Properties Near 33 Transport Drive Bennington, VT

Restore Properties
Exceptional Commercial Real Estate. This outstanding investment & business opportunity in the heart of historic Bennington, offers a package of two beautifully and totally updated and restored historic 19th century buildings with plenty of style, character, and multiple options. High visibility due to the 8,000-12,000 daily traffic count. Excellent lease income from the famous 100 Pleasant St. deli. 125 North St. contains 2,225 SF on two floors plus attic and full basement, all renovated in 2001. Both buildings are fully air-conditioned and heated with gas. Parking is ideal here thanks to the adjacent municipal parking lot plus on street parking, plus another much larger public parking lot across North St. For investors, the income from the existing Deli lease would cover a significant portion of a new acquisition loan and the seller is open to a lease on 125 North St. The parcel cannot be subdivided however the two buildings could be converted to condos and thus one or both buildings could be sold separately. Bennington is the anchor for the southwest side of Vermont, bordering Massachusetts to the south and NY to the east. Home of Bennington College and the Southwestern Vermont Medical Center, multiple small manufacturing businesses, and a busy commercial center. These two excellent turn-key buildings in a prime location offered for the first time in over 50 years will fit the ideal needs and goals of an enterprising entrepreneur investor.
Here's your chance to own a high visibility valuable piece of commercial property on bustling Northside Drive. This unique opportunity includes four separate buildings on one parcel, offering strong rental income and incredible flexibility for business or investment use. Whether you're an entrepreneur looking to live where you work, start a new from scratch, or expand your business footprint, this property delivers. The property has it all. A residential unit, a commercial storefront, a business store front, and additional outbuilding ready for use or income. With over 15,000 cars passing by daily, the location offers excellent visibility, ample signage options, and is situated right in the heart of the commercial shopping district. This is where the community comes to shop, work, and connect making it an ideal place to plant your business roots Don't miss this rare chance to establish yourself in one of the busiest and most sought after commercial areas in our community. Contact us today to schedule your private showing.
Industrial / Commercial Opportunity – 33 Transport Drive, Bennington, VT Outstanding opportunity to acquire a versatile commercial building situated on 4.5 acres in one of Bennington’s established industrial corridors. This property offers functionality, accessibility, and room for expansion, making it ideal for owner-users, contractors, distribution operations, or light industrial businesses. The building features four heated loading docks, providing efficient year-round shipping and receiving capabilities. Additional storage space supports warehouse or operational needs, while the showroom/storefront area offers a professional customer-facing presence. The layout also includes two private offices and a bathroom, creating a practical balance between administrative and operational space. The site is serviced by a paved driveway with ample room for truck maneuverability, equipment storage, or future development. With 4.5 acres, there is significant potential for expansion, outdoor storage, or additional structures (subject to local approvals). Located on Transport Drive, the property benefits from strong accessibility to regional routes and proximity to other commercial and industrial users. This is a rare opportunity to secure a well-located industrial property with loading capacity, land, and flexibility in Bennington’s commercial market.
Located in the heart of the bustling downtown district on Main Street, this versatile, solid built concrete commercial building offers a rare and exciting investment or owner-occupier opportunity. This property is designed for maximum adaptability, featuring a blend of professional and industrial spaces to suit a wide range of business needs. Key Features Include: Professional Space: Dedicated office space and a well-appointed conference room for meetings and collaborative work. Recently renovated with new flooring and breakroom space. Industrial Capacity: A large, easily accessible warehouse space, ideal for storage, production, or logistics. Development Potential: The property holds significant potential for conversion into premium living space, a multi-family residential income component, or a dynamic shared office area on the upper level, offering the highest and best use options adaptable to the new owner's visions. Solid Construction: Built with durable, solid built concrete for lasting quality and peace of mind. Renovation Ready: Layout design is complete for a new kitchen and four modern baths, allowing the new owner to move quickly through the remaining build-out phase. A fantastic location with flexible configurations, this unique commercial asset is ready for its next chapter.
BRING YOUR BUSINESS TO THE HEART OF SHAFTSBURY! Discover an investment opportunity in this prime multi-use commercial opportunity in the heart of Shaftsbury! This historic 1850 building, known as the “Shaftsbury Country Store Building”, offers a unique blend of character, history, and high traffic count. Located on a highly visible stretch of Historic Route 7A, this iconic Vermont landmark has been a central part of the community for over 170 years. The property features ~ 2,800 sq. ft. of updated, versatile commercial space—perfect for a café, gallery, boutique, or office—with excellent visibility. The space features charming historic details and is ready for your business to thrive. In addition to the commercial space, the property includes 2 income-producing rental apartments. The first is a spacious, multi-level unit with 3 bedrooms, a generous living room, a large eat-in kitchen, and bonus areas ideal for a home office or studio—plus breathtaking mountain views from a large private deck. The recently updated front apartment features a sunny, open-concept layout with 3 bedrooms, perfect for tenants seeking comfort and convenience. Both apartments feature in-unit laundry. Seize this extraordinary opportunity to own a piece of Vermont history, combine your business ambitions with investment potential, and become part of the Shaftsbury community. Whether you're an entrepreneur or investor, this property offers an opportunity to set down roots and grow. We invite your inquiry

© 2026 Northern New England Real Estate Network, Inc. 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 NNEREN. Subject to errors, omissions, prior sale, change or withdrawal without notice.