165 Chestnut St · New York, NY 11208

$1,299,000

9 bd · 3.0 ba · 3,444 sqft · MultiFamily public records · 112 Days on market

Built 1901

---

Why this score? — see what drove the D+ grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +16.1/30.0
• ARV discount +7.5/15.0
• DSCR +5.0/10.0
• Schools +5.0/10.0
• Rent growth +4.0/5.0
• Livability +3.8/5.0
• 1% rule +3.4/10.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 3 units. confirmed

Listing remarks MLS

Extraordinary multi-family investment property just hitting the market right in the heart of Cypress Hills! This amazing 3-family home is an enormous building, with well over 3,000 square feet of living space; with 3 above-ground levels and one level step-down at walk-in ground level, this is a really big home! The breakdown of living space is impressive; with 2-4-bedroom apartments and a third 3-bedroom unit on the walk-in level. Altogether, with an extra bathroom in the basement, it's a whopping 11 beds, 4 baths total! Imagine the revenue for 3 very large, income producing rental units! Rarely do we see such exceptional opportunities. The top floor is the most updated and modern of the three, first two floors might benefit from an upgrade, making this a home-improvement delight! Most appealing is its location near the train station in Cypress Hills, directly between Ridgewood and Fulton Avenues, a couple of blocks from Atlantic Avenue and just a short 2-minute walk from the J and Z.

Key facts

• Private backyard
• Full basement
• Three separate units

Tags

• PRIVATE BACKYARD
• FULL BASEMENT
• THREE SEPARATE UNITS
• PRIME BROOKLYN LOCATION

What this means for you Summary

Snapshot

• This is a 3 × 3-bed/1.0-bath units multifamily listed at $1.30M.

Deal economics

• 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).
• Recommended offer: $1.10M (15.5% below list) — sets the bar for 1% rule.
• 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.

Location & tenants

• 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).
• 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).
• 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.

Forward outlook

• 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.
• Kings County population projected at +13% by 2050 — modest demand growth; plan on rents tracking national, not racing it.

Negotiation context

• It's been on market 112 days — a 9% lower offer ($1.18M) is reasonable based on typical stale-listing flexibility.
• 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.

Risks & watch-outs

• Watch-outs: built in 1901 — expect roof / HVAC / electrical / plumbing capex.
• 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.

Recommended offer $1,097,200 (15.5% below list)

Questions for the listing agent

1. 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?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1901 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. 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?
8. 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?
9. 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?
10. 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.
11. 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.
12. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 0.84% ✗
• Cap rate: 6.90%
• Cash-on-cash: 2.18%
• DSCR: 1.10
• GRM: 9.9

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 6.14% rent growth · sell at horizon

5-year hold

• IRR: -9.7%
• Equity multiple: 0.63×
• Total profit: $-133,119
• Equity at exit: $193,685

10-year hold

• IRR: 3.1%
• Equity multiple: 1.26×
• Total profit: $92,981
• Equity at exit: $112,314

Cash invested: $363,720 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (CITY): 0 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City New York: 0 Strongly Tenant-Friendly · D+34

Rent Stabilization Code; HSTPA; 6+ months in housing court.

Methodology + full state rankings →

ZIP-level market 11208

• Rents YoY: 6.1%
• Active inventory: 193
• Price-to-rent: 29.6×

Monthly cashflow live

• Estimated rent: $10,972 high
• Mortgage (P&I): −$6,812
• Tax from tax record: −$654 /mo · $7,851/yr
• Insurance: −$541
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,304
• Net cashflow: $660

Break-even live

Break-even rent $10,136

Max offer price $1,299,000

Occupancy floor 89%

Sensitivity live

Price	-10% $1,396	-5% $1,028	+0% $660	+5% $293	+10% $-75
Rent	-10% $-207	-5% $227	+0% $660	+5% $1,094	+10% $1,527
Rate	-1.0pp $1,314	-0.5pp $991	base $660	+0.5pp $324	+1.0pp $-19

3-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 3× units	3	1	$10,974
Total (3 units)			$10,972

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $324,750
• Closing costs: $38,970
• Reserves months: —
• Total cash needed: —

Listing history 10 events

1. 2026-01-01
   status Pending
2. 2026-01-01
   historical
3. 2025-09-11
   price $1,299,000
4. 2025-09-09
   listed $1,300,000 Active
5. 2024-06-07
   historical $3,600
6. 2024-05-29
   listed $3,600
7. 2023-05-26
   historical
8. 2022-11-10
   soldstatus $950,000 Closed 999-char remark

   Show marketing remark (999 chars)

   Extraordinary multi-family investment property just hitting the market right in the heart of Cypress Hills! This amazing 3-family home is an enormous building, with well over 3,000 square feet of living space; with 3 above-ground levels and one level step-down at walk-in ground level, this is a really big home! The breakdown of living space is impressive; with 2-4-bedroom apartments and a third 3-bedroom unit on the walk-in level. Altogether, with an extra bathroom in the basement, it's a whopping 11 beds, 4 baths total! Imagine the revenue for 3 very large, income producing rental units! Rarely do we see such exceptional opportunities. The top floor is the most updated and modern of the three, first two floors might benefit from an upgrade, making this a home-improvement delight! Most appealing is its location near the train station in Cypress Hills, directly between Ridgewood and Fulton Avenues, a couple of blocks from Atlantic Avenue and just a short 2-minute walk from the J and Z.

