290 Windward Rd

Orient, NY 11957

$2,499,999C

5 bd · 4.0 ba · 4,200 sqft · Built 2023 · SingleFamily · Active · 481 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $21,998/mo
• Mortgage (P&I): −$13,110
• Tax + insurance: −$2,263
• HOA: −$0
• Vac / Maint / Mgmt: −$4,619
• Net cashflow: $2,005/mo
• Annual: $24,062/yr
• Cap rate: 7.26%
• Cash-on-cash: 3.44%
• DSCR: 1.15
• 1% rule: 0.88%
• Cash to close: $700,000

Investor read

• This is a 5-bed/4.0-bath single-family listed at $2.50M.
• At list price, monthly cash flow is $2k ($24k/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 $2.20M (12.0% below list).
• It's been on market 481 days — a 12% lower offer ($2.20M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $2.20M (12.0% below list) — sets the bar for 1% rule.
• In year one you build about $267k of equity ($17k loan paydown + $250k appreciation (10.0% local appreciation)).
• Location reads 57/100 on livability (#1,080 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Oysterponds Union Free School District (rural): math 30% / reading 60% proficiency, ranked #506 of 755 in NY (top 67%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 4% free/reduced lunch — higher-income household profile.
• Zoned schools: Oysterponds Elementary School (math 54% / reading 64%, grade B-, #745 of 2,108 statewide, top 39%, 80 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Zoned-school proficiency averages 60% at this address vs 45% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Oysterponds Union Free School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 25 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals lingering (median 46d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% 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.
• 4 sale attempts since 2y ago; this cycle's ask has dropped $199k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $300k; list at $2.50M implies a 733% gain — meaningful room to come down on a strong offer.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $700k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$430k 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

• It's been on market 481 days. Have you received any prior offers? Is the seller open to a 12% 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.
• 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.