# 33 Oak Street, Brattleboro, VT 05301 > **TL;DR:** residential multi family, $375,000 ($91/sqft), built 1860, 4,116 sqft. Est. $2,005/mo. Listed 184 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $375,000 | | Price/sqft | $91 | | Square Feet | 4,116 | | Year Built | 1860 | | Lot Size | 17,424 sqft (0.40 acres) | | Stories | 3 | | Property Type | Residential Multi Family (Other) | | Status | Active | | Days on Market | 184 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,896 | | Estimated Insurance | $109 | | **Total** | **$2,005** | ## Property Highlights - Built in 1860 - 0.40 acre lot - 3 stories ## Description ### Agent Description This is a rare opportunity to take over a multi-family redevelopment project in the heart of Brattleboro. Situated on a 0.40-acre site, the property features a vacant three-story building that has already been gutted and fully remediated for lead paint. With municipal zoning approvals already in place to expand from 8 to 13 units and full architectural plans included with the sale, the time-consuming planning and permitting phase is behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing in a neighborhood characterized by strong rental demand and near-zero vacancy. The financial incentives lined up for this project provide substantial non-dilutive equity. The purchase includes access to $317,500 in VHIP funds ($130,000 for the 8 original units and $187,500 for the 5 expansion units), a $125,000 Downtown State Tax Credit that can be utilized directly or sold to a lender at 90% face value, and an estimated $60,000 in weatherization incentives. A recent appraisal strongly supports a robust finished valuation, offering a clear path to equity. The project is also well-suited for a phased renovation approach, allowing units to be completed and leased in stages to generate immediate cash flow during construction. The seller is motivated and open to creative financing options for qualified buyers. This is a unique chance to transform a prime downtown parcel into a vibrant, high-yield community asset with enthusiastic neighborhood backing. Complete project documentation, including architectural plans as well as as-is and as-completed appraisals, is available in a shared data room. Proof of funds or a commercial pre-approval is required prior to scheduling a showing or receiving the full diligence file. ## Location - **Address:** 33 Oak Street, Brattleboro, VT 05301 - **County:** VT-Windham - **Coordinates:** 42.85424227, -72.56273345 - **Google Maps:** https://www.google.com/maps?q=42.85424227,-72.56273345 ## Virtual Tour & Media - **Video Tour:** https://tour.primemls.com/33-Oak-Street-Brattleboro-VT-05301/unbranded ## Listing Agent - **Name:** Kate Barry - **Brokerage:** eXp Realty LLC - **Broker Phone:** (802) 868-6367 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/33-Oak-St_Brattleboro_VT_05301_M37162-89938?f=listhub&s=NNERENNH&m=5086282&c=propsimple) ## Photos ![33 Oak Street - Photo 1](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3473959032r.jpg) ![33 Oak Street - Photo 2](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f515874251r.jpg) ![33 Oak Street - Photo 3](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2476772147r.jpg) ![33 Oak Street - Photo 4](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2107073524r.jpg) ![33 Oak Street - Photo 5](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3588782265r.jpg) ![33 Oak Street - Photo 6](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2863419r.jpg) ![33 Oak Street - Photo 7](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f1329570240r.jpg) ![33 Oak Street - Photo 8](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f4126290402r.jpg) ![33 Oak Street - Photo 9](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3437296744r.jpg) ![33 Oak Street - Photo 10](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3213832060r.jpg) ![33 Oak Street - Photo 11](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2347988306r.jpg) ![33 Oak Street - Photo 12](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2033970110r.jpg) ![33 Oak Street - Photo 13](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f4097177856r.jpg) ![33 Oak Street - Photo 14](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f1704605473r.jpg) ![33 Oak Street - Photo 15](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f1066555551r.jpg) ![33 Oak Street - Photo 16](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2780781681r.jpg) ![33 Oak Street - Photo 17](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f1554145501r.jpg) ![33 Oak Street - Photo 18](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2269348528r.jpg) ![33 Oak Street - Photo 19](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3094417429r.jpg) ![33 Oak Street - Photo 20](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f441631124r.jpg) ![33 Oak Street - Photo 21](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3906132030r.jpg) ![33 Oak Street - Photo 22](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3971526051r.jpg) ![33 Oak Street - Photo 23](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3946490418r.jpg) ![33 Oak Street - Photo 24](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f692301032r.jpg) ![33 Oak Street - Photo 25](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f3518086258r.jpg) ![33 Oak Street - Photo 26](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2380819887r.jpg) ![33 Oak Street - Photo 27](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f2719175390r.jpg) ![33 Oak Street - Photo 28](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f676801076r.jpg) ![33 Oak Street - Photo 29](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f1274886562r.jpg) ![33 Oak Street - Photo 30](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f4014333841r.jpg) ![33 Oak Street - Photo 31](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f965932347r.jpg) ![33 Oak Street - Photo 32](http://lh.rdcpix.com/bfcef9715cf8ab3164935deef63effabl-f4114953739r.jpg) --- **MLS#:** 5086282 | **Updated:** 2026-10-28 **Source:** listhub *Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/33-oak-street-brattleboro-vt-05301-2080bed230264ed2a7e81d3b2c7b9f86) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/33-oak-street-brattleboro-vt-05301-2080bed230264ed2a7e81d3b2c7b9f86#listing", "url": "https://staging.propertysimple.ai/listing/33-oak-street-brattleboro-vt-05301-2080bed230264ed2a7e81d3b2c7b9f86", "name": "33 Oak Street, Brattleboro, VT 05301", "description": "This is a rare opportunity to take over a multi-family redevelopment project in the heart of Brattleboro. Situated on a 0.40-acre site, the property features a vacant three-story building that has already been gutted and fully remediated for lead paint. With municipal zoning approvals already in place to expand from 8 to 13 units and full architectural plans included with the sale, the time-consuming planning and permitting phase is behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing in a neighborhood characterized by strong rental demand and near-zero vacancy. The financial incentives lined up for this project provide substantial non-dilutive equity. The purchase includes access to $317,500 in VHIP funds ($130,000 for the 8 original units and $187,500 for the 5 expansion units), a $125,000 Downtown State Tax Credit that can be utilized directly or sold to a lender at 90% face value, and an estimated $60,000 in weatherization incentives. A recent appraisal strongly supports a robust finished valuation, offering a clear path to equity. The project is also well-suited for a phased renovation approach, allowing units to be completed and leased in stages to generate immediate cash flow during construction. The seller is motivated and open to creative financing options for qualified buyers. This is a unique chance to transform a prime downtown parcel into a vibrant, high-yield community asset with enthusiastic neighborhood backing. Complete project documentation, including architectural plans as well as as-is and as-completed appraisals, is available in a shared data room. 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