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5237 Kaskaskia Road, Waterloo, IL, 62298

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!

Subdivision: Old Town

List Price

$ 370,000

Status

Active

Days on market

0

MLS#

26025534

Bedrooms

0

Full baths

0

Subdivision

Old Town

County

Monroe-IL

Property Type

Commercial Sale

Type

Commercial Sale

Additional Information

Property Tax (2023)

$1,414

Recent Nearby Sales in 62298

Last 6 closed homes in this zip.

Address Bd/Ba SqFt List Sold Closed
217 Magnolia Avenue, Waterloo, IL 62298 4/2 2,900 $275,000 $240,000
87.3% of ask
Sep 4, 2026
6269 Maeystown Road, Waterloo, IL 62298 3/1 840 $199,999 $350,000
175% of ask
Sep 2, 2026
612 Legacy Drive, Waterloo, IL 62298 0/0 -- $85,500 $85,500
100% of ask
Sep 2, 2026
306 S Market Street, Waterloo, IL 62298 3/2 896 $225,000 $220,000
97.8% of ask
Sep 1, 2026
1615 State Route 156, Waterloo, IL 62298 3/1 1,350 $190,000 $175,000
92.1% of ask
Aug 31, 2026
7812 White Tail Circle, Waterloo, IL 62298 4/4 3,300 $825,000 $810,000
98.2% of ask
Aug 31, 2026

Price & Listing History

Listed for sale
Apr 27, 2026 at $370,000
Current status: Active
As of Jul 27, 2026 · $370,000

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