23 Bacon Rd

Head of the Harbor, NY 11780

$1,399,999B

5 bd · 5.0 ba · 5,393 sqft · Built 1960 · SingleFamily · Pending · 233 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $20,000/mo
• Mortgage (P&I): −$7,342
• Tax + insurance: −$2,490
• HOA: −$0
• Vac / Maint / Mgmt: −$4,200
• Net cashflow: $5,968/mo
• Annual: $71,615/yr
• Cap rate: 11.41%
• Cash-on-cash: 18.27%
• DSCR: 1.81
• 1% rule: 1.43%
• Cash to close: $392,000

Investor read

• This is a 5-bed/5.0-bath single-family listed at $1.40M.
• At list price, monthly cash flow is $6k ($72k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.40M).
• It's been on market 233 days — a 12% lower offer ($1.23M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.23M (12.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $10k of loan paydown is wiped out by about $42k of value loss. Plan a longer hold.
• Location reads 64/100 on livability (#719 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Smithtown Central School District (suburban): math 71% / reading 70% proficiency, ranked #86 of 590 in NY (top 15%) — strong family-tenant draw, lease renewals of 3-5y typical; only 5% free/reduced lunch — higher-income household profile.
• Zoned schools: Saint James Elementary School (math 62% / reading 67%, grade B, #591 of 2,108 statewide, top 31%, 474 students, 15% FRL); Nesaquake Middle School (math 44% / reading 67%, grade B-, #211 of 729 statewide, top 29%, 473 students, 10% FRL); Smithtown High School East (math 96% / reading 82%, grade A+, #288 of 1,100 statewide, top 27%, 1,475 students, 12% FRL).
• Market conditions: 124 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• 4 sale attempts since 2y 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.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $392k cash investment doubles in ~7 years — after that, you're playing with house money.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Questions for listing agent

• It's been on market 233 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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 B-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.