Brattleboro, VT | 59 Highland Street

Christie's International Real Estate
$319,000
MLS#: 5109552
2
# of Units
1,883
Total Sq Ft
0.29
Acres
$5,800
Taxes
General Property Information
Property Status
Active
Price
$319, 000
Property Type
Multi-Family
County
VT-Windham
Agency / Brokerage
Rebecca Seymour
Brattleboro Area Realty
List Date
9/11/2026 8:00 PM
Acres
0.29
# of Units
2

Description

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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Town Market Snapshot

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Features
# of Units
2
Year Built
1876
Parking
Detached, Driveway, Garage
Road Frontage
94
# of Electric Meters
2
Sq Ft (Above Ground)
1,883
Sq Ft (Below Ground)
0
Total Sq Ft
1,883
Land Description
Sidewalks, Near Shopping, Neighborhood, Near Public Transport, Near Hospital, Near School(s)
Elementary School
Brattleboro Elem Schools
Middle School
Brattleboro Area Middle School
High School
Brattleboro High School
Taxes
$5,800
Unit Information

Unit 1

# Rooms
5
# Bedrooms
1
# Baths
1
Sq. Ft.
0
Floor
1
Monthly Rent
$2,200

Unit 2

# Rooms
4
# Bedrooms
1
# Baths
1
Sq. Ft.
0
Floor
2/3
Monthly Rent
$1,800

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