150 Oak St

Winsted, CT 06098

$579,000B-

9 bd · 5.0 ba · 5,233 sqft · Built 1924 · MultiFamily · Active · 50 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $8,179/mo
• Mortgage (P&I): −$3,036
• Tax + insurance: −$724
• HOA: −$0
• Vac / Maint / Mgmt: −$1,718
• Net cashflow: $2,701/mo
• Annual: $32,409/yr
• Cap rate: 11.89%
• Cash-on-cash: 19.99%
• DSCR: 1.89
• 1% rule: 1.41%
• Cash to close: $162,120

Investor read

• This is a 4×2bd/1.6ba + 1×3bd/1.5ba units multifamily listed at $579k.
• At list price, monthly cash flow is $3k ($32k/yr) — positive. Per door: $540/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($8k rent vs $579k).
• It's been on market 50 days — a 3% lower offer ($562k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $562k (3.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $17k of value loss. Plan a longer hold.
• Location reads 80/100 on livability (#25 in CT, #1,955 nationally) — a professional / high-income tenant draw. Strengths: housing A+, health & safety A+, cost of living A; Watch: amenities F, employment D-.
• Winchester School District (town): math 53% / reading 49% proficiency, ranked #131 of 192 in CT (top 68%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Watch-outs: built in 1924 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 61 active listings in the ZIP; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).
• 7 sale attempts since 19y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $341k; list at $579k implies a 70% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $162k cash investment doubles in ~7 years — after that, you're playing with house money.
• Cap rate 11.9% vs local median 4.1% in Winsted — 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 $8,179/mo this rent would consume 148% of the median local household income ($66k/yr) (locally 576% 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 50 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
• What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
• Built in 1924 — 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.
• 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.