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.

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.

This beautifully maintained 1920s building is located in the heart of downtown Bennington. Lovingly cared for and meticulously maintained, 211 School Street is ready for the next entrepreneur, medical professional, or visionary to make it their own. For decades, the main level operated as a successful orthodontic office and its layout still lends itself perfectly to a range of professional or commercial uses. The first floor features a welcoming reception and waiting area, several patient rooms, functional workspaces, a private office, and a convenient 1/2 bath. The thoughtful design makes it ideal for health and wellness practices, boutique businesses, or creative studios. Upstairs, a bright and inviting 2BR/1BA apartment offers additional value and flexibility. Complete with a full kitchen and laundry hookups, the apartment has its own separate entrance making it perfect for owner-occupancy, short-term rental, or steady long-term income. Just a block away from shops, cafés, and restaurants, this property enjoys all the benefits of downtown convenience while being tucked away on a quieter street, ideal for clients seeking discretion or professionals who value a peaceful setting. The building is impeccable with a dry basement and generous parking for clients or tenants. With multiple permitted uses, this is a rare opportunity to live upstairs while running your business below, or to invest in a versatile, income-producing property in Bennington's thriving downtown!

OPEN HOUSE 8/30 from 10am-12pm. Spectacular and unexpected! Originally built in 1920 on the corner of Main & Benmont, moved here in 1987. Stunning details that you don't see in modern buildings today: tin ceilings, oversized windows and thick doors, natural woodwork, and dramatic arches framing the center hall. It's truly breathtaking in person... photos don't do it justice. You'll expect an old stone foundation with dirt floor, but since it was moved downtown in the 80s this beauty was set on a new poured concrete foundation, delivering the best of both worlds: character + good bones. Currently leased to an insurance company, the space offers a turn-key opportunity for a new or existing business to step inside and get right to work. Zoning allows for retail, personal or professional services, lodging, food/drink/entertainment, educational, and place of worship. All furnishings are included. Layout provides three private offices, break/file room, four open concept workspaces and a half bath. Or reimagine as mixed use such as a retail store or studio on the main level with individual offices (co-working) or gorgeous apartment upstairs (to rent or live in yourself). Located directly across from the splashpad and Thompson Stage, enjoy the sounds of laughter and music, or take a short walk to the multitude of awesome eateries downtown. Parking on street or in nearby municipal parking lot. This is an incredible value and opportunity!

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.

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.

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.

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.

Multi-building campus with income today and big 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 work includes new roofs, new gym build-out, updated electric, sprinklers, heating, and fire/smoke systems. Sports facility—1st floor: brand-new full-size basketball/futsal/volleyball courts; lounges and offices; gift shop; multiple locker rooms with showers; trainer room; Fair Play Café and a permitted commercial kitchen (about $50k in equipment); theater/dance area; game/yoga rooms; laundry/maintenance. 2nd floor: large 3BR/2BA apartment, storage/maintenance, and eight former classrooms converted to sleeping areas (~60 beds). 3rd floor: three 1BR coach apartments, players’ lounge, equipment room, and eight additional sleeping rooms (~60 beds) with two 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, and electric; primary suite, two additional bedrooms, second living room, laundry, two additional baths with showers, and finished basement. Keep current income (YMCA, parking, annex) while pursuing concept plans showing up to ~36 apartments across the campus, subject to municipal approvals. Shown by appointment.