Middlebury, IN Homes for Sale under $500,000

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

Welcome to this beautiful 3-bedroom 3-bath home offering over 2,800 square feet of finished living! Step inside to a bright, open-concept layout designed for comfortable everyday living and effortless entertaining. The spacious living area flows beautifully into a sun-filled four-season sunroom overlooking the backyard, creating the perfect place to relax and enjoy the outdoors from the comfort

Toni Bontrager Berkshire Hathaway HomeServices Elkhart

Welcome to comfortable, low-maintenance living in Winding River Estates! Built in 2021 and situated on a spacious 0.4-acre lot, this beautifully maintained 3-bedroom, 2-bath home offers comfortable, low-maintenance living in one of Middlebury’s most inviting neighborhoods. The bright, open-concept floor plan creates an easy flow throughout the main living areas, while the charming kitchen

Marlynn Mast Keller Williams Realty Group

**OPEN HOUSE Thursday 8/20 FROM 4-6PM** 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

Nubia Cruz eXp Realty, LLC

Welcome home to this beautifully maintained 3-bedroom, 2-bath home nestled on a quiet street in one of Middlebury’s desirable neighborhoods. Conveniently located near schools, this move-in-ready home offers the perfect combination of comfort, convenience, and future potential. Inside, you’ll find an inviting layout featuring a spacious primary suite, updated stainless steel appliances, and newer

Chantel Boone RE/MAX Results

AUCTION! This property to sell at phone bid auction with bidding to end on September 22 at 5pm. The posted price is the starting bid not the buy it now price. This 3 bedroom 2 bath home has had many recent updates with the latest having the attached garage being converted over to a large family room. The home currently does not have electricity but does have some natural gas lighting throughout.

Jesse Riegsecker Bright Star Real Estate Services LLC

Completely updated Middlebury Landmark beauty, walkable to downtown! Over 3500 square feet. 4-Bedroom Colonial with first-floor primary suite. This home is built for entertaining. The first floor offers a completely updated kitchen, with room for a table. New cabinets, counters, fixtures, and stainless steel appliances. Tremendous dining and living room spaces to host any event. The first-floor

Timothy Sullivan Baird & Warner Res. Sales Inc.

**REDUCED PRICE-SELLER ISN'T PLAYING AROUND** 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

Kim Vuittonet Cressy & Everett- Goshen

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

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

Jami Stamm Coldwell Banker Real Estate Group

Phone bid auction ending October 6th, at 4:00 PM! The price listed is the starting bid, not the buy it now price. Nestled in the countryside of Middlebury, this 3-acre property combines comfortable living, self-sufficiency, and room for work and play. The home features an updated living room, hickory kitchen cabinets, and a spacious deck overlooking the scenic backyard and woods. Equipped for

Leon Kramer Bright Star Real Estate Services LLC