66 Hillside Dr E

Sag Harbor, NY 11963

$4,700,000D+

6 bd · 7.0 ba · 4,519 sqft · Built 2025 · Land · Active · 303 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $29,830/mo
• Mortgage (P&I): −$24,647
• Tax + insurance: −$7,833
• HOA: −$0
• Vac / Maint / Mgmt: −$6,264
• Net cashflow: $-8,915/mo
• Annual: $-106,978/yr
• Cap rate: 4.02%
• Cash-on-cash: -8.13%
• DSCR: 0.64
• 1% rule: 0.63%
• Cash to close: $1,316,000

Investor read

• This is a 6-bed/7.0-bath land listed at $4.70M.
• At list price, monthly cash flow is $-9k ($-107k/yr) — negative.
• To cash-flow at today's rent, offer at most $3.41M (27.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $2.98M (36.5% below list).
• It's been on market 303 days — a 12% lower offer ($4.14M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $2.98M (36.5% below list) — sets the bar for 1% rule.
• In year one you build about $464k of equity ($32k loan paydown + $432k 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.
• Market conditions: Rents rising fast (+10.8%/yr); 65 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 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.
• 3 sale attempts since 3y ago; this cycle's ask has dropped $295k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $1.43M; list at $4.70M implies a 230% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$745k 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 $29,830/mo this rent would consume 280% 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

• 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 303 days. Have you received any prior offers? Is the seller open to a 37% 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.
• 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.
• 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.