A rare opportunity to acquire a fully occupied, well-maintained mixed-use property in one of Chester's most recognizable village locations. The front portion of the building is leased as professional office space for $5,000 per month, with the commercial tenant responsible for heat and electricity. The tenant has expressed interest in entering into a significantly longer-term lease, with the lease length and additional terms to be negotiated directly with the next owner. The property includes four additional residential units, all currently rented, including one leased by the commercial tenant for employee housing. Detailed income, expense, and lease information is available through your agent. Carefully maintained over the years, the building requires no known major upgrades or repairs and is ready for its next owner. More than sufficient parking is available on both sides of the building, along with abundant storage throughout the property, including basement garage space. Its location just off the historic Chester Village Green provides excellent visibility and steady Main Street traffic for commercial use, while remaining comfortable and quiet for residential tenants. Local shops, restaurants, and village amenities are all nearby, and Chester's iconic Swinging Bridge, the Williams River, and its scenic footpath are less than a quarter mile away at the end of School Street. With established tenants, multiple income streams, ample parking and storage, and an outstanding village location, 23 School Street offers an exceptional opportunity to step into a strong-performing property from day one.

Listing Tools

Property Details of 23 School Street

Property Details

Interior Features

Exterior Features

Utilities and Appliances

Other Details

Map Location

Driving Directions

Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 25, 2026 6:37 AM UTC

 

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Brattleboro Area Realty. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.