72 Woolsey St · New Haven, CT 06513

$400,000

4 bd · 2.0 ba · 2,066 sqft · MultiFamily public records · 12 Days on market

Built 1900 3,484 sqft lot Est $357k · 12% over

---

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 +21.4/30.0
• DSCR +6.8/10.0
• 1% rule +5.6/10.0
• Livability +4.0/5.0
• Rent growth +3.5/5.0
• Condition / age +2.5/5.0
• ARV discount +2.1/15.0
• Schools +1.5/10.0
• Appreciation +0.0/10.0

Multi-family units

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

Listing remarks MLS

Charming and well-kept two-unit property with separate utilities. Both units offer functional layouts with great natural light and a shared backyard. Conveniently located near downtown, Yale, public transportation, and local amenities. A solid opportunity for investors or buyers looking for rental income.

Key facts

• Multi family home
• 3,484 sq ft lot
• Built 1900

Tags

• FAIR HAVEN NEIGHBORHOOD
• STRONG RENTAL POTENTIAL
• EXCELLENT COMMUTER ACCESS
• MULTI FAMILY HOME

Property features AI

Exterior

• Utilities: Public water connected; Public sewer connected
• Home design: Multi-family (2-family) property
• Construction: Frame construction; Concrete foundation; Built prior to public record living area of 2066
• Exterior features: Level lot; Vinyl siding; Asphalt shingle roof

Interior

• Bedrooms: 6 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Hot air heat; Natural gas-fired heating; Natural gas domestic hot water
• Interior features: Full basement

What this means for you Summary

Snapshot

• This is a 2 × 3-bed/1.0-bath units multifamily listed at $400k.

Deal economics

• At list price, monthly cash flow is $591 ($7k/yr) — positive. Per door: $295/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $400k).
• Cap rate 8.1% vs local median 4.9% 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; 39 comparable units currently listed for rent nearby; rentals at typical pace (median 20d on market — plan ~3-4 weeks tenant-placement turnaround); 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• At $4,236/mo this rent would consume 105% 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 $12k of value loss. Plan a longer hold.

Negotiation context

• Only 12 days on market — expect competitive offers; lowballing is unlikely to land.
• 8 sale attempts since 23y 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.

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 $400,000

Questions for the listing agent

1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
3. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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?
7. 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?
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: 1.06% ✓
• Cap rate: 8.07%
• Cash-on-cash: 6.33%
• DSCR: 1.28
• GRM: 7.9

CMA / ARV

• ARV (on-the-fly): $357,418
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
213 Saltonstall Ave	0.19mi	5/2.0 (+1)	1,920 (-7%)	3mo	$325,000	$169	72
169 James St	0.08mi	5/3.0 (+1)	2,255 (+9%)	2mo	$376,000	$167	70
439 Lombard St	0.52mi	4/2.0	1,996 (-3%)	4mo	$440,000	$220	67
175 James St	0.08mi	5/3.0 (+1)	2,263 (+10%)	7mo	$400,000	$177	66
187 Wolcott St	0.10mi	4/2.0	1,812 (-12%)	18mo	$270,000	$149	59
422 Blatchley Ave	0.44mi	5/3.0 (+1)	2,220 (+8%)	7mo	$449,900	$203	52
71 Houston St	0.44mi	5/2.0 (+1)	2,296 (+11%)	6mo	$515,000	$224	51
255 Front St	0.74mi	4/2.0	2,160 (+4%)	14mo	$575,000	$266	46
366 Quinnipiac Ave	0.75mi	4/2.0	1,914 (-7%)	12mo	$330,000	$172	43
533 Quinnipiac Ave	0.72mi	5/2.5 (+1)	2,257 (+9%)	6mo	$391,500	$173	39
197 Farren Ave	0.73mi	4/2.0	1,848 (-11%)	13mo	$320,000	$173	38
315 Lombard St	0.61mi	5/2.0 (+1)	2,362 (+14%)	11mo	$395,000	$167	34

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: -5.3%
• Equity multiple: 0.80×
• Total profit: $-22,299
• Equity at exit: $59,641

10-year hold

• IRR: 5.7%
• Equity multiple: 1.44×
• Total profit: $49,543
• Equity at exit: $34,585

Cash invested: $112,000 (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: 15.7×

