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$625,000
4 Baths ⋅ 202628997 MLS ⋅ Steve Miller
This all-brick church in a peaceful Middlebury setting offers seating for 175-200 (up to 220) and an elevator serving all three levels for full accessibility. Recent updates include a roof (approx. 3 years), driveway (approx. 2 years), and updated bathrooms, along with 2 new central air units (3 total), and LED lighting throughout. The building also includes multiple classrooms, a kitchen, and Fellowship Hall. 1.91 total acres, including two buildable lots — perfect for expansion, additional parking or sold to reduce investment.

206 Mill St, Middlebury

Listing courtesy of Steve Miller from RE/MAX Results. Office: 574-533-9581
$374,900
3 Beds ⋅ 1 Baths ⋅ 202622865 MLS ⋅ 1,990 SqFt. ⋅ Joshua Lenker
**OPEN HOUSE Sunday, September 13th 2-4PM** Peace is all you will think of at this home. Nestled on 1 acre in the desirable Middlebury area, this 3-bedroom, 1-bath retreat offers a perfect blend of comfort, privacy, and potential. Just seconds from Stone Lake, the property is currently a successful Airbnb and a proven income-producing opportunity. It is ideal as a full-time residence, weekend getaway, or investment. Inside, the layout includes a unique catwalk connecting the upstairs bedrooms, offering an open view that overlooks the living room below and adds character to the space. The property also features a brand-new well. Unwind on the covered porch, enjoy cozy evenings around the fire pit, and take advantage of the attached garage. Surrounded by nature in a peaceful, quiet setting, yet still close to all that Middlebury has to offer. This home is a rare find.

10281 County Road 4, Middlebury

Listing courtesy of Joshua Lenker from McKinnies Realty, LLC Elkhart. Cell: 574-215-4959
$695,000
4 Beds ⋅ 2 Baths ⋅ 202618544 MLS ⋅ 3,052 SqFt. ⋅ Leon Kramer
Here's an opportunity to own a versatile country property featuring two homes, a barn, and approximately 3 acres of pasture in Middlebury! Ideal for multi-generational living, hobby farming, or income potential. The primary residence offers 4 bedrooms and 2 full baths, a spacious living room with wood-burning fireplace, and a walkout basement complete with kitchenette, den, and additional bedroom. Recent updates include a new roof in 2025. Additional features include a large laundry/washroom, mudroom with sink and closet, and two decks for outdoor enjoyment. The second home includes 4 bedrooms, 1 full bath, and in-floor heat throughout, providing comfortable living or rental potential. Property is well-equipped with energy-efficient systems, including 15 solar panels, 48V system with two 300 Ah batteries, a 16-kW diesel generator backup and natural gas boiler heat. The 48’ x 32’ barn (built in 2020) is ideal for livestock or equestrian use and features 4 box stalls, 5 tie stalls, wash bay, and tack room. The property includes 2 geothermal waterers, a garden shed, apple trees, and raspberry plants. A unique rural property with flexible use and excellent homesteading potential—don’t miss this opportunity! The main home is wired for electricity - seller is willing to restore to NIPSCO power with a good offer.

57051 County Road 33, Middlebury

Listing courtesy of Leon Kramer from Bright Star Real Estate Services LLC. office: 574-821-7653
$425,000
4 Beds ⋅ 5 Baths ⋅ 202629722 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm
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!

435 S Main St, Middlebury

Listing courtesy of Jami Stamm from Coldwell Banker Real Estate Group. Cell: 574-596-4868

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.