About This Home

This 2-bedroom, 2-bathroom single family at 59 Highland Street in Brattleboro, VT is listed for $319,000 ($169 per sqft). Built in 1876, the home offers 1,883 sqft of living space on a 0.29 acres lot.

Key Features

  • Built in 1876
  • 0.29 acre lot
  • 3 stories

Property Details

3 stories
2 full
1-car garage
1876
Listing Description

Sited at the top of the hill in one of Brattleboro's 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 and town assessed 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!!

Monthly Cost Estimate

$1,706/mo

20% down · 6.5% · 30 years

Principal$231
Interest$1,382
Insurance$93

Estimates only. Actual payments may vary.

Location

59 Highland Street

Brattleboro, VT 05301

Features & Amenities

Exterior Features

Garden SpaceNatural ShadeCovered Porch

Property Details

Flooring

WoodVinyl

Construction

Wood Exterior

Outdoor Features

Porch

Heating

Forced Air

Appliances

DryerRefrigeratorWasherElectric Stove

Questions & Answers

This 2-bedroom, 2-bathroom single family at 59 Highland Street is listed at $319,000 ($169/sqft). The estimated monthly payment is $1,706 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1876, 0.29 acre lot, 3 stories. Exterior Features: Garden Space, Natural Shade, Covered Porch.

This property is listed by Rebecca Seymour.

RS

Rebecca Seymour

Agent at Brattleboro Area Realty

Listed by Brattleboro Area Realty · Broker phone: (802) 257-1335 · View on Broker Site · Broker website

MLS# 5109553· Source: PrimeMLS· 49 days on PropertySimple

Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

59 Highland Street, Brattleboro, VT 05301

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