Monthly cashflow live

• Estimated rent: $4,236 high
• Mortgage (P&I): −$2,098
• Tax from tax record: −$491 /mo · $5,895/yr
• Insurance: −$167
• HOA: −$0
• Vacancy / Maint / Mgmt: −$890
• Net cashflow: $591

Break-even live

Break-even rent $3,488

Max offer price $400,000

Occupancy floor 81%

Sensitivity live

Price	-10% $817	-5% $704	+0% $591	+5% $478	+10% $364
Rent	-10% $256	-5% $424	+0% $591	+5% $758	+10% $926
Rate	-1.0pp $792	-0.5pp $693	base $591	+0.5pp $487	+1.0pp $382

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

Units	Beds	Baths	Est. rent
▸ 2× units	3	1	$4,236
Total (2 units)			$4,236

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: $100,000
• Closing costs: $12,000
• Reserves months: —
• Total cash needed: —

Rent comps 39 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	45d	1	0.08mi
262 Lloyd St Unit 1 New Haven, CT	3.0	2.0	1460	$2,400	$1.64	4d	1	0.10mi
295 Lloyd St Unit 2 New Haven, CT	4.0	2.0	2621	$2,400	$0.92	4d	1	0.15mi
18 Woolsey St New Haven, CT	5.0	2.0	1446	$2,900	$2.01	12d	1	0.17mi
115 Lloyd St #2 New Haven, CT	4.0	2.0	2100	$2,500	$1.19	45d	1	0.24mi
426 Poplar St Unit 2 New Haven, CT	4.0	2.0	1405	$1,800	$1.28	4d	1	0.40mi
426 Poplar St New Haven, CT	3.0	1.0	1658	$1,800	$1.09	45d	1	0.40mi
39 Houston St Unit 2 New Haven, CT	3.0	1.0	2863	$2,200	$0.77	45d	1	0.44mi
37 E Pearl St New Haven, CT	3.0	1.0	1600	$2,595	$1.62	45d	1	0.50mi
441 Chapel St Unit 2A1 (shared) New Haven, CT	4.0	4.0	2151	$3,600	$1.67	4d	1	0.67mi
199 English St Unit 2 New Haven, CT	3.0	1.0	2776	$2,000	$0.72	45d	1	0.67mi
902 State St #2 New Haven, CT	3.0	2.5	1950	$3,750	$1.92	24d	1	0.72mi
28 Edwards St Unit 2 New Haven, CT	4.0	2.0	1800	$3,850	$2.14	15d	1	0.75mi
54 Mechanic St Unit 2nd floor New Haven, CT	4.0	2.0	1412	$3,600	$2.55	45d	1	0.77mi
31 Clark St New Haven, CT	4.0	2.0	1694	$4,200	$2.48	4d	1	0.80mi
48 Lyon St Unit 1 New Haven, CT	3.0	1.0	1402	$2,950	$2.10	20d	1	0.82mi
300 Humphrey St Unit 2 New Haven, CT	3.0	2.0	2868	$3,295	$1.15	45d	1	0.82mi
318 Front St Unit one New Haven, CT	3.0	1.5	1400	$3,100	$2.21	22d	1	0.84mi
120 Downing St Unit 3 New Haven, CT	3.0	2.0	1800	$2,450	$1.36	45d	1	0.85mi
315 Humphrey St Unit A New Haven, CT	4.0	3.5	2465	$4,500	$1.83	4d	1	0.85mi
59 Clark St New Haven, CT	4.0	1.0	1541	$3,250	$2.11	24d	1	0.85mi
526 Chapel St Unit B New Haven, CT	3.0	2.0	1450	$3,500	$2.41	22d	1	0.86mi
30 Trumbull St New Haven, CT	5.0	4.0	2668	$5,000	$1.87	4d	1	0.96mi
367 Orange St New Haven, CT	3.0	1.0–2.0	1075	$4,973	$4.63	4d	43	0.99mi
506 Orange St Unit 2 New Haven, CT	3.0	1.5	1553	$3,600	$2.32	45d	1	0.99mi
399 Orange St New Haven, CT	4.0	1.5	1650	$3,200	$1.94	12d	1	0.99mi
395 Orange St Unit 2 New Haven, CT	4.0	1.5	1650	$3,000	$1.82	45d	1	0.99mi
239 Bradley St Unit 1 New Haven, CT	3.0	1.0	1982	$3,650	$1.84	45d	1	1.06mi
54 Trumbull St Unit 54-1 New Haven, CT	5.0	2.5	2250	$6,695	$2.98	15d	1	1.07mi
67 Trumbull St New Haven, CT	4.0	1.0	1400	$3,200	$2.29	12d	1	1.11mi
87 Union St New Haven, CT	4.0	1.0–4.0	959	$5,543	$5.78	4d	16	1.12mi
904 Quinnipiac Ave New Haven, CT	3.0	1.5	2125	$3,298	$1.55	4d	1	1.14mi
68 Anderson St Unit A New Haven, CT	3.0	2.5	1693	$4,500	$2.66	45d	1	1.14mi
251 Edwards St Unit 2 New Haven, CT	4.0	1.5	1522	$3,900	$2.56	4d	1	1.18mi
813 Chapel St Unit 817-2B New Haven, CT	3.0	2.0	1446	$2,745	$1.90	45d	1	1.23mi
339 Willow St Unit 1 New Haven, CT	4.0	2.0	2163	$4,050	$1.87	12d	1	1.30mi
420 Whitney Ave New Haven, CT	3.0–4.0	2.0–3.0	1800	$4,700	$2.61	12d	2	1.33mi
420 Whitney Ave Unit 424-3B New Haven, CT	4.0	3.0	1800	$4,700	$2.61	4d	1	1.33mi
56 Mansfield St Unit 1 New Haven, CT	3.0	1.0	2759	$2,800	$1.01	45d	1	1.43mi

