59 Highland StreetBrattleboro, VT 05301MLS Number 5109553

Price: $319,000
Est. Mortgage of $/month
1 Day on Market

Sited at the top of the hill in one of Brattleboros 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 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!!

More Info

Tax Information

Tax Year2025

Location

Building Number59
StreetHighland Street
TownBrattleboro
StateVT
Zip05301
CountyWindham
DistrictBrattleboro School District
Elementary SchoolBrattleboro Elem Schools
Junior HighBrattleboro Area Middle School
High SchoolBrattleboro High School
Flood Zone Y/NNo
Address59 Highland Street

Interior

Room 1 TypeEat-in Kitchen
Room 1 Level1
FloorsVinyl, Wood
Room 2 TypeLiving Room
Room 2 Level1
Room 3 TypeOffice/Study
Room 3 Level1
Room 4 TypeBathroom Full
Room 4 Level1
Room 5 TypeBedroom
Room 5 Level1
Stories3
Room 6 TypeBedroom
Room 6 Level2
Room 7 TypeFamily Room
Room 7 Level2
Room 8 TypeEat-in Kitchen
Room 8 Level2
Room 9 TypeBathroom Full
Room 9 Level2
Room 10 TypeBonus Room
Room 10 Level3

Parking

Parking Spaces1
GarageYes

Building

Year Built1876
Building ConstructionWood Exterior
ConstructionFixer
Property StyleVictorian
Bedrooms2
Bathroom2
Total Baths2
Total Rooms9
Square Feet1,883
APX Unfin Below Grade962
BasementBulkhead, Concrete, Concrete Floor, Full, Insulated, Storage Space
FoundationBrick, Stone

Exterior

Exterior FeaturesGarden Space, Natural Shade, Covered Porch
Exterior Coloryellow
RoofMembrane, Slate

Amenities

PricePerSqFt169.41

Legal

Taxes$5,800
Tax ReductionNo
ZoningRes
Surveyed Y/NUnknown

Rooms

Full Bath2

Basic Information

MLS Number5109553
MLS StatusComing Soon
Virtual TourView Tour
StatusCMS
Property TypeSingle Family
List Price$319,000
Listing Agent NameRebecca Seymour
Broker NameBrattleboro Area Realty

Property

Acreage0.29
Lot DescriptionCurbing, Landscaped, Mountain View, Sidewalks, In Town, Near Shopping, Neighborhood, Near Public Transport, Near Hospital, Near School(s)
AreaVT-Windham
DrivewayGravel
RoadsPublic
Road Frontage94

Utilities

Heat SystemForced Air
WaterPublic
SewerPublic
Electric100 Amp Service
UtilitiesCable at Site

Other

SeasonalNo
Page512
Date Listed09/12/2026

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, non-commercial 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 13, 2026 7:07 AM UTC

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59 Highland StreetBrattleboro, VT 05301MLS Number 5109553

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