Middlebury Real Estate

Welcome to Middlebury, Indiana—a charming township nestled in the heart of Elkhart County. Known for its picturesque landscapes and tight-knit community, Middlebury offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

With a population of just over 3,000 residents, Middlebury exudes a warm, welcoming atmosphere. The township is steeped in rich Amish heritage, which is evident in its local culture, community events, and even the delicious homemade baked goods available at local markets. The surrounding countryside, with its rolling hills and lush farmland, provides a serene backdrop for outdoor enthusiasts and families alike.

Middlebury boasts a thriving local economy, supported by a variety of businesses, from quaint shops to larger manufacturers. The township is also home to top-rated schools, ensuring that families have access to quality education. Residents enjoy a variety of recreational opportunities, including parks, walking trails, and community sports leagues, fostering an active and engaged lifestyle.

The township hosts several annual events, such as the Middlebury Summer Festival, where locals and visitors come together to celebrate with food, music, and fun activities for all ages. With a strong sense of community and a commitment to preserving its cultural heritage, Middlebury is more than just a place to live; it’s a place to thrive.

Whether you're looking to settle down or invest in a property, Middlebury offers a delightful blend of tranquility and opportunity. Come discover why this charming township is the perfect place to create lasting memories and build your dream life!

Newest Listings in Middlebury

$649,900

4 Beds ⋅ 4 Baths ⋅ 202636820 MLS ⋅ 3,841 SqFt. ⋅ Steve Miller

Built by Town & Country Builders, this beautiful home offers timeless quality in one of the area's most sought-after neighborhoods. Set on a private, wooded lot within walking distance to parks and the Pumpkin Vine Trail. Four bedrooms each include a private bath, plus a bonus room ideal as a 5th bedroom, for a total of 3.5 bathrooms. Hand-scraped hardwood floors and granite kitchen countertops add warmth and quality throughout. The lower level includes a hot tub connection on the patio access, plus rough-in plumbing for a fourth full bathroom. Enjoy outdoor living on the screened porch overlooking the backyard, complete with a natural gas grill hookup. A spacious 3 car attached garage completes the package, along with a roof installed just three years ago. Don't miss your opportunity to call this exceptional Highland Woods property home!

211 Greenfield Dr, Middlebury

Listing courtesy of Steve Miller from RE/MAX Results. Office: 574-533-9581

$699,000

5 Beds ⋅ 4 Baths ⋅ 202636797 MLS ⋅ 3,582 SqFt. ⋅ Kylee Sulkowski

Welcome home to 217 Greenfield Dr — in Middlebury's Northridge school district, set on a wooded, professionally landscaped lot, this is a home that needs neither updating nor more space, which isn't something you find often at this price. From the moment you step inside, vaulted ceilings in the living and dining rooms set the tone: open and bright, with light pouring through room after room and pooling across the oak flooring. The kitchen has been outfitted with all-new appliances, including a professional-series stove, complete with a pot filler at the range, built-in reverse osmosis filtration, and a double pull-out trash system —the kind of conveniences you'll appreciate every single day. All new energy efficient windows, doors, and garage door in 2026, plus a brand new 2025 composite deck, mean the big-ticket updates are already done — this is a home to move into, not renovate. Then there's the layout most houses simply don't offer: a main-level primary suite for single-story ease, three additional bedrooms upstairs sharing a full bath and arranged around a large loft landing that overlooks the living room below, and a finished walk-out basement with its own second living suite and private office — space for guests, extended family, or a work-from-home setup that doesn't feel like an afterthought. A double-sided fireplace warms both the basement living area and the office, while a second fireplace anchors the formal living room upstairs. Step outside from the lower level and you'll find a second patio — a shaded, private spot to sit out and enjoy even the hottest afternoons. Storage is never an issue, with two oversized storage rooms in the basement and closets throughout, and the 2-car garage adds an epoxy floor and extra workspace for projects or hobbies. Outside, mature woods and a live walnut tree give the backyard a quiet, established feel, along with an irrigation system, and a landscaped dog area tucked behind the shrubbery means even your pets have their own space. The sale includes the adjacent lot, adding extra privacy and breathing room around the home. 217 Greenfield Dr offers a rare combination: real space, real updates, and a layout built for how families actually live, in one of the area's most desired school districts. Schedule your private showing — homes like this don't stay quiet for long.

217 Greenfield Dr, Middlebury

Listing courtesy of Kylee Sulkowski from White Hat Realty Group, LLC.

