43 Gardiners Bay Dr

Shelter Island, NY 11964

$3,625,000B+

5 bd · 4.5 ba · 6,106 sqft · Built 1985 · SingleFamily · Active · 5 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $75,000/mo
• Mortgage (P&I): −$19,010
• Tax + insurance: −$6,042
• HOA: −$0
• Vac / Maint / Mgmt: −$15,750
• Net cashflow: $34,198/mo
• Annual: $410,381/yr
• Cap rate: 17.61%
• Cash-on-cash: 40.43%
• DSCR: 2.80
• 1% rule: 2.07%
• Cash to close: $1,015,000

Investor read

• This is a 5-bed/4.5-bath single-family listed at $3.62M.
• At list price, monthly cash flow is $34k ($410k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($75k rent vs $3.62M).
• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• In year one you build about $96k of equity ($25k loan paydown + $71k 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: 40 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 13y 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 $815k; list at $3.62M implies a 345% gain — meaningful room to come down on a strong offer.
• At projected returns (2.0% appreciation + 3.0% rent growth), your $1.01M cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$245k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Questions for listing agent

• 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.