38 Pleasure Dr

Flanders, NY 11901

$775,000C+

4 bd · 2.0 ba · 1,600 sqft · Built 1860 · SingleFamily · Active · 4 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $24,682/mo
• Mortgage (P&I): −$4,064
• Tax + insurance: −$759
• HOA: −$0
• Vac / Maint / Mgmt: −$5,183
• Net cashflow: $14,676/mo
• Annual: $176,108/yr
• Cap rate: 29.02%
• Cash-on-cash: 81.16%
• DSCR: 4.61
• 1% rule: 3.18%
• Cash to close: $217,000

Investor read

• This is a 4-bed/2.0-bath single-family listed at $775k.
• At list price, monthly cash flow is $15k ($176k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($25k rent vs $775k).
• Only 4 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $23k of value loss. Plan a longer hold.
• Location reads 56/100 on livability (#1,107 in NY) — a working-class tenant base; expect higher turnover. Strengths: employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Riverhead Central School District (suburban): math 34% / reading 48% proficiency, ranked #489 of 590 in NY (top 83%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Phillips Avenue School (math 17% / reading 32%, grade F, #1,846 of 2,108 statewide, top 91%, 578 students, 50% FRL); Riverhead Middle School (math 18% / reading 35%, grade F, #594 of 729 statewide, top 81%, 827 students, 57% FRL); Riverhead Senior High School (math 80% / reading 86%, grade A, #440 of 1,100 statewide, top 40%, 2,001 students, 52% FRL).
• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 192 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.
• 2 sale attempts since 14y 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 $438k; list at $775k implies a 77% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $217k cash investment doubles in ~2 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 1860 — 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.
• Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
• 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.