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$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
$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
$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
$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
$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
$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.

$90,000
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
$450,000
4 Beds ⋅ 2 Baths ⋅ 202630219 MLS ⋅ 1,566 SqFt. ⋅ Leon Kramer
Phone bid auction ending Thursday, September 10th, at 4:00 PM! The price listed is the starting bid, not the buy it now price. Enjoy country living on a quiet backroad just minutes from town! This 4-bedroom, 2-bath home features a new metal roof and an updated kitchen. Relax on the covered front porch or enjoy the privacy of the fenced backyard. The property offers a unique blend of efficiency and rural charm with a solar panel array, a 48-volt solar system, 7-battery storage, and LP gas lights already plumbed throughout the home. Equestrian enthusiasts and hobby farmers will appreciate the impressive 40' x 72' barn featuring 3 box stalls, 3 tie stalls, a tack room, workshop area, and hay mow. An attached 40' x 52' garage provides abundant space for vehicles, projects, or storage. The pasture and wooded acreage create an ideal setting for animals and outdoor recreation, with frequent deer sightings adding to the natural beauty of the property. Conveniently located just 2 miles from IN-13, this peaceful rural retreat offers the perfect combination of space, functionality, and country tranquility. Attend one of the open houses on Thursdays, August 6,13,20, & 27 from 3-5 PM.

51134 County Road 37, Middlebury

Listing courtesy of Leon Kramer from Bright Star Real Estate Services LLC. office: 574-821-7653
$89,900
202609839 MLS ⋅ Nicolas Wyse
One of the last remaining building sites in Cedar Creek—and truly an exceptional opportunity. This nearly 1.5-acre parcel offers an ideal setting for a walkout basement, with topography and layout that lend themselves perfectly to your future build. Located at the rear of the subdivision, the property provides a sense of privacy while still being part of an established community. A rare chance to secure a premium homesite in a highly desirable location in Middlebury.

55902 Little Creek Ln, Middlebury

Listing courtesy of Nicolas Wyse from RE/MAX Results. Office: 574-533-9581
$617,500
4 Beds ⋅ 3 Baths ⋅ 202626923 MLS ⋅ 2,571 SqFt. ⋅ Steve Miller
**Lakefront on 3.67 Acres – Hunter Lake!** One-owner home in popular Middlebury schools. 4 bed, 2.5 bath with wood-burning fireplace in the family room. Appliances just 2 years old. Unfinished walk-out basement is a blank slate. Enjoy lake views from the private backyard, 12x20 porch, and screened lakeside gazebo. 24x30 barn with horse stalls. Lakefront + acreage + top schools — a rare find!

10416 State Road 120, Middlebury

Listing courtesy of Steve Miller from RE/MAX Results. Office: 574-533-9581
$575,000
5 Beds ⋅ 3 Baths ⋅ 202621264 MLS ⋅ 2,584 SqFt. ⋅ Nicolas Wyse
Brand-new construction featuring 4-5 Bedrooms, 3 Full Bathrooms, and a desirable split-bedroom floor plan. The open-concept living area offers plenty of room to gather, while the upstairs bonus space provides flexibility for a home office, recreation room, hobby area, or additional living space. The kitchen comes complete with a full appliance package, and additional upgrades include a water softener and on-demand hot water heater. Enjoy low-maintenance living with slab construction, plus a covered front porch and an oversized covered rear patio overlooking neighboring woods for a peaceful and private setting. Move-in ready with modern finishes throughout.

13120 Bear Creek Ct, Middlebury

Listing courtesy of Nicolas Wyse from RE/MAX Results. Office: 574-533-9581
$4,999,900
6 Beds ⋅ 7 Baths ⋅ 202614607 MLS ⋅ 12,367 SqFt. ⋅ Stephen Smith
Set on over 38 private acres in Middleburry, this remarkable 2018 Fireside Homes estate offers more than 12,000 sq ft of thoughtfully designed living space, combining luxury, privacy, and exceptional craftsmanship. A gated entrance opens to a long drive filled with natural beauty and wildlife. Inside, the home showcases extensive custom hardwoods and cabinetry, along with a fully integrated smart home system that seamlessly manages lighting, security, and entertainment. At the heart of the home, the commercial-grade chef's kitchen stands out with its custom Italian design, premium Gaggenau appliances, multiple ovens, dual dishwashers, built-in espresso system, and an oversized hidden pantry for added function and storage. The main level study offers a refined workspace with rich cherry paneling, herringbone flooring, and a private reading loft accessed by a hidden spiral staircase, exclusively reachable from the study or the primary suite. The main floor primary suite is designed as a true retreat, featuring vaulted ceilings, a two-sided fireplace, private sitting area with deck, and a spa-like bath with heated flooring, walk-in shower, and a walk-in closet with ample storage. The lower level is built for entertaining, with a custom bar, temperature-controlled wine cellar and tasting room, and a spacious gathering area designed for watching sporting events or hosting guests. A dedicated movie theater with professional-grade acoustics, luxury seating, and high-end projection creates an immersive experience. Outdoor living is equally impressive, with multiple covered decks/patios and a fully equipped grilling area. A private spa retreat set within the woods features a sauna, cold plunge, and a wood-fired hot tub, creating a resort-like experience just steps from home. This is only a glimpse into the level of detail and design that truly defines this extraordinary estate. Schedule your private showing to fully experience everything this remarkable property has to offer!

54420 County Road 33rd Rd, Middlebury

Listing courtesy of Stephen Smith from Irish Realty. steve.smith@irishrealty.net
$1,390,000
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
$349,000
3 Beds ⋅ 3 Baths ⋅ 202624968 MLS ⋅ 1,970 SqFt. ⋅ Carlos Avelar
Modern style meets everyday comfort in this beautifully refreshed home. Step inside to a bright, airy foyer and discover luxury vinyl plank flooring that flows throughout most of the main level. The open-concept design creates a seamless connection between the living spaces, perfect for both entertaining and daily life. The stunning kitchen features crisp white cabinetry with crown molding, stainless steel appliances, and a spacious center island that serves as the heart of the home—ideal for meal prep, casual dining, and gathering with friends and family. Just beyond, the inviting living room offers plenty of space to unwind, highlighted by a cozy gas fireplace and abundant natural light. Upstairs, the spacious primary suite provides a private retreat complete with an en-suite bath and a large walk-in closet. The finished basement expands your living options with a flexible bonus room featuring an egress window—perfect for a home office, gym, guest space, or potential fourth bedroom—plus a generous recreation room with a second fireplace for the ultimate movie nights and game-day gatherings. With its clean lines, neutral palette, and move-in-ready appeal, this home offers the perfect blend of style, function, and versatility. Schedule your private showing today and experience it for yourself. The sale of this property is subject to Seller find suitable property to move!

12853 King Fish Ct, Middlebury

Listing courtesy of Carlos Avelar from Fenix Realty, LLC. Cell: 574-849-9022

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.