165 Chestnut St

New York, NY 11208

$1,299,000D+

9 bd · 3.0 ba · 3,444 sqft · Built 1901 · MultiFamily · Pending · 112 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $10,972/mo
• Mortgage (P&I): −$6,812
• Tax + insurance: −$1,196
• HOA: −$0
• Vac / Maint / Mgmt: −$2,304
• Net cashflow: $660/mo
• Annual: $7,923/yr
• Cap rate: 6.90%
• Cash-on-cash: 2.18%
• DSCR: 1.10
• 1% rule: 0.84%
• Cash to close: $363,720

Investor read

• This is a 3 × 3-bed/1.0-bath units multifamily listed at $1.30M.
• At list price, monthly cash flow is $660 ($8k/yr) — positive. Per door: $220/mo.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.10M (15.5% below list).
• It's been on market 112 days — a 9% lower offer ($1.18M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.10M (15.5% below list) — sets the bar for 1% rule.
• Local home prices are declining (-3.0%/yr); year-one equity from $9k of loan paydown is wiped out by about $39k of value loss. Plan a longer hold.
• Location reads 75/100 on livability (#268 in NY, #4,188 nationally) — a middle-class / working-renter tenant base. Strengths: amenities A+, commute A+, health & safety A; Watch: crime F, cost of living F.
• Zoned schools: Elm Tree Elementary School (math 27% / reading 52%, grade F, #1,444 of 2,108 statewide, top 71%, 806 students, 94% FRL); Jhs 383 Philippa Schuyler (math 32% / reading 67%, grade C, #280 of 729 statewide, top 40%, 822 students, 85% FRL); Midwood High School (math 94% / reading 96%, grade A+, #83 of 1,100 statewide, top 8%, 4,062 students, 73% FRL).
• Watch-outs: built in 1901 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+6.1%/yr); 193 active listings in the ZIP; 10,063 units permitted in Kings County in 2024 (9,789 in 5+ unit buildings).
• Kings County population projected at +13% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• 3 sale attempts since 4y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $950k; 37% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Climate carrying-cost: major wind risk, 39% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 6.9% vs local median 2.6% in New York — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.
• At $10,972/mo this rent would consume 212% of the median local household income ($62k/yr) (locally 7574% 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 112 days. Have you received any prior offers? Is the seller open to a 16% concession, seller financing, or rate buy-down credit?
• Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
• What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
• Built in 1901 — 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 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?
• Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?