744 Canaan Road Rd #23

Bridgeport, CT 06610

$59,000B-

2 bd · 1.0 ba · 650 sqft · Built 1956 · Condo · Active · 62 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,731/mo
• Mortgage (P&I): −$309
• Tax + insurance: −$98
• HOA: −$584
• Vac / Maint / Mgmt: −$364
• Net cashflow: $376/mo
• Annual: $4,510/yr
• Cap rate: 13.94%
• Cash-on-cash: 27.30%
• DSCR: 2.21
• 1% rule: 2.93%
• Cash to close: $16,520

Investor read

• This is a 2-bed/1.0-bath condo listed at $59k.
• At list price, monthly cash flow is $376 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $59k).
• It's been on market 62 days — a 6% lower offer ($55k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $55k (6.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $408 of loan paydown is wiped out by about $2k of value loss. Plan a longer hold.
• Location reads 81/100 on livability (#15 in CT, #1,374 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, health & safety A+; Watch: crime C-, employment D+, schools D-.
• Bridgeport School District (urban): math 9% / reading 19% proficiency, ranked #151 of 153 in CT (top 99%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 97% free/reduced lunch — lower-income household profile, screen leases tightly.
• Watch-outs: HOA is 34% of rent; built in 1956 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 68 active listings in the ZIP; 22 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 852 units permitted in Greater Bridgeport Planning Region in 2024 (698 in 5+ unit buildings).
• 5 sale attempts since 15y 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 $24k; list at $59k implies a 146% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $17k cash investment doubles in ~5 years — after that, you're playing with house money.
• Climate carrying-cost: major wind risk, 51% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 13.9% vs local median 5.0% in Bridgeport — 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.
• This rent runs 40% of the median local income ($52k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• It's been on market 62 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
• Built in 1956 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
• 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?
• 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.