfort. With

  Elizabeth Garcia Blackrock Real Estate Services

  1329 N 375 E, Chesterton, IN 46304
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  /28

  $315,000

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  2513 Springdale St, Chesterton, IN 46304

  Welcome to your maintenance-free oasis in the desirable Springdale neighborhood of Chesterton, Indiana. This bright and inviting home offers 2 bedrooms and 2 bathrooms, plus a versatile office space and a sunroom that bathes the home in natural light. The open-concept kitchen features granite countertops, modern appliances, and ample counter space--perfect for entertaining or everyday living.

  Elizabeth Garcia Blackrock Real Estate Services

  2513 Springdale St, Chesterton, IN 46304
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  /32

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,046 Sq Ft

  399 Conestoga Dr, Chesterton, IN 46304

  This charming 3-bedroom, 2-bathroom home in the conveniently located Olde Towne Subdivision is waiting for you! Step inside and be greeted by an open living area featuring vaulted ceilings and a cozy gas fireplace, perfect for relaxing evenings. The kitchen comes fully equipped with all appliances included, making your move-in seamless. Just off the back of the house, a lovely wood deck overlooks

  Vince Kisala Coldwell Banker Real Estate Gr

  399 Conestoga Dr, Chesterton, IN 46304
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  /58

  $459,000

  • 4 Beds
  • 4 Baths
  • 3,260 Sq Ft

  1521 Birdie Way, Chesterton, IN 46304

  WOW! Immaculate 2-Story with finished basement & 3-car garage in a great neighborhood. Main level offers an inviting foyer with coat closet, office, an open concept kitchen with an abundance of cabinets, granite countertops, island with electrical, undermount sink with window overlooking the backyard, pantry and all appliances included, dining area with sliders to composite decking, living room

  Judith Posiadlik McColly Real Estate

  1521 Birdie Way, Chesterton, IN 46304
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  /20

  $174,900

  • 2 Beds
  • 1 Bath
  • 1,228 Sq Ft

  2121 Tupelo Ln, Chesterton, IN 46304

  Move-in ready, maintenance-free main-floor condo with a 1-car garage! A bright, open-concept living area features a cozy gas fireplace, and two new sliding doors to a private patio & your new backyard. The updated kitchen offers a brand-new quartz countertop, deep sink, pantry, and abundant cabinetry. Down the hall are two generous bedrooms, including a primary bedroom with a walk-in closet, an

  Nikola Trajceski Listing Leaders

  2121 Tupelo Ln, Chesterton, IN 46304
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  /24

  $254,900

  • 3 Beds
  • 1 Bath
  • 1,238 Sq Ft

  308 Rankin St, Chesterton, IN 46304

  Beautifully updated 3 Bedroom Ranch with hardwood and ceramic tile floors throughout. Kitchen features maple cabinetry, quartz counter top and all appliances. Loads of windows offering natural lighting. Brand new roof on house and 2.5 car garage, bath updated, partial basement with interior and exterior access. Move in ready!

  Cheryl Bonin CHERYL Real Estate Services, L

  308 Rankin St, Chesterton, IN 46304
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  /24

  $309,000

  • 2 Beds
  • 1 Bath
  • 1,692 Sq Ft

  1325 Indian Boundary Rd, Chesterton, IN 46304

  This two-bedroom, one-bath ranch home sits on a spacious 3.94-acre lot with apple, pear, and cherry trees and offers a cozy, comfortable living space. Featuring a welcoming wood-burning fireplace in the living room, the home exudes warmth and character. The fenced backyard provides privacy and plenty of room for outdoor activities, while the enclosed porch is perfect for entertaining. With a

  

  Paul Boyter

  McColly Real Estate

  (219) 355-2358

  1325 Indian Boundary Rd, Chesterton, IN 46304
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  /28

  $385,000

  • 5 Beds
  • 3 Baths
  • 2,232 Sq Ft

  1008 Preserve Ln, Chesterton, IN 46304

  Stunning 5 bedroom 3 full bath home built in 2023. Discover your dream home in the highly sought-after Preserve neighborhood of Chesterton! This nearly new construction offers modern luxury, spacious design, and an unbeatable location in the Liberty Township area. The eat in kitchen offers granite counter tops, a large island with seating for four and a nice backsplash. All bedrooms offer walk in

