Middlebury Real Estate

Welcome to Middlebury, Indiana – a charming town that beautifully blends small-town warmth with a vibrant community spirit. Nestled in the heart of Elkhart County, Middlebury is renowned for its picturesque landscapes, friendly neighbors, and rich cultural heritage. With a population of just over 3,500 residents, this quaint town offers a peaceful retreat while providing easy access to larger urban centers.

Middlebury is perhaps best known for its thriving Amish community, which adds a unique flavor to the area. Visitors and locals alike can enjoy delicious homemade goods from local markets, explore handcrafted furniture, or take a scenic drive through the countryside to witness the beautiful farms and rolling hills. The town’s annual events, such as the Middlebury Community Fair, showcase the vibrant culture and foster a sense of camaraderie among residents.

Outdoor enthusiasts will find plenty to love in Middlebury. The town is surrounded by beautiful parks and nature trails, perfect for hiking, biking, or simply enjoying a leisurely stroll. The nearby rivers and lakes provide ample opportunities for fishing and boating, ensuring that adventure is never far away.

Middlebury also boasts a strong sense of community, with excellent schools, friendly local businesses, and numerous recreational programs that cater to all ages. Whether you’re looking to raise a family, retire in peace, or simply find a welcoming place to call home, Middlebury offers a delightful blend of tranquility and charm. Come discover the hidden gem of Indiana, where every day feels like a warm embrace!

Newest Listings in Middlebury

$474,900

3 Beds ⋅ 4 Baths ⋅ 202637625 MLS ⋅ 3,729 SqFt. ⋅ Allison Miller

Over 3,700 sq. ft. of total living space on a beautiful 1.06-acre lot in a quiet cul-de-sac! This meticulously maintained, sprawling ranch offers exceptional space, versatility, and numerous updates. The main level features a gorgeous, spacious kitchen with stone countertops, wine fridge, abundant cabinetry, stainless steel appliance and engineered hardwood flooring that flows throughout much of the home. Enjoy both a large family room with brick fireplace and separate living room, along with 3 bedrooms and 2.5 baths. The beautifully updated primary suite features a fireplace and an upgraded bath with fully tiled shower, and heated tile floors. Step outside to enjoy the peaceful pond views from the impressive 34' x 24' deck or relax in the 27' x 13' screened porch with hot tub—perfect for entertaining or unwinding. With beautifully landscaped and irrigated 1.06 acre yard it provides space for out door activities or entertaining. The walk-out lower level adds tremendous versatility with a full kitchen, private bath, rec room, laundry facilities, and a potential bedroom area (currently without egress). This level offers an excellent opportunity for extended family, mother-in-law suite, guests, hobbies, or potential rental income. Garage space is truly exceptional, featuring a 3-stall garage plus an enormous heated basement garage/storage area measuring approximately 29' x 50'. Laundry facilities are conveniently available on both levels. Recent improvements include a new roof in 2023 and new on-demand water heater in 2025, along with numerous updates throughout. With its generous lot, flexible floor plan, extensive garage space, pond views, and outstanding outdoor living areas, this unique property offers a rare combination of comfort, functionality, and opportunity.

1116 Erin Ct, Middlebury

Listing courtesy of Allison Miller from Century 21 Circle. Office: 574-293-2121

$575,000

5 Beds ⋅ 4 Baths ⋅ 202637090 MLS ⋅ 4,216 SqFt. ⋅ Scott Bradshaw

Enjoy space, privacy, and exceptional versatility on 3.31 acres in Middlebury Community Schools. This expansive 5-bedroom, 4-bath home features a large rear addition completed in 2011, providing an impressive amount of flexible living space. The main level offers two primary suites, two additional bedrooms, and a convenient laundry room. The updated kitchen includes granite countertops, stainless-steel appliances, abundant cabinetry, and an open connection to the living area. One primary suite features a spacious walk-in closet and a distinctive river-rock shower. The finished walkout basement adds a fifth bedroom, bathroom, extensive recreation and gathering space, storage, and direct backyard access. Outside, enjoy the large deck, patio, above-ground pool, mature trees, and peaceful country setting. The property also includes an attached garage, a heated 24' x 40' detached building, and a large 30' x 60' pole barn built in 2024. A rare opportunity combining comfortable living, acreage, and outstanding space for vehicles, equipment, hobbies, or a workshop.

12330 County Road 4th St, Middlebury

Listing courtesy of Scott Bradshaw from HomeFront Realty, LLC. hfr.scott@gmail.com

$69,900

2 Beds ⋅ 1 Baths ⋅ 202636919 MLS ⋅ 1,232 SqFt. ⋅ Deanna Wilcox-Moen

Looking for a project in Middlebury? Here is your chance! Located right next to Stone Lake, this cottage is ready for you to bring it back to life. Loads of potential here! Nice, wooded lot plus a 10x24 barn. Home needs a full renovation and is being sold as-is. There is a spacious eat in kitchen and living room with fireplace, 1 bedroom and 1 bath on the main level. Bath has been gutted. Bonus room on the main level with no closet, could be an office or small bedroom. Upstairs there is another bedroom and a large landing area. Vinyl replacement windows have been installed.

51855 E County Line Rd Unit Lot 5, Middlebury

Listing courtesy of Deanna Wilcox-Moen from Realty Experts LLC. Cell: 574-202-7653

$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.

$925,000

5 Beds ⋅ 4 Baths ⋅ 202634859 MLS ⋅ 4,283 SqFt. ⋅ Lisa Schrock

This one truly has it all! If you have been looking for your own slice of heaven, this newer-construction home is the one you have been waiting for. Situated on 4.85 acres, with a beautiful creek flowing through the property and stock tank pool for relaxing. The spacious home features 5 bedrooms, 3.5 baths, and a well-designed open-concept floor plan. The primary suite offers a large private bath complete with a relaxing soaker tub. The kitchen is both stylish and functional, featuring quartz countertops and two pantry areas for ample storage.The finished basement provides even more living space with a dedicated workout room, daylight windows, bar area, and an additional bedroom and bath. Newer construction with a like-new feel, plenty of space, and a peaceful setting make this property a rare find.

14212 County Road 8, Middlebury

Listing courtesy of Lisa Schrock from Berkshire Hathaway HomeServices Elkhart. Office: 574-293-1010

$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

$345,000

3 Beds ⋅ 2 Baths ⋅ 202634463 MLS ⋅ 1,450 SqFt. ⋅ Marlynn Mast

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 provides the perfect space for everyday meals and entertaining. Outside, enjoy the fully fenced backyard, ideal for pets, play, and relaxing. Downstairs, the full unfinished basement offers exceptional potential to significantly expand the home’s living space. With plumbing already in place for a third bathroom and an egress window included, the basement is ready to be transformed into additional bedrooms, a recreation room, home office, or whatever best suits your needs. Located in Winding Waters Subdivision just north of Middlebury, this home offers a peaceful country setting on a quiet road while remaining within the highly regarded Northridge School District. If you haven’t explored Winding Waters yet, you’ll want to, this is a wonderful place to call home!

12825 Sunfish Dr, Middlebury

Listing courtesy of Marlynn Mast from Keller Williams Realty Group. marlynnmast@gmail.com

$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

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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.