56 Woolsey St · New Haven, CT 06513

$380,000

5 bd · 3.0 ba · 1,920 sqft · MultiFamily public records · 41 Days on market

Built 1900 6,534 sqft lot Est $334k · 14% over

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Why this score? — see what drove the C+ 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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Livability +4.0/5.0
• Rent growth +3.5/5.0
• Condition / age +2.5/5.0
• Schools +1.5/10.0
• ARV discount +1.3/15.0
• 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

Multi-family with ample parking and potential for a four car garage as the foundation is already set. A newer roof that is one year old. Three units that are in fair condition and producing $50,400 annually, completely rented on a month to month basis. Whether you are looking for a steady cash flow or your own slice of ownership in New Haven. Do not waste any time folks this one is bigger on the inside.

Key facts

• Completely rented
• Ample parking
• Newer roof

Tags

• AMPLE PARKING
• NEWER ROOF
• THREE UNITS
• STEADY CASH FLOW
• COMPLETELY RENTED

What this means for you Summary

Snapshot

• This is a 3 × 2-bed/1.0-bath units multifamily listed at $380k.

Deal economics

• At list price, monthly cash flow is $2k ($22k/yr) — positive. Per door: $607/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $380k).
• Recommended offer: $369k (3.0% below list) — sets the bar for market timing.
• Cap rate 12.0% vs local median 4.5% in New Haven — 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 79/100 on livability (#31 in CT, #2,190 nationally) — a middle-class / working-renter tenant base. Strengths: amenities A+, commute A+, health & safety A+; Watch: schools D+, employment D, crime F.
• New Haven School District (urban): math 12% / reading 25% proficiency, ranked #147 of 153 in CT (top 96%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 66% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: Rents rising fast (+4.1%/yr); 102 active listings in the ZIP; 23 comparable units currently listed for rent nearby; rentals leasing fast (median 12d on market — plan ~1-2 weeks tenant-placement turnaround); 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• At $5,794/mo this rent would consume 143% of the median local household income ($48k/yr) (locally 2664% 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 $3k of loan paydown is wiped out by about $11k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 4.1% rent growth), your $106k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 41 days — a 3% lower offer ($369k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 20y ago; this cycle's ask is 9% above the opening price — seller raised mid-cycle; expect resistance to lowballs.
• Current owner paid $14k; list at $380k implies a 2614% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 56% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $368,600 (3.0% below list)

Questions for the listing agent

1. It's been on market 41 days. Have you received any prior offers? Is the seller open to a 3% 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 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
7. 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?
8. 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.
9. 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.
10. 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: 1.52% ✓
• Cap rate: 12.04%
• Cash-on-cash: 20.54%
• DSCR: 1.91
• GRM: 5.5

CMA / ARV

• ARV (on-the-fly): $334,080
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
213 Saltonstall Ave	0.22mi	5/2.0	1,920 (0%)	3mo	$325,000	$169	84
206 Saltonstall Ave	0.24mi	6/2.0 (+1)	1,980 (+3%)	1mo	$365,000	$184	73
72 Woolsey St	0.06mi	6/2.0 (+1)	2,066 (+8%)	7mo	$360,000	$174	70
14 Market St	0.24mi	6/3.0 (+1)	2,054 (+7%)	10mo	$385,000	$187	63
73 Main St	0.43mi	6/3.0 (+1)	1,800 (-6%)	3mo	$365,000	$203	62
229 Exchange St	0.12mi	6/2.0 (+1)	2,080 (+8%)	13mo	$329,000	$158	60
439 Lombard St	0.51mi	4/2.0 (-1)	1,996 (+4%)	4mo	$440,000	$220	58
85 Pierpont St	0.29mi	4/2.0 (-1)	1,704 (-11%)	5mo	$170,000	$100	54
366 Quinnipiac Ave	0.71mi	4/2.0 (-1)	1,914 (-0%)	12mo	$330,000	$172	48
16 Mill River St	0.54mi	6/2.0 (+1)	1,750 (-9%)	6mo	$365,000	$209	46
464 Blatchley Ave	0.52mi	6/2.0 (+1)	2,156 (+12%)	4mo	$365,000	$169	43
197 Farren Ave	0.69mi	4/2.0 (-1)	1,848 (-4%)	13mo	$320,000	$173	42

