20 Rolling Hill Rd

Old Westbury, NY 11568

$2,499,000D

5 bd · 3.0 ba · 4,482 sqft · Built 1960 · SingleFamily · Active · 405 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $10,000/mo
• Mortgage (P&I): −$13,105
• Tax + insurance: −$3,756
• HOA: −$0
• Vac / Maint / Mgmt: −$2,100
• Net cashflow: $-8,961/mo
• Annual: $-107,535/yr
• Cap rate: 1.99%
• Cash-on-cash: -15.37%
• DSCR: 0.32
• 1% rule: 0.40%
• Cash to close: $699,720

Investor read

• This is a 5-bed/3.0-bath single-family listed at $2.50M.
• At list price, monthly cash flow is $-9k ($-108k/yr) — negative.
• To cash-flow at today's rent, offer at most $916k (63.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.00M (60.0% below list).
• It's been on market 405 days — a 12% lower offer ($2.20M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $916k (63.3% below list) — sets the bar for cash-flow.
• In year one you build about $267k of equity ($17k loan paydown + $250k appreciation (10.0% local appreciation)).
• Location reads 65/100 on livability (#714 in NY) — a middle-class / working-renter tenant base. Strengths: schools A+, crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Jericho Union Free School District (suburban): math 91% / reading 86% proficiency, ranked #7 of 590 in NY (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 3% free/reduced lunch — higher-income household profile.
• Market conditions: 40 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 824 units permitted in Nassau County in 2024 (153 in 5+ unit buildings).
• Nassau County population projected at +7% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• 3 sale attempts since 14y ago; this cycle's ask has dropped $801k (24%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $435k; list at $2.50M implies a 474% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$429k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: major wind risk, 63% chance of damaging wind over 30y; extreme-heat days projected 7→14/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 405 days. Have you received any prior offers? Is the seller open to a 63% concession, seller financing, or rate buy-down credit?
• Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.
• Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
• 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.