Chesterton, IN Homes

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  /24

  $419,999

  • 4 Beds
  • 3.5 Baths
  • 2,992 Sq Ft

  2131 Pepperbush Ave, Chesterton, IN 46304

  Move-In Ready in Westwood Manor - Chesterton's desired Subdivision! Nestled in the award-winning Duneland School District, this beautifully maintained home is ready for you to move in and enjoy. Boasting 4 bedrooms, 4 bathrooms, a loft office area, and a finished basement with a versatile flex room that could serve as a 5th bedroom, office, or game room, this home offers space for every need. The

  

  Jason Moon

  Trueblood Real Estate, LLC

  (219) 348-8090

  2131 Pepperbush Ave, Chesterton, IN 46304
• Explore Chesterton

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  /50

  $1,497 - $3,301 per month

  Eagle Crossing Luxury Apartment Homes

  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.

  2113 Kelle Dr, 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 $451,592

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  544 Windridge Dr, Chesterton, IN 46304
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  /73

  Est $1,524,179 Not Listed For Sale

  1420 Ryder Rd, Chesterton, IN 46304

  • 4 Beds
  • 4.5 Baths
  • 5,776 Sq Ft
  • Built 2015

  1420 Ryder Rd, Chesterton, IN 46304

  Last Sold Summary

  • 5% Above List Price
  • $251/SF
  • 9 Days On Market

  Last Sold Price $1,450,000

  Last Listing Agent Tami Bianco @properties/Christie's Intl RE
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  /46

  $599,000

  • 4 Beds
  • 3 Baths
  • 3,066 Sq Ft

  1650 Hogan Ave, Chesterton, IN 46304

  Located in the desirable Sand Creek community, this stunning 4-bedroom, 3-bath home seamlessly blends luxury, comfort, and modern updates. The home features LED lighting throughout, hardwood floors, crown molding, and a stone fireplace just five years old. The main floor and upper level both include convenient laundry areas, while the huge primary suite offers a tray ceiling, brand-new carpet,

  

  Paul Boyter

  McColly Real Estate

  (219) 342-2742

  1650 Hogan Ave, Chesterton, IN 46304
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  /15

  $2,350 per month

  • 3 Beds
  • 2.5 Baths
  • 1,727 Sq Ft
  • Townhouse for Rent

  1239 Fox Hollow Dr, Chesterton, IN 46304

  Maintenance free 3 bedroom/2.5 bath townhome for rent near the Indiana Dunes. Over 1700 sq ft of living space. Primary suite has private bath and walk-in-closet. 2 car garage, brand new driveway, and corner lot overlooking neighborhood park. Enjoy the convenience and comfort of maintenance free living with provided lawn care and snow removal. Just minutes to parks, the Dunes, Porter Beach,

  Amy Redman Dunes Realty, LLC

  1239 Fox Hollow Dr, 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 $1,013,145

  Last Listing Agent Stefanie Neal BHHS Indiana Realty

  1458 Spyglass Cir, Chesterton, IN 46304
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  /51

  Est $787,981 Not Listed For Sale

  1125 Ryder Rd, Chesterton, IN 46304

  • 4 Beds
  • 5 Baths
  • 4,482 Sq Ft
  • Built 1999

  1125 Ryder Rd, Chesterton, IN 46304

  Last Sold Summary

  • 5% Above List Price
  • $167/SF
  • 25 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Stefanie Neal BHHS Indiana Realty
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  /23

  $291,000 Pending

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

  1807 W Porter Ave, Chesterton, IN 46304

  Don't miss this one!! See the updated pictures! Seller has been chipping away at his list! 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 some updates and is ready for your personal touch! Step inside and see the possibilities! The

