Imagine owning a charming home just steps from the heart of one of Northern Indiana's most beloved tourist destinations. Located on historic Main Street in the quaint town of Middlebury, this property offers the ideal setting for a short-term rental, boutique Airbnb, or weekend getaway. The home sits on the Pumpkinvine Nature Trail and is just minutes away from Shipshewana's famous flea market and auctions, the Essenhaus Inn & Restaurant, Amish countryside tours, and endless opportunities for shopping, dining, and outdoor recreation. Whether visitors are coming for a girls' weekend, cycling adventure, Amish country experience, or Notre Dame football weekend, this location places them in the center of it all. Picture cozy gathering spaces, 4 thoughtfully designed bedrooms, and charming outdoor areas where guests can unwind after a day of exploring. With Middlebury's year-round tourism and limited boutique lodging options, this property presents an exciting opportunity to generate income while owning a piece of one of Indiana's most picturesque small towns. Whether you're looking to expand your investment portfolio or create a destination property with lasting appeal, this property offers location, charm, and exceptional Airbnb potential in one of the Midwest's hidden gems. All with a bonus apartment that could be rented!

Listing Tools

Property Details of 435 S Main Street

Property Details

Interior Features

Community

Map Location

IDX information provided by the Indiana Regional MLS. Data was last updated on this website at July 24, 2026 8:29 AM UTC. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Abram Christianson. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.