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435 S Main Street, 
Middlebury, IN 46540

$425,000


4

Beds


5

Baths


4,112

Sq Ft


Multi-Family

Active

Last updated:

October 22, 2026, 03:11 PM

MLS#

202629722

Source:

Indiana Regional MLS

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About This Home

435 S Main Street

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!

Home Facts

Multi-Family

5 Baths

4 Bedrooms

Built in 1900

Subdivision & Development:

None

Price Summary

425,000

$103 per Sq. Ft.

MLS #:

202629722

Last Updated:

October 22, 2026, 03:11 PM

Added:

5 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

5

Interior

Living Area:

4,112 Sq. Ft.


Structure

Structure

Architectural Style:

Two Story

Building Area:

4,112 Sq. Ft.

Year Built:

1900


Lot

Lot Size (Sq. Ft):

24,829


Finances & Disclosures

Finances

Price:

$425,000

Price per Sq. Ft:

$103 per Sq. Ft.

435 S Main Street
Source:Indiana Regional MLS
IRMLS 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. IRMLS Data is deemed reliable but is not guaranteed accurate by the MLS. IRMLS information provided by the Indiana Regional MLS. Copyright 2026 Indiana Regional MLS LLC.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.