  Veronica Wilson Boulder Bay Realty Group

  1008 Preserve Ln, Chesterton, IN 46304
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  /33

  $359,900 Open Sat 10AM - 12PM

  • 3 Beds
  • 3 Baths
  • 1,866 Sq Ft

  17 E 900 N, Chesterton, IN 46304

  Charming Farmhouse on 2 Acres in Chesterton Welcome to this beautiful 3-bedroom, 3-bath farmhouse set on a serene 2-acre lot in Chesterton. This home blends classic character with modern updates -- including new flooring, fresh paint, and an updated upstairs bathroom. Enjoy a spacious yard perfect for entertaining, gardening, or simply relaxing under the open sky. The property also includes a

  Amy Wright @properties/Christie's Intl RE

  17 E 900 N, Chesterton, IN 46304
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  /19

  $237,900

  • 3 Beds
  • 1 Bath
  • 1,433 Sq Ft

  319 Michigami Trail, Chesterton, IN 46304

  Move right in and start enjoying Chesterton living! This spacious three-bedroom ranch offers a bright and inviting layout with a large living room and an oversized kitchen complete with a dishwasher and plenty of space to cook, gather, and entertain. Each bedroom offers comfortable dimensions-- the primary suite spans an impressive 19x11 ft! An additional large flex room provides endless options

  Charles Vanderstelt Listing Leaders

  319 Michigami Trail, Chesterton, IN 46304
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  /27

  $449,900

  • 4 Beds
  • 3.5 Baths
  • 3,112 Sq Ft

  353 Cherry Hills Dr, Chesterton, IN 46304

  Welcome Home! Come take a look at all of the updates and amenities including custom kitchen and bathrooms, upstairs laundry, ceiling fans in all of the bedrooms and a master suite with a tray ceiling and fireplace. Sump pump was replaced in 2025, Hot water heater in 2024, Roof, Furnace and A/C in 2023. Close to the Indiana Dunes, walking paths, park and expressways for easy commuting. Nothing to

  Teri Healy HomeSmart Legacy

  353 Cherry Hills Dr, Chesterton, IN 46304
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  /21

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,443 Sq Ft

  1887 Jacob Ln, Chesterton, IN 46304

  Welcome to 1887 Jacob Ln., a move-in ready home providing full main floor living where comfort meets convenience in the heart of Chesterton. This three-bedroom residence invites you in with a welcoming foyer that opens to an airy, open-concept living space. The oversized living room flows seamlessly into the eat-in kitchen, complete with stainless steel appliances including a dishwasher, creating

  Charles Vanderstelt Listing Leaders

  1887 Jacob Ln, Chesterton, IN 46304
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  /23

  $544,000

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  2011 Timberwood Ln, Chesterton, IN 46304

  Step inside and fall in love! This Easton Park home delivers all the charm, function, and "wow" factor you've been searching for. Bright engineered hardwood floors, elegant wainscoting, and a stone fireplace set the tone for stylish comfort. The gourmet kitchen is every cook's happy place with quartz countertops, 42" cabinets, roll-out shelving, and a walk-in pantry big enough for your secret

  Larry Hitz Berkshire Hathaway Homeservices Executive Group

  2011 Timberwood Ln, Chesterton, IN 46304
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  /37

  $324,900

  • 4 Beds
  • 2 Baths
  • 1,827 Sq Ft

  1226 Dogwood Dr, Chesterton, IN 46304

  Extensive Updates Throughout! This home has been beautifully remodeled with numerous recent improvements, including: Interior Upgrades: New paint in master bedroom, master bath, and fish tank room. Downstairs bedroom features new paneling. Utility room has a new floor. New doors and trim installed throughout most of the home. Main Floor Bathroom: Completely remodeled with an oversized tub, new

  Nicole Pleasant Listing Leaders

  1226 Dogwood Dr, Chesterton, IN 46304
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  /21

  $435,777

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  2332 Hickory Grove St, Chesterton, IN 46304

