Properties Near 442 East Main Street Middlebury, VT

This classic village home is in a great location! Situated on South St., with sidewalks on both sides of the historical street as you head into town. You have no doubt driven by this home and admired its handsome Colonial facade many times. A brand new natural gas boiler has been installed! From the front door you enter into the living room space, with wood floors that continue throughout the home. A pellet stove makes things extra cozy, and built in bookcases line one wall of this space. A den allows for an additional living area, perfect for tv watching. A formal dining room is adjacent to the kitchen which is at the rear of the home, leading to the back yard. An office, 3/4 bathroom and laundry room/pantry round out this floor. Upstairs you will find three bedrooms and an additional 3/4 bath. The large, level lot provides space for your gardens, and is fenced in for privacy and keeping pets safe. Walk to downtown Middlebury for shopping, restaurants, library or the many events that take place all year long! Middlebury College is also within walking distance, so you can enjoy sporting events, walk the trails around the campus or check out the museum, theater or musical performances. Porter Hospital is just down the road as well. In town living at its best!

Spacious East Middlebury Ranch on 1.20 Acres with Mountain Views Set on a generous 1.20-acre lot with a beautiful Green Mountain backdrop, this inviting ranch-style home offers comfort, flexibility, and room to grow. The property includes an attached two-car garage plus a separate detached building—perfect for hobbies, a workshop, or a small business—complete with its own power supply. Home has many new upgrades, new windows, new roof, new siding (concrete James hardy), new heating system VT GAS, new electrical and new deck! Inside, the bright and open living space features a sunny three-season sunroom that flows into the dining area and kitchen. The main level includes a full bathroom, while a convenient half bath is located on the finished lower level. The lower level provides excellent versatility for additional living space, whether you need room for guests, extended family, or recreation. Enjoy the ease of being close to East Middlebury amenities, including a bakery, convenience stores, the post office, and more. Outdoor enthusiasts will appreciate quick access to skiing, hiking, and snowmobiling trails. The expansive yard offers ample space for gardening, play areas, and pets. This spacious lot also offers the potential for subdivision to create an additional building lot, giving buyers even more opportunity. A wonderful chance to enjoy space, comfort, and flexibility in a desirable location.

This inviting home offers a bright, comfortable layout designed for easy everyday living. The main level flows naturally between the kitchen, dining and living spaces, creating a welcoming environment for gatherings or quiet evenings at home. The updated kitchen blends the convenience of modern living with the charm and character of an older home. Upstairs, a large full bath serves the bedroom level, providing both space and functionality. Outside, the fenced-in backyard is ideal for pets, play or gardening. The garage adds valuable storage and parking. Set on a small, manageable lot the property offers quick access to town amenities and is just a short drive to the Middlebury Snow Bowl. The location is ideal for commuting to Rutland or Burlington as well. The sidewalks in front of the house make it easy to enjoy a morning walk or an evening stroll. This home delivers comfort, practicality, and a great location.

Warm and inviting 3 bedroom, 2 bath home with a generous family room and bright, comfortable living room in a peaceful country setting bordering the Green Mountain National Forest. Enjoy a welcoming yard with abundant wildlife and old-growth apple trees just outside your windows. The spacious first-floor primary ensuite features a jetted tub and radiant floor heat. The second floor offers two additional bedrooms and a den for flexible use. Recent updates include a remodeled family room, lighting and electrical upgrades, mudroom with direct garage access, and a fenced-in play yard. Mini homestead potential with a barn, which is currently housing chickens and a fenced garden space ideal for growing your own food, well protected from wildlife. Ample storage with attached garage, barn, and shed. Ideally located minutes to Lake Dunmore, Middlebury, and Brandon with dining, shopping, arts, and recreation nearby. Lovingly maintained and filled with warmth, this home has been a special place for the current owners and is ready to welcome new memories.

Discover this stunning end-unit condominium nestled in one of Middlebury's most charming neighborhoods — where thoughtful updates, effortless living, and a peaceful natural setting come together beautifully. The main level is designed for ease and comfort, featuring an open-concept living and dining area bathed in natural light from expansive windows and sliding doors. Step outside onto your private deck to enjoy the fresh Vermont air, whether basking in the sun or relaxing in the shade beneath a retractable awning. A cozy gas stove anchors the living space, creating a warm and inviting atmosphere year-round. The bright, well-appointed kitchen offers stainless steel appliances, a gas range, and generous counter space — perfect for both everyday meals and entertaining guests. Two spacious bedrooms and a full bathroom complete the main floor, all with no stairs, making for truly convenient single-level living. Downstairs, a finished bonus room provides endless possibilities complemented by an additional ¾ bathroom, in-unit laundry, and abundant storage and workspace. Recent updates include beautiful hardwood floors, fresh paint, and more. Outside, enjoy serene views overlooking a lush lawn framed by mature trees, a detached garage for added convenience, and wonderful outdoor space to call your own. Ideally situated close to downtown Middlebury, top-rated schools, shopping, and world-class outdoor recreation — this one truly has it all. Schedule your showing today!