13 Winthrop Rd #24

Shelter Island Heights, NY 11964

$499,000D-

1 bd · 1.0 ba · 39,964 sqft · Built 1980 · Condo · Active · 88 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $3,888/mo
• Mortgage (P&I): −$2,617
• Tax + insurance: −$832
• HOA: −$0
• Vac / Maint / Mgmt: −$816
• Net cashflow: $-377/mo
• Annual: $-4,527/yr
• Cap rate: 5.39%
• Cash-on-cash: -3.24%
• DSCR: 0.86
• 1% rule: 0.78%
• Cash to close: $139,720

Investor read

• This is a 1-bed/1.0-bath condo listed at $499k.
• At list price, monthly cash flow is $-377 ($-5k/yr) — negative.
• To cash-flow at today's rent, offer at most $444k (10.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $389k (22.1% below list).
• It's been on market 88 days — a 6% lower offer ($469k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $389k (22.1% below list) — sets the bar for 1% rule.
• In year one you build about $13k of equity ($3k loan paydown + $10k 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; 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 ~$34k 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 88 days. Have you received any prior offers? Is the seller open to a 22% concession, seller financing, or rate buy-down credit?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• 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?
• This sits on a lake — are riparian / water-frontage rights deeded with the parcel? Any dock permits, shoreline easements, or HOA water-use restrictions?
• What's the documented flood / surge / shoreline-erosion history here (FEMA AND non-FEMA — e.g., storm surge, creek backup, septic-field saturation)?