Properties Near 53 High Street Middlebury, VT

FLEXIBLE ZONING, MIXED USE ALLOWING FOR BOTH RESIDENTIAL OR COMMERCIAL OPPORTUNITY. Welcome to this charming 3-bedroom, 1.5-bathroom split-level home in the heart of Middlebury, VT. Set in a peaceful neighborhood surrounded by trees and well-spaced homes, this property offers both privacy and convenience. Step onto the inviting covered front porch and make your way inside to a cozy living room with beautiful hardwood flooring and a classic brick fireplace. The kitchen features updated appliances, including a stainless steel refrigerator and gas range, plus ample cabinet space. The sunny dining area flows nicely into the spacious back deck—recently painted with brand-new railings—perfect for outdoor meals or relaxing after a long day. Big, airy bedrooms provide plenty of space for rest or work-from-home comfort, all conveniently located near a full bathroom and generous storage. The lower level includes a partially finished room, perfect for a game room, gym, or family hangout, plus a versatile bonus area with direct access to the garage—ideal for snowy Vermont mornings. Outdoor updates include replacement of several fascia boards and newer siding around the chimney. Just steps from the TAM Trail for hiking and dog walks, and within walking distance to popular local restaurants, this home also enjoys easy access to town amenities like grocery stores, shops, and workplaces. A wonderful blend of quiet living with town convenience—this Middlebury gem won’t last long!

Sweet cape with easy access to everything that the wonderful town of Middlebury offers! This house has a good sized living room, first floor bedroom, kitchen and full bath on the main floor. Upstairs are three more rooms PLUS a large landing spot that might be a perfect office or play space. The enclosed porch faces south and is a big enough space for a table and chairs, flower pots or another lounge space! Heating unit (furnace) and hot water tank (on demand) were installed in 2024 by Champlain Valley P&H. If you prefer natural gas, the line is at the house ready for hookup. Basement has a concrete floor and a walkup entry. Small gardens around the house bring a pop of color and are easy maintenance!

Investment Opportunity!! What was once a barn in the early 1900's is now 2 apartments. This property could be converted back to a singe family or remain as is for multi-generational living. It could also be used as a rental or think big and start over and build your dream home. Inside you will find 2 one bedroom apartments and stairs to the top floor which needs renovation. Wonderful views and sunsets from all 3 floors looking West over Middlebury proper and the Adirondacks, for spectacular sunsets! A short distance to groceries and the Co-op and Chipman Hill Park is a few hundred feet away! Lots of beautiful trees were planted above the house by the current owners including 2 walnut trees, pinyon pines and a willow tree. A deck off the back of the house overlooks the back yard where there is enough room for terraced gardening. Bring your imagination and see what this house has to offer in this amazing location in Middlebury!

This quaint two-bedroom, one-bath home is located on 1.6 acres in the picturesque Vermont town of New Haven. The current owner has completed many updates to the home itself as well as the large level lot which offers outdoor space suitable for all manner of outdoor activities. The property includes garden beds, a fire pit area, a brand new shed, and movable chicken coop! The two-bay garage provides additional overhead storage and can be used as a workshop, exercise room, or for vehicle parking. A truly versatile space for all your endeavors! The property is located just a short distance from the Trail Around Middlebury (TAM) for hiking and biking as well as Otter Creek’s Belden Falls for easy water access for fishing, kayaking or canoeing. Just a few minutes drive from Middlebury center and a short trip to Vergennes and Burlington beyond, this property offers both a sense of privacy and convenient access to nearby necessities. In addition, the acreage provides ample opportunities for landscaping projects or outdoor recreation. Mature shade and fruit bearing trees, along with open fields create an inviting atmosphere perfect for gatherings or peaceful solitude. Plenty of space to increase the homestead if desired. Inside, an upgraded entryway sets a welcoming tone for guests arriving at the home and upgrades bring both style and functionality, making it easy to host family dinners or entertain friends. Schedule your showing today and experience this special spot!

You'll have to get your thinking cap on but once you see the views to the West from this property you'll be glad you did. A classic Vermont farmhouse in need of a total renovation/restoration OR a viable building lot with a State of VT wastewater permit in place for a new septic system. Town subdivision has been approved by the Town of Middlebury (had been part of the adjacent farm where they hay and keep some beef cows). Currently, the water line is shared with the farm, a minor permit amendment would be needed to go across the road to the main water line. Existing line from the neighboring barn is not likely viable for long term use.