$325,000

3 Beds ⋅ 2 Baths ⋅ 202635455 MLS ⋅ 1,791 SqFt. ⋅ Leon Kramer

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 homesteading and outdoor enjoyment, the property includes gardens, grapes, raspberries, a chicken coop, a horse shelter, pasture, food plot, hunting blind, and privacy screening along the woodland edge. Whether you're raising animals, gardening, hunting, or simply enjoying nature, this property is ready for your lifestyle. A 40' x 56' insulated outbuilding provides exceptional storage and workspace, complete with workshop area, floor drain, root cellar, hay storage, hydrant, and refrigerator. The solar power system with battery backup adds efficiency and peace of mind, making this a truly versatile and sustainable country property. Attend one of the open houses on Tuesdays, September 8,15,22, and 29, from 3-5 PM.

14340 County Road 12, Middlebury

Listing courtesy of Leon Kramer from Bright Star Real Estate Services LLC. office: 574-821-7653

$420,000

3 Beds ⋅ 3 Baths ⋅ 202635356 MLS ⋅ 2,864 SqFt. ⋅ Toni Bontrager

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 of home. The main level features convenient laundry, beautiful wood flooring, and a spacious primary suite that overlooks the picturesque backyard. The updated primary bathroom offers a fresh, modern feel with a ceramic tile shower and thoughtful finishes. Step outside to discover your own private backyard retreat, complete with a beautiful in-ground pool, this home offers the perfect combination of comfort, style, and outdoor enjoyment. Come and see what this wonderful home has to offer!

1006 Hidden Meadow Ln, Middlebury

Listing courtesy of Toni Bontrager from Berkshire Hathaway HomeServices Elkhart. Office: 574-293-1010

$700,000

4 Beds ⋅ 5 Baths ⋅ 202633832 MLS ⋅ 3,696 SqFt. ⋅ Jesse Riegsecker

AUCTION!! This amazing 20 acre property is set to sell at Phone Bid auction with bidding to end on September 24th at 5pm. The posted amount is the starting bid not the buy it now price. This home has 4 bedrooms and 3.5 baths and has been completely updated as of the last few years. The home has coffered ceilings in many of the rooms and 3 of the bedrooms all have their own en-suites! The finished walkout basement has the 4th bedroom and its own bathroom. The home has a large wrap around porch which is perfect to relax and over look the property. There is also a 30x40 pole building on the property. The property has a nice pond and has multiple elevated deer blinds and has a rich history of large amounts of deer and turkey! The property also borders the Jesse & Agnes Riegsecker Natural Area which is 200+ acres to enjoy. Auction Open house dates are set for August 24 - Sept 3-10-17 from 3-5pm.

55750 County Road 33, Middlebury

Listing courtesy of Jesse Riegsecker from Bright Star Real Estate Services LLC. office: 574-821-7653

$400,000

3 Beds ⋅ 2 Baths ⋅ 202633274 MLS ⋅ 1,594 SqFt. ⋅ John Wainwright

This home is nestled within the highly desirable Middlebury School District. This exceptional ranch home offers the perfect blend of country serenity and modern convenience, situated on 3.59 acres of land tucked in near a major thoroughfare. Complete with a concrete approach to the garage and a covered front concrete porch that beckons you to sit back and enjoy the peaceful surroundings. Inside, the main level features 3 spacious bedrooms, 2 bathrooms, updated kitchen, large living area, dining area, and a sliding patio door to your private back deck designed for effortless relaxation. Enjoy your retaining wall garden as well as a seamlessly designed, paver-lined outdoor fire pit area and a dedicated picnic space, creating the ultimate setup for cozy evening bonfires and weekend gatherings under the stars. Car enthusiasts and hobbyists will fall in love with the attached garage, which uniquely boasts its own direct stairway down to a full, expansive basement that is bursting with untapped potential. Already equipped with two egress windows for a possible 4th and 5th bedroom, and pre-plumbed for a 3rd bathroom. This lower level offers an excellent opportunity to double your square footage and customize your dream layout. Also included is a utility shed for your outdoor gardening and lawn tools. Nice landscaping, some mature trees, and lots of birds & wildlife!!

12028 County Road 18, Middlebury

Listing courtesy of John Wainwright from Lewis & Lambright Inc.

