90 Peconic Ave

Shelter Island Heights, NY 11964

$4,800,000B+

5 bd · 3.5 ba · 3,325 sqft · Built 1985 · SingleFamily · Active · 16 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $75,000/mo
• Mortgage (P&I): −$25,172
• Tax + insurance: −$8,000
• HOA: −$6
• Vac / Maint / Mgmt: −$15,750
• Net cashflow: $26,072/mo
• Annual: $312,867/yr
• Cap rate: 12.81%
• Cash-on-cash: 23.28%
• DSCR: 2.04
• 1% rule: 1.56%
• Cash to close: $1,344,000

Investor read

• This is a 5-bed/3.5-bath single-family listed at $4.80M.
• At list price, monthly cash flow is $26k ($313k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($75k rent vs $4.80M).
• It's been on market 16 days — a 2% lower offer ($4.73M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $4.73M (1.5% below list) — sets the bar for market timing.
• In year one you build about $128k of equity ($33k loan paydown + $94k appreciation (2.0% local appreciation)).
• Location reads 56/100 on livability (#1,120 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Shelter Island Union Free School District (rural): math 40% / reading 45% proficiency, ranked #546 of 755 in NY (top 72%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 39 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.
• 3 sale attempts since 7y 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 (2.0% appreciation + 3.0% rent growth), your $1.34M cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$324k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Questions for listing agent

• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• 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.