Middlebury Real Estate

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

52808 New York Dr, Middlebury
$65,000
3 Beds ⋅ 2 Baths ⋅ 202645627 MLS ⋅ 1,456 SqFt. ⋅ Susan Beyler
Calling all investors, flippers, or handy buyers! This is a great opportunity with excellent potential for rental, flip, or to renovate your own home in a desirable location. Home is cleaned out and ready for rehab. The seller is accepting cash-only, offers from buyers prepared to close quickly. The seller has never lived in the home and does not have information on the property. Buyers and their agents are responsible for verifying room dimensions, square footage, zoning, utilities, and school details.

52808 New York Dr, Middlebury

Listing courtesy of Susan Beyler from Harbor & Lake Real Estate. info@harborandlake.com
221 Greenfield Dr, Middlebury
$600,000
3 Beds ⋅ 5 Baths ⋅ 202645258 MLS ⋅ 4,331 SqFt. ⋅ Allison Miller
Welcome to this charming, expansive and beautifully appointed home offering over 4,300 finished square feet of versatile living space, 3 potentially 4 bedrooms, 3 full baths, and 2 half baths! Designed for both everyday comfort and entertaining, the open floor plan blends generous living spaces with thoughtful updates and timeless charm. The heart of the home is the stunning chef's kitchen, renovated in 2022 and featuring quartz countertops, high-end appliances, tiled backsplash, abundant pull-out cabinetry, a massive center island, peninsula with additional seating, open wood shelving, and a convenient pot filler above the range. The kitchen flows seamlessly into the spacious living room, complete with a cozy fireplace, while a formal dining room offers the perfect setting for gatherings. A main-floor office provides an ideal work-from-home space. Hardwood flooring extends throughout the main level, complemented by a convenient mudroom with half bath and an additional half bath in the main living area. Upstairs, retreat to the oversized primary suite featuring elegant tray ceilings and a beautifully renovated (2023) ensuite bath with dual vanities, soaking tub, tiled shower, and a large walk-in closet. Two additional generously sized bedrooms offer unique dormer spaces that add character and functionality. The second full bath is thoughtfully designed with two vanities and a separate toilet and shower area, making busy mornings easier for everyone. Upstairs carpeting was replaced in 2023. The enormous walk-out basement offers endless possibilities for recreation, relaxation, and entertaining, with dedicated areas for ping pong and pool tables, a bar, TV lounge, full bath, and an additional flexible room that could serve as a potential fourth bedroom, hobby room, or private retreat. Step outside to the patio and enjoy easy access to the outdoors. Situated on two lots totaling an impressive 1.023 acres, this property offers room to spread out, entertain, and enjoy the privacy of the wooded setting. Outdoor features include a spacious 21' x 11' wood deck, a charming wraparound front porch perfect for relaxing or gathering with friends, and plenty of yard space to enjoy. With over 4,300 finished square feet, an abundance of entertaining space, extensive updates, and a desirable setting on two lots, this home offers the space, flexibility, and lifestyle you've been looking for!

221 Greenfield Dr, Middlebury

Listing courtesy of Allison Miller from Century 21 Circle. Office: 574-293-2121
104 Southern Cross Dr, Middlebury
$329,900
4 Beds ⋅ 2 Baths ⋅ 202645096 MLS ⋅ 1,520 SqFt. ⋅ David Book
OPEN HOUSE SUNDAY NOVEMBER 8TH 2 TO 4. Beautiful well maintained home in desirable Middlebury! This 4 bedroom 2 full bath home is well updated and has tons of character, especially the beautifully landscaped almost half acre lot with hot tube and firepit area, 3 car garage and plenty of storage gives this home everything a family would need! Come see it soon as it won't last long!

104 Southern Cross Dr, Middlebury

Listing courtesy of David Book from Book Real Estate Services, LLC.

500 N Main St, Middlebury
$8,350,000
2 Baths ⋅ 202643020 MLS ⋅ Brad Hooley
33.4 acres of land zoned M-2 with city water and sewer to the site. This property includes the original very nice farm house with a 4 car garage and barn workshop. Extensive pre-development engineering work and plans have been done and are available, including typo maps, drainage site plan as well as building and parking elevations 1306 feet of road frontage,