  Beautifully Updated Home in Coffee Creek! Welcome to this stylish and move-in-ready home, that blends modern updates with comfortable everyday living. Step inside to find a freshly updated kitchen with sleek finishes, featuring brand-new stainless steel appliances and quartz counters offering space perfect for cooking and entertaining. Plus....plenty of cabinet space, with a list of convenient

  Valeri McClelland Realty Executives Premier

  2332 Hickory Grove St, Chesterton, IN 46304
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  /33

  $549,900

  • 5 Beds
  • 4 Baths
  • 2,648 Sq Ft

  2335 Legend Cir E, Chesterton, IN 46304

  Maintenance Free Living on the trail in Coffee Creek! This tastefully updated townhome offers Main level living with added bonuses! On the main level you will find a spacious living room, well appointed kitchen, Primary EnSuite, additional bed and full bath, laundry, deck and screen porch. Upstairs offers an additional EnSuite and massive walk-in, the lower level has two more additional bedrooms,

  Alexis Metcalf Seramur Properties, LLC

  2335 Legend Cir E, Chesterton, IN 46304
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  /27

  $379,900

  • 4 Beds
  • 2.5 Baths
  • 2,484 Sq Ft

  1609 S 5th St, Chesterton, IN 46304

  Welcome home to this well maintained 4 bedroom gem, perfectly situated near Chesterton schools, the Indiana Dunes, shopping, and great dining. The main level primary suite features a walk-in closet and a private ensuite bath for added comfort. Beautiful hardwood floors flow throughout the main level, complemented by a bright and inviting living room with vaulted ceilings and a cozy fireplace. The

  Julee Kwiatkowski Realty Executives Premier

  1609 S 5th St, Chesterton, IN 46304
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  /29

  $379,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,393 Sq Ft

  24 Karner Blue Ct, Chesterton, IN 46034

  New construction home in The Preserve, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! Welcome home to over 2300 sq. ft. of open floor plan. The front entry greets guests and leads past a den, which will have French doors, and a powder bath, into a large great room, open to dining nook and kitchen. Dining

  Allen Edwin Homes Builder

  24 Karner Blue Ct, Chesterton, IN 46034
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  /41

  $594,900 New Construction

  • 3 Beds
  • 4 Baths
  • 2,580 Sq Ft

  5 Golf Wood Rd, Chesterton, IN 46304

  Rare opportunity to own a special retreat situated along the boundary of the Indiana Dunes National Park, just one mile from the Lake Michigan shore. Wooded surroundings combine with a modern aesthetic and effortless access to the South Shore Line (Chicago to South Bend) to deliver peaceful living. The house has an open concept floorplan with large windows and light throughout. Three bedrooms

  Arlene Beglin Arlene Beglin Real Estate

  5 Golf Wood Rd, Chesterton, IN 46304
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  $439,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  28 Karner Blue Ct, Chesterton, IN 46304

  New construction home in The Preserve, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! Welcome home, to over 2,700 sq. ft. of living space that seamlessly blends space with style. The large two-story foyer greets you and leads past a den or study continuing into the expansive great room and large dining

  Allen Edwin Homes Builder

  28 Karner Blue Ct, Chesterton, IN 46304
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  /23

  $419,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,954 Sq Ft

  1617 Melanie Ln, Chesterton, IN 46304

  PRIME LOCATION! Discover luxurious living in this highly desirable golf course community. This fabulous new listing boasts 3 bedrooms, 3 bathrooms, a perfect mix of sophistication, coziness, and awe-inspiring views! Get ready to be amazed by the grand master suite with its high cathedral ceilings and spacious walk-in closet. Indulge in the luxurious custom tile shower with a sleek glass enclosure

  Stacey Matthys Brokerworks Group

  1617 Melanie Ln, Chesterton, IN 46304
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  /21

  $295,000

  • 4 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  1817 W Porter Ave, Chesterton, IN 46304

  Move-in Ready! This spacious 4 bedroom, 2.5 bath Bi-Level is ready for new owners! Freshly painted interior and brand new carpet throughout. The stylish kitchen features a new backsplash and brand new stainless appliances. The dining area opens through a new sliding glass door that leads to the deck. The primary bedroom offers a 3/4 bath, while the full bath has been beautifully updated. The

