58 Oak St

Brattleboro, VT 05301

$625,000
Price
5
Beds
3,748 Sq. Ft.
$167 / Sq. Ft.
3,748
Sq. Ft.
$167
per Sq. Ft.

Description

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,...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.
  1. Listed by Rebecca Seymour • Brattleboro Area Realty

Property Details for 58 Oak Street

Zoning
res
LISTING UPDATED: 09/26/2025 11:17 AM

Property Details for 58 Oak Street

StatusActive
MLS #5060836
Days on Market103
Taxes$8,090 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1880
Lot Size0.25 AC / 10,890 SF
CountyWindham County

Location

Listing Courtesy of Brattleboro Area Realty
Add your commute

Building Information for 58 Oak Street

Stories2Year Built1880Building Size-Lot Size0.25 AC / 10,890 SF

Payment Calculator

$3,763 per month

30 year fixed, 6.28% Interest

Principal and Interest

$3,088

Property Taxes

$674

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 58 Oak Street

Summary
Location and General Information
  • City: Brattleboro
  • County: VT-Windham
  • Directions: Corner of Oak and Howard, driveway on Howard.
  • Latitude: 42.854910000000999
  • Longitude: -72.563474999999997
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05301
Taxes and HOA Information
  • SPAN Number: 081-025-14119
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Corner, Curbing, Landscaped, Sidewalks, Walking Trails, In Town, Near Shopping, Neighborhood, Near Public Transportatn, Near School(s)
  • Lot Size Acres: 0.25
  • Road Frontage Length: 219.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1880
Utilities
  • Electric: 100 Amp Service
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable Available, Telephone Available
  • Internet: Cable Internet
Interior and Exterior Features
Exterior Features
  • Color: Yellow
  • Construction Materials: Clapboard Exterior
  • Roof: Shingle, Slate
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Unfinished
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Full Bathroom, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Full Bathroom, Level 2: Laundry Room
  • Flooring: Tile, Vinyl, Wood
  • Heating: Baseboard
  • Cooling: None
  • Total Stories: 2
Room Information
Room 1
  • Room Dimensions: 14.5x15.5
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 15x15
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 15x16
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Dimensions: 13x15
  • Room Level: 1
  • Room Type: Bedroom
Room 5
  • Room Level: 1
  • Room Type: Bathroom Full
Room 6
  • Room Dimensions: 15x15
  • Room Level: 2
  • Room Type: Bedroom
Room 7
  • Room Dimensions: 10x12.5
  • Room Level: 2
  • Room Type: Bedroom
Room 8
  • Room Dimensions: 14x14.5
  • Room Level: 2
  • Room Type: Bedroom
Room 9
  • Room Level: 2
  • Room Type: Bathroom Full
Room 10
  • Room Dimensions: 15x15
  • Room Level: 2
  • Room Type: Laundry Room

Property History for 58 Oak Street

DateEvent & SourcePriceAppreciation
Sep 11, 2025

Listed (Active)

New England Real Estate Network #5060836

$625,000—
Sep 21, 2023

Sold (Public Record)

Public Record #1526045346

$595,000—
Sep 21, 2023

Sold

New England Real Estate Network #4961927

$595,000—
Sep 21, 2023

Pending

New England Real Estate Network #4961927

—
Aug 9, 2023

Active Under Contract

New England Real Estate Network #4961927

—
Jul 19, 2023

Listed (Active)

New England Real Estate Network #4961927

$595,000—
May 22, 2010

Expired

New England Real Estate Network #3052345

—
Mar 15, 2008

Listed (Active)

New England Real Estate Network #3052345

$345,000—
Mar 15, 2008

Listed (Active)

New England Real Estate Network #3052343

$345,000—
Aug 1, 2000

Sold

New England Real Estate Network #3002419

$141,750—
Jun 22, 2000

Pending

New England Real Estate Network #3002419

—
May 22, 2000

Listed (Active)

New England Real Estate Network #3002419

$149,000—
DateEvent & SourcePrice
09/11/2025

Listed (Active)

New England Real Estate Network #5060836

$625,000
09/21/2023

Sold (Public Record)

Public Record #1526045346

$595,000
09/21/2023

Sold

New England Real Estate Network #4961927

$595,000
09/21/2023

Pending

New England Real Estate Network #4961927

—
08/09/2023

Active Under Contract

New England Real Estate Network #4961927

—
07/19/2023

Listed (Active)

New England Real Estate Network #4961927

$595,000
05/22/2010

Expired

New England Real Estate Network #3052345

—
03/15/2008

Listed (Active)

New England Real Estate Network #3052345

$345,000
03/15/2008

Listed (Active)

New England Real Estate Network #3052343

$345,000
08/01/2000

Sold

New England Real Estate Network #3002419

$141,750
06/22/2000

Pending

New England Real Estate Network #3002419

—
05/22/2000

Listed (Active)

New England Real Estate Network #3002419

$149,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 58 Oak Street

Taxable ValueLand$52,000Additions$216,790Total$268,790
Tax Record2024$8,728 ($727 / month)
Home Facts
Baths4Total Finished SqFt3,748 SqFtAbove Grade Finished SqFt3,748 SqFtStories2Lot Size10,890 SqFtStyleTriplexYear Built1880CountyWINDHAMAPN(025) 00275243.000

Schools near 58 Oak Street

This home is within Windham Southeast Unified Union School District #96.
Rating
School
Type
Grades
Distance
Canal Street/Oak Grove Schools
Public - PK to 6
Brattleboro Area Middle School
Public - 7 to 8
Brattleboro Senior Uhsd #6
Public - 9 to 12
Windham Regional Career Center
Public - 9 to 12
Rating
School
Distance
Canal Street/Oak Grove Schools
PublicPK to 6

Brattleboro Area Middle School
Public7 to 8

Brattleboro Senior Uhsd #6
Public9 to 12

Windham Regional Career Center
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 58 Oak Street, Brattleboro, VT 05301

58 Oak Street is a single family home for sale in Brattleboro, VT 05301. This property was listed for sale on September 11, 2025 by Brattleboro Area Realty, it's currently listed at $625,000. It has been on the market for a total of 103 days and was last sold on September 21, 2023. This listing's school district is Windham Southeast Unified Union School District #96. Nearby schools include Canal Street/Oak Grove Schools, Brattleboro Area Middle School and Brattleboro Senior Uhsd #6. 58 Oak Street is a 5-bed, 4-bath, 3,748 sqft single family home built in 1880.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Brattleboro Area Realty

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 12/24/2025 02:25 AM