Chesterton, IN Homes

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  /58

  $290,000

  $30K PRICE DROP

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

  214 Woodlawn Ave, Chesterton, IN 46304

  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

  

  Aaron Bagsby

  Keller Williams Realty - LAF

  214 Woodlawn Ave, Chesterton, IN 46304
• Explore Chesterton

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  /50

  Starting at $1,497 Per Month

  • 1 - 3 Beds

  2113 Kelle Dr, Chesterton, IN 46304

  Inside beautiful Coffee Creek is a luxury community like no other. We are ideally situated and near all shopping, dining, and between I-80/90 Toll Rd and I-94. Appointed with numerous luxurious details, ease of living, privacy, and style.

  Eagle Crossing Luxury Apartment Homes

  

  2113 Kelle Dr, Chesterton, IN 46304
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  /25

  $246,250

  Sold Jul 06, 2026

  511 S 22nd St, Chesterton, IN 46304

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Above List Price
  • $220/SF
  • 1 Day On Market

  Current Estimated Value $232,567

  Last Listing Agent Jeana Consier Realty Executives Premier

  511 S 22nd St, Chesterton, IN 46304
• 

  

  

  /10

  Est $130,350

  Not Listed For Sale

  1050 Kilarney Rd, Chesterton, IN 46304

  1050 Kilarney Rd, Chesterton, IN 46304

  Last Sold Summary

  • 434 Days On Market

  Last Listing Agent Jenn Marinangeli @properties/Christie's Intl RE
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  /26

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,445 Sq Ft

  318 Village Square, Chesterton, IN 46304

  Charming Duneland Schools Townhome: Welcome home to 318 Village Square, a beautifully maintained 3-bedroom, 1.75-bath townhome tucked inside The Village in Burns Harbor -- Northwest Indiana's award-winning, walkable neighborhood.This low-maintenance townhome offers the perfect blend of comfortable everyday living and small-town charm, all within the highly rated Duneland School District. Step

  

  Lisa Gaff

  White Hat Realty Group, LLC

  318 Village Square, Chesterton, IN 46304
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  /31

  Starting at $1,100 Per Month

  • 1 - 2 Beds

  111 W Taylor St, Chesterton, IN 46304

  Heat, water, garbage, sewer and cooking gas included with rent. Deer Run is conveniently located within the beautiful town of Chesterton, but is surrounded by woods. Residents enjoy the peace and quiet of nature, while still having the convenience of nearby shopping. Many residents take advantage of the quick access to I 94 and the South Shore Rail line to Chicago.This community features

  Deer Run Apartments

  111 W Taylor St, Chesterton, IN 46304
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  /47

  $289,900

  Sold Jul 24, 2026

  612 S Jackson Blvd, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1967

  Last Sold Summary

  • $222/SF
  • 4 Days On Market

  Current Estimated Value $285,117

  Last Listing Agent Nick Scalise Listing Leaders

  612 S Jackson Blvd, Chesterton, IN 46304
• 

  

  /27

  Est $404,922

  Not Listed For Sale

  1381 Dixon Pkwy, Chesterton, IN 46304

  • 3 Beds
  • 3 Baths
  • 2,512 Sq Ft
  • Built 1996

  1381 Dixon Pkwy, Chesterton, IN 46304

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Meghan Maddox MTM Realty Group
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  /44

  $425,000

  • 4 Beds
  • 3.5 Baths
  • 2,360 Sq Ft

  455 Woodlawn Ave Unit 457, Chesterton, IN 46304

  Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining

  

  Paul Boyter

  McColly Real Estate

  455 Woodlawn Ave Unit 457, Chesterton, IN 46304
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  /13

  $1,900

  Total Monthly Price

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  1116 Penny Ln, Chesterton, IN 46304

  Welcome home to this beautifully renovated 3-bedroom, 1.5-bath duplex in Chesterton! Enjoy a modern kitchen with stainless steel appliances, brand-new cabinets, butcher block countertops, and cozy built-in booth seating. New LVP flooring runs throughout, and the updated bathroom features fresh tile finishes.Relax on the front deck, take advantage of in-unit washer/dryer, a heated garage, and

