# 5237 Kaskaskia Road, Waterloo, IL 62298 > **TL;DR:** commercial, $370,000, built 1939. > A/C. Est. $1,979/mo. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $370,000 | | Year Built | 1939 | | Lot Size | 15,329 sqft (0.35 acres) | | Stories | 1 | | Property Type | Commercial (Other) | | Status | Active | | Days on Market | 0 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,871 | | Estimated Insurance | $108 | | **Total** | **$1,979** | ## Key Amenities - A/C ## Property Highlights - Built in 1939 - 0.35 acre lot ## Description ### Agent Description ALL ABOARD THE CRAZY TRAIN! This is your rare opportunity to own a well-established and much-loved local watering hole just a short, well-traveled drive outside of thriving Waterloo. The Crazy Train Saloon and Grill is a turn-key bar and restaurant that has earned its place as a local favorite for decades. With its laid-back vibe, welcoming atmosphere, and reputation for great food and cold drinks, this isn't just a business-it's a destination where memories are made and regulars feel like family. Patrons come from miles around for the area's favorite fried chicken-made fresh using a signature recipe that will transfer with the sale, along with all other beloved house recipes. The sale also includes all digital assets (website, social media, branding), fixtures, furnishings, and equipment, allowing a seamless transition into ownership and continued operation without missing a beat. The property boasts numerous updates, including major kitchen upgrades and enhanced systems throughout. While gambling machines are currently on-site, they are not included in the sale but may be transferrable pending appropriate licensing and regulatory approvals. This is a rare chance to take the wheel of a fully operational, community-supported business with loyal clientele and proven success. Financials will be made available to qualified buyers with a Letter of Intent or written offer accompanied by proof of financing. Don't miss your chance to keep the Crazy Train rolling! ## Location - **Address:** 5237 Kaskaskia Road, Waterloo, IL 62298 - **County:** Monroe - **Neighborhood:** Old Town - **Coordinates:** 38.268747, -90.153466 - **Google Maps:** https://www.google.com/maps?q=38.268747,-90.153466 ## Listing Agent - **Name:** Linda Frierdich - **Brokerage:** Century 21 Advantage Real Estate Inc - **Phone:** (618) 281-7621 - **Broker Phone:** (618) 281-7621 - **Listing URL:** [View original listing](https://listings.listhub.net/pages/MARISMO/26025534/?channel=propsimple) ## Photos ![5237 Kaskaskia Road - Photo 1](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3496155435r.jpg) ![5237 Kaskaskia Road - Photo 2](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f760144412r.jpg) ![5237 Kaskaskia Road - Photo 3](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f755111963r.jpg) ![5237 Kaskaskia Road - Photo 4](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f464595061r.jpg) ![5237 Kaskaskia Road - Photo 5](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f703545234r.jpg) ![5237 Kaskaskia Road - Photo 6](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1082632097r.jpg) ![5237 Kaskaskia Road - Photo 7](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2989639843r.jpg) ![5237 Kaskaskia Road - Photo 8](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1005705021r.jpg) ![5237 Kaskaskia Road - Photo 9](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1437767815r.jpg) ![5237 Kaskaskia Road - Photo 10](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2107830931r.jpg) ![5237 Kaskaskia Road - Photo 11](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2346673652r.jpg) ![5237 Kaskaskia Road - Photo 12](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3001004953r.jpg) ![5237 Kaskaskia Road - Photo 13](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1554408381r.jpg) ![5237 Kaskaskia Road - Photo 14](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1869076732r.jpg) ![5237 Kaskaskia Road - Photo 15](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f547092701r.jpg) ![5237 Kaskaskia Road - Photo 16](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2225002499r.jpg) ![5237 Kaskaskia Road - Photo 17](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3691000808r.jpg) ![5237 Kaskaskia Road - Photo 18](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f4256108434r.jpg) ![5237 Kaskaskia Road - Photo 19](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f287112192r.jpg) ![5237 Kaskaskia Road - Photo 20](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1343899726r.jpg) ![5237 Kaskaskia Road - Photo 21](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f548462755r.jpg) ![5237 Kaskaskia Road - Photo 22](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3602106039r.jpg) ![5237 Kaskaskia Road - Photo 23](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3363790623r.jpg) ![5237 Kaskaskia Road - Photo 24](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f829291166r.jpg) ![5237 Kaskaskia Road - Photo 25](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2163285365r.jpg) ![5237 Kaskaskia Road - Photo 26](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2831231253r.jpg) ![5237 Kaskaskia Road - Photo 27](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1801056379r.jpg) ![5237 Kaskaskia Road - Photo 28](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3708771957r.jpg) ![5237 Kaskaskia Road - Photo 29](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f3429435210r.jpg) ![5237 Kaskaskia Road - Photo 30](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2312666261r.jpg) ![5237 Kaskaskia Road - Photo 31](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1713789307r.jpg) ![5237 Kaskaskia Road - Photo 32](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2535255307r.jpg) ![5237 Kaskaskia Road - Photo 33](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f4215392091r.jpg) ![5237 Kaskaskia Road - Photo 34](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1781684413r.jpg) ![5237 Kaskaskia Road - Photo 35](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f1250291171r.jpg) ![5237 Kaskaskia Road - Photo 36](http://lh.rdcpix.com/80572cd09806d10cedd0ce66666327ael-f2359334344r.jpg) --- **MLS#:** 26025534 | **Updated:** 2026-09-02 **Source:** listhub *Copyright © 2026 Mid America Regional Information Systems, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/5237-kaskaskia-road-waterloo-il-62298-26025534) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/5237-kaskaskia-road-waterloo-il-62298-26025534#listing", "url": "https://www.propertysimple.ai/listing/5237-kaskaskia-road-waterloo-il-62298-26025534", "name": "5237 Kaskaskia Road, Waterloo, IL 62298", "description": "ALL ABOARD THE CRAZY TRAIN! This is your rare opportunity to own a well-established and much-loved local watering hole just a short, well-traveled drive outside of thriving Waterloo. The Crazy Train Saloon and Grill is a turn-key bar and restaurant that has earned its place as a local favorite for decades. With its laid-back vibe, welcoming atmosphere, and reputation for great food and cold drinks, this isn't just a business-it's a destination where memories are made and regulars feel like family. Patrons come from miles around for the area's favorite fried chicken-made fresh using a signature recipe that will transfer with the sale, along with all other beloved house recipes. The sale also includes all digital assets (website, social media, branding), fixtures, furnishings, and equipment, allowing a seamless transition into ownership and continued operation without missing a beat. The property boasts numerous updates, including major kitchen upgrades and enhanced systems throughout. While gambling machines are currently on-site, they are not included in the sale but may be transferrable pending appropriate licensing and regulatory approvals. This is a rare chance to take the wheel of a fully operational, community-supported business with loyal clientele and proven success. 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