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Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro-home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and oversized wavy glass windows that bathe the interior in natural light. The 1st floor is bright and inviting, with a sun-filled dining room and a living room featuring a propane insert for warmth and ambiance. For accessibility, there is a 1st floor full bathroom and bedroom with historic curved wall. The gracious staircase brings you to a reading nook on the landing, 3 bedrooms, and a full bath with a clawfoot tub. The large laundry room offers flexibility to double as a studio, craft, or hobby space. The property also features two accessory apartments, offering excellent income potential or space for guests or extended family. A detached barn has storage above, and plenty off-street parking. The yard has been extensively and thoughtfully landscaped with lush, low-maintenance perennials, stone patios, and garden pathways. A private sauna nestled among the gardens creates a peaceful retreat a after a busy day.This exceptional property is a rare find-gracefully blending history, function, and opportunity in one of Brattleboro's most coveted locations. Being offered as a single family home.

More Info

Tax Information

  • Tax Year2025

Location

  • Building Number58
  • StreetOak 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
  • Address58 Oak Street

Interior

  • Interior FeaturesIn-Law/Accessory Dwelling, Kitchen Island, Natural Light
  • Room 1 TypeKitchen
  • Room 1 Level1
  • Room 1 Dimensions14.5x15.5
  • FloorsTile, Vinyl, Wood
  • Room 2 TypeDining Room
  • Room 2 Level1
  • Room 2 Dimensions15x15
  • Room 3 TypeLiving Room
  • Room 3 Level1
  • Room 3 Dimensions15x16
  • Room 4 TypeBedroom
  • Room 4 Level1
  • Room 4 Dimensions13x15
  • Room 5 TypeBathroom Full
  • Room 5 Level1
  • Stories2
  • Room 6 TypeBedroom
  • Room 6 Level2
  • Room 6 Dimensions15x15
  • Room 7 TypeBedroom
  • Room 7 Level2
  • Room 7 Dimensions10x12.5
  • Room 8 TypeBedroom
  • Room 8 Level2
  • Room 8 Dimensions14x14.5
  • Room 9 TypeBathroom Full
  • Room 9 Level2
  • Room 10 TypeLaundry Room
  • Room 10 Level2
  • Room 10 Dimensions15x15

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionDriveway, Garage

Building

  • Year Built1880
  • Building ConstructionClapboard Exterior
  • ConstructionExisting
  • Property StyleVictorian
  • Bedrooms5
  • Bathroom4
  • Total Baths4
  • Total Rooms15
  • Square Feet3,748
  • APX Unfin Below Grade1874
  • BasementUnfinished
  • FoundationBrick, Fieldstone

Exterior

  • Exterior FeaturesDeck, Full Fence, Garden Space, Natural Shade, Sauna
  • Exterior ColorYellow
  • RoofShingle, Slate

Amenities

  • PricePerSqFt166.76

Rooms

  • Full Bath4

Basic Information

  • MLS Number5060836
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$625,000
  • Listing Agent NameRebecca Seymour
  • Broker NameBrattleboro Area Realty

Property

  • Acreage0.25
  • Lot DescriptionCorner, Curbing, Landscaped, Sidewalks, Walking Trails, In Town, Near Shopping, Neighborhood, Near Public Transportatn, Near School(s)
  • AreaVT-Windham
  • DrivewayPaved
  • RoadsPublic
  • Road Frontage219

Utilities

  • Heat SystemBaseboard
  • WaterPublic
  • SewerPublic
  • Electric100 Amp Service
  • UtilitiesCable Available, Telephone Available

Other

  • Delayed ShowingsNo
  • SeasonalNo
  • Page18
  • Date Listed09/11/2025
  • View Count1

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Copyright 2025 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 November 12, 2025 8:54 AM EST

 

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