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 306-8062

  1807 W Porter Ave, Chesterton, IN 46304
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  /20

  $1,275 - $1,750 per month

  The Enclave

  1 - 2 Beds

  2135 Dickinson Rd, Chesterton, IN 46304

  The Enclave is a luxurious apartment community nestled in Coffee Creek Center. Our rental properties include one bedroom and two bedroom floor plans. Select floor plans come with garages. Experience outstanding amenities and remarkable features paired with all Coffee Creek Center's advantages. Welcome to a place where nature, luxury and convenience unite, offering you a unique and exciting living

  2135 Dickinson Rd, Chesterton, IN 46304
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  /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 $350,486

  70 Fairmont Dr, Chesterton, IN 46304
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  /24

  Est $287,712 Not Listed For Sale

  114 S 14th St, Chesterton, IN 46304

  • 3 Beds
  • 1.5 Baths
  • 2,688 Sq Ft
  • Built 1925

  114 S 14th St, Chesterton, IN 46304

  Last Sold Summary

  • 188% Above List Price
  • $37/SF
  • 152 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Dan Robinson Crosstown Real Estate, Inc.
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  /49

  $2,950,000

  • 5 Beds
  • 9.5 Baths
  • 17,178 Sq Ft

  1700 Littler Dr, Chesterton, IN 46304

  Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, craftsmanship, and prestige define this extraordinary 5-bedroom, 10-bathroom estate, located just one hour from Chicago in the exclusive Sand Creek community. Designed and built in 2003 by renowned interior designer and architect David Julian, this custom masterpiece offers breathtaking golf course views of

  

  John Reagan

  Blackrock Real Estate Services

  (219) 259-5914

  1700 Littler Dr, Chesterton, IN 46304
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  /13

  $1,300 per month

  • 1 Bed
  • 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
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  /21

  $466,143 Sold Apr 09, 2025

  1622 Melanie Ln, Chesterton, IN 46304

  • 3 Beds
  • 3 Baths
  • 1,954 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Above List Price
  • $239/SF
  • 0 Days On Market

  Current Estimated Value $469,347

  Last Listing Agent Michelle Renninger Better Homes and Gardens Real

  1622 Melanie Ln, Chesterton, IN 46304
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  /18

  Est $202,405 Not Listed For Sale

  1343 Park Ave, Chesterton, IN 46304

  • 2 Beds
  • 1 Bath
  • 1,107 Sq Ft
  • Built 1913

  1343 Park Ave, Chesterton, IN 46304

  Last Sold Summary

  • 12% Above List Price
  • $163/SF
  • 4 Days On Market

  Last Sold Price $180,000

  Last Listing Agent Julie Dube New Chapter Real Estate
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  /11

  $58,000

  • Land
  • 0.22 Acre
  • $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

  (317) 961-8462

  27 Karner Blue Ct, Chesterton, IN 46034
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  /20

  $992 - $1,194 per month

  State Place Apartment Homes

  1 - 3 Beds

  1623 Westchester Ave, Chesterton, IN 46304

  Quiet location and minutes to South Shore Train, State Place Apartments feature a central location just west of the 49 Bypass, and close to Lake Michigan, shopping and bike trails. Move-in today and see what real hospitality feels like!

  1623 Westchester Ave, Chesterton, IN 46304
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  /23

  $389,900 Sold Jul 28, 2025

  361 Watertower Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,859 Sq Ft
  • Built 1990

  Last Sold Summary

  • $210/SF
  • 4 Days On Market

  Current Estimated Value $387,866

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  361 Watertower Dr, Chesterton, IN 46304
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  /51

  Est $290,665 Not Listed For Sale

  401 Jefferson Ave, Chesterton, IN 46304

  • 4 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1910

  401 Jefferson Ave, Chesterton, IN 46304

  Last Sold Summary

  • 5% Above List Price
  • $131/SF
  • 6 Days On Market

  Last Sold Price $277,000

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC
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  /5

  $389,000

  • Land
  • 1.44 Acres
  • $270,139 per Acre

  1022 N Old State Road 49, Chesterton, IN 46304

  This 1.44 acre lot is located close to the Indiana Toll Road, I-94, the South Shore train station, The Indiana Dunes State Park, and the Indiana Dunes National Park. Across Highway 49 you will find Culver's, AJ's Pizza, Popeye's, Dunkin Donuts, Hilton Garden Inn, Bob Evans, and multiple medical and office buildings.

