39 Pinetop Dr

Shirley, NY 11967

$669,000D

4 bd · 3.5 ba · 2,832 sqft · Built 1957 · SingleFamily · Active · 39 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,843/mo
• Mortgage (P&I): −$3,508
• Tax + insurance: −$1,104
• HOA: −$0
• Vac / Maint / Mgmt: −$1,227
• Net cashflow: $3/mo
• Annual: $39/yr
• Cap rate: 6.30%
• Cash-on-cash: 0.02%
• DSCR: 1.00
• 1% rule: 0.87%
• Cash to close: $187,320

Investor read

• This is a 4-bed/3.5-bath single-family listed at $669k.
• At list price, monthly cash flow is $3 ($39/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $584k (12.7% below list).
• It's been on market 39 days — a 3% lower offer ($649k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $584k (12.7% below list) — sets the bar for 1% rule.
• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $20k of value loss. Plan a longer hold.
• Location reads 62/100 on livability (#886 in NY) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+; Watch: crime D+, amenities F, commute F.
• William Floyd Union Free School District (suburban): math 48% / reading 57% proficiency, ranked #309 of 590 in NY (top 52%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: William Floyd Elementary School (math 48% / reading 54%, grade C-, #1,047 of 2,108 statewide, top 50%, 742 students, 54% FRL); William Floyd Middle School (math 36% / reading 47%, grade F, #394 of 729 statewide, top 55%, 1,053 students, 54% FRL); William Floyd High School (math 65% / reading 87%, grade A-, #616 of 1,100 statewide, top 57%, 3,013 students, 54% FRL).
• Watch-outs: built in 1957 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 185 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.
• 3 sale attempts since 4y 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 $350k; list at $669k implies a 91% gain — meaningful room to come down on a strong offer.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.
• Cap rate 6.3% vs local median 4.8% in Shirley — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Questions for listing agent

• It's been on market 39 days. Have you received any prior offers? Is the seller open to a 13% concession, seller financing, or rate buy-down credit?
• Built in 1957 — 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?
• Crime grade is D in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
• 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.