For Sale
Multi family home for sale at 59 Highland St, Brattleboro, VT 05301 | MLS# 5109552 | Listing updated on 2026-10-27
Photo 1 of Multi family home for sale at 59 Highland St, Brattleboro, VT 05301 | MLS# 5109552 | Listing updated on 2026-10-27
Photo 2 of Multi family home for sale at 59 Highland St, Brattleboro, VT 05301 | MLS# 5109552 | Listing updated on 2026-10-27
Photo 3 of Multi family home for sale at 59 Highland St, Brattleboro, VT 05301 | MLS# 5109552 | Listing updated on 2026-10-27
Photo 4 of Multi family home for sale at 59 Highland St, Brattleboro, VT 05301 | MLS# 5109552 | Listing updated on 2026-10-27
45+
Beds Icon

Street View

Listed by: Rebecca Seymour | Brattleboro Area Realty (802) 257-1335

$319,000

Monthly Est:$1,588

  • Beds Icon-- Bed
  • Beds Icon
    -- Bath
  • Beds Icon1,883sqft

59 Highland St, Brattleboro, VT 05301

$1,588/moEst:

Get Pre-Approved

  • Multi Family

  • Built in 1876

  • $-- HOA

  • 12,632 sqft lot

  • $169/sq.ft

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 on
e-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!

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 27, 2026 at 8:19 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5109552 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Vt Windham County

  • City

    Brattleboro

  • Neighborhood

    --

  • Year Built

    1876

  • HOA Fees

    -

  • Finished Area

    1,883 sqft

  • Lot Size

    12,632 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5109552

  • MLS Status

    (10) Active - Active

  • Days on Market

    51

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedroom: --

    Bathroom: --

Interior

  • Exterior Features

    Garden, Natural Shade, Covered Porch

  • Appliances

    Electric Water Heater

  • Heating

    Forced Air

  • Sewer

    Public

  • Cooling

    None

  • Flooring

    Vinyl, Wood

Construction

  • Year Built

    Year Built: 1876

  • Home type

    Multi Family

  • Roof

    Membrane, Slate

  • Construction Materials

    Wood Siding

  • Foundation Details

    Brick/mortar, Fieldstone

  • Architectural Style

    Victorian

  • Property Condition

    Existing

Utilities & Energy

  • Electric

    100 Amp Service

  • Basement

    Bulkhead, Concrete Floor, Full, Insulated, Storage Space, Unfinished

  • Water Source

    Public

  • Parking Features

    Detached, Driveway, Garage

  • Utilities

    Cable At Site, Propane

Other Features

  • Lot Features

    Sidewalks, Near Shopping, Neighborhood, Near Public Transit, Near Hospital, Near School(s)

Price History

DateEventPrice

10/27/2026

Source: mls_logoNEREN/Prime MLS-NH #5109553

Listed for Sale

$319,000

$169/sqft

Nearby Homes

Based on information from PrimeMLS Inc. through Nov 02, 2026, 02:16PM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Nov 02, 2026, 02:16PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content