Middlebury Homes with Two Story Style

Welcome to Middlebury, Indiana—a charming township nestled in the heart of Elkhart County, where the warm spirit of community meets the beauty of rural living. Known for its picturesque landscapes and friendly atmosphere, Middlebury offers a delightful blend of small-town charm and modern conveniences. With a rich heritage and a vibrant local culture, this town is perfect for families, retirees, and anyone seeking a peaceful, yet engaging lifestyle.

Middlebury is renowned for its excellent schools, beautiful parks, and a variety of local shops and restaurants that create a strong sense of community. The township also hosts several annual events that bring residents together, from seasonal festivals to farmers' markets, making it easy to connect with neighbors and enjoy the local flavor.

When it comes to housing, Middlebury boasts a selection of stunning two-story homes that cater to diverse tastes and lifestyles. These spacious residences are designed with both comfort and functionality in mind, often featuring open floor plans, ample natural light, and beautifully landscaped yards. The two-story style offers the perfect balance of privacy and togetherness, with bedrooms often located on the upper level, allowing for a peaceful retreat while still keeping family members close.

Whether you're looking for a cozy family home or a stylish space to entertain, Middlebury's two-story homes provide the ideal backdrop for creating lasting memories. Embrace the charm of this delightful township and discover the perfect place to call home in Middlebury, IN!

Newest Middlebury Homes with Two Story Style

$460,000

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 Street, Middlebury

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

$299,900

4 Beds ⋅ 1 Baths ⋅ 202629465 MLS ⋅ 3,384 SqFt. ⋅ Jennea Schirr

Step back in time and bring your vision to life with one of Middlebury’s most recognizable historic homes—the Krider nursery family home. Originally built in 1890, this remarkable property showcases a beautiful blend of Second Empire and Italianate architecture while offering an incredible opportunity to complete the restoration of a true local landmark. Situated on approximately 1.5 acres, the home has already undergone extensive structural and mechanical improvements, including all new electrical, a new electrical panel, new gas, water, and electrical service lines, a new metal roof (2017), basement tuck-pointing and the exterior of home. Home offers original hardwood flooring. City water has already been run to the property and simply needs to be activated. Inside, you’ll find timeless character at every turn, including a spacious study, formal dining room, an expansive enclosed wraparound porch featuring a log fireplace, and original architectural details waiting to be showcased. The current kitchen plans are at the rear of the home, with plans already envisioned for a future addition that would include a pantry and main-level bedroom. Upstairs offers space for four bedrooms and space for 2 bathrooms, seller envisioned a jack and Jill for one. Upstairs has a loft area with built-in bookshelf. Original shutters for the windows remain stored in the attic, preserving even more of the home’s historic charm. Additional improvements include a restored carport and detached garage. Whether you’re dreaming of restoring a grand historic residence, creating a bed and breakfast, or owning one of Middlebury’s most iconic homes, the Krider House offers a rare opportunity to finish a remarkable restoration while honoring its rich history. Home is being sold in its current condition. Buyer to verify all measurements, zoning, intended use, and historical preservation requirements, if applicable.

313 Bristol Avenue, Middlebury

Listing courtesy of Jennea Schirr from McKinnies Realty, LLC Elkhart. Cell: 574-215-9291

$1,200,000

6 Beds ⋅ 6 Baths ⋅ 202629033 MLS ⋅ 7,320 SqFt. ⋅ Julie Thatcher

Welcome to this extraordinary custom all-brick estate nestled in the heart of Middlebury's prestigious Highland Woods subdivision. Perched atop the area's rolling hills, this exceptional Town & Country-built residence offers more than 6,000 square feet of beautifully finished living space and has been completely transformed with over $800,000 in luxurious updates completed within the past two years. Step inside the stunning foyer and discover impeccable craftsmanship and designer finishes throughout. The inviting lodge-inspired family room features a striking stone fireplace, while the spectacular custom kitchen is a true showpiece with premium finishes, abundant storage, and a hidden butler's pantry. The adjoining buffet and beverage area makes entertaining effortless, whether hosting holidays in the formal dining room or enjoying casual meals in the bright breakfast area overlooking your private back yard. You will love the spacious mudroom/laundry room. The perfect "drop spot" for coats, or backpacks. The main-level den/office with gorgeous custom woodwork provides the perfect work-from-home space. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and oversized tiled shower. Three additional bedrooms include a Jack-and-Jill bath with a walk-in shower and a third full bath with tub. The lower level is designed for entertaining with a custom kitchen, stone accents, a spacious family room with a second fireplace, bar area, two additional bedrooms, a fourth full bath, and a stunning wine room where fireside entertaining is at your fingertips for game nights, gatherings, or relaxing with friends. Outside, enjoy a private backyard surrounded by mature trees and abundant wildlife, along with a newly constructed deck ideal for outdoor living and entertaining. Beyond its beautiful finishes, this home offers peace of mind with new roof, windows, updated mechanicals, and a heated three-car attached garage. Every detail has been thoughtfully updated, and nothing has been overlooked. This is a rare opportunity to own one of Middlebury's finest homes.

