Listing Details

Brattleboro, VT 05301 59 Highland Street

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Presented By: Rebecca Seymour with Brattleboro Area Realty;
  • PrimeMLS - 85 - NH
  • MLS# 5109552
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Disclaimer: The information contained in this listing has not been verified by Halliday Real Estate and should be verified by the buyer.
  • Beds • 2
  • Baths • 2
  • SQFT • 1,883
  • Garage • 1

Home Details

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!
Presented By: Rebecca Seymour with Brattleboro Area Realty;

Interior Features for 59 Highland Street

Bedrooms

Unit 1 Bedrooms1
Unit 2 Bedrooms1

Bathrooms

Total Full Baths2

Other Interior Features

Unit 1 Lease TermOther
Total Ranges2
Total Refrigerators2
Unit 1 StatusLeased
Unit 2 StatusVacant
InternetHigh Speed Intrnt at Site
Total Finished Area1883
Total Water Heaters2
Total 3+ BR Units
Total 2 BR Units
Total 1 BR Units2
Basement Access TypeInterior
BasementYes
Basement DescriptionBulkhead, Concrete Floor, Full, Insulated, Storage Space, Unfinished
FlooringVinyl, Wood
Total Number of Units2

Other Rooms

Unit 2 Rooms4
Unit 1 Rooms5

General for 59 Highland Street

AppliancesElectric Water Heater
CityBrattleboro
Construction MaterialsWood Siding
CoolingNone
CovenantsNo
DOM4
DirectionsAccess from Washington Street or Central Street. See sign at top of Highland St.
Electric100 Amp Service
Elementary SchoolBrattleboro Elem Schools
Flood ZoneNo
GarageYes
HeatingForced Air
High SchoolBrattleboro High School
Last Updated09/15/2026 15:50:37
Middle SchoolBrattleboro Area Middle School
Price Per Sq Ft Total AG169.41
Property ClassMulti-Family
Property ConditionExisting
Road FrontageYes
RoofMembrane, Slate
School DistrictWindham Southeast
SeasonalNo
Separate UtilitiesYes
SewerPublic
Status Detail0
Stories Count2.5
StyleVictorian
Tax Year2025
Total Heat Units2
Total Rooms Above Ground9
Unit 1 Level Number1
Unit 2 Level Number2/3
UtilitiesCable at Site, Propane
Year Built1876
ZoningRes

Exterior for 59 Highland Street

Coloryellow
DrivewayGravel
Exterior AmenitiesGarden Space, Natural Shade, Covered Porch
Foundation Brick, Fieldstone
Garage Capacity1
Lot FeaturesSidewalks, Near Shopping, Neighborhood, Near Public Transport, Near Hospital, Near School(s)
Lot Size Area0.29
Lot Size Square Feet12632
Parking FeaturesDetached, Driveway, Garage
Road Frontage Length94
Road Frontage TypePublic
SurveyedUnknown
Total Electric Meters2
Water SourcePublic

Additional Details

Price History

Schools

Middle School Brattleboro Area Middle School
High School Brattleboro High School
Elementary School Brattleboro Elem Schools

Sadie Halliday

REALTOR
Price $319,000
MLS#5109552
Property Type Multi-Family
Phone 603.660.2321
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