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59 Highland Street, 
Brattleboro, VT 05301

$319,000


2

Beds


2

Baths


1,883

Sq Ft


Multi-Family

Active

Listed by

Rebecca Seymour

Brattleboro Area Realty

802-257-1335

Last updated:

November 4, 2026, 12:38 PM

MLS#

5109552

Source:

PrimeMLS

About This Home

59 Highland Street

Arguably one of the coolest houses in town! Perched at the top of the hill in one of Brattleboro’s desirable, close-to-town neighborhoods, this mini Victorian is an incredibly special property offering a rare blend of character, charm, 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. Inside, the home is filled with original character, including high ceilings, original wood floors, and great natural light. Currently configured as a two-family property, the first floor offers a 1–2 bedroom apartment that is ready to go, while the second floor features a one-bedroom apartment with unique gothic arched windows. Above it all, the third-floor turret room creates a truly magical bonus space unlike anything you’ll find in an ordinary home. The mature perennial plantings around the home create a beautiful escape all year. The detached garage could be converted for more living space or additional income potential. The property does need exterior maintenance, offering an opportunity for the right buyer to restore this one-of-a-kind home over time. Rent the first floor to generate income while living comfortably on the second floor tackling improvements as your budget and vision allow. With its income potential, flexible layout, exceptional architectural character, and fantastic location, this would be an investment worth making. Restore this magical little Victorian to its former glory and make it your own!

Home Facts

Multi-Family

2 Baths

2 Bedrooms

Built in 1876

Price Summary

319,000

$169 per Sq. Ft.

MLS #:

5109552

Last Updated:

November 4, 2026, 12:38 PM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,883 Sq. Ft.


Structure

Structure

Building Area:

2,845 Sq. Ft.

Year Built:

1876


Lot

Lot Size (Sq. Ft):

12,632


Finances & Disclosures

Finances

Price:

$319,000

Price per Sq. Ft:

$169 per Sq. Ft.

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Copyright 2026 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated November 4, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.