Middlebury Homes under $500,000

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Newest Middlebury Homes under $500,000

$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. Come see why it could be the perfect place to call home!

13086 Bear Creek Ct, Middlebury

Listing courtesy of Laurie Ladow from Cressy & Everett - South Bend. Cell: 574-532-8779

$325,000

5 Beds ⋅ 2 Baths ⋅ 202640412 MLS ⋅ 2,736 SqFt. ⋅ Craig Blough

Large Middlebury farmhouse on 1.55 acres. This 5-bedroom, 2-bathroom farmhouse has very large rooms, many updates, a wraparound porch, and offers a great opportunity with plenty of space to tailor to your individual family needs at a great price point in Middlebury Schools. The dining, kitchen, and living areas are large and the flow seemlessly from one to the next, providing a nice balance of open concept and defined spaces. The primary bedroom features an ensuite bathroom. The upstairs bedrooms are quite large with a secondary full bathroom serving the four upstairs bedrooms. The attic space is accessible by a dedicated stairway and could be finished for additional bonus space like a play room, craft room, or mancave. The basement offers a canning space, updated mechanicals, and additional space for storage or sprawl. The 36'x28' detached 2-car garage is spacious and has electric. The 54'x36' hip-roof has an additional 54'x36' lean-to and is served by a frost free water hydrant and electric as well. The barn has a hay mow with drops on both outside walls and is a blank slate for your farmette. The old milk house would make a neat garden shed, and the possibilities with the spacious yard are endless.

53805 County Road 43, Middlebury

Listing courtesy of Craig Blough from Bartel & Company. Cell: 574-596-9890

$274,900

3 Beds ⋅ 3 Baths ⋅ 202640234 MLS ⋅ 2,848 SqFt. ⋅ Toni Bontrager

RIGHT IN THE HEART OF MIDDLEBURY! Welcome to a property filled with character, history, and endless possibilities. Located right in the heart of Middlebury, this unique property offers the flexibility to be used as residential home, commercial space, or potentially a combination of both, depending on the applicable zoning and approvals. The property has been used as an office for numerous years, but its original Charm is still evident throughout. Upstairs, you will find three bedrooms, a possible kitchenette area, and a separate entrance, providing the potential for the upper level to function as an apartment or additional living space. The natural woodwork dating back to the early 1900's is truly equisite, adding warmth and character that simply can't be duplicated in newer construction. A beautiful brick fireplace, once the heart of the family room, is another reminder of he home's rich history. The basement adds even more opportunity with a finished recreation room and additional space for storage or future use. There are currently no appliances giving the next owner the opportunity to design the kitchen and living spaces to fit their vision. Whether you are looking for a unique home, an office, and investment property, or a property wth the potential for multiple uses, this one deserves a look. The possibilities are endless!!

112 S Main St, Middlebury

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

$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

$289,900

3 Beds ⋅ 2 Baths ⋅ 202639202 MLS ⋅ 2,116 SqFt. ⋅ Allison Miller

Updated, spacious, and ideally located! This 3-bedroom (potential 4th bedroom in the basement with installation of a egress), 2-bath home sits on a full 1-acre lot and is located in the Middlebury School District. Step inside to find extensive updates throughout, including a new kitchen with white cabinets, flooring throughout, white trim, doors, and fresh paint. The finished basement adds valuable additional living space for entertaining, storage, potential 4th bedroom (no egress) and much more. The main-floor laundry provides everyday convenience immediately off the kitchen. A new roof adds to the list of recent improvements and offers peace of mind. Outside, enjoy the covered back patio enjoying morning sunrises, expansive 1-acre setting and shed for additional storage. The property also includes a 1-stall garage and is conveniently located near town, shopping, and walking trails. With its extensive updates, generous lot, and convenient location, this home is ready to welcome its next owner!

928 S Main St, Middlebury

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

$474,900

4 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 (with 4th room without egress in basement home is a walk out and does have multiple exit locations) 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

$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

$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

$354,900

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.