59 Highland Street, Brattleboro, VT 05301

• 2 baths |
• 2,845 sqft

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!

Listing Status:

Active

Date Added:

September 12, 2026

Data Last Updated:

September 20, 2026 at 7:56AM

Listing Office:

Brattleboro Area Realty : 802-257-1335

Listing Agent:

Rebecca Seymour : 802-257-1335 : rebecca@realtyvermont.com

MLS ID:

5109552

Interior

• Appliances: Electric Water Heater
• Basement: BulkheadConcrete FloorFullInsulatedStorage SpaceUnfinished
• Flooring: VinylWood
• A/C: None
• Heating: Forced Air

Exterior

• General: Garden SpaceNatural ShadeCovered Porch
• Style: Victorian
• Parking: DetachedDrivewayGarage

Construction

• Roofing: MembraneSlate
• General: Wood SidingBrickFieldstone

Location

• Road/Access: Public
• School District: Windham Southeast
• County: Windham

Lot

• Driveway: Gravel
• Zoning: Res

Utilities

• Utilities: Cable at SitePropane
• Water: Public
• Sewer: Public