59 Highland StreetBrattleboro, VT 05301MLS Number 5109552

  • Price: $319,000
  • Est. Mortgage of $/month
  • 1 Day on Market
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%
$/month over payments
Federal 30-year interest rate: 6.76% last updated on Sep 10, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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CMS
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  • 0.29Acreage
  • 2Bathrooms
  • 1876Year Built
  • 1,883Square Feet

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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!
Listed by Rebecca Seymour of Brattleboro Area Realty

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More Info

Tax Information

  • Tax Year2025

Building

  • Year Built1876
  • Building ConstructionWood Siding
  • StyleVictorian
  • Units2
  • Unit 1 Bath1
  • Unit 1 Bedrooms1
  • Unit 1 Floor Location1
  • Unit 1 Total Rooms5
  • Unit 2 Bath1
  • Unit 2 Bedrooms1
  • Unit 2 Floor Location2/3
  • Unit 2 Total Rooms4
  • # of 1 Bedrooms2
  • Bathroom2
  • Total Baths2
  • Basement
    • Bulkhead
    • Concrete Floor
    • Full
    • Insulated
    • Storage Space
    • Unfinished
  • FoundationBrick, Fieldstone

Other

  • Taxes$5,800
  • Seasonal Y/NNo
  • Date Listed09/12/2026
  • Unit 1 Deposit$2,200
  • Unit 2 Rent Amount$1,800

Basic Information

  • Virtual TourView Tour
  • StatusCMS
  • List Price$319,000
  • Date Price Change09/12/2026
  • MLS Number5109552
  • MLS StatusComing Soon

Property

  • Acreage0.29
  • GarageYes
  • Parking Spaces1
  • Lot Description
    • Near Hospital
    • Near Public Transport
    • Near School(s)
    • Near Shopping
    • Neighborhood
    • Sidewalks
  • Square Feet1,883
  • APX Fin AG Sqft1,883
  • Road Frontage94
  • RoadsPublic
  • AreaVT-Windham

Amenities

  • Exterior AmenitiesGarden Space, Natural Shade, Covered Porch
  • PricePerSqFt169.41

Location

  • TownBrattleboro
  • StateVT
  • Zip05301
  • CountyWindham
  • ZoningRes
  • Elementary SchoolBrattleboro Elem Schools
  • Junior HighBrattleboro Area Middle School
  • High SchoolBrattleboro High School
  • Address59 Highland Street
  • Flood Zone Y/NNo

Interior

  • FloorsVinyl, Wood

Exterior

  • RoofMembrane, Slate
  • Exterior Coloryellow

Utilities

  • Heat SystemForced Air
  • WaterPublic
  • Water HeaterElectric Water Heater
  • Electric100 Amp Service
  • SewerPublic
  • UtilitiesCable at Site, Propane
Bellville Realty
Bellville Realty
Office: 802-257-7979
16 Harmony Place
Brattleboro, VT 05301
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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 September 13, 2026 7:07 AM UTC

 

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