  Debra Lightfoot McColly Real Estate

  1817 W Porter Ave, Chesterton, IN 46304
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  /21

  $264,900

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  2009 W Porter Ave, Chesterton, IN 46304

  Set in a prime location, this ranch home has been remodeled and is ready for you to move in! Discover this beautiful 4-bedroom, 2-bath home, offering 1,664 square feet of living space. KEY FEATURES include- Kitchen: The large kitchen features newer cabinets, tiled backsplash, an island with seating, butcher block top, and all appliances. The kitchen opens into the flexible dining room, which can

  Julie Elisha McColly Real Estate

  2009 W Porter Ave, Chesterton, IN 46304
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  /4

  $114,900

  • Land
  • 2.52 Acres
  • $45,595 per Acre

  383 E 1050 N, Chesterton, IN 46304

  Beautiful Wooded 2.52-Acre Homesite in Chesterton Schools Build your dream home on this 2.52-acre wooded parcel located in the desirable Chesterton School District. Nestled among mature trees, this peaceful property offers the perfect blend of privacy and natural beauty -- yet it's conveniently close to major highways, shopping, and all that Chesterton has to offer. With plenty of room for your

  Claudia Miller Forrest Century 21 Circle

  383 E 1050 N, Chesterton, IN 46304
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  /2

  $85,000

  • Land
  • 0.74 Acre
  • $115,489 per Acre

  1475 Snead Ave, Chesterton, IN 46304

  ALL OFFERS WILL BE LOOKED AT!! Gorgeous vacant lot located in Sand Creek. Build your DREAM HOME! So many possibilities.

  Karen Maynard McColly Real Estate

  1475 Snead Ave, Chesterton, IN 46304
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  /20

  $368,900

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  882 Argyle Ct, Chesterton, IN 46304

  Built in 2024 and nestled in a peaceful cul-de-sac, this stunning two-story home offers the perfect blend of modern design and everyday comfort. With 4 spacious bedrooms and 2.5 baths, there's room for everyone to spread out and feel at home. Step inside to an open-concept main floor that's ideal for entertaining--whether you're hosting game night or enjoying a quiet evening in. The kitchen flows

  Kari Rooney Realty Executives Premier

  882 Argyle Ct, Chesterton, IN 46304
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  /33

  $285,000 Open Sat 11AM - 2PM

  • 2 Beds
  • 1.5 Baths
  • 1,506 Sq Ft

  422 Jefferson Ave, Chesterton, IN 46304

  Old-World Charm Meets Modern Comfort in a Prime Location! Step back in time while enjoying every modern convenience in this absolutely charming 1.5-story Cape Cod home, built in 1910. This home perfectly blends old-world flair with contemporary living, offering 2 bedrooms and 1.5 bathrooms in a highly sought-after area. Inside, you'll be captivated by the architectural details. The open-concept

  Derek Durish Haven Realty

  422 Jefferson Ave, Chesterton, IN 46304
• 

  

  /21

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  315 Franklin St, Chesterton, IN 46304

  Location, location, location, Stately Brick home with welcoming front porch. Inside boosts of original hardwood, and beautiful leaded glass windows, Kitchen has some updates with all appliances staying. Walking upstairs you will admire the beautiful woodwork, All four bedrooms are light and airy. This home has a large landscaped lot, with sidewalks that can take you to the many bike trails and

  Marcia Forcey McColly Real Estate

  315 Franklin St, Chesterton, IN 46304
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  /15

  $180,000

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  2111 Tupelo Ln, Chesterton, IN 46304

  MOTIVATED SELLER!! Welcome to this charming 2-bedroom, 1-bath MAIN-level condo in the heart of Chesterton! Situated on a desirable corner unit, this home offers extra privacy and maintenance-free living -- say goodbye to lawn care and snow removal. Step inside and you'll love the bright and open feel, with newer LVP flooring flowing throughout. The kitchen is stocked with plenty of cabinet

  Jacquelyn Brubaker Coldwell Banker Real Estate Gr

  2111 Tupelo Ln, Chesterton, IN 46304

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