257 Saint John St · New Haven, CT 06511

$749,500

4 bd · 3.0 ba · 2,728 sqft · MultiFamily public records · 21 Days on market

Built 1900 5,662 sqft lot Est $786k · at est.

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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 +26.7/30.0
• ARV discount +9.6/15.0
• DSCR +9.1/10.0
• 1% rule +7.3/10.0
• Livability +4.0/5.0
• Rent growth +3.2/5.0
• Condition / age +2.5/5.0
• 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: 3 units. confirmed

Listing remarks MLS

This wonderful three family is on a quiet one-way street in the Wooster Square area. The house has been lovingly maintained by a long term owner. The first floor unit has five rooms. The living room has a high ceiling, fantastic cast iron moldings and pocket doors. There is a spacious dining room, updated kitchen with good work and storage space, two bedrooms and a bath. The apartment has gas heat and central air conditioning. The second floor offers two good condition apartments, a three room one bedroom unit and a two room one bedroom apartment. Each unit has its own heat and electric. There is one hot water heater and the owner pays the cost of this. The yard has a garden area plus a two car garage. This Wooster Square neighborhood is close to Yale, YNHH, the train station, a weekly farmer's market, downtown New Haven and is part of the Yale Homebuyer area. Ideal for an investor or an owner occupant.

Key facts

• High ceiling
• Pocket doors
• Spacious dining room

Tags

• QUIET ONE-WAY STREET
• HIGH CEILING
• CAST IRON MOLDINGS
• POCKET DOORS
• SPACIOUS DINING ROOM
• UPDATED KITCHEN

What this means for you Summary

Snapshot

• This is a 3 × 4-bed/3.0-bath units multifamily listed at $750k.

Deal economics

• At list price, monthly cash flow is $2k ($24k/yr) — positive. Per door: $673/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($9k rent vs $750k).
• Recommended offer: $738k (1.5% below list) — sets the bar for market timing.
• Cap rate 9.5% 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 (+2.6%/yr); 140 active listings in the ZIP; 32 comparable units currently listed for rent nearby; rentals at typical pace (median 25d on market — plan ~3-4 weeks tenant-placement turnaround); 41% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• At $9,198/mo this rent would consume 184% of the median local household income ($60k/yr) (locally 4999% 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 $5k of loan paydown is wiped out by about $22k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 2.6% rent growth), your $210k cash investment doubles in ~10 years — after that, you're playing with house money.

Negotiation context

• It's been on market 21 days — a 2% lower offer ($738k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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 $240k; list at $750k implies a 212% 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, 60% 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 $738,257 (1.5% below list)

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. 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.
8. 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.
9. 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: 1.23% ✓
• Cap rate: 9.52%
• Cash-on-cash: 11.54%
• DSCR: 1.51
• GRM: 6.8

CMA / ARV

• ARV (on-the-fly): $785,664
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
257 Saint John St	0.00mi	4/3.0	2,728 (0%)	1mo	$740,000	$271	100
32 Trumbull St	0.34mi	4/3.0	2,736 (+0%)	9mo	$827,500	$302	76
99 Olive St	0.17mi	5/3.0 (+1)	2,885 (+6%)	6mo	$950,000	$329	72
30 Lyon St	0.13mi	3/3.0 (-1)	2,880 (+6%)	15mo	$700,000	$243	67
117 Olive St	0.14mi	4/3.0	2,372 (-13%)	13mo	$613,000	$258	61
85-87 Bishop St	0.69mi	4/4.0	2,698 (-1%)	2mo	$960,000	$356	61
34 Trumbull St	0.34mi	4/4.0	2,664 (-2%)	20mo	$830,000	$312	59
545 Orange St	0.56mi	4/4.0	2,880 (+6%)	9mo	$963,000	$334	53
407 Temple St	0.47mi	5/3.0 (+1)	3,036 (+11%)	12mo	$875,000	$288	45
198 James St	0.71mi	5/3.0 (+1)	2,711 (-1%)	23mo	$315,000	$116	42
18 Eld St	0.41mi	5/4.0 (+1)	2,998 (+10%)	20mo	$725,000	$242	39
173 James St	0.74mi	5/3.0 (+1)	2,324 (-15%)	20mo	$410,000	$176	19

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 · 2.6% rent growth · sell at horizon

5-year hold

• IRR: 0.4%
• Equity multiple: 1.02×
• Total profit: $3,575
• Equity at exit: $111,753

10-year hold

• IRR: 9.7%
• Equity multiple: 1.74×
• Total profit: $154,347
• Equity at exit: $64,803

Cash invested: $209,860 (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 06511

• Home prices YoY: -20.8%
• Rents YoY: 2.6%
• Active inventory: 140
• Price-to-rent: 20.4×

Monthly cashflow live

• Estimated rent: $9,198 high
• Mortgage (P&I): −$3,930
• Tax from tax record: −$1,006 /mo · $12,067/yr
• Insurance: −$312
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,932
• Net cashflow: $2,018

Break-even live

Break-even rent $6,643

Max offer price $749,500

Occupancy floor 73%

Sensitivity live

Price	-10% $2,442	-5% $2,230	+0% $2,018	+5% $1,806	+10% $1,594
Rent	-10% $1,291	-5% $1,655	+0% $2,018	+5% $2,381	+10% $2,745
Rate	-1.0pp $2,396	-0.5pp $2,209	base $2,018	+0.5pp $1,824	+1.0pp $1,626

