33 Oak St

Brattleboro, VT 05301

$495,000C-

None bd · None ba · 4,116 sqft · Built 1860 · MultiFamily · Active · 49 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $22,677/mo
• Mortgage (P&I): −$2,596
• Tax + insurance: −$756
• HOA: −$0
• Vac / Maint / Mgmt: −$4,762
• Net cashflow: $14,563/mo
• Annual: $174,751/yr
• Cap rate: 41.60%
• Cash-on-cash: 126.08%
• DSCR: 6.61
• 1% rule: 4.58%
• Cash to close: $138,600

Investor read

• This is a multifamily listed at $495k.
• At list price, monthly cash flow is $15k ($175k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $495k).
• It's been on market 49 days — a 3% lower offer ($480k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $480k (3.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $15k of value loss. Plan a longer hold.
• Location reads 67/100 on livability (#42 in VT) — a middle-class / working-renter tenant base. Strengths: schools A+, health & safety A+, cost of living B; Watch: crime F, amenities D-, commute F.
• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 82 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 188 units permitted in Windham County in 2024 (0 in 5+ unit buildings).
• Windham County population projected at -26% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• Current owner paid $350k; 41% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $139k cash investment doubles in ~1 year — after that, you're playing with house money.
• Cap rate 41.6% vs local median 4.5% in Brattleboro — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.
• At $22,677/mo this rent would consume 413% of the median local household income ($66k/yr) (locally 594% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• It's been on market 49 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Built in 1860 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
• Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
• What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
• What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
• How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.