Middlebury, IN Homes for Sale

Open House Scheduled for August 23 1-3pm! A stone bridge and layered landscaping set the tone for this private 5.8-acre estate near downtown Middlebury. Inside, the home has been modernized—redesigned and furnished for a part-time retreat, though fully equipped for year-round living. Vaulted ceilings, high windows, and lit beams draw light into the open-concept living area and kitchen, where

Jesse Riegsecker Bright Star Real Estate Services LLC

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

Location, location, location, on main street in the heart of Middlebury with .80 acre in the Northridge school system. Step inside this beautifully updated meticulously kept home and take in the charm. This home offers 4 bedrooms with the Master on the main floor with walk in closet and fireplace, and sliding glass door that opens to your deck. Full bath and there is a bonus room that can be your

Kimberlie Whitsel The LT Group Real Estate

Stunning 5-Acre Estate with Pond, Pool, and Oversized Heated Workshop – A Dream Hobbyist’s Shop & now available at an even better value:) Welcome to your private slice of paradise, nestled on 5 beautifully maintained acres with abundant wildlife including deer, hawks, ducks, turkeys, and more. The serene backdrop includes a peaceful stream at the rear of the property, a fully stocked 1⁄2-acre

Daryle Lambright RE/MAX Results

Step into modern elegance with this stunning 2-story home in the highly sought-after Winding River subdivision in Middlebury, built in 2022 and located within the top-rated Middlebury School District. Offering 2,100 sq. ft. of thoughtfully designed living space, this home features 3 spacious bedrooms, 2.5 bathrooms, and a seamless open-concept layout perfect for everyday living and entertaining.

Natashia Bontrager McKinnies Realty, LLC

Welcome to your peaceful country homestead! This beautiful walkout ranch offers 3 bedrooms and 2 bathrooms on the main level, plus an additional finished room in the fully finished basement—perfect for a home office, gym, or guest space. Sitting on nearly one acre, this property provides the ideal blend of country living with the convenience of being just a short drive from Downtown Middlebury

Crystal Miller RE/MAX Results

Tucked away on nearly 10 acres in Middlebury, this 2022 custom stick-built home offers a peaceful retreat with space and modern comfort throughout. With approximately 6,000 sq. ft., 5 bedrooms, and 4 total baths, there’s room for family, guests, and more. The open main level centers around a wood burning fireplace and features radiant heated floors that extend through the entire home and the

Brianna Gilbert Keller Williams Realty Group

Nestled on just under 2 acres, this unique property offers privacy in town — you won’t even realize you’re in town! Featuring 4 full bedrooms and 3 full baths, including a finished walkout basement with an additional bedroom and full baths, this home provides plenty of room for family and guests. Step outside to enjoy a patio just outside the walkout basement. The property also includes a

The Hostetler Team Bright Star Real Estate Services LLC

Discover affordable new home living at Tall Oaks #5, a charming 2-bedroom, 1-bath manufactured home featuring 672 square feet of modern comfort. Located in the peaceful Tall Oaks Manufactured Home Community off County Road 4 near scenic Stone Lake, this cozy home is perfect for anyone looking for low-maintenance living in a friendly neighborhood. This brand-new home offers a bright, open-concept

Frank Sheppard Thrive Communities, LLC

Open House Saturday 12/6/2025 12-2PM. Welcome home to this beautifully updated quad-level home in the sought-after Middlebury School District! Featuring 3 bedrooms and 21⁄2 bathrooms, this home combines space, style, and comfort in one perfect package. Step inside to discover brand new carpet on the upper level and newer flooring throughout the rest of the home. The main level features soaring

Courtney Barber McKinnies Realty, LLC Elkhart

Start Showing Date: 12/20/2025 Bring in the New Year in this 3 bedroom, 3 bathroom home on a cul-de-sac in Middlebury. The kitchen has a breakfast bar, and all kitchen appliances will stay. The large master bedroom has an en-suite bath. Laundry is on the main floor for convienent access. Washer and dryer will stay. Plenty of room for entertaining upstairs and downstairs. Downstairs has a large

Amber Hapner Coldwell Banker Real Estate Group

Welcome home to Tall Oaks #16, a brand-new 2-bedroom, 2-bath manufactured home offering style, efficiency, and comfort. Located in the peaceful Tall Oaks Manufactured Home Community just off County Road 4 near scenic Stone Lake, this home combines modern finishes with low-maintenance living. Step inside to a bright, open-concept floor plan featuring energy-efficient construction and a modern

Frank Sheppard Thrive Communities, LLC

Charming Downtown Middlebury Living! Nestled on a desirable corner lot in the heart of downtown Middlebury, this home offers unbeatable walkability to the coffee shop, library, playground, parks, and post office. Step inside to a welcoming entryway highlighted by a beautiful wood staircase. The spacious living room flows into a versatile bonus space complete with built-in cabinets—perfect for an

Stephen Schemenauer Keller Williams Realty Group

What an excellent opportunity! This home is nestled in a serene rural Subdivision within the Middlebury school district on a large spacious lot! The main floor offers 3 bedroom, 2 bathrooms, while the lower level features kitchen, bedroom, full bathroom,small office,and expansive family room complete with projector for your movie nights!

Mike Parson Hallmark Excellence Realty

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.