16 Shelterlands Path

Shelter Island, NY 11964

$1,175,000D

4 bd · 3.0 ba · 1,950 sqft · Built 1988 · SingleFamily · Pending · 58 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $7,200/mo
• Mortgage (P&I): −$6,162
• Tax + insurance: −$909
• HOA: −$4
• Vac / Maint / Mgmt: −$1,512
• Net cashflow: $-1,387/mo
• Annual: $-16,638/yr
• Cap rate: 4.88%
• Cash-on-cash: -5.06%
• DSCR: 0.77
• 1% rule: 0.61%
• Cash to close: $329,000

Investor read

• This is a 4-bed/3.0-bath single-family listed at $1.18M.
• At list price, monthly cash flow is $-1k ($-17k/yr) — negative.
• To cash-flow at today's rent, offer at most $930k (20.8% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $720k (38.7% below list).
• It's been on market 58 days — a 3% lower offer ($1.14M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $720k (38.7% below list) — sets the bar for 1% rule.
• In year one you build about $31k of equity ($8k loan paydown + $23k 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; 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.
• By year 3, paydown + projected appreciation supports a ~$79k 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 do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
• It's been on market 58 days. Have you received any prior offers? Is the seller open to a 39% 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?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
• 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.