500 N Main St, Middlebury

Listing courtesy of Brad Hooley from Bartel & Company. Office: 574-825-2115
13086 Bear Creek Ct, Middlebury
$475,000
4 Beds ⋅ 4 Baths ⋅ 202641153 MLS ⋅ 3,006 SqFt. ⋅ Laurie Ladow
Ready to love where you live? This beautifully maintained 4-bedroom, 3.5-bath home in prestigious Cedar Creek offers the space, updates, and comfort you’ve been looking for. Conveniently located in a cul de sac with a large yard. Step inside to gorgeous hardwood floors and an inviting open floor plan designed for both everyday living and entertaining. The spacious kitchen features solid-surface countertops, a prep island, and plenty of storage, while the living room’s gas-log fireplace with built-ins creates the perfect spot to relax. The beautiful primary suite offers a private retreat with a soaking tub and walk-in shower. Three additional bedrooms provide plenty of room for family, guests, or a home office. The walk-out lower level adds valuable living space with a family room and full bath. Outside, enjoy the composite deck, lower level patio, and a beautifully maintained lawn with a sprinkler system. Beautifully cared for and move-in ready, this Cedar Creek home checks all the boxes. Taxes will be substantially lower with Homestead Exemption.

13086 Bear Creek Ct, Middlebury

Listing courtesy of Laurie Ladow from Cressy & Everett - South Bend. Cell: 574-532-8779
115 Greenfield Dr, Middlebury
$434,900
3 Beds ⋅ 3 Baths ⋅ 202622750 MLS ⋅ 3,304 SqFt. ⋅ Andrew Myers
Sprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schools! This 3-bedroom, 2.5-bath home has over 3,300 finished square feet with an open layout, spacious living areas, a cozy fireplace and spacious fenced-in backyard with patio. It features solid hardwood floors, a stunning primary suite with walk-in closet, and main-level laundry. The partially finished basement provides additional living space and tons of potential with an additional 1,500+ unfinished square feet. Recent updates include brand new HVAC furnace and central A/C (2026) new roof (2022), stainless steel appliances (2022), reverse osmosis water filtration system, and many other recent upgrades throughout.

115 Greenfield Dr, Middlebury

Listing courtesy of Andrew Myers from Myers Trust Real Estate. Office: 574-875-5149
211 Greenfield Dr, 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
55755 Little Creek Ln, Middlebury
$615,000
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
13889 Adirondack Ct, Middlebury
$789,900
5 Beds ⋅ 4 Baths ⋅ 202632257 MLS ⋅ 4,473 SqFt. ⋅ Toni Bontrager
ELEGANCE MEETS COMFORT IN THIS EXCEPTIONAL MIDDLEBURY HOME. Welcome to this stunning 5 bedroom, 3 1/2 bath home nestled in The Summit, beautifully situated on a park-like setting at the end of a peaceful cup-de-sac. Offering over 4,600 sq ft. of thoughtfully designed living space, this meticulously maintained home blends timeless elegance with everyday comfort. The heart of the home is the beautifully appointed kitchen, featuring Wellborn soft-close custom cabinetry, a new GE Profile appliance package, double ovens, granite countertops, and a classic subway tile backsplash. The ML showcases gorgeous engineered hardwood flooring, neutral greige paint throughout, 5 3/4 trim/baseboards, recessed LED lighting and ceiling fans in every room. The inviting living are features a beautiful gas fireplace flanked by custom built-in cabinetry. The ML office is both stylish & functional, complete with built-ins & USB wall plugs. The spacious primary suite offers thoughtful custom touches, including built-in dresser bump out & wall mounted nightstands, that maximize both style & functionality. Additional features include: solid-core doors, split-door to the lower level, and a dedicated fenced dog run with turf & a convenient dog door. The fully fenced backyard offers peaceful, wooded view & exceptional privacy, along w/extensive landscaping, & custom fire pit. An oversized stamped-concrete patio provides the perfect space for entertaining or relaxing outdoors. The home is equipped with Navian tankless water heater. From beautiful finishes & custom cabinetry to the private outdoor retreat & thoughtful details throughout, this home has been exceptionally cared for and is truly move-in ready.

13889 Adirondack Ct, Middlebury

Listing courtesy of Toni Bontrager from Berkshire Hathaway HomeServices Elkhart. Office: 574-293-1010
606 Claudia Ln, Middlebury
$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
V/L County Road 28 ***, Middlebury
$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
53982 Midnight, Middlebury
$94,900
201452503 MLS ⋅ David Singell
Private, secluded, wooded. Borders Morning Star Nature Preserve.

53982 Midnight, Middlebury

Listing courtesy of David Singell from Myers Trust Real Estate. Cell: 574-536-1191
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IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by IRMLS as amended from time to time.


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.


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