Bennington Vermont Real Estate

It's time to retire! Do you want to take over this cornerstone shop, the largest independently-owned art supply store in Vermont? Steeped in history and brimming with character, Jay's Art Shop & Frame Gallery presents a rare opportunity to own a piece of Bennington's rich heritage. Established in 1972, this beloved local institution has been a fixture of the community for over 50 years. Nestled within the walls of the beautifully preserved Drysdale building that dates back to 1865 and boasts approximately 5000 square feet of retail space, plus the same in basement storage. Jay's Art Shop & Frame Gallery offers a delightful combination of historical charm and modern convenience. Ample retail space with flexible layout options: Original wooden floors that showcase the building's history Captivating storefront windows, perfect for showcasing unique art pieces and merchandise. Off-street parking with an adjacent lot for customers As you step inside, you're greeted by an inviting and well-organized interior that houses an impressive collection of art supplies, custom framing services, clothing, greeting cards, and more. The store's 10 distinct departments offer something for everyone, making it a go-to destination for locals and tourists alike. This exceptional business is within walking distance of a myriad of local shops, ensuring a steady stream of foot traffic. Don't miss this opportunity to own a cherished piece of Bennington history. *This is a business listing only*

Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a prime spot to establish or expand your business. Upstairs, you’ll find a generously sized 2-3 bedroom, 1 bathroom apartment spanning approximately 1,250 square feet. Whether you choose to live above your business or rent it out for additional income, the upper-level unit offers comfort and flexibility with plenty of natural light and charm. This property is perfect for an entrepreneur looking to live and work in the same location or an investor seeking strong rental potential in a vibrant downtown setting.

Step into Bennington’s past with the Norton-Fenton House, a distinguished Greek Revival building located at 206–208 Pleasant Street in the heart of the Downtown Historic District. Built in 1838, this stately structure was originally constructed as a double home for Judge Luman Norton and his daughter and son-in-law. The Norton family was deeply involved in Bennington’s celebrated pottery industry, and their legacy is woven into the fabric of the town’s history. Over the years, this building has served many purposes, most recently as the longtime home of Heritage Family Credit Union. Today, it offers over 6,200 square feet of flexible space, ideal for continued commercial use, adaptive reuse, or mixed-use redevelopment. Its tall windows, symmetrical façade, and classic proportions exemplify the elegance of Greek Revival architecture, while its solid construction and historic charm make it a standout in the downtown landscape. Perfectly situated just steps from Main Street, the property is surrounded by restaurants, shops, galleries, and civic amenities. It benefits from high visibility, steady foot traffic, and easy access to public parking. As a contributing structure in Bennington’s Downtown Historic District, the Norton-Fenton House may also be eligible for historic preservation tax credits and incentives.

Located in the heart of downtown Bennington VT sits this 15,000 plus sq. ft. commercial/office/retail building. This versatile building is able to conform to many uses and configurations. Currently there are two anchor tenants on the main level street front retail spaces and a large open warehouse in the back with its own access from a back (Union Street) that is approx. 4,000 sq. ft. with overhead door and other access for deliveries/ parking. This space has 3-phase power, tall ceilings and a ton of potential including indoor parking if the second floor was to be built out into residential units. Significant renovations have been completed to the interior and exterior of the building. The fire suppression system and alarm has been completely redone, the electrical system is new to the second floor, heating system upgrades, on demand HW system upgrades, electrical upgrades, membrane roofing and much more. The second floor could add a tremendous residential income component to the property and could result in a very attractive CAP rate. It is prepped with HVAC ducts, wiring, plumbing and is sprinkled. This space could also be utilized as professional office space. A beautiful building in great condition in a fantastic location with highest and best use options that are adaptable to the new owner's visions.

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.

738 sqft. restaurant building and a 384 sqft indoor dining space on approximately .75 acres at 100 Depot Street, Bennington VT. Located in the heart of Downtown Bennington and in the Opportunity Zone, this property has great redevelopment potential. Prominent corner lot with Town water and sewer. Adjacent lot to the North is also available (MLS: 4968625).

Great opportunity to own this highly visible piece of commercial property! Commercial expansion is happening all around this property and traffic patterns consistently pass by.

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.

