Properties Near 425 Main Street Bennington, VT

Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great room anchored by an impressive floor-to-ceiling fireplace, with a loft above that overlooks the space and adds architectural interest. The thoughtfully designed layout includes three bedrooms, highlighted by an incredibly spacious primary suite featuring a walk-in closet and a luxurious en suite bath with soaking tub and double vanities. The main level also offers two additional bedrooms, a full bath, and convenient first-floor laundry. A bright breakfast nook provides the perfect spot to start your day, while the back deck overlooks the lush gardens, creating an ideal setting for outdoor entertaining or quiet relaxation. The inviting front sitting porch, complete with a charming fish pond, enhances the home's peaceful appeal. Additional features include an attached oversized two-car garage, a home office, large workshop and sweeping mountain views that complete this exceptional property. A rare opportunity to enjoy privacy, natural beauty, and timeless craftsmanship in one remarkable setting.

Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors, and a low-maintenance lifestyle ideal for year-round enjoyment. The kitchen is appointed with granite countertops and a convenient slider leading directly to the deck-perfect for easy outdoor grilling. The walk-out lower level offers exceptional flexibility, featuring a large family room, cozy library area, cedar closet, and an expansive craft room or office that could easily be converted into an additional bedroom. With its layout and private access, the lower level presents great potential for an in-law apartment. A standout feature is the 10x26 workshop, complete with a dust collection system already in place—ideal for woodworking or hobbyists. The home is equipped with central air, 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. Additional highlights include a partially fenced yard and an attached two-car garage, completing this well-rounded and inviting property.

15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R & D, climate controlled storage, or if you are a service provider company (electrical, plumbing and heating, etc.) in need of more space for at grade storage of inventory, vehicles and offices with easy access it is ideal space to run a service business from. Significant renovations have been completed to the interior 2nd floor of the building. This space is roughly 6,000 sq ft and is a blank slate at present but has been prepped for a residential buildout including plumbing for bathrooms, fire alarm and full sprinkler system, electrical service and other new systems in place. Informal plans have configured 2 to 7 possible apartments in this space depending on size and cost vs. income analysis OR possibly a large in-town owners' residence with skiing, hiking and other year-round outdoor recreational opportunities in the Green Mountain National Forest and Lakes and Rivers within it just a short drive away. Final state and local permits required for finalized development plan. This space combined with the flex space and retail storefronts along main street would be an ideal mixed-use income property. If creating value and optimizing income with creative development of a fantastic building is intriguing, this is an unbelievable and very unique opportunity. At this price point it would be challenging to find another commercial/residential building of this size and condition with this much potential to be solid income property with tremendous equity gain in a very quick timeframe.

A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors lead to a charming screened porch, perfect for relaxing or entertaining. The upper level offers three bedrooms, including a spacious primary suite with a private ensuite bath, as well as an additional full bathroom. A separate first-floor bedroom w/living space is currently being used as an in-law suite with its own private feel, offering excellent potential for guest accommodations, multigenerational living, or possible Airbnb/rental income. Sliding doors open to a stone patio and a semi-wooded backyard offering privacy and seclusion. Additional highlights include a large attached two-car garage, a semi-finished basement with ample storage space, a newer roof and gutters, paved driveway with drainage system, newer garage door, and updated furnace. The major improvements have already been taken care of — simply move in and enjoy. Schedule your showing today!

This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today’s lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a warm and functional space for cooking and gathering. The expansive primary suite is a true retreat, complete with an oversized walk-in shower, double vanity with granite countertop, and abundant space to unwind. Three additional guest bedrooms and a full guest bath provide flexibility for family, guests, or home office needs. The finished attic is perfect for a playroom or creative space and the home offers abundant storage throughout. Step outside to enjoy the brand-new expansive deck overlooking the yard, along with a shed and additional outbuilding for hobbies, gardening, or extra storage. Located in the Clarks Woods neighborhood, this charming home is convenient to the country club, hospital, and other local amenities while offering the comfort of a lovely residential setting. 0.33 acre.