$319,000
 $1,712 est/mo Sourced by Back At You

59 Highland Street,Brattleboro, VT 05301

Brattleboro, VT 05301

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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!

Details

MLS #5109552
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
Status(30) Under Contract - Pending
Year1876
Days On Site27
Listing Provided ByBrattleboro Area Realty | Rebecca Seymour

Features

Garage1
BasementY
Story(s)2
Units2
ZoningRes
Acreage0.29

Interior

CoolingNone
HeatingForced Air
AppliancesElectric Water Heater

Exterior

Exterior FeaturesGarden, Natural Shade, Covered Porch
RoofMembrane, Slate
Construction MaterialsWood Siding
Foundation DetailsBrick/Mortar, Fieldstone
Lot FeaturesSidewalks, Near Shopping, Neighborhood, Near Public Transit, Near Hospital, Near School(s)

Parking

Garage Yes / NoYes
Parking FeaturesDetached, Driveway, Garage

Utilities

UtilitiesCable at Site, Propane
Electric100 Amp Service
SewerPublic

Taxes

Tax Annual Amount5800
Tax Year2025

Area Information

StateVT
CountyWindham
CityBrattleboro
Zip Code05301
AreaVT Windham
School DistrictWindham Southeast
Elementary SchoolBrattleboro Elem Schools
High SchoolBrattleboro High School
Listing VS Median (in 05301)
Price:
$319,000
low | high
Med:
$899,800
100% of Average
On site:
27
low | high
Med:
485
5.567010309278% of Average
Sourced by Back At You

Market Activity 05301

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Learn More About This Property

StateVT
CountyWindham
CityBrattleboro
Zip Code05301
AreaVT Windham
School DistrictWindham Southeast
Elementary SchoolBrattleboro Elem Schools
High SchoolBrattleboro High School
Listing VS Median (in 05301)
Price:
$319,000
low | high
Med:
$899,800
100% of Average
On site:
27
low | high
Med:
485
5.567010309278% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $239K - $398K
sqft: 0 - 0
Nearby Listings Property ImageNearby Listings Details
59 Highland Street Property Photo 1
$319,000
59 Highland Street
Brattleboro, VT 05301
Listing Updated: October 5, 2026 at 10:22:36 AM PDT