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Listed by: Rebecca Seymour | Brattleboro Area Realty (802) 257-1335
$319,000
Monthly Est:$1,588
-- Bed
- -- Bath
1,883sqft
59 Highland St, Brattleboro, VT 05301
$319,000
$1,588/moEst:
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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 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!
- Houzeo last checked: 12 hours ago
- Listing updated: October 27, 2026 at 8:19 pm
- Source: NEREN/Prime MLS-NH | MLS#: 5109552

Property Details
Status
Active
Type
Multi Family
No. of Stories
-
County
City
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

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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
| Date | Event | Price |
|---|---|---|
10/27/2026 Source: | Listed for Sale | $319,000 $169/sqft |
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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.
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