12 Terry Dr

Shelter Island, NY 11964

$2,950,000A-

5 bd · 4.5 ba · 4,200 sqft · Built 2016 · SingleFamily · Active · 72 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $53,363/mo
• Mortgage (P&I): −$15,470
• Tax + insurance: −$4,917
• HOA: −$15
• Vac / Maint / Mgmt: −$11,206
• Net cashflow: $21,755/mo
• Annual: $261,058/yr
• Cap rate: 15.14%
• Cash-on-cash: 31.61%
• DSCR: 2.41
• 1% rule: 1.81%
• Cash to close: $826,000

Investor read

• This is a 5-bed/4.5-bath single-family listed at $2.95M. Condition is rated good.
• At list price, monthly cash flow is $22k ($261k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($53k rent vs $2.95M).
• It's been on market 72 days — a 6% lower offer ($2.77M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $2.77M (6.0% below list) — sets the bar for market timing.
• In year one you build about $78k of equity ($20k loan paydown + $58k appreciation (2.0% local appreciation)).
• Location reads 60/100 on livability (#998 in NY) — a middle-class / working-renter tenant base. 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; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 23d on market — plan ~3-4 weeks tenant-placement turnaround); 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.
• At projected returns (2.0% appreciation + 3.0% rent growth), your $826k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$199k 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

• It's been on market 72 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• 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.
• 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.