Property Type:
Commercial
Square Footage:
3,725
Lot Size (sq. ft.):
5,227
Status:
Active
Current Price:
$590,000
List Date:
4/20/2026
Last Modified:
4/20/2026
Overview
Description
This remarkable investment opportunity in the heart of the historic town of Bennington offers the future owner two beautifully and totally updated and restored historic 19th century buildings with plenty of style, character, and multiple options. The prominent North St. location stands out to the 8,000-12,000 daily traffic count passing by assuring outstanding visibility. Continue leasing to the existing business or locate a new business or professional office here while also receiving the income from the leased building next door housing a locally famous deli. 125 North St. contains 2,225 SF on two floors plus attic and full basement, all renovated in 2001. Also completely renovated in 2001, 100 Pleasant St. contains 1,500 SF on two floors.
Supplements:
Originally a small barn for what was once the adjacent old firehouse, it is now a very attractive and popular deli with added seating on the front patio and on the second floor. Also, the upstairs includes bathrooms and features a bar making this an ideal space for special events and parties. Both buildings are fully air-conditioned and heated with
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Originally a small barn for what was once the adjacent old firehouse, it is now a very attractive and popular deli with added seating on the front patio and on the second floor. Also, the upstairs includes bathrooms and features a bar making this an ideal space for special events and parties. Both buildings are fully air-conditioned and heated with gas. Parking, a challenge for many other in-town buildings, is ideal here thanks to the municipal parking lot directly across Pleasant St. plus on street parking, plus another much larger public parking lot just off North St. on the opposite side. This means plenty of available parking without the expense of maintaining a parking lot for the owner and businesses here.
For pure investors, the income from the existing lease with Deli will cover a significant portion of a new acquisition loan. In addition, the seller is open to a lease on 125 North St.
The parcel on which the two buildings stand is too small to qualify for subdivision under the zoning regulations however the property could be divided using a condo conversion approach allowing the sale of one or both buildings under a condominium structure of ownership.
Bennington, like its cousin in the south-east side of the state, Brattleboro, is the anchor for the south end 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, Bennington provides a local based
The two separate buildings, dating from the late 19th century, were purchased in 1977 by the current owners and completely renovated and then expanded in 2000. All systems were new as of the renovations in 2000 and later.
This first time offering in over 50 years of two excellent turn-key buildings in a prime location will fit the ideal needs and goals of an enterprising entrepreneur investor.
Last Updated: April - 20 - 2026
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