9. 2022-03-11
   status Pending 999-char remark

   Show marketing remark (999 chars)

   Extraordinary multi-family investment property just hitting the market right in the heart of Cypress Hills! This amazing 3-family home is an enormous building, with well over 3,000 square feet of living space; with 3 above-ground levels and one level step-down at walk-in ground level, this is a really big home! The breakdown of living space is impressive; with 2-4-bedroom apartments and a third 3-bedroom unit on the walk-in level. Altogether, with an extra bathroom in the basement, it's a whopping 11 beds, 4 baths total! Imagine the revenue for 3 very large, income producing rental units! Rarely do we see such exceptional opportunities. The top floor is the most updated and modern of the three, first two floors might benefit from an upgrade, making this a home-improvement delight! Most appealing is its location near the train station in Cypress Hills, directly between Ridgewood and Fulton Avenues, a couple of blocks from Atlantic Avenue and just a short 2-minute walk from the J and Z.

10. 2022-01-24
    listed $940,000 Active 999-char remark

    Show marketing remark (999 chars)

    Extraordinary multi-family investment property just hitting the market right in the heart of Cypress Hills! This amazing 3-family home is an enormous building, with well over 3,000 square feet of living space; with 3 above-ground levels and one level step-down at walk-in ground level, this is a really big home! The breakdown of living space is impressive; with 2-4-bedroom apartments and a third 3-bedroom unit on the walk-in level. Altogether, with an extra bathroom in the basement, it's a whopping 11 beds, 4 baths total! Imagine the revenue for 3 very large, income producing rental units! Rarely do we see such exceptional opportunities. The top floor is the most updated and modern of the three, first two floors might benefit from an upgrade, making this a home-improvement delight! Most appealing is its location near the train station in Cypress Hills, directly between Ridgewood and Fulton Avenues, a couple of blocks from Atlantic Avenue and just a short 2-minute walk from the J and Z.

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $7,851 · $654/mo
• Projected year-2 tax: $14,902 · $1,242/mo
• Expected delta: +$7,051/yr (+$588/mo · 89.8%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥99°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 39% chance of damaging wind over 30 yrs
• 🫁 Air quality 5/10 Major 6 unhealthy d/yr today · 8 by 30 yrs out

Taxation est. · year 1

• Rental income: $131,664
• − Mortgage interest: −$72,764
• − Property taxes: −$7,851
• − Insurance: −$6,495
• − Repairs & maintenance: −$10,533
• − Management: −$10,533
• − Depreciation: −$37,789
• Taxable loss: −$14,302
• Est. tax savings @ 24.0%: +$3,432
• After-tax cash flow: $11,355/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

No district data.

Livability — New York

• Score: 75/100
• State rank: #268
• US rank: #4188

Category grades

Amenities A+ Commute A+ Cost of living F Crime F Employment A- Housing C+ Health & safety A User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: New York, NY
• County: Kings County · 2,614,986 people
• City population: 7,731,280
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 105,428
• Household income: $62,077
• Rent vs Own: 75.1% rent · 24.9% own
• Severe rent burden: 7574.0

Population outlook (Kings County) Hauer SSP2

• Today (2025): 2,847,441 people
• By 2030: 2,937,006 · +3.1%
• By 2040: 3,095,491 · +8.7%
• By 2050: 3,228,968 · +13.4%
• By 2075: 3,321,723 · +16.7%
• By 2100: 3,111,387 · +9.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.66)
• Race & ethnicity: Black 42% Hispanic / Latino 39% Asian 10% Two or more races 8% White 3%
• Hispanic origin (detail): Mexican 2% Puerto Rican 9% Dominican 16%
• Common ancestry: Hispanic 1%
• Foreign-born: 40% · Canada, China, Mexico
• Languages at home: 48% English-only · Spanish 36% Other Indo-European 11% French/Haitian/Cajun 1%

Political lean MEDSL · Kings

• 2024 margin: Solid D (+44.0) · D 72.0% · R 28.0%
• 2008→2024 swing: -15.5pp toward R · 2008: 59.4pp · 2024: 44.0pp
• All cycles: 2024: D+44.0 2020: D+54.8 2016: D+61.8 2012: D+63.9 2008: D+59.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -546.38%
• Current HPI: 376.1489
• Rent YoY: ▲ 6.14%
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+38.2% since first listed

10 events — show timeline

• 2026-01-01 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-01-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-09-11 Price Changed $1,299,000 OneKey® MLS as Distributed by MLS Grid
• 2025-09-09 Listed $1,300,000 OneKey® MLS as Distributed by MLS Grid
• 2024-06-07 Rental Removed $3,600 ONEKEY
• 2024-05-29 Listed for Rent $3,600 ONEKEY
• 2023-05-26 Rental Removed — ONEKEY
• 2022-11-10 Sold (MLS) $950,000 OneKey® MLS as Distributed by MLS Grid
• 2022-03-11 Pending — OneKey® MLS as Distributed by MLS Grid
• 2022-01-24 Listed $940,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+5.1%/yr

Latest (2025): $7,851 · +3.3% YoY. Source: county tax records.