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59 Highland Street, 
Brattleboro, VT 05301

$319,000


2

Beds


2

Baths


1,883

Sq Ft


Single Family

Active

Listed by

Rebecca Seymour

Brattleboro Area Realty

802-257-1335

Last updated:

September 17, 2026, 10:33 AM

MLS#

5109553

Source:

PrimeMLS

About This Home

59 Highland Street

Sited at the top of the hill in one of Brattleboro's 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 and town assessed 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!!

Home Facts

Single Family

2 Baths

2 Bedrooms

Built in 1876

Price Summary

319,000

$169 per Sq. Ft.

MLS #:

5109553

Last Updated:

September 17, 2026, 10:33 AM

Added:

5 day(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 September 17, 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.