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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
$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
$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.

$299,900
4 Beds ⋅ 2 Baths ⋅ 202631868 MLS ⋅ 2,055 SqFt. ⋅ David Rogers
NEW PRICE! OPEN HOUSE 8/23, 2-4pm. Stop by and see us! Set on a quiet street in the heart of downtown Middlebury, this beautiful 1900s farmhouse is a well-recognized part of this small community and offers genuine character and charm. Featuring 3-4 bedrooms and 2 full baths, the 2,055 sq/ft of living space is spread across two stories and includes the kind of period details and warmth that modern builds simply don't offer. The sellers have poured their hearts into the outdoor living areas with a new covered patio space that creates a shaded gathering spot and a large, raised garden bed ready for vegetables and flowers. The large & charming front porch invites you to spend slow mornings in a rocking chair with a cup of coffee while watching the world pass by. This property is as practical as it is charming. An oversized 2-car garage, a 20'×30' outbuilding, and generous parking make it an ideal home for a hobbyist, a growing family, or anyone who wants room for tools, toys, and projects. The outbuilding alone offers serious workshop or storage potential. The detached structures and spacious lot add a flexibility most homes in this price range simply don't have. Located in a friendly small town with convenient access to area amenities, this home pairs small-town comfort with real utility. If you value character, outdoor space, and room to spread out, this one is worth a look.

209 Bristol Ave, Middlebury

Listing courtesy of David Rogers from Cressy & Everett- Elkhart. Cell: 574-849-6822
$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
$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
$364,900
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
$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
$425,000
4 Beds ⋅ 6 Baths ⋅ 202619303 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm
Located in the heart of downtown in endearing Middlebury, the possibilities in this home are ENDLESS! The upper two levels were once a Bed & Breakfast, with 4 Bedrooms and 5 baths. The lower level has a separate entrance with entirely separate living quarters! The historic charm exudes in the two upper levels. Rich woodwork, a butlers pantry and the original fireplace provide character that is rare to find! The yard is spacious and backs up to the extremely popular Pumpkinvine Trail, great for walking and biking enthusiasts! This is a rare gem! Don't miss your chance to make it your own! *Property had water in the basement and has been professionally remedied. The flooring has been removed and the seller is offering a $3,000 flooring allowance with an acceptable offer.

435 S Main St, Middlebury

Listing courtesy of Jami Stamm from Coldwell Banker Real Estate Group. Cell: 574-596-4868
$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
$800,000
5 Beds ⋅ 5 Baths ⋅ 202629655 MLS ⋅ 4,908 SqFt. ⋅ Alex Bernth
Welcome to 13283 Cedar Creek Drive, where timeless design, impressive amenities, and exceptional comfort come together. The beautifully landscaped brick exterior leads into a bright and inviting interior highlighted by soaring vaulted ceilings, spacious living areas, and newer flooring throughout much of the home. Major improvements provide added comfort and peace of mind, including a newer roof, updated HVAC system, whole-home generator, and tankless water heater offering endless hot water. A central vacuum system adds another layer of everyday convenience. A dedicated home office provides a quiet place to work, while the exercise room offers flexible space for fitness or hobbies. The finished basement creates the ultimate entertainment retreat, complete with a projector and screen for memorable movie nights at home. Step outside and discover a private backyard with an inground pool, offering the perfect setting for summer gatherings, relaxing afternoons, and evenings spent outdoors. The hot tub may also be negotiated separately. Offering privacy, thoughtful updates, versatile living spaces, and an exceptional collection of amenities, this remarkable Middlebury home is designed for both comfortable everyday living and effortless entertaining.

13283 Cedar Creek Dr, Middlebury

Listing courtesy of Alex Bernth from eXp Realty, LLC.

$1,200,000
6 Beds ⋅ 6 Baths ⋅ 202629033 MLS ⋅ 6,412 SqFt. ⋅ Julie Thatcher
Welcome to this extraordinary custom all-brick estate nestled in the heart of Middlebury's prestigious Highland Woods subdivision. Perched atop the area's rolling hills, this exceptional Town & Country-built residence offers more than 6,000 square feet of beautifully finished living space and has been completely transformed with over $800,000 in luxurious updates completed within the past two years. Step inside the stunning foyer and discover impeccable craftsmanship and designer finishes throughout. The inviting lodge-inspired family room features a striking stone fireplace, while the spectacular custom kitchen is a true showpiece with premium finishes, abundant storage, and a hidden butler's pantry. The adjoining buffet and beverage area makes entertaining effortless, whether hosting holidays in the formal dining room or enjoying casual meals in the bright breakfast area overlooking your private back yard. You will love the spacious mudroom/laundry room. The perfect "drop spot" for coats, or backpacks. The main-level den/office with gorgeous custom woodwork provides the perfect work-from-home space. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and oversized tiled shower. Three additional bedrooms include a Jack-and-Jill bath with a walk-in shower and a third full bath with tub. The lower level is designed for entertaining with a custom kitchen, stone accents, a spacious family room with a second fireplace, bar area, two additional bedrooms, a fourth full bath, and a stunning wine room where fireside entertaining is at your fingertips for game nights, gatherings, or relaxing with friends. Outside, enjoy a private backyard surrounded by mature trees and abundant wildlife, along with a newly constructed deck ideal for outdoor living and entertaining. Beyond its beautiful finishes, this home offers peace of mind with new roof, windows, updated mechanicals, and a heated three-car attached garage. Every detail has been thoughtfully updated, and nothing has been overlooked. This is a rare opportunity to own one of Middlebury's finest homes.

