# 59 Highland Street, Brattleboro, VT 05301

> **TL;DR:** 2bd/2ba single family, $319,000 ($169/sqft), built 1876, 1,883 sqft.
> 1-car garage. Est. $1,706/mo. Listed 51 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $319,000 |
| Price/sqft | $169 |
| Bedrooms | 2 |
| Bathrooms | 2 full |
| Square Feet | 1,883 |
| Year Built | 1876 |
| Lot Size | 12,632 sqft (0.29 acres) |
| Stories | 3 |
| Garage | 1-car |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 51 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $1,613 |
| Estimated Insurance | $93 |
| **Total** | **$1,706** |

## Nearby Schools

- **Elementary:** Brattleboro Elem Schools
- **Middle:** Brattleboro Area Middle School
- **High:** Brattleboro High School

## Key Amenities

- 1-car garage

## Property Highlights

- Built in 1876
- 0.29 acre lot
- 3 stories

## Description

### Agent 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!!

## Location

- **Address:** 59 Highland Street, Brattleboro, VT 05301
- **County:** VT-Windham
- **Coordinates:** 42.845074, -72.560461
- **Google Maps:** https://www.google.com/maps?q=42.845074,-72.560461

## Virtual Tour & Media

- **Video Tour:** https://tour.primemls.com/59-Highland-Street-Brattleboro-VT-05301/unbranded

## Listing Agent

- **Name:** Rebecca Seymour
- **Brokerage:** Brattleboro Area Realty
- **Broker Phone:** (802) 257-1335
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/59-Highland-St_Brattleboro_VT_05301_M93463-64248?f=listhub&s=NNERENNH&m=5109553&c=propsimple)

## Photos

![59 Highland Street - Photo 1](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2524396884r.jpg)

![59 Highland Street - Photo 2](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3618476131r.jpg)

![59 Highland Street - Photo 3](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f409615012r.jpg)

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![59 Highland Street - Photo 5](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3979126010r.jpg)

![59 Highland Street - Photo 6](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f4167022578r.jpg)

![59 Highland Street - Photo 7](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f398130936r.jpg)

![59 Highland Street - Photo 8](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3400220580r.jpg)

![59 Highland Street - Photo 9](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3672708340r.jpg)

![59 Highland Street - Photo 10](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2582220771r.jpg)

![59 Highland Street - Photo 11](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f608449937r.jpg)

![59 Highland Street - Photo 12](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f67226620r.jpg)

![59 Highland Street - Photo 13](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3650317651r.jpg)

![59 Highland Street - Photo 14](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f37235519r.jpg)

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![59 Highland Street - Photo 17](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3963114730r.jpg)

![59 Highland Street - Photo 18](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3840091946r.jpg)

![59 Highland Street - Photo 19](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3825735163r.jpg)

![59 Highland Street - Photo 20](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3770190846r.jpg)

![59 Highland Street - Photo 21](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2270151257r.jpg)

![59 Highland Street - Photo 22](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3849390429r.jpg)

![59 Highland Street - Photo 23](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f858175087r.jpg)

![59 Highland Street - Photo 24](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2161203487r.jpg)

![59 Highland Street - Photo 25](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1020453849r.jpg)

![59 Highland Street - Photo 26](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1785722879r.jpg)

![59 Highland Street - Photo 27](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1153047586r.jpg)

![59 Highland Street - Photo 28](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1728276536r.jpg)

![59 Highland Street - Photo 29](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f4026899543r.jpg)

![59 Highland Street - Photo 30](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2503627053r.jpg)

![59 Highland Street - Photo 31](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1597022675r.jpg)

![59 Highland Street - Photo 32](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f3621948765r.jpg)

![59 Highland Street - Photo 33](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2978064993r.jpg)

![59 Highland Street - Photo 34](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f419828060r.jpg)

![59 Highland Street - Photo 35](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1159227278r.jpg)

![59 Highland Street - Photo 36](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f4054818998r.jpg)

![59 Highland Street - Photo 37](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2605017393r.jpg)

![59 Highland Street - Photo 38](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f194775329r.jpg)

![59 Highland Street - Photo 39](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1889060523r.jpg)

![59 Highland Street - Photo 40](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2781447342r.jpg)

![59 Highland Street - Photo 41](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2396659840r.jpg)

![59 Highland Street - Photo 42](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f4242882243r.jpg)

![59 Highland Street - Photo 43](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f1448401173r.jpg)

![59 Highland Street - Photo 44](http://lh.rdcpix.com/9b4059f4eadfa06a71987d3374d8d6c7l-f2906251938r.jpg)

---

**MLS#:** 5109553 | **Updated:** 2026-10-27
**Source:** listhub

*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.*

[View on PropertySimple](https://staging.propertysimple.ai/listing/59-highland-street-brattleboro-vt-05301-aa2e510d7df44585a00104c9042b885f)

---

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```