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 4.12% rent growth · sell at horizon

5-year hold

• IRR: 14.2%
• Equity multiple: 1.58×
• Total profit: $61,200
• Equity at exit: $56,659

10-year hold

• IRR: 23.8%
• Equity multiple: 3.17×
• Total profit: $231,064
• Equity at exit: $32,855

Cash invested: $106,400 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Connecticut: 27 Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

Methodology + full state rankings →

ZIP-level market 06513

• Home prices YoY: -7.8%
• Rents YoY: 4.1%
• Active inventory: 102
• Price-to-rent: 16.4×

Monthly cashflow live

• Estimated rent: $5,794 high
• Mortgage (P&I): −$1,993
• Tax from tax record: −$605 /mo · $7,257/yr
• Insurance: −$158
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,217
• Net cashflow: $1,821

Break-even live

Break-even rent $3,488

Max offer price $380,000

Occupancy floor 64%

Sensitivity live

Price	-10% $2,037	-5% $1,929	+0% $1,821	+5% $1,714	+10% $1,606
Rent	-10% $1,364	-5% $1,593	+0% $1,821	+5% $2,050	+10% $2,279
Rate	-1.0pp $2,013	-0.5pp $1,918	base $1,821	+0.5pp $1,723	+1.0pp $1,623

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

Units	Beds	Baths	Est. rent
▸ 3× units	2	1	$5,793
Total (3 units)			$5,794

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: $95,000
• Closing costs: $11,400
• Reserves months: —
• Total cash needed: —

Rent comps 23 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
302 Exchange St Unit 2 New Haven, CT	5.0	2.0	1800	$2,500	$1.39	44d	1	0.09mi
18 Woolsey St New Haven, CT	5.0	2.0	1446	$2,900	$2.01	12d	1	0.11mi
18 Woolsey St New Haven, CT	6.0	2.0	1446	$3,000	$2.07	44d	1	0.11mi
295 Lloyd St Unit 2 New Haven, CT	4.0	2.0	2621	$2,400	$0.92	3d	1	0.16mi
115 Lloyd St #2 New Haven, CT	4.0	2.0	2100	$2,500	$1.19	44d	1	0.24mi
139 Poplar St New Haven, CT	6.0	1.0	1673	$3,100	$1.85	44d	1	0.25mi
426 Poplar St Unit 2 New Haven, CT	4.0	2.0	1405	$1,800	$1.28	3d	1	0.38mi
441 Chapel St Unit 2A1 (shared) New Haven, CT	4.0	4.0	2151	$3,600	$1.67	3d	1	0.71mi
28 Edwards St Unit 2 New Haven, CT	4.0	2.0	1800	$3,850	$2.14	15d	1	0.78mi
54 Mechanic St Unit 2nd floor New Haven, CT	4.0	2.0	1412	$3,600	$2.55	44d	1	0.80mi
31 Clark St New Haven, CT	4.0	2.0	1694	$4,200	$2.48	4d	1	0.84mi
315 Humphrey St Unit A New Haven, CT	4.0	3.5	2465	$4,500	$1.83	4d	1	0.89mi
59 Clark St New Haven, CT	4.0	1.0	1541	$3,250	$2.11	24d	1	0.90mi
399 Orange St New Haven, CT	4.0	1.5	1650	$3,200	$1.94	12d	1	1.04mi
395 Orange St Unit 2 New Haven, CT	4.0	1.5	1650	$3,000	$1.82	44d	1	1.04mi
54 Trumbull St Unit 54-1 New Haven, CT	5.0	2.5	2250	$6,695	$2.98	15d	1	1.12mi
67 Trumbull St New Haven, CT	4.0	1.0	1400	$3,200	$2.29	12d	1	1.16mi
87 Union St New Haven, CT	4.0	1.0–4.0	959	$5,543	$5.78	4d	16	1.16mi
250 Willow St #3 New Haven, CT	4.0	2.0	1234	$3,600	$2.92	4d	1	1.18mi
251 Edwards St Unit 2 New Haven, CT	4.0	1.5	1522	$3,900	$2.56	4d	1	1.22mi
339 Willow St Unit 1 New Haven, CT	4.0	2.0	2163	$4,050	$1.87	12d	1	1.33mi
420 Whitney Ave New Haven, CT	3.0–4.0	2.0–3.0	1800	$4,700	$2.61	12d	2	1.37mi
420 Whitney Ave Unit 424-3B New Haven, CT	4.0	3.0	1800	$4,700	$2.61	4d	1	1.37mi