  1116 Penny Ln, Chesterton, IN 46304
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  /9

  $282,000

  Sold Jul 15, 2026

  403 Sand Creek Dr N, Chesterton, IN 46304

  • 2 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Above List Price
  • $156/SF
  • 1 Day On Market

  Last Listing Agent Regina Dotto White Hat Realty Group, LLC

  403 Sand Creek Dr N, Chesterton, IN 46304
• 

  

  /22

  Est $241,382

  Not Listed For Sale

  2234 Texas St, Chesterton, IN 46304

  • 2 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • Built 1997

  2234 Texas St, Chesterton, IN 46304

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Patty Raffin McColly Real Estate
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  /52

  $490,000

  $15K PRICE INCREASE Pending

  • 4 Beds
  • 2.5 Baths
  • 3,797 Sq Ft

  300 Sandpiper Dr, Chesterton, IN 46304

  Tucked into one of Chesterton's most sought-after subdivisions, this 4-bedroom, 2.5-bath home offers the space, comfort, and setting that make Duneland Cove such a special place to call home. From the moment you arrive, you'll feel the pride of ownership throughout -- and the tree-lined backyard sets the tone for what living here is really about. Step inside to a layout built for everyday living

  

  Lisa Gaff

  White Hat Realty Group, LLC

  300 Sandpiper Dr, Chesterton, IN 46304
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  /11

  $1,450

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  812 S 14th St Unit 1 unit (Duplex)), Chesterton, IN 46304

  Comfortable house 1 half of duplex.2 bedrooms, 1 bathroom, laundry room, kitchen, living room, front porch, front yard and driveway, backyard, 1 shed.Air conditioner and hitting.

  812 S 14th St Unit 1 unit (Duplex)), Chesterton, IN 46304
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  /52

  $460,000

  Sold Oct 10, 2025

  544 Windridge Dr, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,261 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 85 Days On Market

  Current Estimated Value $453,819

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  544 Windridge Dr, Chesterton, IN 46304
• 

  

  /27

  Est $306,529

  Not Listed For Sale

  2470 Springdale St, Chesterton, IN 46304

  • 2 Beds
  • 2 Baths
  • 1,477 Sq Ft
  • Built 2021

  2470 Springdale St, Chesterton, IN 46304

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Gus Morquecho Realty Executives Premier
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  /44

  $649,500

  Open Sat 11AM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 5,128 Sq Ft

  1429 Calais Ct, Chesterton, IN 46304

  Welcome to 1429 Calais Court, a beautifully maintained home nestled in the sought-after Sand Creek community of Chesterton. Offering the perfect blend of comfort, convenience, and low-maintenance living, this home is ideal for anyone looking to enjoy a relaxed lifestyle in one of Northwest Indiana's premier neighborhoods. Step inside to find a bright, inviting floor plan with spacious living

  

  Lisa Gaff

  White Hat Realty Group, LLC

  1429 Calais Ct, Chesterton, IN 46304
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  /14

  $2,200

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • House for Rent

  750 Elm Ct, Chesterton, IN 46304

  *Available 7/25/26 * This 3 Bedroom/2 Bath Ranch home is in a quiet neighborhood in the Duneland School community. This home features: 1.5 car garage, a four season room, a patio, hardwood floors, large fenced-in yard and a finished basement where 1 of the bedrooms and 1 bathroom are located. This home is on a 3/4 acre lot. Fireplaces are not to be used. NO PETS This rental is unfurnished

  750 Elm Ct, Chesterton, IN 46304
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  /53

  $1,000,000

  Sold Feb 27, 2026

  1458 Spyglass Cir, Chesterton, IN 46304

  • 6 Beds
  • 5.5 Baths
  • 7,047 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $142/SF
  • 8 Days On Market

  Current Estimated Value $1,056,183

  Last Listing Agent Stefanie Neal BHHS Indiana Realty

  1458 Spyglass Cir, Chesterton, IN 46304
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  /28

  Not Listed For Sale

  815 Idlewild Ln, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,415 Sq Ft
  • Built 2025

  815 Idlewild Ln, Chesterton, IN 46304

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Michelle Renninger Brokerworks Group
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  /5