  

  Paul Boyter

  McColly Real Estate

  (219) 533-0714

  1022 N Old State Road 49, Chesterton, IN 46304
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  /18

  $2,200 per month

  • 2 Beds
  • 2.5 Baths
  • 1,666 Sq Ft
  • House for Rent

  1205 Saratoga Ln, Chesterton, IN 46304

  This maintenance free, 2-story condo unit with its 2+ bedrooms has over 1600 sqft of living space. Main floor primary bdrm has attached 3/4 bath with views of the front fenced courtyard. Center hall shared bath with main floor 2nd bedroom also is within steps away from the main level laundry room and open vaulted living room with adjacent dine-in kitchen. The upper level loft space can also be

  Patty Raffin McColly Real Estate

  1205 Saratoga Ln, Chesterton, IN 46304
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  /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
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  /22

  Est $255,819 Not Listed For Sale

  516 E Morgan Ave, Chesterton, IN 46304

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1954

  516 E Morgan Ave, Chesterton, IN 46304

  Last Sold Summary

  • 3% Above List Price
  • $201/SF
  • 18 Days On Market

  Last Sold Price $247,900

  Last Listing Agent Milenda Simerlein McColly Real Estate
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  /22

  $424,900 Pending

  • 4 Beds
  • 4 Baths
  • 2,160 Sq Ft

  2130 Westchester Ave Unit 32, Chesterton, IN 46304

  Well-maintained duplex with a strong rental history and excellent owner-occupant opportunity! One side was recently vacated after a long-term tenant of over 20 years, making it perfect to live in one unit and rent the other for additional income. Each spacious unit features 2 bedrooms, 2 full bathrooms, a one-car garage, private laundry room, and its own deck for outdoor enjoyment. The interiors

  

  Paul Boyter

  McColly Real Estate

  (219) 544-5843

  2130 Westchester Ave Unit 32, Chesterton, IN 46304
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  /19

  $1,545 per month

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

  2014 Washington Ave, Chesterton, IN 46304

  Property Id: 2003480Welcome to a beautifully updated 2-bedroom, 1.5-bath two-story townhome located in a quiet residential area of Chesterton.This home offers the layout renters prefer — bedrooms upstairs for privacy and comfortable living space on the main level — along with modern finishes and easy maintenance.The kitchen features quartz countertops and stainless steel

  2014 Washington Ave, Chesterton, IN 46304
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  /39

  $511,000 Sold Jan 21, 2026

  4131 Abercrombie Dr, Chesterton, IN 46304

  • 4 Beds
  • 3.5 Baths
  • 3,780 Sq Ft
  • Built 2007

  Last Sold Summary

  • $135/SF
  • 7 Days On Market

  Current Estimated Value $506,253

  Last Listing Agent Claudia Miller Forrest Century 21 Circle

  4131 Abercrombie Dr, Chesterton, IN 46304
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  /5

  Est $399,829 Not Listed For Sale

  1065 N 400 E, Chesterton, IN 46304

  • 1 Bed
  • Built 1964

  1065 N 400 E, Chesterton, IN 46304

  Last Sold Summary

  • 4% Above List Price
  • $670/SF
  • 7 Days On Market

  Last Sold Price $386,000

  Last Listing Agent Roxanne Gottleber RE/MAX
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  /12

  $58,000

  • Land
  • 0.19 Acre
  • $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

  (317) 751-5447

  47 Karner Blue Ct, Chesterton, IN 46034
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  /13

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,226 Sq Ft
  • Condo for Rent

