Middlebury Vermont Real Estate

Welcome home to this well-maintained Skyline mobile home offering comfortable, convenient living with thoughtful accessibility features. The property features a paved driveway for easy parking and access, along with handicap-accessible features designed to make everyday living more comfortable and convenient.With a practical layout and welcoming living spaces, this home offers an excellent opportunity for anyone looking for affordable, low-maintenance living. The paved driveway provides easy year-round access, while the accessibility features add valuable convenience for a variety of buyers. Come take a look and see all this home has to offer!
Exceptional redevelopment opportunity in East Middlebury for either commercial or residential uses. Bring your vision to life at 51 Ossie Road, a unique property with a long-standing history as the home of Otter East Bakery. For decades, this well-known location served as a successful food production facility, making it an excellent opportunity for entrepreneurs, investors, or business owners looking to establish or expand their operations. Situated on 0.29 acres in the heart of East Middlebury, the 2,088-square-foot building is connected to municipal water and serviced by an on-site septic system. The property also offers ample parking, a charming yard with mature apple trees, and would make a wonderful primary residence or residential rental property. Following a recent fire, the building has been fully gutted, creating a blank canvas for redevelopment into a home or rental property. Whether you’re looking to restore the existing structure, customize the space to meet your needs, or pursue a complete build-to-suit project, this property offers outstanding potential. Available as-is or as a build-to-suit opportunity, 51 Ossie Road is a rare chance to create a space tailored to your vision in a highly visible and established East Middlebury location. Property Highlights: Former home of the renowned Otter East Bakery Decades of established food production use 2,088 SF commercial building 0.29-acre lot Municipal water and on-site septic Ample on-site parking Attractive yard with mature apple trees
Welcome to this well-maintained home offering comfortable one-level living on 1.4 wooded acres in a peaceful country setting. With over 1,800 square feet of living space, this 3-bedroom, 2-bath home features a spacious layout with generously sized rooms and plenty of opportunity to make it your own. The primary suite offers a private bath and ample closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Surrounded by mature trees, the property offers a peaceful setting with space to enjoy the outdoors, whether gardening, relaxing, or simply appreciating the privacy of the wooded landscape. Whether you're a first-time homebuyer, looking to downsize, or searching for an affordable property with room to personalize over time, this home presents an excellent opportunity with all that Middlebury has to offer. Conveniently located just minutes from downtown Middlebury, shopping, dining, Middlebury College, and outdoor recreation. Don't miss your chance to make this property your own. Schedule your showing today!
This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with ¾ bathroom. Upstairs, you'll find three additional bedrooms, along with a bonus room that was previously used as a laundry room and still retains its hookups. The electrical system has been updated, and a new hot water tank was installed in 2024. Perched above the road on the edge of Buttolph Acres, this corner-lot property features a welcoming front porch and a spacious fenced side yard. Sidewalks right outside the front door lead all the way to Middlebury's public schools and provide convenient access to downtown shops, restaurants, and amenities. This is a rare chance to own a classic Middlebury home at a price point that leaves room to make it your own. Comfortable to live in while you make improvements, the home offers tremendous potential for buyers with vision. Whether you're searching for your next home, your next project, or an investment opportunity, this property invites you to breathe new life into a classic home in one of Middlebury's most convenient areas. The zoning may provide added flexibility for certain residential, office, service, or lodging uses, creating even more possibilities for future owners - buyers are encouraged to explore this further.
Set on a picturesque 1.1-acre corner lot with a country feel, this beautifully maintained 1800s home offers the perfect blend of historic character, thoughtful updates, and exceptional versatility. The spacious, renovated eat-in kitchen serves as the heart of the home, featuring custom cabinetry, stainless-steel appliances, and plenty of room for gathering. The first floor also offers a generous living room with a wood stove and direct access to the backyard. A full bathroom with laundry hookups and a den with a fireplace complete the main level. Recently remodeled, the den could easily serve as a home office, formal sitting room, or playroom. Upstairs, you’ll find three bedrooms, including a spacious primary bedroom with an adjoining bonus room already equipped with plumbing beneath the floor. This flexible space offers the opportunity to create a dream walk-in closet, private nursery, home office, or future en suite bathroom. A second laundry area and three-quarter bathroom complete the upper level. Major improvements completed within the past eight years include a new roof, water heater, front deck, and extensive landscaping that has transformed the yard into a more functional outdoor space. The possibilities continue with an impressive collection of outbuildings. The attached garage offers space for three or more vehicles while still leaving room for storage or a workshop. A detached one-car garage and an additional barn with room for two more vehicles, multiple storage areas, hobby space, or potential home-business use provide incredible flexibility. Enjoy a country setting while remaining only 10 minutes from Middlebury College, Porter Medical Center, downtown Middlebury, local restaurants, shops, schools, and everyday amenities. Whether you’re looking for room to grow, space to work from home, extensive garage and workshop space, or a historic Middlebury property with endless potential, this one-of-a-kind home is ready to welcome its next owners.