Listing history 9 events

1. 2026-06-21
   days on market $400,000 Active 12 DOM
2. 2026-06-18
   days on market $400,000 Active 9 DOM
3. 2026-06-17
   days on market $400,000 Active 8 DOM
4. 2026-06-16
   days on market $400,000 Active 7 DOM
5. 2026-06-15
   days on market $400,000 Active 6 DOM
6. 2026-06-14
   days on market $400,000 Active 4 DOM
7. 2026-06-13
   days on market $400,000 Active 3 DOM
8. 2026-06-09
   remarks 595-char remark
9. 2026-06-09
   listed $400,000 Active 1 DOM

ⓘ 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: $5,895 · $491/mo
• Projected year-2 tax: $7,228 · $602/mo
• Expected delta: +$1,332/yr (+$111/mo · 22.6%)

ⓘ 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: $50,832
• − Mortgage interest: −$22,406
• − Property taxes: −$5,895
• − Insurance: −$2,000
• − Repairs & maintenance: −$4,067
• − Management: −$4,067
• − Depreciation: −$11,636
• Taxable income: $761
• Est. tax owed @ 24.0%: −$183
• After-tax cash flow: $6,908/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

+701.6% since first listed

21 events — show timeline

• 2026-05-27 Listed $400,000 Smart MLS
• 2025-11-20 Sold (MLS) $360,000 Smart MLS
• 2025-05-29 Pending — Smart MLS
• 2025-04-28 Listed $380,000 Smart MLS
• 2024-12-18 Listing Removed — Smart MLS
• 2024-10-31 Listed $350,000 Smart MLS
• 2024-10-16 Listing Removed — Smart MLS
• 2024-08-16 Listed $350,000 Smart MLS
• 2021-05-04 Sold (Public Records) $250,000 Public Records
• 2021-04-06 Sold (MLS) $250,000 Smart MLS
• 2021-01-14 Listed $249,000 Smart MLS
• 2009-01-16 Sold (Public Records) $187,000 Public Records
• 2009-01-15 Listing Removed — Smart MLS
• 2008-11-01 Listed $189,900 Smart MLS
• 2006-11-21 Listing Removed — Smart MLS
• 2006-08-21 Listed $250,000 Smart MLS
• 2005-03-23 Sold (Public Records) $148,682 Public Records
• 2003-11-13 Sold (Public Records) $150,000 Public Records
• 2003-03-12 Sold (Public Records) $37,400 Public Records
• 2003-03-11 Sold (MLS) $37,400 Smart MLS
• 2003-01-18 Listed $49,900 Smart MLS

Property tax history

+8.2%/yr

Latest (2023): $5,895 · -6.4% YoY. Source: county tax records.