  122 Jeffrey St Unit 122JeffreySt, Chesterton, IN 46304

  Charming Updated Duplex in Chesterton Schools | 2BR/1.5BA | Recently RenovatedWelcome to 122 Jeffrey St, a beautifully updated second-floor duplex unit in a quiet Chesterton neighborhood. This 2-bedroom, 1.5-bathroom home boasts a full interior refresh, perfect for modern living.Key Features & Recent Updates: Modern Kitchen: Equipped with brand-new stainless-steel

  122 Jeffrey St Unit 122JeffreySt, Chesterton, IN 46304
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  /32

  $515,000 Sold Dec 12, 2025

  997 N 250 E, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Above List Price
  • $197/SF
  • 2 Days On Market

  Current Estimated Value $520,583

  Last Listing Agent Kayla Jones Listing Leaders

  997 N 250 E, Chesterton, IN 46304
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  /20

  Est $504,674 Not Listed For Sale

  1540 Sand Wedge Cir, Chesterton, IN 46304

  • 4 Beds
  • 4 Baths
  • 2,863 Sq Ft
  • Built 2010

  1540 Sand Wedge Cir, Chesterton, IN 46304

  Last Sold Summary

  • 10% Above List Price
  • $160/SF
  • 3 Days On Market

  Last Sold Price $457,000

  Last Listing Agent Jason Newman @ Properties
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  /14

  $54,000

  • Land
  • 0.19 Acre
  • $284,211 per Acre

  1005 Preserve Ln, Chesterton, IN 46304

  Phase 3 is now open and ready for building. Lot 93 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

  (219) 419-4506

  1005 Preserve Ln, Chesterton, IN 46304
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  /22

  $327,500 Sold Nov 26, 2025

  809 Olde Towne Square, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $244/SF
  • 24 Days On Market

  Current Estimated Value $328,162

  Last Listing Agent Amanda Klimczak Realty Executives Premier

  809 Olde Towne Square, Chesterton, IN 46304
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  /25

  Est $422,984 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

  • 8% Above List Price
  • $181/SF
  • 93 Days On Market

  Last Sold Price $392,900

  Last Listing Agent Dianne Cline McColly Real Estate
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  /20

  $274,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  225 Dogwood Dr, Chesterton, IN 46304

  Well-maintained 3-bedroom, 2-bath ranch home offering approximately 1,316 finished square feet, ideally situated on a nice-sized corner lot in the desirable Wake Robin subdivision. This thoughtfully laid-out home features a spacious living room highlighted by oversized windows that fill the space with natural light, complemented by hardwood flooring throughout much of the home. The functional

  

  Amy Blanton

  Better Homes and Gardens Real

  (219) 419-7735

  225 Dogwood Dr, Chesterton, IN 46304
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  /15

  $167,000 Sold Jun 05, 2025

  1102 Saratoga Ln, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft
  • Built 1979

  Last Sold Summary

  • 16% Below List Price
  • $117/SF
  • 132 Days On Market

  Current Estimated Value $177,420

  Last Listing Agent Catherine Craigin Kasl Century 21 Circle

  1102 Saratoga Ln, Chesterton, IN 46304
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  /19

  Est $457,816 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

  • 5% Above List Price
  • $272/SF
  • 4 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Tiffany Dowling Keller Williams Preferred Real
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  /23

  $285,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,561 Sq Ft

  1201 Tower Ln, Chesterton, IN 46304

  Discover the perfect blend of comfort, convenience, and coastal charm in this beautiful 1,500-square-foot townhome in the heart of Porter, Indiana--just moments from the shores of Porter Beach. This spacious 3-bedroom, 2.5-bath home offers the ideal layout for everyday living and entertaining. The huge primary suite is a true retreat, complete with a private en suite bathroom and generous closet

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 217-1857

  1201 Tower Ln, Chesterton, IN 46304
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  /56

  $345,000 Sold Feb 27, 2026

  781 David Blvd, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 2,515 Sq Ft
  • Built 1998

  Last Sold Summary

  • $137/SF

  Current Estimated Value $350,430

  Last Listing Agent Shelly Grimm White Hat Realty Group, LLC

  781 David Blvd, Chesterton, IN 46304

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