Welcome to your next home,10 Case Street, a charming 3-bedroom, 2-bath home dating back to 1840. Filled with character and warmth, this home features beautiful wood floors and the timeless appeal of an older Vermont property. Outside, there is plenty of garden space to create your own outdoor retreat, whether you envision flower gardens, vegetables, entertaining areas, or simply a peaceful place to enjoy the seasons. Conveniently located in East Middlebury, this home is just a short distance from the post office, gas station, and the historic Waybury Inn, making everyday errands and local amenities easily accessible. Enjoy the close-knit feel of East Middlebury while being just minutes from everything Middlebury has to offer. A wonderful opportunity to own a historic Vermont home with character, usable outdoor space, and a convenient location!
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled using mini-split technology and will include a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, a laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details!
The Middlebury River is your backyard! Lovingly held by the same family for 60 years, this rambling Cape sits on a level, south-facing acre with approximately 140 feet of river frontage. Enjoy the soothing sounds of the river, mature shade, and a welcoming, walkable community. The front deck offers another spot to relax outdoors. The easily accessible main level features approximately 2,000 square feet, including a sunny kitchen with a newer quartz-topped island, cooktop, and dishwasher, plus a charming pantry with sink, refrigerator, and workspace. The kitchen opens to a dining room with built-ins. The living room features wide pine floors and a newer glass-front woodstove. Two spacious bedrooms, a renovated primary bath with walk-in shower, a second full bath, laundry, office, and sewing room complete the main floor. Upstairs, two additional rooms await updating and offer possibilities for bedrooms, studio space, or storage. The attached two-car garage includes additional space for hobbies or a workshop. Updates include a newer roof, windows, Buderus boiler, and circuit breakers. Conveniently located across from the Sarah Partridge Library, tennis courts, and recreation park, and within walking distance of the historic Waybury Inn and a convenience store. A special opportunity to enjoy riverside living with village amenities close at hand!The generous one-acre lot may offer potential for subdivision, subject to official town approval and all applicable requirements.
This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck, the perfect place to entertain, relax, and take in views of your own private slice of Vermont. Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings. The spacious home is conveniently located just minutes from Middlebury College, Porter Medical Center, and the Middlebury Natural Foods Co-op, while Burlington International Airport is only 52 minutes away. The oversized two-car garage provides ample room for vehicles, hobbies, and storage, with an additional separate workshop or storage area located at the rear. Outdoor enthusiasts will also appreciate the home's close proximity to several walking trails and recreation opportunities.
Set on 10 private acres, this charming log home offers the perfect balance of privacy, open lawn, and wooded surroundings, creating a peaceful Vermont retreat just 10 minutes from downtown Middlebury. Inside, the warm wood interior, high ceilings, and skylights fill the home with an abundance of natural light, creating a bright and inviting atmosphere throughout. The open-concept living room, dining area, and kitchen flow seamlessly together, making the home ideal for both everyday living and entertaining. With two bedrooms one on each level, and a three-quarter bathroom on each floor, the thoughtfully designed layout provides privacy and convenience. First-floor laundry is tucked neatly into the bathroom, while the spacious landing at the top of the stairs offers flexible space for a home office, reading nook, workout area, or hobby room. The full insulated basement provides exceptional storage with the potential to suit a variety of future needs. Outside, the property features a beautiful mix of open land and woods, offering endless opportunities for gardening, recreation, hobby farming, or simply enjoying Vermont's natural beauty. A classic barn adds both character and practical storage, while the large covered front porch and concrete patio create the perfect spaces to relax, entertain, or take in the peaceful surroundings. Combining rustic charm with everyday functionality, this inviting property offers the privacy of country living while remaining just minutes from the shops, restaurants, and amenities of downtown Middlebury.
