59 Highland StreetBrattleboro, VT 05301MLS Number 5109553

  • Price: $319,000
  • Est. Mortgage of $/month
  • 7 Days on Market
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Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
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59 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 0530159 Highland Street Brattleboro VT 05301
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  • 2Bedrooms
  • 0.29Acreage
  • 2Bathrooms
  • 1876Year Built

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Listed by Rebecca Seymour of Brattleboro Area Realty
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!!

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More Info

Basic Information

  • PricePerSqFt169.41

Basic Information

  • MLS Number5109553
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$319,000
  • Listing Agent NameRebecca Seymour
  • Broker NameBrattleboro Area Realty

Property

  • Acreage0.29
  • Lot DescriptionCurbing, Landscaped, Mountain View, Sidewalks, In Town, Near Shopping, Neighborhood, Near Public Transport, Near Hospital, Near School(s)
  • AreaVT-Windham
  • DrivewayGravel
  • RoadsPublic
  • Road Frontage94

Utilities

  • Heat SystemForced Air
  • WaterPublic
  • SewerPublic
  • Electric100 Amp Service
  • UtilitiesCable at Site

Tax Information

  • Tax Year2025

Rooms

  • Full Bath2

Building

  • Year Built1876
  • Building ConstructionWood Exterior
  • ConstructionFixer
  • Property StyleVictorian
  • Bedrooms2
  • Bathroom2
  • Total Baths2
  • Total Rooms9
  • Square Feet1,883
  • APX Unfin Below Grade962
  • BasementBulkhead, Concrete, Concrete Floor, Full, Insulated, Storage Space
  • FoundationBrick, Stone

Exterior

  • Exterior FeaturesGarden Space, Natural Shade, Covered Porch
  • Exterior Coloryellow
  • RoofMembrane, Slate

Legal

  • Taxes$5,800
  • Tax ReductionNo
  • ZoningRes
  • Surveyed Y/NUnknown

Other

  • SeasonalNo
  • Page512
  • Date Listed09/12/2026

Parking

  • Parking Spaces1
  • GarageYes

Location

  • Building Number59
  • StreetHighland Street
  • TownBrattleboro
  • StateVT
  • Zip05301
  • CountyWindham
  • DistrictBrattleboro School District
  • Elementary SchoolBrattleboro Elem Schools
  • Junior HighBrattleboro Area Middle School
  • High SchoolBrattleboro High School
  • Flood Zone Y/NNo
  • Address59 Highland Street

Interior

  • Room 1 TypeEat-in Kitchen
  • Room 1 Level1
  • FloorsVinyl, Wood
  • Room 2 TypeLiving Room
  • Room 2 Level1
  • Room 3 TypeOffice/Study
  • Room 3 Level1
  • Room 4 TypeBathroom Full
  • Room 4 Level1
  • Room 5 TypeBedroom
  • Room 5 Level1
  • Stories3
  • Room 6 TypeBedroom
  • Room 6 Level2
  • Room 7 TypeFamily Room
  • Room 7 Level2
  • Room 8 TypeEat-in Kitchen
  • Room 8 Level2
  • Room 9 TypeBathroom Full
  • Room 9 Level2
  • Room 10 TypeBonus Room
  • Room 10 Level3
Dave Chenette | Chenette Real Estate

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Dave Chenette | Chenette Real Estate
Office: 802-264-1991
9 Roberts Ct
Milton, VT 05468
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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 18, 2026 1:09 PM UTC

 

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