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54725 County Road 33, Middlebury
$1,249,999
5 Beds ⋅ 5 Baths ⋅ 202624521 MLS ⋅ 6,370 SqFt. ⋅ Chantel Boone
Set on over 17 private acres in Middlebury, this open-concept split-bedroom luxury home blends modern comfort with natural beauty in a truly serene setting. A 1-acre pond, fed by a fresh sandy creek, offers year-round enjoyment for fishing, swimming, and peaceful waterfront views surrounded by mature woods and abundant wildlife. Inside, the home features a bright, flowing layout designed for both everyday living and entertaining. The eat-in kitchen showcases solid custom alderwood cabinetry, granite countertops, and a large island that anchors the space beautifully. Thoughtful updates continue throughout, including new windows, roof, and chimney (2023), a new septic system (2025), and freshly painted cedar exterior (2025). The living spaces extend outdoors with a screened-in porch and a Trex deck complete with an awning—perfect for relaxing while overlooking the pond and natural landscape. Electric blinds with Bluetooth remote control add a modern touch of convenience throughout the home. A brick fireplace creates a warm focal point and can easily be converted to gas if desired. Practical features include a generator capable of powering essential systems such as HVAC and refrigerators, ensuring comfort during outages. A large outbuilding provides excellent storage, workspace, or hobby potential, and additional equipment is available for purchase with the home. This 5 bed/4.5 bath property offers a rare combination of privacy, updated luxury, and recreational land—all in a picturesque setting designed for both relaxation and function.

54725 County Road 33, Middlebury

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

13998 Shavano Peak Dr, Middlebury
$1,175,000
4 Beds ⋅ 5 Baths ⋅ 202636321 MLS ⋅ 4,903 SqFt. ⋅ Tammy Kmitta
Custom Luxury on 3.35 Acres! Located in the beautiful and sought-after Summit subdivision, this exceptional custom-built home sits on 3.35 beautifully landscaped acres surrounded by mature woods, offering privacy, quality craftsmanship, and an impressive array of amenities. Striking glass-arched entry doors welcome you into a home showcasing beautiful hardwood floors, coffered ceilings, solid wood doors, and custom details throughout. The great room features a stunning gas fireplace with built-ins. It flows seamlessly into the dining area and gourmet kitchen, complete with quartz countertops, an oversized island, generous pantry space, a wine refrigerator, and an inviting eat-in area. The covered patio extends the living space outdoors, with a beautiful fireplace and grilling area with granite countertops. The split-bedroom design provides privacy, with the spacious primary suite featuring a soaking tub, an impressive walk-in shower, dual vanities, a generous walk-in closet, and a separate water closet. Additional bedrooms share a well-appointed Jack-and-Jill bath. The finished lower level is designed for entertaining and relaxation, featuring a wet bar with granite countertops, a wine refrigerator, and seating for four, along with a lounge/conversation room, an exercise room, an office/craft room with built-ins, a bedroom, and a full bath. The exceptional custom home theater room is truly something to experience. Offers tiered seating, motorized leather chairs, LED-lit cup holders, and a fully immersive Dolby Atmos surround sound with in-wall speakers and dual sub-woofers. A walk-out leads directly to the saltwater hot tub and outdoor space. The oversized three-car garage includes water hookups for convenient vehicle cleaning. The extraordinary 40' x 64' heated outbuilding features 14-foot doors, a loft with stairs and a motorized lift for moving and storing heavier items, a dog wash station, a half bath, specialty outlets for RVs and equipment, and an attached air compressor with dryer. Just outside the outbuilding is an RV dump station. An exceptional space for vehicles, RVs, equipment, hobbies, collections, workshop projects, or storage. A Sonos home audio system with 5 zones extends throughout the home and outdoor spaces. With so many exceptional features and custom details, this property truly needs to be experienced in person!

13998 Shavano Peak Dr, Middlebury

Listing courtesy of Tammy Kmitta from RE/MAX Results. Cell: 574-536-4778

14212 County Road 8, Middlebury
$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

55750 County Road 33, Middlebury
$900,000
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

53660 Forest Lakes Dr, Middlebury
$715,000
5 Beds ⋅ 4 Baths ⋅ 202631921 MLS ⋅ 3,333 SqFt. ⋅ Nate Paulus
Welcome to your private waterfront sanctuary on Forest Lakes Drive. Set on nearly 2 secluded acres at the end of a quiet Middlebury cul-de-sac, this exceptional 5-bedroom, 3.5-bath East Lake home offers direct water access to canoe, kayak, and fish right from your private dock. Enjoy stunning water views from multiple vantage points, including the bright and inviting 3-season room—an ideal spot to take in the morning sun. The home features 5 bedrooms and 3.5 bathrooms, highlighted by a main-floor primary suite complete with a walk-in closet and convenient main-floor laundry. The vaulted ceiling in the living room with a stone fireplace creates an open, airy feel, while the walkout basement expands your living space. As a bonus, there is and a sauna for ultimate relaxation. Step outside to your own backyard oasis featuring an in-ground pool, perfect for entertaining or unwinding in total privacy. Additional highlights include a 3-stall garage, storage shed, and major mechanical updates with a furnace and A/C just 3 years old and a roof approximately 8 years old. All of this in a prime location with close proximity to Shipshewana, Middlebury, and the Indiana Toll Road—making it easy to enjoy both peaceful lake living and convenient access to nearby amenities.

53660 Forest Lakes Dr, Middlebury

Listing courtesy of Nate Paulus from R1 Property Group LLC.

1116 Erin Ct, Middlebury
$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

14340 County Road 12, Middlebury
$425,000
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

1006 Hidden Meadow Ln, Middlebury
$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

111 River Park Dr, Middlebury
$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 (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

928 S Main St, Middlebury
$289,900
3 Beds ⋅ 2 Baths ⋅ 202639202 MLS ⋅ 2,116 SqFt. ⋅ Allison Miller
***Open House October 11th 1-3PM*** 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

112 S Main St, Middlebury
$274,900
3 Baths ⋅ 202640237 MLS ⋅ 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

112 S Main St, Middlebury
$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

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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