Located in the heart of Middlebury, this home has been thoughtfully updated and improved upon by the current owners, turn-key ready for its next owner. This is a ranch style home, perfect for single-floor living. With new Quartz kitchen countertops, new appliances, new kitchen sink, and new flooring, the kitchen that once was divided by a wall now generously opens up to the living room, where a wood burning fireplace invites cozy nights. New insulation in the living room wall keeps the house warm, while a new mini-split allows cooler summers. A sweet sunroom has been finished to be year-round space with new energy efficient windows, insulation, walls and floors, and will be your favorite spot to hang out. The sunroom overlooks the spacious backyard, privately enclosed by evergreens. Down the hall are three bedrooms, all complete with new flooring. New lighting fixtures and new ceilings to eliminate popcorn were installed throughout the first floor. A full bath has two sinks, a bathtub, and stone tile detailing. Laundry is conveniently on the same floor. The finished lower level is perfect for games, office space, or additional family room. A 1/2 bath on this floor is handy, and a laundry hook-up is available. Located in the sought after Buttolph acres neighborhood, the half an acre lot allows plenty of space for gardening, pets, and outdoor enjoyment. You can easily walk to grocery stores, recreational facilities, multiple TAM trails, shops and all that Middlebury has to offer!
Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Qualified pricing - check with your agent to see if you qualify! Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
This 4 bedroom, 2 bath cape is tucked into a nice, quiet Middlebury neighborhood. It's been lovingly cared for by the same family since the beginning, with many upgrades over the years including a huge primary suite over the garage. The upstairs bedrooms are all spacious and inviting, with an additional bedroom on the 1st floor. The briight living room is open to the dining room, with a glass door leading to the back deck, the perfetct place for morning coffee or bbq's. Enjoy the tranquility of this home, and also the convenience being only a few mins from town.
Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple possiblities such as a home based occupation or bed and breakfast. With a total of 5 bedrooms, 5 bathrooms and over 3600 finished square feet, there is so much opportunity to personalize a layout that best suits your wants and needs. The rear of the home is part of a newer addition that includes a 1 bedroom apartment with 3/4 bathroom, living room and office. Adjacent to the apartment is a 2 car garage that was also part of this addition. Above both is a large timber frame family or primary bedroom with vaulted ceilings, custom built ins, and a 3/4 bathroom. The property is priced well below recent appraisal at just over $150/square foot to enable the new owner to create their own vision of this historic home with exterior updates. Conveniently walkable to all of Middlebury's downtown offerings. Imagine village living at its best!
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled using mini-split technology and will include a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, a laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details!
Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills the air as you relax on your porch or savor a warm summer evening by the firepit. This classic Vermont farmhouse has been beautifully updated inside with a gorgeous custom kitchen complete with high end appliances that are a work of art. A 48" Italian gas range, Big Chill fridge and a handmade Moroccan brass faucet are just a few of the details! Custom cabinetry includes a bespoke island that is the center of the chef's domain. Throughout the home thoughtful design choices are around every corner. With an acceptable offer, the house can be sold mostly furnished! Wood floors throughout, and natural light is in abundance. A first floor bedroom and fully remodeled bath make one level living possible. The living and dining rooms feature built in cabinetry, and a wood burning fireplace is a focal point in the living room for cozy nights. Three additional bedrooms and another fully remodeled bath are upstairs, along with an office and large laundry room with hand stenciled floors. An attached sunporch is on the back of the home, with a cool bar for an amazing entertaining space. Walk outside and the magic begins there. Mature plantings, fruit trees, berry bushes, and open lawn space lead you back to the river. Nicely protected with a stone retaining wall, there are steps up and over to a cool riverside sitting area. From here you can cool off, sit and enjoy a cold drink, or just enjoy the soothing sounds of the river. Walking distance to the Waybury Inn for a delicious meal, or walk to the East Middlebury gorge, a beautiful and popular swimming hole. Tennis courts, library and a playground are nearby too! 8 miles (12 minutes) to the Snow Bowl for skiing in the winter. 5 miles (10 minutes) to Lake Dunmore for swimming in the summer. Enjoy the abundant hiking trails in the area as well! ALTHOUGH THIRD PARTY SITES SUCH AS ZILLOW SHOW OTHERWISE, THIS HOUSE IS NOT IN A FLOOD ZONE.
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

© 2026 PrimeMLS. All rights reserved. This information is deemed reliable but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of PrimeMLS. Subject to errors, omissions, prior sale, change or withdrawal without notice.