69 Hillside Dr E

Sag Harbor, NY 11963

$1,490,000A-

3 bd · 2.0 ba · 3,843 sqft · Built 1954 · SingleFamily · Pending · 429 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $22,932/mo
• Mortgage (P&I): −$7,814
• Tax + insurance: −$969
• HOA: −$0
• Vac / Maint / Mgmt: −$4,816
• Net cashflow: $9,334/mo
• Annual: $112,005/yr
• Cap rate: 13.81%
• Cash-on-cash: 26.85%
• DSCR: 2.19
• 1% rule: 1.54%
• Cash to close: $417,200

Investor read

• This is a 3-bed/2.0-bath single-family listed at $1.49M.
• At list price, monthly cash flow is $9k ($112k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $1.49M).
• It's been on market 429 days — a 12% lower offer ($1.31M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.31M (12.0% below list) — sets the bar for market timing.
• In year one you build about $147k of equity ($10k loan paydown + $137k appreciation (9.2% local appreciation)).
• Location reads 70/100 on livability (#427 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety A; Watch: amenities F, commute F, cost of living F.
• Sag Harbor Union Free School District (suburban): math 54% / reading 70% proficiency, ranked #175 of 590 in NY (top 30%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Zoned schools: Sag Harbor Elementary School (math 47% / reading 72%, grade B-, #745 of 2,108 statewide, top 39%, 426 students, 22% FRL); Pierson Middle/High School (math 61% / reading 72%, grade B, #763 of 1,100 statewide, top 69%, 525 students, 25% FRL) — zoned schools average 24% FRL vs 8% district-wide (16 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Watch-outs: built in 1954 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+10.8%/yr); 65 active listings in the ZIP; high-income renter base; 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 2y ago; this cycle's ask has dropped $105k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• At projected returns (9.2% appreciation + 8.0% rent growth), your $417k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$236k 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 — expect insurance premiums to compound above CPI over the hold.
• At $22,932/mo this rent would consume 215% of the median local household income ($128k/yr) (locally 95% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• It's been on market 429 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1954 — 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?
• 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.