39 Webb St

New Haven, CT 06517

$350,000C+

4 bd · 2.0 ba · 2,076 sqft · Built 1925 · MultiFamily · Under Contract · 3 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $4,227/mo
• Mortgage (P&I): −$1,835
• Tax + insurance: −$808
• HOA: −$0
• Vac / Maint / Mgmt: −$888
• Net cashflow: $696/mo
• Annual: $8,349/yr
• Cap rate: 8.68%
• Cash-on-cash: 8.52%
• DSCR: 1.38
• 1% rule: 1.21%
• Cash to close: $98,000

Investor read

• This is a 2 × 2-bed/1.5-bath units multifamily listed at $350k.
• At list price, monthly cash flow is $696 ($8k/yr) — positive. Per door: $348/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $350k).
• Only 3 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $10k 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.
• Hamden School District (suburban): math 30% / reading 43% proficiency, ranked #106 of 153 in CT (top 69%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Watch-outs: built in 1925 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents flat; 84 active listings in the ZIP; 22 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); 41% of comp listings sitting > 30 days — soft ceiling on asking rent; solid renter incomes; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• Current owner paid $240k; 46% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Climate carrying-cost: major wind risk, 54% 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 8.7% vs local median 4.8% 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 $4,227/mo this rent would consume 49% of the median local household income ($105k/yr) (locally 531% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• 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 1925 — 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.
• 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.