108 Dewitt St

New Haven, CT 06519

$485,000C

5 bd · 3.0 ba · 2,330 sqft · Built 1900 · MultiFamily · Under Contract · 37 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,145/mo
• Mortgage (P&I): −$2,543
• Tax + insurance: −$635
• HOA: −$0
• Vac / Maint / Mgmt: −$1,080
• Net cashflow: $886/mo
• Annual: $10,629/yr
• Cap rate: 8.48%
• Cash-on-cash: 7.83%
• DSCR: 1.35
• 1% rule: 1.06%
• Cash to close: $135,800

Investor read

• This is a 1×4bd/1.5ba + 1×5bd/1.5ba units multifamily listed at $485k.
• At list price, monthly cash flow is $886 ($11k/yr) — positive. Per door: $443/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $485k).
• It's been on market 37 days — a 3% lower offer ($470k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $470k (3.0% below list) — sets the bar for market timing.
• In year one you build about $51k of equity ($3k loan paydown + $48k appreciation (9.8% local appreciation)).
• 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 (+3.3%/yr); 46 active listings in the ZIP; 15 comparable units currently listed for rent nearby; rentals at typical pace (median 14d on market — plan ~3-4 weeks tenant-placement turnaround); 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• 6 sale attempts since 22y 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 $121k; list at $485k implies a 301% gain — meaningful room to come down on a strong offer.
• At projected returns (9.8% appreciation + 3.3% rent growth), your $136k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$82k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• 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 8.5% 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 $5,145/mo this rent would consume 124% of the median local household income ($50k/yr) (locally 1321% 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 37 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.