Darren McGovern
REALTOR®
BEDS2
BATHS2 full
SQUARE FEET1,883
MLS#5109552
STATUSActive
PROPERTY TYPEMulti Unit - Multiple
SCHOOLWindham Southeast
Listing Courtesy of:
Brattleboro Area Realty
Agency Phone: 802-257-1335
Associate Name: Rebecca Seymour
Property 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!
Property Features
Property Type: Multi Unit - Multiple
Basement: Yes
Basement: Bulkhead, Concrete Floor, Full, Insulated, Storage Space, Unfinished
Cooling: None
Garage: 1
Heating: Forced Air
Home Style: Victorian
Lot Size: 0.29 Acres
Roof Type: Membrane, Slate
Stories: 2.5
Taxes: $5,800
Year Built: 1876
Units
Unit 1:
Bathroom(s): 1
Bedrooms: 1
Rent: $2200.00
Unit 2:
Bathroom(s): 1
Bedrooms: 1
Rent: $1800.00
Amenities
Garden Space
Natural Shade
Covered Porch
Feature Descriptions
Color: yellow
Construction: Wood Siding
Days on Site: 3
Driveway: Gravel
Driveway: Gravel
Electric: 100 Amp Service
Exterior: Wood Siding
Flood Zone: No
Flooring: Vinyl, Wood
Foundation: Brick, Fieldstone
Foundation: Brick, Fieldstone
Lot: Sidewalks, Near Shopping, Neighborhood, Near Public Transport, Near Hospital, Near School(s)
Parking: Detached, Driveway, Garage
Roads: Public
Sewer: Public
Sq. Ft. Total Finished: 1883
Total Stories: 2.5
Units: 2
Water: Public
Zoning: Res
Local Schools
High School: Brattleboro High School
Middle School: Brattleboro Area Middle School
Elementary School: Brattleboro Elem Schools
School District: Windham Southeast
Listed By / Shown By
Listed By
Agency Name: Brattleboro Area Realty
Agent Name: Rebecca Seymour
Agency Phone: 802-257-1335
Shown By
Agent Name: Darren McGovern
Agent Phone: (800) 741-1540
Agency Title: Better Homes and Gardens Real Estate The Masiello Group
TOUR THIS HOME
Choose a date and time to see 59 Highland Street, Brattleboro, VT 05301.
I will get in touch with you shortly.
Estimate Your Payment
Estimated Payment
$ 1,286.33 per month $709.96 Principal & Interest $483.33 Property Tax $93.04 Homeowner's Insurance
Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. 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 2026-09-14 23:32:57 
59 Highland Street | MLS# 5109552
This multi-family property located at 59 Highland Street, Brattleboro, VT 05301 is currently listed for sale with an asking price of $319,000. Highland Street is located within the Windham Southeast school district. Search Brattleboro real estate on darrenmcgovern.masiellogrouprealestate.com today.