56 Woolsey St

New Haven, CT 06513

$380,000C+

5 bd · 3.0 ba · 1,920 sqft · Built 1900 · MultiFamily · Under Contract · 41 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,794/mo
• Mortgage (P&I): −$1,993
• Tax + insurance: −$763
• HOA: −$0
• Vac / Maint / Mgmt: −$1,217
• Net cashflow: $1,821/mo
• Annual: $21,857/yr
• Cap rate: 12.04%
• Cash-on-cash: 20.54%
• DSCR: 1.91
• 1% rule: 1.52%
• Cash to close: $106,400

Investor read

• This is a 3 × 2-bed/1.0-bath units multifamily listed at $380k.
• At list price, monthly cash flow is $2k ($22k/yr) — positive. Per door: $607/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $380k).
• It's been on market 41 days — a 3% lower offer ($369k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $369k (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 $11k of value loss. Plan a longer hold.
• Location reads 79/100 on livability (#31 in CT, #2,190 nationally) — a middle-class / working-renter tenant base. Strengths: amenities A+, commute A+, health & safety A+; Watch: schools D+, employment D, crime F.
• New Haven School District (urban): math 12% / reading 25% proficiency, ranked #147 of 153 in CT (top 96%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 66% free/reduced lunch — lower-income household profile, screen leases tightly.
• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+4.1%/yr); 102 active listings in the ZIP; 23 comparable units currently listed for rent nearby; rentals leasing fast (median 13d on market — plan ~1-2 weeks tenant-placement turnaround); 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• 3 sale attempts since 20y ago; this cycle's ask is 9% above the opening price — seller raised mid-cycle; expect resistance to lowballs.
• Current owner paid $14k; list at $380k implies a 2614% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 4.1% rent growth), your $106k cash investment doubles in ~6 years — after that, you're playing with house money.
• Climate carrying-cost: major wind risk, 56% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 12.0% vs local median 4.9% in New Haven — 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 $5,794/mo this rent would consume 143% of the median local household income ($48k/yr) (locally 2664% 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 41 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 1900 — 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 D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
• 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.