205 Greenfield Drive, Middlebury

Listing courtesy of Julie Thatcher from Coldwell Banker Real Estate Group. 574-522-2822

$209,900

4 Beds ⋅ 1 Baths ⋅ 202628938 MLS ⋅ 2,484 SqFt. ⋅ Daryle Lambright

Historic Character Meets Opportunity:)! Nestled in the heart of Middlebury, this classic 4 BR, 1 BA two-story home is rich with timeless architectural details and ready for its next chapter. The inviting wraparound porch welcomes you inside, where an original staircase, tall ceilings, spacious living and dining rooms, and beautiful historic trim showcase the character only a classic home can offer. Recent improvements provide an excellent foundation for future updates, including updated electrical, new windows (2015), a high-efficiency furnace and central air (2019), a durable metal roof, and some updated lighting and ceiling fans. Situated on nearly a half-acre, this rare in-town property features a detached 1-car garage, a barn with its own workshop, mature shade trees, and room to enjoy. Newer washer and dryer are included. Being offered As-Is, this is a wonderful opportunity to restore, personalize, and build equity while preserving the timeless charm of a classic Middlebury home.

411 S Main Street, Middlebury

Listing courtesy of Daryle Lambright from RE/MAX Results. Cell: 574-238-4587

$399,900

5 Beds ⋅ 3 Baths ⋅ 202625894 MLS ⋅ 2,400 SqFt. ⋅ Liliana Ballge

Spacious secluded home two story home with 5 bedrooms and 3 baths! Tucked away in a wooded setting with trails, this inviting home offers the perfect blend of peaceful surroundings and 8 minutes from town in Middlebury schools. The upstairs features 3 bedrooms, 2 baths, an open-concept kitchen, dining, and living space filled with natural light and a laundry room. The downstairs offers a second living area with 2 bedrooms, a full bath, and storage space. Enjoy additional space in oversized 2 car attached, finished, and heated garage and the 3 decks offer a relaxing retreat to come home to. Peace of mind items include a new septic field system installed in 2020; metal roof installed in 2017; and furnace, central air, and gas water heater from 2015, plus newer stainless steel appliances. Schedule your showing today!

13452 County Road 12 Lot 3, Middlebury

Listing courtesy of Liliana Ballge from McKinnies Realty, LLC Elkhart. Cell: 574-312-5222

$575,000

5 Beds ⋅ 3 Baths ⋅ 202621264 MLS ⋅ 2,584 SqFt. ⋅ Nicolas Wyse

Brand-new construction featuring 4-5 Bedrooms, 3 Full Bathrooms, and a desirable split-bedroom floor plan. The open-concept living area offers plenty of room to gather, while the upstairs bonus space provides flexibility for a home office, recreation room, hobby area, or additional living space. The kitchen comes complete with a full appliance package, and additional upgrades include a water softener and on-demand hot water heater. Enjoy low-maintenance living with slab construction, plus a covered front porch and an oversized covered rear patio overlooking neighboring woods for a peaceful and private setting. Move-in ready with modern finishes throughout.

13120 Bear Creek Court, Middlebury

Listing courtesy of Nicolas Wyse from RE/MAX Results. Office: 574-533-9581

$460,000

4 Beds ⋅ 6 Baths ⋅ 202619303 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm

Located in the heart of downtown in endearing Middlebury, the possibilities in this home are ENDLESS! The upper two levels were once a Bed & Breakfast, with 4 Bedrooms and 5 baths. The lower level has a separate entrance with entirely separate living quarters! The historic charm exudes in the two upper levels. Rich woodwork, a butlers pantry and the original fireplace provide character that is rare to find! The yard is spacious and backs up to the extremely popular Pumpkinvine Trail, great for walking and biking enthusiasts! This is a rare gem! Don't miss your chance to make it your own!

435 S Main Street, Middlebury

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

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IDX information is provided by the Indiana Regional MLS and is exclusively for the 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.

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