Middlebury Homes under $350,000

Welcome to Middlebury, Vermont, a picturesque town nestled in the heart of Addison County. Known for its charming New England character, Middlebury boasts a vibrant community, rich history, and stunning natural beauty. With the Green Mountains as a backdrop, this quaint town offers a perfect blend of small-town charm and modern amenities.

Middlebury is home to Middlebury College, which adds a youthful energy to the area, hosting various cultural events, art exhibitions, and outdoor activities throughout the year. The town’s historic downtown area is lined with delightful shops, cafes, and restaurants, making it a wonderful place to explore on foot. Nature enthusiasts will appreciate the abundance of outdoor recreational opportunities, from hiking and biking in the warmer months to skiing and snowshoeing in the winter.

For those looking to call Middlebury home, you’ll be pleased to discover a range of charming homes available for under $350,000. Whether you’re a first-time buyer or seeking a cozy getaway, there are options to suit every lifestyle. From quaint historic homes to modern townhouses, you’ll find properties that reflect the town's unique character and charm.

Living in Middlebury means embracing a community that values both tradition and innovation, where neighbors become friends and the beauty of Vermont is just outside your door. Come explore the possibilities of making this enchanting town your home!

Newest Middlebury Homes under $350,000

$91,000

3 Beds ⋅ 1 Baths ⋅ 5112826 MLS

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!

46 Monarch Ct, Middlebury

$264,000

2 Beds ⋅ 1 Baths ⋅ 5106773 MLS

NEW REDUCED PRICE! MOTIVATED SELLER! TAKE A LOOK TODAY! LET'S MAKE THIS PROPERTY WORK FOR YOU!! You could be all in for under $2k/ month to live in the heart of Middlebury! This is with the estimations of $43/mo. for insurance, $278/mo. for taxes, $160/mo. for the HOA and then your mortgage payment with 20% down. Welcome to 36 Seymour Street, Unit 1, a charming first floor 2-bedroom, 1-bath condo offering 1,024 square feet of comfortable living space in a convenient Middlebury location. Inside, you'll find a functional layout with a spacious kitchen and dining area, hardwood and tile flooring, and the added convenience of first-floor laundry. Two well-sized bedrooms provide flexibility for everyday living, or guests. An additional room could be fit up as a home office, a huge closet or some additional inside storage space. Outside, enjoy a covered porch with privacy fencing, patio, and garden space, while the unfinished basement provides additional room for storage. The low $160 monthly association fee includes landscaping, plowing, and trash removal, helping make day-to-day maintenance a little easier. The location is a standout, offering convenient access to everything Middlebury has to offer. Downtown is home to locally owned shops, restaurants, cafes, a movie theater, library, and other community amenities. Middlebury College adds arts, cultural events, and recreational opportunities to the area, while the Trail Around Middlebury provides miles of trails for walking, running, and biking. With shopping, dining, schools, recreation, and everyday necessities all nearby, this condo offers a great opportunity to enjoy the convenience and character of one of Addison County's most vibrant communities.

36 Seymour St Unit 1, Middlebury

$225,000

5104820 MLS

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

51 Ossie Rd, Middlebury

$173,000

2 Beds ⋅ 2 Baths ⋅ 5103821 MLS

OPPORTUNITY IS KNOCKING! With a little sweat equity, you can unlock the potential of this 2 bedroom, 2 bath condo being sold in an estate sale "As Is." The home features two generously sized bedrooms, a comfortable living room, and a kitchen with an island that overlooks the dining area and opens to the deck. A walk-in pantry, half bath down, and full bath up add convenience. The laundry room is located in the full basement which provides abundant storage and room for multiple uses. This property is an improvement project including flooring, painting, some trim work and heat (boiler not connected). The estate administrator has never occupied the property, so there is limited knowledge of the home. Located conveniently in a desirable college town, this condo is close to the local hospital, schools, shopping, dining, and other everyday conveniences. Although an improvement project, where do you find this price in Middlebury?? You can make this baby shine!!

3 Woodbridge Ln Unit 3, Middlebury

$279,000

3 Beds ⋅ 2 Baths ⋅ 5101809 MLS

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!

76 N Forty Ln, Middlebury

$237,500

3 Beds ⋅ 1 Baths ⋅ 5101704 MLS

Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. This location is ideal for easy access to local shops, restaurants and parks and offers low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating a fresh and inviting space to call home. The three spacious bedrooms provide flexibility for guests or a home office, while the full bath is designed for everyday ease. Step outside to enjoy the newly built back deck, perfect for relaxing with your morning coffee, entertaining friends, or enjoying Vermont's changing seasons. A full basement offers abundant storage space, giving you plenty of room for seasonal gear, hobbies, or extra belongings. Conveniently located just minutes from downtown Middlebury, you'll have easy access to local shops, restaurants, parks, schools, and all the charm this vibrant Vermont community has to offer. With its recent updates, generous storage, and excellent location, this condo is a wonderful opportunity to enjoy comfortable living in the heart of Addison County.

11 Ledgewood Ct, Middlebury

$280,000

4 Beds ⋅ 2 Baths ⋅ 5099999 MLS

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.

89 Court St, Middlebury

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