74 Chester St

Bridgehampton, NY 11932

$5,995,000C

6 bd · 5.5 ba · 5,450 sqft · Built 2026 · SingleFamily · Active · 192 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $54,506/mo
• Mortgage (P&I): −$31,438
• Tax + insurance: −$9,992
• HOA: −$0
• Vac / Maint / Mgmt: −$11,446
• Net cashflow: $1,630/mo
• Annual: $19,554/yr
• Cap rate: 6.62%
• Cash-on-cash: 1.16%
• DSCR: 1.05
• 1% rule: 0.91%
• Cash to close: $1,678,600

Investor read

• This is a 6-bed/5.5-bath single-family listed at $6.00M. Condition is rated excellent.
• At list price, monthly cash flow is $2k ($20k/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 $5.45M (9.1% below list).
• It's been on market 192 days — a 12% lower offer ($5.28M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $5.28M (12.0% below list) — sets the bar for market timing.
• In year one you build about $641k of equity ($41k loan paydown + $600k appreciation (10.0% local appreciation)).
• Location reads 62/100 on livability (#874 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, schools B; Watch: amenities F, commute F, cost of living F.
• Bridgehampton Union Free School District (rural): math 50% / reading 40% proficiency, ranked #511 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 24 active listings in the ZIP; 2 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.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $1.68M cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$1.03M 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.
• At $54,506/mo this rent would consume 377% of the median local household income ($174k/yr) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• It's been on market 192 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.
• Schools are B-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.