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33 Oak Street, Brattleboro, VT 05301

VT-Windham County

Key Facts

9,232Sq Ft
1860Year Built
0.40Lot (acres)
3Stories

Description

This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing. The financial incentives currently lined up for this project are significant. The sale includes access to VHIP funds : 8 original units $130,000 and the 5 new units $187,500. Additionally, there is a $125,000 Downtown State Tax Credit that can be used directly or sold to a bank at 90% face value, plus an estimated $60,000 in weatherization incentives. A recent appraisal supports a strong finished value, offering a clear path to equity for an investor. Located in a neighborhood with high rental demand and a low vacancy rate, this property is in an ideal location and could also be renovated one stage at a time so that units could go live and start generating cash flow. A lot of leg work has already been done, and the entire community wants to see this building come alive again with residents. This part of Brattleboro is thriving and this is truly the opportunity to take the worst house in the best neighborhood and turn it into affordable housing that generates a positive return. All project documents, including architect plans and both as-is and as-complete appraisals, are available in a shared Drive file. Please note that proof of funds or a commercial pre-approval is required before scheduling a showing or receiving the full data room.

Property Information

Property Type

Residential Income

Sub-Type

Multi Family

Style

Multi-Family

Year Built

1860

Stories

3

Living Area

9,232 sq ft

Lot Size

0.40 acres

Zoning

RM / M

Days on Market

11

MLS® Listing#

5086282

Property Features

Cooling

None

Heating

OilHot Water

Basement

Dirt FloorWalk-Up AccessFull

Parking

Gravel

Lot Features

Level

Construction

Frame

Roof

MetalSlate

Utilities

None

Sewer

Public Sewer

Water Source

Public

Financial Details

Annual Taxes

$11,956

Tax year 2024

Affordability Calculator

$107,000

Estimated monthly payment

$2,847/mo

Principal $428,000 · Est. interest $597,098 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Brattleboro, VT

$325,532
Median Listing Price
83
Median Days on Market
1,872
Median Sq Ft
$177
Median Price / Sq Ft
75
Active Listings
  • This home’s price is 64% above the area median.
  • Its price per sq ft is 67% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Brattleboro, VT.

Location

Map showing the location of 33 Oak Street, Brattleboro, VT 05301

Points of Interest in Brattleboro, VT

Showing the Brattleboro area map.

Nearby Schools

  • Green Street School

    Elementary · 0.2 mi away

  • Canal Street Headstart

    School · 0.4 mi away

  • Esteyville School

    School · 0.6 mi away

  • Neighborhood Schoolhouse

    School · 0.7 mi away

  • Vermont Wilderness School

    School · 1.0 mi away

  • The Garland School

    School · 1.0 mi away

  • Austine School

    School · 1.0 mi away

  • Inspire for Autism

    School · 1.0 mi away

  • Oak Grove School

    Elementary · 1.0 mi away

  • Winston Prouty Center

    School · 1.1 mi away

  • Brattleboro Union High School

    Secondary · 1.3 mi away

  • Brattleboro Area Middle School

    Secondary · 1.3 mi away

  • Windham Regional Career Center

    Secondary · 1.3 mi away

  • Liberty High School

    Secondary · 1.5 mi away

  • Hilltop Montessori School

    Elementary · 1.8 mi away

  • Academy School

    Elementary · 1.8 mi away

  • West Bee Nursery School

    Elementary · 1.8 mi away

  • Chesterfield Central School

    Elementary · 5.2 mi away

  • Dummerston Schools

    Elementary · 5.6 mi away

  • Hinsdale Elementary School

    Elementary · 5.8 mi away

Commute Calculator

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Nearby Homes

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Similar Home Values

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Moving Cost Estimate

EXIT Agents in Brattleboro

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by NEREN. MLS® Listing#5086282. © 2026EXIT Realty®. All rights reserved.