Middlebury, IN Homes for Sale under $500,000

MOVE RIGHT IN to this 3 BR 3 bath cape code style home in convenient Middlebury location. You'll appreciate the spacious rooms, the open kitchen and dining area. Kitchen has abundant cabinets, breakfast bar, pantry, built-in desk and the appliances are inlcuded. Large living room, open stairway leads to 2 upper bedrooms and a full bath. Primary bedroom has adjoining bath w/ a double vanity. Main

Sheila Showalter RE/MAX Results

This well-maintained bi-level home offers the perfect blend of comfort, style, and functionality. Step inside to find a beautifully remodeled kitchen (2018) featuring granite countertops, an abundance of cabinetry, and modern finishes—ideal for cooking and entertaining. The upper living area boasts brand-new carpet installed in 2025, creating a fresh and inviting atmosphere. Enjoy peace of mind

Lisa Schrock Berkshire Hathaway HomeServices Elkhart

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

Jennea Schirr McKinnies Realty, LLC Elkhart

Middlebury living at it's finest! This gorgeous brick home features 3 bedrooms and 3.5 baths and a spacious 3,729 sq.ft. of living area! The main level offers a fully redone kitchen and master bathroom with new flooring throughout! Step into the enclosed deck to your personal hot tub retreat or onto the redone back deck for that morning cup of joe overlooking your pond waterfront! Fully finished

Michael Patka Grogg Martin Realty

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

Daryle Lambright RE/MAX Results

Located along State Road 120, this nicely-maintained home sits on 1.5 acres and offers plenty of room to enjoy both indoors and out. Major updates include a new furnace, central air conditioning, water heater, and gutters in 2023, along with a metal roof installed in 2020. The water softener and garage door are both less than one year old. With many of the major mechanical and exterior

Nubia Cruz eXp Realty, LLC

Charming Move In Ready 3-bedroom, single-story home in Middlebury with an assumable balance of $94k at 3.25% offering comfortable living in a convenient location. The practical layout features inviting living spaces, spacious bedrooms, and plenty of potential to make it your own. Outside, enjoy the added value of a pool and pole barn, providing space to relax, entertain, or pursue your hobbies.

Geoff Cavender eXp Realty, LLC

Beautiful 2019 ranch in a peaceful neighborhood with a country setting just minutes from downtown Middlebury! This 3 bedroom (split floorplan), 2 bath home has thoughtfully designed living space with an attached 2 car garage that is insulated and heated. The open floor plan is perfect for everday living and entertaining. All appliances will stay, along with a whole house water filtration system.

Kathy McMillan Berkshire Hathaway HomeServices Elkhart

MOTIVATED SELLERS! Welcome to this summer ready home on Sunset Dr. You will love the space, updates and amenities that come together to make this home. Offering 1992 square feet of above grade square footage plus a finished basement! Enjoy the large family room with natural woodwork, large windows and lots of natural light. Home features updated white kitchen, 3 spacious bedrooms, bonus room in

Kelly Dyksen Rooted Realty

LOOKING FOR THE LAKE LIFE? Enjoy lakefront living on sought-after Stone Lake with this 3-bedroom, 1-bath home offering year-round spectacular views and a relaxed lakeside setting. Large windows and inviting four seasons room capture the beauty of the water and bring the outdoors in, creating the perfect backdrop for everyday living or weekend getaways. Inside, the home features warm, lived-in

Kim Vuittonet Cressy & Everett- Goshen

Phone bid auction ending Thursday, September 10th, at 4:00 PM! The price listed is the starting bid, not the buy it now price. Enjoy country living on a quiet backroad just minutes from town! This 4-bedroom, 2-bath home features a new metal roof and an updated kitchen. Relax on the covered front porch or enjoy the privacy of the fenced backyard. The property offers a unique blend of efficiency

Leon Kramer Bright Star Real Estate Services LLC

This classic 3 Bed 3 Full Baths has everything you need, and more! Every room has been freshly painted, new light fixtures, new carpet and LVT waterproof flooring, new appliances, the lower level was completely remodeled and ready for new owners. The roof is 2 years old, the furnace and AC less than 4 years old. This quad level has all the bedrooms as well as two full baths on the upper level.

Kristin Bales Listing Leaders, NCI-Plymouth

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

Jami Stamm Coldwell Banker Real Estate Group

Welcome to effortless living in the desirable River Park Villas! This beautifully maintained villa offers 2 bedrooms plus a dedicated office or den, providing the flexibility today’s buyers are looking for. The thoughtfully designed floor plan features spacious living areas filled with natural light, a well-appointed kitchen with abundant cabinetry, ample counter space, and a pantry, plus a

Jennea Schirr McKinnies Realty, LLC Elkhart

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

Josh Lenker McKinnies Realty, LLC Elkhart