  $110,000

  • Land
  • 1.36 Acres
  • $80,882 per Acre

  369 Ridgeview Dr, Chesterton, IN 46304

  Imagine your dream home nestled among the trees on this beautiful 1.36-acre corner lot at 369 Ridgeview Drive. Located in Woodridge Hills, a private Jackson Township community known for its spacious wooded homesites and impressive custom residences, this property offers the rare opportunity to create a home designed entirely around your lifestyle. The generous corner setting provides flexibility

  

  Lisa Gaff

  White Hat Realty Group, LLC

  369 Ridgeview Dr, Chesterton, IN 46304
• 

  

  /13

  $1,300 Per Month

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • House for Rent

  1101 Jefferson Ave Unit 6, Chesterton, IN 46304

  Move-in ready 2-bedroom, 1-bath apartment available now at Porter Ridge Apartments in Chesterton. This spacious unit features a private balcony, perfect for enjoying the outdoors. Rent includes water, sewer, and trash, plus a storage locker conveniently located in the laundry room with coin-operated washer/dryer access. Rent: 1,300/month Security Deposit: 1,300 Pets welcome with 25/month fee

  Jordan Williams VIA Realty

  1101 Jefferson Ave Unit 6, Chesterton, IN 46304
• 

  

  /15

  $367,991

  Sold Sep 10, 2025

  70 Fairmont Dr, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $183/SF
  • 20 Days On Market

  Current Estimated Value $357,037

  70 Fairmont Dr, Chesterton, IN 46304
• 

  

  /29

  Est $441,941

  Not Listed For Sale

  2585 Dunbar St, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,042 Sq Ft
  • Built 2019

  2585 Dunbar St, Chesterton, IN 46304

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Ashley Tezak Realty Executives Premier
• 

  

  /21

  $225,000

  Open Sat 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  206 Fieldstone Dr, Chesterton, IN 46304

  Welcome to this well-maintained 2-bedroom, 1.75-bath condo in the desirable Summer Tree community! Offering the convenience of low-maintenance living, this home is perfect for those looking to spend less time on upkeep and more time enjoying life. The thoughtfully designed ranch floor plan provides comfortable living spaces, spacious bedrooms, and the convenience of two bathrooms. Lawn care and

  

  Lisa Gaff

  White Hat Realty Group, LLC

  206 Fieldstone Dr, Chesterton, IN 46304
• 

  

  /14

  $1,695 Per Month

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • House for Rent

  257 S 20th St, Chesterton, IN 46304

  Prospective tenants are NOT REQUIRED TO PAY 3rd Party Application fees. ALL applications MUST be submitted via the PMI NWI website. Applications submitted through 3RD PARTY websites/vendors WILL NOT BE ACCEPTED.PLEASE SUBMIT ANY QUESTIONS THROUGH THE "REQUEST A TOUR", "CHECK AVAILABILITY" or other contact options provided.Welcome home to this charming 3-bedroom, 1-bath home in the

  257 S 20th St, Chesterton, IN 46304
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  /31

  $365,000

  Sold Apr 27, 2026

  3431 Drivers Way, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,717 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Above List Price
  • $213/SF
  • 4 Days On Market

  Current Estimated Value $361,174

  Last Listing Agent Debra Lightfoot McColly Real Estate

  3431 Drivers Way, Chesterton, IN 46304
• 

  

  /40

  Est $459,186

  Not Listed For Sale

  221 Trailcreek Dr, Chesterton, IN 46304

  • 5 Beds
  • 2.5 Baths
  • 3,208 Sq Ft
  • Built 2014

  221 Trailcreek Dr, Chesterton, IN 46304

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Erica Kendera Brokerworks Group
• 

  