Listing history 11 events

1. 2025-12-15
   status Under Contract
2. 2025-11-06
   price $380,000
3. 2025-11-04
   listed $350,000 Active
4. 2024-03-17
   historical
5. 2023-12-07
   price $380,000
6. 2023-11-09
   listed $385,000 Active
7. 2006-12-08
   historical
8. 2006-06-09
   listed $289,900
9. 1998-08-07
   soldstatus $14,000
10. 1995-11-28
    soldstatus $15,000
11. 1995-11-06
    soldstatus $12,500

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $7,257 · $605/mo
• Projected year-2 tax: $7,694 · $641/mo
• Expected delta: +$438/yr (+$36/mo · 6.0%)

ⓘ 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 7/10 Severe 7 d/yr ≥99°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 56% 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: $69,528
• − Mortgage interest: −$21,286
• − Property taxes: −$7,257
• − Insurance: −$1,900
• − Repairs & maintenance: −$5,562
• − Management: −$5,562
• − Depreciation: −$11,055
• Taxable income: $16,906
• Est. tax owed @ 24.0%: −$4,057
• After-tax cash flow: $17,800/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)

• District: New Haven School District
• NCES district ID: 0902790
• Math proficiency: 12% ▼ -10.00%
• Reading proficiency: 25% ▼ -10.00%
• Median HH income: $38,058
• Composite: 15.48/100
• National rank: #9308
• State rank: #147 of 153 in CT

Livability — New Haven

• Score: 79/100
• State rank: #31
• US rank: #2190

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: New Haven, CT
• County: New Haven County · 688,236 people
• City population: 132,813
• Metro: New Haven-Milford, CT
• Population (ZIP): 38,888
• Household income: $48,500
• Rent vs Own: 59.7% rent · 40.3% own
• Severe rent burden: 2664.0

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.66)
• Race & ethnicity: Hispanic / Latino 47% White 26% Black 22% Two or more races 12% Asian 1%
• Hispanic origin (detail): Mexican 7% Puerto Rican 25% Dominican 2%
• Common ancestry: Romanian 2% Lithuanian 1% Slovak 1%
• Foreign-born: 17% · Canada, Jamaica, South Korea
• Languages at home: 56% English-only · Spanish 39% Other Indo-European 1% Russian/Polish/Slavic 1%

Political lean MEDSL · South Central Connecticut

• 2024 margin: Strong D (+20.1) · D 59.0% · R 38.9% · Other 2.1%
• All cycles: 2024: D+20.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -30.87%
• Current HPI: 364.006
• Rent YoY: ▲ 4.12%
• Metro: New Haven-Milford, CT
• State GDP YoY: ▲ 1.06%
• F500 in state: 38

Industry mix (Fortune 500 HQ in CT)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$38B
▸Insurance	3	$71B
▸Financial Services	2	$25B
▸Transportation / Logistics	2	$18B
▸Healthcare	1	$247B
▸Telecommunications	1	$55B

Price history

+2940.0% since first listed

11 events — show timeline

• 2025-12-15 Pending — Smart MLS
• 2025-11-06 Price Changed $380,000 Smart MLS
• 2025-11-04 Listed $350,000 Smart MLS
• 2024-03-17 Listing Removed — Smart MLS
• 2023-12-07 Price Changed $380,000 Smart MLS
• 2023-11-09 Listed $385,000 Smart MLS
• 2006-12-08 Listing Removed — Smart MLS
• 2006-06-09 Listed $289,900 Smart MLS
• 1998-08-07 Sold (Public Records) $14,000 Public Records
• 1995-11-28 Sold (Public Records) $15,000 Public Records
• 1995-11-06 Sold (Public Records) $12,500 Public Records

Property tax history

+6.8%/yr

Latest (2023): $7,257 · -6.4% YoY. Source: county tax records.