205 Greenfield Dr, Middlebury

Listing courtesy of Julie Thatcher from Coldwell Banker Real Estate Group.

$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
$374,900
3 Beds ⋅ 1 Baths ⋅ 202622865 MLS ⋅ 1,990 SqFt. ⋅ Joshua Lenker
**OPEN HOUSE Sunday, September 13th 2-4PM** Peace is all you will think of at this home. Nestled on 1 acre in the desirable Middlebury area, this 3-bedroom, 1-bath retreat offers a perfect blend of comfort, privacy, and potential. Just seconds from Stone Lake, the property is currently a successful Airbnb and a proven income-producing opportunity. It is ideal as a full-time residence, weekend getaway, or investment. Inside, the layout includes a unique catwalk connecting the upstairs bedrooms, offering an open view that overlooks the living room below and adds character to the space. The property also features a brand-new well. Unwind on the covered porch, enjoy cozy evenings around the fire pit, and take advantage of the attached garage. Surrounded by nature in a peaceful, quiet setting, yet still close to all that Middlebury has to offer. This home is a rare find.

10281 County Road 4, Middlebury

Listing courtesy of Joshua Lenker from McKinnies Realty, LLC Elkhart. Cell: 574-215-4959
$695,000
4 Beds ⋅ 2 Baths ⋅ 202618544 MLS ⋅ 3,052 SqFt. ⋅ Leon Kramer
Here's an opportunity to own a versatile country property featuring two homes, a barn, and approximately 3 acres of pasture in Middlebury! Ideal for multi-generational living, hobby farming, or income potential. The primary residence offers 4 bedrooms and 2 full baths, a spacious living room with wood-burning fireplace, and a walkout basement complete with kitchenette, den, and additional bedroom. Recent updates include a new roof in 2025. Additional features include a large laundry/washroom, mudroom with sink and closet, and two decks for outdoor enjoyment. The second home includes 4 bedrooms, 1 full bath, and in-floor heat throughout, providing comfortable living or rental potential. Property is well-equipped with energy-efficient systems, including 15 solar panels, 48V system with two 300 Ah batteries, a 16-kW diesel generator backup and natural gas boiler heat. The 48’ x 32’ barn (built in 2020) is ideal for livestock or equestrian use and features 4 box stalls, 5 tie stalls, wash bay, and tack room. The property includes 2 geothermal waterers, a garden shed, apple trees, and raspberry plants. A unique rural property with flexible use and excellent homesteading potential—don’t miss this opportunity! The main home is wired for electricity - seller is willing to restore to NIPSCO power with a good offer.

57051 County Road 33, Middlebury

Listing courtesy of Leon Kramer from Bright Star Real Estate Services LLC. office: 574-821-7653
$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
$425,000
4 Beds ⋅ 5 Baths ⋅ 202629722 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm
Imagine owning a charming home just steps from the heart of one of Northern Indiana's most beloved tourist destinations. Located on historic Main Street in the quaint town of Middlebury, this property offers the ideal setting for a short-term rental, boutique Airbnb, or weekend getaway. The home sits on the Pumpkinvine Nature Trail and is just minutes away from Shipshewana's famous flea market and auctions, the Essenhaus Inn & Restaurant, Amish countryside tours, and endless opportunities for shopping, dining, and outdoor recreation. Whether visitors are coming for a girls' weekend, cycling adventure, Amish country experience, or Notre Dame football weekend, this location places them in the center of it all. Picture cozy gathering spaces, 4 thoughtfully designed bedrooms, and charming outdoor areas where guests can unwind after a day of exploring. With Middlebury's year-round tourism and limited boutique lodging options, this property presents an exciting opportunity to generate income while owning a piece of one of Indiana's most picturesque small towns. Whether you're looking to expand your investment portfolio or create a destination property with lasting appeal, this property offers location, charm, and exceptional Airbnb potential in one of the Midwest's hidden gems. All with a bonus apartment that could be rented!

435 S Main St, Middlebury

Listing courtesy of Jami Stamm from Coldwell Banker Real Estate Group. Cell: 574-596-4868

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.