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

4 Beds ⋅ 4 Baths ⋅ 202641153 MLS ⋅ 3,006 SqFt. ⋅ Laurie Ladow

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

13086 Bear Creek Ct, Middlebury

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

$274,900

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!!

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

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.

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

***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!

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

$474,900

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.

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

$279,900

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!

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

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.

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

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.

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

$399,000

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.

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

$425,000

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!

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