  /24

  $465,000

  • 3 Beds
  • 3.5 Baths
  • 3,199 Sq Ft

  1077 Mission Hills Ct, Chesterton, IN 46304

  Now available in Sand Creek--currently the only townhouse on the market! Located in one of Northwest Indiana's premier golf course communities, Sand Creek offers beautifully maintained surroundings, mature trees, and an upscale lifestyle just minutes from downtown Chesterton and the Indiana Dunes. This beautifully updated three-bedroom home features a fully remodeled open concept main level and

  

  Jason Moon

  Trueblood Real Estate, LLC

  1077 Mission Hills Ct, Chesterton, IN 46304
• 

  

  /32

  $435,000

  Sold May 27, 2026

  4221 Burlwood Dr, Chesterton, IN 46304

  • 3 Beds
  • 3 Baths
  • 3,384 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $129/SF
  • 22 Days On Market

  Current Estimated Value $437,365

  Last Listing Agent Jennifer Miga McColly Real Estate

  4221 Burlwood Dr, Chesterton, IN 46304
• 

  

  /10

  Not Listed For Sale

  0 E 1300 N, Chesterton, IN 46304

  0 E 1300 N, Chesterton, IN 46304

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Crystal Peraza-Grah Better Homes and Gardens Real
• 

  

  /11

  $58,000

  • Land
  • 9,583 Sq Ft
  • $263,636 per Acre

  27 Karner Blue Ct, Chesterton, IN 46034

  Phase 3 is now open and ready for building. Lot 69 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

  

  Paul Boyter

  McColly Real Estate

  27 Karner Blue Ct, Chesterton, IN 46034
• 

  

  /13

  $319,991

  Sold Aug 22, 2025

  881 Argyle Ct, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 1,455 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $220/SF
  • 8 Days On Market

  881 Argyle Ct, Chesterton, IN 46304
• 

  

  /25

  Est $256,500

  Not Listed For Sale

  945 S 5th St Unit 101, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1925

  945 S 5th St Unit 101, Chesterton, IN 46304

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Patty Raffin McColly Real Estate
• 

  

  /12

  $58,000

  • Land
  • 8,276 Sq Ft
  • $305,263 per Acre

  47 Karner Blue Ct, Chesterton, IN 46034

  Phase 3 is now open and ready for building. Lot 86 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

  

  Paul Boyter

  McColly Real Estate

  47 Karner Blue Ct, Chesterton, IN 46034
• 

  

  /26

  $264,900

  Sold May 21, 2026

  204 Wagner Rd, Chesterton, IN 46304

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1977

  Last Sold Summary

  • $210/SF
  • 19 Days On Market

  Current Estimated Value $259,870

  Last Listing Agent John Barlow White Hat Realty Group, LLC

  204 Wagner Rd, Chesterton, IN 46304
• 

  

  /25

  Est $410,650

  Not Listed For Sale

  2432 Legend Cir, Chesterton, IN 46304

  • 4 Beds
  • 2 Baths
  • 2,169 Sq Ft
  • Built 2012

  2432 Legend Cir, Chesterton, IN 46304

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Dianne Cline McColly Real Estate
• 

  

  /3

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  860 Quail Ridge Cir, Chesterton, IN 46304

  Welcome to the undeveloped phase of the desirable Hunters Glen Subdivision in Porter, Indiana--an excellent opportunity for builders or investors. This offering includes 8 spacious, wooded lots plus 2 additional parcels designated for roads and drainage infrastructure. Nestled in a peaceful, natural setting, this subdivision combines privacy with convenience. With easy access to I-94 and the

  

  Paul Boyter

  McColly Real Estate

  860 Quail Ridge Cir, Chesterton, IN 46304
• 

  /2

  $220,000

  Sold May 07, 2026

  1939 Chamborde Ln, Chesterton, IN 46304

  • Land
  • 1.08 Acres
  • $203,704 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Stefanie Neal BHHS Indiana Realty

  1939 Chamborde Ln, Chesterton, IN 46304
• 

  

  /19

  Est $429,104

  Not Listed For Sale

  886 Saint Andrews Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2020

  886 Saint Andrews Dr, Chesterton, IN 46304

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Tiffany Dowling Keller Williams Preferred Real

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