21 Wilderness Rd

Nissequogue, NY 11780

$1,850,000C+

4 bd · 2.5 ba · 2,841 sqft · Built 1966 · SingleFamily · Active · 22 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $34,160/mo
• Mortgage (P&I): −$9,702
• Tax + insurance: −$2,271
• HOA: −$0
• Vac / Maint / Mgmt: −$7,174
• Net cashflow: $15,014/mo
• Annual: $180,167/yr
• Cap rate: 16.03%
• Cash-on-cash: 34.78%
• DSCR: 2.55
• 1% rule: 1.85%
• Cash to close: $518,000

Investor read

• This is a 4-bed/2.5-bath single-family listed at $1.85M.
• At list price, monthly cash flow is $15k ($180k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($34k rent vs $1.85M).
• It's been on market 22 days — a 2% lower offer ($1.82M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.82M (1.5% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $13k of loan paydown is wiped out by about $56k of value loss. Plan a longer hold.
• Location reads 58/100 on livability (#1,056 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: housing D+, amenities F, commute F.
• Smithtown Central School District (suburban): math 71% / reading 70% proficiency, ranked #86 of 590 in NY (top 15%) — strong family-tenant draw, lease renewals of 3-5y typical; only 5% free/reduced lunch — higher-income household profile.
• Market conditions: 123 active listings in the ZIP; 2 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.
• 5 sale attempts since 13y ago; this cycle's ask has dropped $100k (5%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $790k; list at $1.85M implies a 134% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $518k cash investment doubles in ~4 years — after that, you're playing with house money.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Questions for listing agent

• Built in 1966 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.