44 Upper State St

North Haven, CT 06473

$269,000C+

3 bd · 1.0 ba · 1,290 sqft · Built 1954 · SingleFamily · Under Contract · 23 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,897/mo
• Mortgage (P&I): −$1,411
• Tax + insurance: −$540
• HOA: −$0
• Vac / Maint / Mgmt: −$608
• Net cashflow: $338/mo
• Annual: $4,054/yr
• Cap rate: 7.80%
• Cash-on-cash: 5.38%
• DSCR: 1.24
• 1% rule: 1.08%
• Cash to close: $75,320

Investor read

• This is a 3-bed/1.0-bath single-family listed at $269k.
• At list price, monthly cash flow is $338 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $269k).
• It's been on market 23 days — a 2% lower offer ($265k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $265k (1.5% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $8k of value loss. Plan a longer hold.
• Location reads 78/100 on livability (#39 in CT, #2,723 nationally) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety A+; Watch: amenities F, commute F, cost of living D-.
• North Haven School District (suburban): math 49% / reading 64% proficiency, ranked #55 of 153 in CT (top 36%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Watch-outs: built in 1954 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 77 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals at typical pace (median 15d 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).
• 2 sale attempts 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.
• Cap rate 7.8% vs local median 4.0% in North 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.

Questions for listing agent

• Built in 1954 — 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?
• 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 for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.