Welcome to The Eddington House Inn – a quintessential country Bed & Breakfast nestled in the heart of the charming Village of North Bennington. This inviting property offers the perfect blend of historic character, modern comfort, and endless possibilities. Ideally located within walking distance to Bennington College, the Park McCullough Historic Governor’s Mansion, Lake Paran, and the acclaimed Pangaea restaurant, this location is as convenient as it is picturesque. The front portion of the home is currently operating as the Inn, featuring four well-appointed bedrooms (two with private baths), a cozy living room ideal for reading or relaxing, and a welcoming kitchen/dining area perfect for gathering guests. Attached to the Inn is a converted barn that serves as the owner's private quarters. This spacious and sunlit space includes two bedrooms, one bath, soaring ceilings, and stunning mountain views. A versatile shop/storage/studio area connects the two dwellings and can be customized to suit your needs—yet each space also enjoys its own private entrance for flexibility and privacy. This unique property offers multiple use options: Continue operating a successful B&B with owner's residence Make the Inn your private home and rent out the barn Create a multi-generational family retreat Offered fully furnished, the Inn is turnkey ready—ready for your vision and lifestyle. Don't miss this rare opportunity to own a piece of Vermont charm and hospitality.

Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more desirable. On the corner of Bennington's many street festivals and walkable downtown. The main floor is very recognizable as a bank but has been adapted and could meet many possible business solutions. The mezzanine overlooks the main floor and takes in all of the beautiful architecture. The 2nd floor is currently a 4 bedroom, 2 bath residence with well appointed, large spaces. Open a business while living in a lavish residence or use the residence as a rental.The possibilities are endless. A must see property.

Unlock the potential of this fully leased commercial property, situated in the heart of Bennington’s vibrant downtown district. This high-visibility building boasts a prime location on Main Street, offering consistent business exposure. The turnkey property features three well-maintained units, all currently occupied by established tenants, ample on-site parking and proximity to local attractions make this property an attractive spot for retail, office, or service-based businesses.

An exceptional opportunity to acquire the historic South Shire Inn, a meticulously restored Victorian property in the heart of Bennington. Originally built in 1887 by renowned architect William C. Bull, this luxury inn blends classic charm with modern amenities, offering a unique, profitable business for discerning buyers. Established and successful, it operates as a turnkey boutique hotel with beautifully appointed guest rooms, many featuring fireplaces, and inviting common areas, combining Victorian elegance with contemporary comfort. The property includes a restaurant leased to a thriving Thai restaurant, serving lunch and dinner, and is newly zoned for additional uses, including a restaurant, bar/lounge, and catering services on the grounds. This makes it an ideal space for further growth and development. The South Shire Inn has a loyal client base, well-maintained operational systems, and rich history, making it a sought-after destination. Located in Bennington, Vermont, between the cultural attractions of Manchester and the artistic offerings of Williamstown and the Berkshires, it’s a prime location for tourists seeking a diverse New England experience. This is a rare opportunity to own a piece of Bennington’s history with a solid foundation for continued success and growth.

126 Elm Street is a distinguished and iconic property in the heart of Bennington. Currently home to Southern Vermont Residential Care, this grand residence was originally built in 1896 and offers over 7,000 square feet of opportunity. Set on a prominent corner lot with mature landscaping, this striking Queen Anne-style home is one of Vermont’s most architecturally celebrated properties. From its sweeping wraparound porch and covered side entry to its turrets, gables, and distinctive slate roof, the home radiates character and history. Inside, you’ll find spacious rooms with high ceilings, ornate oak woodwork, and original tile fireplaces—each space offering its own charm and timeless craftsmanship. The structure includes numerous bedrooms, common rooms, office spaces, and bathrooms. Located just blocks from downtown Bennington, the property is close to local shops, restaurants, cultural venues, and healthcare facilities. As part of Bennington’s Downtown Historic District, the property may qualify for historic preservation tax credits and other incentives.

Exciting investment opportunity located in the PRIME district of Northside Drive in Bennington, Vermont! Family-owned for over 50 years, this gem boasts an excellent location that combines both charm and convenience for travelers. Located strategically to restaurants, stores and easy access to highways leading to ski areas, Manchester outlets, recreational areas to include Prospect Nordic skiing, Mt.Snow, Stratton, Bromley, the Long Trail, golfing, the Harriman Reservoir and so much more. The Knotty Pine Motel offers generous upgrades such as gorgeous concrete stamping surrounding the pool and walkways, pleasing esthetic exterior and thoughtful decorating within each of the 21 rooms. Each room is tastefully decorated while still maintaining the charm and warmth of the original knotty pine walls. There is a lovely separate owners apartment available in the main house lending many options. This beautifully appointed living space can be occupied by owners/managers, marketed as a rental, or included with the motels offering as an additional motel suite. While currently being a successful business, this property also has the ability to be many other commercially zoned businesses to compliment our continuing growth of Bennington's downtown. Northside Drive is on an upward trajectory with many new investors jumping onboard! This is an opportunity that you will not regret!

Mixed use development site on the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.