Bennington Vermont Real Estate

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.

Mixed-use investment opportunity in the heart of downtown Bennington located along North Street near the Four Corners intersection of Routes 7 and 9. The building consists of six total units including two street-level commercial storefronts with strong visibility and four residential apartments above and to the rear (three two-bedroom units and one one-bedroom unit). The property offers a diverse income stream with both commercial and residential tenants and benefits from its location within Bennington’s Downtown (D) zoning district supporting mixed-use development and active commercial frontage. The building extends deep into the lot with rear access and is conveniently located near public parking. Current rents present potential upside through future lease adjustments, operational improvements, or updates over time. Income, expense, and lease information available to qualified buyers.

A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly larger, brighter, and more versatile. Fresh paint, flooring, LED lighting, and a convenient half bath make it easy to imagine anything from a charming shop to a café, office suite, or creative workspace. The basement offers abundant storage with built-in shelving. Second floor features a beautifully renovated 1-bed, 1-bath apartment completed by prior owner about 10 years ago. Use it as an owner’s residence, rental income, or convert for more commercial space. A walk-up attic provides bonus storage or potential expansion. Practical features include separate entrances, separate electric meters, shared boiler and oil tank (both new in 2020), vinyl siding and windows, architectural shingle roof, town water/sewer, and high-speed internet. Parking areas for both units add convenience. Location is unbeatable – North Street is one of Bennington’s most traveled routes, offering excellent visibility and signage. Enjoy gorgeous mountain views and great neighbors like the Blue Benn Diner, Wassick’s Tire, and the Vermont Veterans Home. Bring your ideas — this place is ready for you!

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.

Exceptional mixed-use opportunity in Bennington’s MU-2 District. Sale includes 307 & 307.5 North Street on one 0.70-acre parcel with approximately 150 feet of frontage along North Street (VT Route 7). The front building (approx. 3,446 SF, c. 1840) is currently configured for professional office use with reception, private offices, meeting rooms, kitchen space, and updated mechanical systems. The detached rear structure (approx. 1,200 SF) is a 3BR residence providing supplemental income or on-site occupancy potential. Flexible zoning supports residential, commercial, or mixed-use configurations (subject to approvals).

c. 1913 historic former carriage house offers approximately 5,208 square feet of finished space on 0.63 acre. The property includes three residential apartments and one retail unit, providing multiple income streams and flexible use options. Retaining its early 20th-century character, the building has been adapted for modern functionality. Located in the Downtown District of Bennington, this property offers potential for expansion or further development, subject to local approvals. A distinctive opportunity to own and enhance a part of Bennington’s historic fabric with existing rental income and commercial possibilities.

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.

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.

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.

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.

UNRIVALED OPPORTUNITY! Own a Piece of History and a Profitable Future! Discover a rare and exceptional opportunity to own a storied commercial property and a thriving business in the heart of downtown. For sale is a well-established and profitable printing company, including all equipment, a loyal customer base, and decades of goodwill. The building itself is a landmark, boasting over 12,000 sq ft of versatile space. It has served the community as a beloved vintage roller rink and a bustling grocery store, and is currently home to a prolific printing press. This history provides character and an adaptable layout for multiple uses. Situated on the largest downtown lot available—over an acre of land—this property offers unparalleled potential for expansion or redevelopment. A dedicated loading dock adds crucial functionality for a wide range of commercial operations. This is your chance to secure a turn-key business and a significant piece of downtown real estate with unlimited upside.

Industrial opportunity in North Bennington. This 44,193 SF steel-frame industrial building sits on 1.47 acres along VT-67A (Water Street) in the Village Industrial corridor. Built in 1967 for manufacturing operations, the property offers open warehouse space with approximately 22’ ceiling height, mezzanine office and storage areas, wet sprinkler system, multiple loading docks, slab-on-grade construction, metal siding and roof, and municipal water and sewer. The building formerly operated as a Chemfab / Saint-Gobain manufacturing facility. A comprehensive VTDEC-approved corrective action program was completed in 2023–2024, including asbestos abatement and interior remediation. A Completion Report dated February 29, 2024 confirms corrective action objectives were achieved. Documentation available upon request. Strategically located approximately one mile south of North Bennington Village and one mile north of downtown Bennington, the property provides direct frontage on VT-67A with strong industrial access and regional connectivity. Ideal for warehouse, light manufacturing, distribution, contractor operations, or redevelopment. Limited industrial inventory available in Bennington County. Buyer to verify square footage, zoning, and permitted uses.

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.

Premier commercial development opportunity along Southwestern Vermont’s busiest traffic corridor. This 2.3± acre offering occupies a highly visible corner location at Northside Drive and Harmon Road, directly across from the base of Harwood Hill (VT Route 7A). With approximately 720 feet of combined road frontage, excellent access, and strong daily traffic counts, this site offers exceptional exposure for a wide range of commercial uses. The property consists of four contiguous parcels with five separate addresses, including two vacant lots (former residential structures removed), a commercial building with two operating businesses, and two income-producing residential units—providing immediate cash flow while allowing for future redevelopment or expansion. Current gross annual rental income totals $61,200, derived from a leased feed store ($1,800/month), a hair salon with booth rentals ($1,150/month), a rented three-bedroom farmhouse ($1,200/month), and a single-wide mobile home ($950/month). Located in the Planned Commercial (PC) Zoning District, the property supports a broad mix of commercial and mixed-use development, with 28 permitted uses by Development Review Board approval, including but not limited to retail, restaurant, indoor recreation, daycare, warehouse, gas station, service businesses, and multi-family housing. Town water and sewer are available, and zoning design standards encourage cohesive site planning, shared access, and pedestrian-friendly layouts—ideal for a modern commercial or mixed-use project. This is a rare opportunity to secure a large, flexible assemblage in one of Bennington’s most visible and strategically located commercial corridors, suitable for immediate income generation, phased redevelopment, or long-term investment.

Seller financing available for qualified buyers. Multi-building campus with income today and substantial redevelopment upside. Approx. 56,000 SF, 3-story indoor sports facility + approx. 22,000 SF, four-story 1889 Old Catamount High School + 2,500 SF renovated annex house. Recent upgrades include new roofs, new gym build-out, updated electrical, sprinklers, heating, and fire/smoke systems. Sports facility: 1st floor features brand-new full-size basketball/futsal/volleyball courts, lounges and offices, gift shop, multiple locker rooms with showers, trainer room, Fair Play Café with permitted commercial kitchen (~$50K in equipment), theater/dance area, game/yoga rooms, and laundry/maintenance. 2nd floor offers a 3BR/2BA apartment, storage, and eight converted classrooms (~60 beds). 3rd floor includes three 1BR coach apartments, players’ lounge, equipment room, and eight additional sleeping rooms (~60 beds) with shared bath/shower rooms. Historic school: reception, offices/classrooms, fitness/yoga rooms, locker rooms, two baseball cages, game room, maintenance areas, plus a fourth-floor historic amphitheater and small courts. Annex house (renovated): new kitchen/appliances, plumbing, furnace, electric; primary suite, two additional bedrooms, living room, laundry, and two baths with showers. Keep current income (YMCA, parking, annex) while pursuing concept plans showing up to ~36 apartments, subject to municipal approvals. Shown by appointment.