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$319,000
New Listing

59 Highland Street
Brattleboro, VT 05301

Multi Family|Coming Soon
2
Beds
2
Total Baths
1,883
SqFt
$169
/SqFt
1876
Built
County:
Windham
Listing courtesy of Rebecca Seymour of Brattleboro Area Realty
Call Now: (978) 710-9388
Is this the listing for you? We can help make it yours.
(978) 710-9388
59 Highland Street59 Highland Street59 Highland Street59 Highland Street
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Monthly Payment (Est.)

$1,455
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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!

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Listing Snapshot
Price 
$319,000
Days On Site 
0 Days
Bedrooms 
2
Inside Area (SqFt) 
1,883 sqft
Total Baths 
2
Full Baths 
N/A
Partial Baths 
N/A
Lot Size 
0.29 Acres
Year Built 
1876
MLS® Number 
5109552
Status 
Coming Soon
Property Tax 
$5,800
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
6 hours agoListing updated with changes from the MLS®
9 hours agoListing first seen on site
General Features
Acres 
0.29
Foundation 
Brick/Mortar
Garage 
Yes
Garage Spaces 
1
Number Of Stories 
2
Parking 
GravelDetachedDrivewayGarage
Parking Spaces 
1
Property Sub Type 
Multi Family
Sewer 
Public Sewer
SqFt Above 
1883
SqFt Total 
2845
Style 
Victorian
Utilities 
Cable Available
Water Source 
Public
Zoning 
Res
Interior Features
Appliances 
Electric Water Heater
Basement 
ConcreteFinishedFullUnfinishedStorage Space
Electric 
100 Amp Service
Flooring 
VinylWood
Heating 
Forced Air
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Exterior Features
Construction Details 
Wood Siding
Patio And Porch 
Porch
Roof 
SlateMembrane
Community Features
School District 
Windham Southeast
Schools
School District
Windham Southeast
Elementary School
Brattleboro Elem Schools
Middle School
Brattleboro Area Middle School
High School
Brattleboro High School
Listing courtesy of Rebecca Seymour of Brattleboro Area Realty



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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Last checked: 2026-09-13 05:06 AM UTC
Neighborhood & Commute
Source: Walkscore
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