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!!
Pending
Listed by: Brattleboro Area Realty • Rebecca Seymour
$319,000
59 Highland Street, Brattleboro, VT 05301
2beds
1,883sqft
Single Family Residence
Built in 1876
0.29 Acres Lot
$312,000 Zestimate®
$169/sqft
$-- HOA
What's special
- 25 days
- 3,373
- 274
Zillow last checked:
Listing updated:
Listed by:
Rebecca Seymour,
Brattleboro Area Realty 802-257-1335
Source: PrimeMLS,MLS#: 5109553
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Forced Air
Cooling
- None
Appliances
- Included: Dryer, Refrigerator, Washer, Electric Stove
Features
- Flooring: Vinyl, Wood
- Basement: Bulkhead,Concrete,Concrete Floor,Full,Insulated,Storage Space,Interior Entry
Interior area
- Total structure area: 2,845
- Total interior livable area: 1,883 sqft
- Finished area above ground: 1,883
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Gravel
- Garage spaces: 1
Features
- Levels: 3
- Stories: 3
- Patio & porch: Covered Porch
- Exterior features: Garden, Natural Shade
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 94
Lot
- Size: 0.29 Acres
- Features: Curbing, Landscaped, Sidewalks, In Town, Near Shopping, Neighborhood, Near Public Transit, Near Hospital, Near School(s)
Details
- Parcel number: 8102513221
- Zoning description: Res
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Wood Exterior
- Foundation: Brick, Stone
- Roof: Membrane,Slate
Condition
- Fixer
- New construction: No
- Year built: 1876
Utilities & green energy
- Electric: 100 Amp Service
- Sewer: Public Sewer
- Utilities for property: Cable at Site
Community & HOA
Location
- Region: Brattleboro
Financial & listing details
- Price per square foot: $169/sqft
- Tax assessed value: $173,840
- Annual tax amount: $5,800
- Date on market: 9/12/2026
- Listing terms: Cash,Conventional
Estimated market value
$312,000
$296,000 - $328,000
$2,353/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/5/2026 | Pending sale | $319,000$169/sqft |
Source:  PrimeMLS #5109553 Report a problem | ||
| 9/14/2026 | Listed for sale | $319,000+14.7%$169/sqft |
Source: PrimeMLS #5109553 Report a problem | ||
| 3/24/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 9/6/2016 | Sold | $278,000-3.8%$148/sqft |
Source: Public Record Report a problem | ||
| 5/13/2016 | Listed for sale | $289,000+31.4%$153/sqft |
Source: Owner Report a problem | ||
| 10/10/2012 | Sold | $220,000$117/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $173,840 |
| 2023 | -- | $173,840 |
| 2022 | -- | $173,840 |
| 2021 | -- | $173,840 |
| 2020 | -- | $173,840 |
| 2019 | -- | $173,840 |
| 2018 | -- | $173,840 |
| 2017 | -- | $173,840 |
| 2016 | -- | $173,840 +9902.3% |
| 2015 | -- | $1,738 |
| 2014 | -- | $1,738 |
| 2013 | -- | $1,738 |
| 2012 | -- | $1,738 |
| 2011 | -- | $1,738 |
| 2010 | -- | $1,738 +0.6% |
| 2009 | -- | $1,727 |
| 2008 | -- | $1,727 |
| 2007 | -- | $1,727 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 05301
Nearby schools
Schools provided by the listing agent
- Elementary: Brattleboro Elem Schools
- Middle: Brattleboro Area Middle School
- High: Brattleboro High School
- District: Brattleboro School District
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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