14 Freds Ln

Shelter Island Heights, NY 11964

$2,485,000D-

4 bd · 3.0 ba · 2,418 sqft · Built 2014 · SingleFamily · Active · 75 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $10,319/mo
• Mortgage (P&I): −$13,032
• Tax + insurance: −$1,730
• HOA: −$0
• Vac / Maint / Mgmt: −$2,167
• Net cashflow: $-6,609/mo
• Annual: $-79,311/yr
• Cap rate: 3.10%
• Cash-on-cash: -11.40%
• DSCR: 0.49
• 1% rule: 0.42%
• Cash to close: $695,800

Investor read

• This is a 4-bed/3.0-bath single-family listed at $2.48M.
• At list price, monthly cash flow is $-7k ($-79k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.32M (47.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.03M (58.5% below list).
• It's been on market 75 days — a 6% lower offer ($2.34M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.03M (58.5% below list) — sets the bar for 1% rule.
• In year one you build about $66k of equity ($17k loan paydown + $49k 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: 40 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 45d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; 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.
• Current owner paid $325k; list at $2.48M implies a 665% gain — meaningful room to come down on a strong offer.
• By year 3, paydown + projected appreciation supports a ~$168k 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 75 days. Have you received any prior offers? Is the seller open to a 58% concession, seller financing, or rate buy-down credit?
• 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.
• 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.