$649,900

4 Beds ⋅ 3 Baths ⋅ 202633095 MLS ⋅ 3,575 SqFt. ⋅ Cyle Jaskolka

Beautifully remodeled home offers an impressive combination of modern updates, spacious living areas, and luxurious amenities. Featuring two large living rooms, there is plenty of space to entertain, relax, or create a dedicated family and gathering area. The remodeled kitchen provides a fresh, updated space for preparing meals and entertaining, while the fireplace adds warmth and character to the home. The finished basement offers additional versatile living space that can be used as a recreation room, gym, media room, or whatever best fits your needs. The home's luxury features continue with a steam shower, heated bathroom floors, and built-in sauna, creating a private spa-like experience. Step outside to enjoy the backyard and its beautiful water feature, adding a peaceful focal point to the outdoor space. With extensive remodeling, generous living areas, a finished basement, and exceptional amenities, this Middlebury property is ready to welcome its next owner. Buyer to verify tax's, square footage, room sizes and schools

55755 Little Creek Ln, Middlebury

Listing courtesy of Cyle Jaskolka from Realty Group Resources. Cell: 574-312-9718

$299,900

4 Beds ⋅ 2 Baths ⋅ 202631868 MLS ⋅ 2,055 SqFt. ⋅ David Rogers

NEW PRICE! OPEN HOUSE 8/23, 2-4pm. Stop by and see us! Set on a quiet street in the heart of downtown Middlebury, this beautiful 1900s farmhouse is a well-recognized part of this small community and offers genuine character and charm. Featuring 3-4 bedrooms and 2 full baths, the 2,055 sq/ft of living space is spread across two stories and includes the kind of period details and warmth that modern builds simply don't offer. The sellers have poured their hearts into the outdoor living areas with a new covered patio space that creates a shaded gathering spot and a large, raised garden bed ready for vegetables and flowers. The large & charming front porch invites you to spend slow mornings in a rocking chair with a cup of coffee while watching the world pass by. This property is as practical as it is charming. An oversized 2-car garage, a 20'×30' outbuilding, and generous parking make it an ideal home for a hobbyist, a growing family, or anyone who wants room for tools, toys, and projects. The outbuilding alone offers serious workshop or storage potential. The detached structures and spacious lot add a flexibility most homes in this price range simply don't have. Located in a friendly small town with convenient access to area amenities, this home pairs small-town comfort with real utility. If you value character, outdoor space, and room to spread out, this one is worth a look.

209 Bristol Ave, Middlebury

Listing courtesy of David Rogers from Cressy & Everett- Elkhart. Cell: 574-849-6822

$279,900

3 Beds ⋅ 2 Baths ⋅ 202631867 MLS ⋅ 1,176 SqFt. ⋅ Chantel Boone

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 mechanicals for added peace of mind. The home has been professionally cleaned and is ready for its next owner to move right in.The full unfinished basement offers an incredible opportunity to nearly double your finished living space, providing endless possibilities for additional bedrooms, a recreation room, home office, or workout area. Whether you’re a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property checks all the boxes. Available for a quick closing with immediate possession, you can start enjoying your new home right away. Don’t miss this fantastic opportunity to own a move-in-ready home in the heart of Middlebury!

606 Claudia Ln, Middlebury

Listing courtesy of Chantel Boone from RE/MAX Results. Cell: 574-202-4408

$199,900

202614096 MLS ⋅ Crystal Miller

Escape to the tranquility of country living with this 6-acre property in the sought-after Middlebury Community School District. Surrounded by open skies and rural charm, this land offers the perfect setting for your dream home, hobby farm, or private getaway. Enjoy the peace and quiet of the countryside while still being just a short drive from local conveniences.

V/L County Road 28 ***, Middlebury

Listing courtesy of Crystal Miller from RE/MAX Results. Cell: 574-607-7156

$364,900

2 Beds ⋅ 3 Baths ⋅ 202629545 MLS ⋅ 2,485 SqFt. ⋅ Jennea Schirr

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 bright sunroom overlooking the peaceful pond—perfect for relaxing year-round. The spacious primary suite offers a private bath and walk-in closet, while main-floor laundry adds everyday convenience. The full basement provides exceptional storage and endless possibilities for additional finished living space, including the potential for two more bedrooms as the home already offers two egress windows. Major updates include a new roof (2024), furnace (2023), central air (2023), and water heater (2018), along with two sump pumps for added peace of mind. Enjoy a truly maintenance-free lifestyle with River Park Villas Association dues of $765 per quarter, which include lawn care, snow removal, exterior maintenance, and exterior property insurance—allowing you more time to enjoy your home and the beautiful surroundings.

111 River Park Dr, Middlebury

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

$299,900

4 Beds ⋅ 1 Baths ⋅ 202629465 MLS ⋅ 2,256 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 Ave, Middlebury

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

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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.