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Courtesy of Rebecca Seymour of Brattleboro Area Realty: .

59 Highland Street

Brattleboro, VT 05301
  • $319,000
  • STATUS: Pending
  • ON SITE: 33 Days
  • MLS #: 5109552
Pending
UPDATED: 52 min ago
$319,000
  • 2
    BEDS
  • 0.29
    ACRES
  • 2
    BATHS
  • 0
    1/2 BATHS
  • 1,883
    SQFT
  • $169
    $/SQFT
Type:
Multi-Family
Built:
1876
County:
Area:

School Information

Elementary School:
School District:

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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© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2026-10-16T15:06:09.527.
www.livingvermont.com/homes/181147052
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59 Highland Street Brattleboro, VT 05301

  • Price: $319,000
  • Status: Pending
  • On Site: 33 Days
  • Updated: 52 min ago
  • MLS #: 5109552
2
Beds
2
Baths
0
½ Baths
0.29
Acres
1,883
SQFT
$169
$/SQFT
1876
Built
County:
Windham
Area:
Brattleboro
Elementary School:
Brattleboro Elem Schools
Middle School:
Brattleboro Area Middle School
High School:
Brattleboro High School
School District:
Windham Southeast
Property 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!
Exterior Features

Architectural Style Victorian Color yellow Construction Materials Wood Siding Driveway Gravel Exterior Features Garden SpaceNatural ShadeCovered Porch Has Garage Yes Lot Features SidewalksNear ShoppingNeighborhoodNear Public TransportNear HospitalNear School(s) Parking DetachedDrivewayGarage Road Frontage Yes Road Frontage Length 94 Roof MembraneSlate

Interior Features

Basement Access Type Interior Basement Description BulkheadConcrete FloorFullInsulatedStorage SpaceUnfinished Cooling None Flooring VinylWood Foundation BrickFieldstone Has Basement Yes Heating Forced Air Total Heated Units 2 Total Ranges 2 Total Refrigerators 2 Total Water Heaters 2 Unit1 Baths 1 Unit2 Baths 1

Property Features

Construction Status Existing Electric 100 Amp Service Flood Zone No Pre Construction No Road Frontage Type Public Seasonal No Separate Utilities Yes Sewer Public Tax Gross Amount 5800 Tax Year 2025 Taxes Tbd No Total Electric Meters 2 Total Leases 1 Total1 Bed Units 2 Total2 Bed Units 0 Total3 Plus Bed Units 0 Unit1 Rental Amount 2200 Unit1 Tenant Pays All Utilities Unit2 Rental Amount 1800 Unit2 Tenant Pays All Utilities Utilities Cable at SitePropane Water Source Public Zoning Res

Courtesy of Rebecca Seymour of Brattleboro Area Realty: .


© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2026-10-16T15:06:09.527.
 
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553 Roosevelt highway suite 200
Colchester VT, 05446