Sited at the top of the hill in one of Brattleboros desirable, close to town, neighborhoods, this mini victorian home is arguably one of the coolest houses in town! Offering a perfect blend of character, comfort, and convenience. Located in a quiet, leafy area close to downtown, where you'll find a vibrant arts scene, great restaurants, shops, food coop, train station, and more. The space features high ceilings, original wood floors, and great light. Currently set up as a two family with a 1-2 bedroom on the first floor, a one bedroom on the second floor with unique arched windows, and a turret room encompassing the third floor. One could make this a single family just by removing the second stove, opening doors, and a change of use, plenty of room for everyone! If rental income would be welcome, the detached garage offers possibility for a tiny home. The established perennial gardens are lovely and provide a tranquil retreat. This house does need exterior maintenance but this would be an investment worth making, restore this magical home to its former beauty!!

Property Details

Interior Features

Exterior Features

Utilities and Appliances

Community

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 13, 2026 7:38 AM UTC

Name

Your Email Address

Phone

Message Send me the deed for 59 Highland Street Brattleboro VT 05301 (ID#:5109553)

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

Name

Your Email Address

Phone

Message Send me the survey or tax map for 59 Highland Street Brattleboro VT 05301 (ID#:5109553)

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

Name

Your Email Address

Phone

Message I would like more information for 59 Highland Street Brattleboro VT 05301 (ID#:5109553)

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

Listing Tools