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

Units	Beds	Baths	Est. rent
▸ 3× units	4	3	$9,198
Total (3 units)			$9,198

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: $187,375
• Closing costs: $22,485
• Reserves months: —
• Total cash needed: —

Rent comps 32 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
441 Chapel St Unit 2A1 (shared) New Haven, CT	4.0	4.0	2151	$3,600	$1.67	3d	1	0.31mi
30 Trumbull St New Haven, CT	5.0	4.0	2668	$5,000	$1.87	4d	1	0.33mi
54 Trumbull St Unit 54-1 New Haven, CT	5.0	2.5	2250	$6,695	$2.98	15d	1	0.42mi
239 Bradley St Unit 1 New Haven, CT	3.0	1.0	1982	$3,650	$1.84	44d	1	0.50mi
300 Humphrey St Unit 2 New Haven, CT	3.0	2.0	2868	$3,295	$1.15	44d	1	0.56mi
902 State St #2 New Haven, CT	3.0	2.5	1950	$3,750	$1.92	24d	1	0.59mi
315 Humphrey St Unit A New Haven, CT	4.0	3.5	2465	$4,500	$1.83	4d	1	0.60mi
28 Edwards St Unit 2 New Haven, CT	4.0	2.0	1800	$3,850	$2.14	15d	1	0.70mi
56 Mansfield St Unit 1 New Haven, CT	3.0	1.0	2759	$2,800	$1.01	44d	1	0.81mi
302 Exchange St Unit 2 New Haven, CT	5.0	2.0	1800	$2,500	$1.39	44d	1	0.84mi
295 Lloyd St Unit 2 New Haven, CT	4.0	2.0	2621	$2,400	$0.92	3d	1	0.86mi
115 Lloyd St #2 New Haven, CT	4.0	2.0	2100	$2,500	$1.19	44d	1	0.89mi
134 Mansfield St New Haven, CT	5.0	2.0	1960	$5,500	$2.81	24d	1	0.95mi
52 Goffe St New Haven, CT	3.0	2.0	1935	$2,600	$1.34	24d	1	0.99mi
43 Howe St New Haven, CT	4.0	2.0	1995	$4,995	$2.50	15d	1	0.99mi
41 Howe St New Haven, CT	4.0	2.0	1795	$3,750	$2.09	44d	1	1.00mi
41 Howe St Apt 2 New Haven, CT	3.0	1.0	1795	$3,200	$1.78	44d	1	1.00mi
41 Howe St Apt 2 New Haven, CT	3.0	1.0	1795	$3,200	$1.78	24d	1	1.00mi
420 Whitney Ave New Haven, CT	3.0–4.0	2.0–3.0	1800	$4,700	$2.61	12d	2	1.06mi
420 Whitney Ave Unit 424-3B New Haven, CT	4.0	3.0	1800	$4,700	$2.61	4d	1	1.06mi
120 Dwight St New Haven, CT	3.0	2.0	1750	$3,175	$1.81	22d	2	1.09mi
339 Willow St Unit 1 New Haven, CT	4.0	2.0	2163	$4,050	$1.87	12d	1	1.15mi
50 Admiral St New Haven, CT	5.0	2.0	2157	$2,700	$1.25	20d	1	1.19mi
47 Dickerman St Unit 1 New Haven, CT	3.0	1.0	3729	$2,100	$0.56	44d	1	1.20mi
55 Admiral St Unit 2 New Haven, CT	5.0	3.0	2000	$3,295	$1.65	24d	1	1.22mi
39 Houston St Unit 2 New Haven, CT	3.0	1.0	2863	$2,200	$0.77	44d	1	1.22mi
57 Houston St Fl 1 New Haven, CT	3.0	1.0	3424	$2,300	$0.67	24d	1	1.23mi
66 Kensington St Unit 2 New Haven, CT	3.0	2.0	1800	$2,100	$1.17	24d	1	1.23mi
34 Cassius St Unit 36 New Haven, CT	5.0	2.0	1872	$2,300	$1.23	44d	1	1.28mi
36 Cassius St New Haven, CT	4.0	1.5	1872	$2,300	$1.23	44d	1	1.29mi
199 English St Unit 2 New Haven, CT	3.0	1.0	2776	$2,000	$0.72	44d	1	1.29mi
347 Sherman Ave New Haven, CT	5.0	3.0	3153	$2,300	$0.73	44d	1	1.47mi

Listing history 5 events

1. 2026-04-02
   status Under Contract 916-char remark

   Show marketing remark (916 chars)

   This wonderful three family is on a quiet one-way street in the Wooster Square area. The house has been lovingly maintained by a long term owner. The first floor unit has five rooms. The living room has a high ceiling, fantastic cast iron moldings and pocket doors. There is a spacious dining room, updated kitchen with good work and storage space, two bedrooms and a bath. The apartment has gas heat and central air conditioning. The second floor offers two good condition apartments, a three room one bedroom unit and a two room one bedroom apartment. Each unit has its own heat and electric. There is one hot water heater and the owner pays the cost of this. The yard has a garden area plus a two car garage. This Wooster Square neighborhood is close to Yale, YNHH, the train station, a weekly farmer's market, downtown New Haven and is part of the Yale Homebuyer area. Ideal for an investor or an owner occupant.

2. 2026-03-12
   listed $749,500 Active 916-char remark

   Show marketing remark (916 chars)

   This wonderful three family is on a quiet one-way street in the Wooster Square area. The house has been lovingly maintained by a long term owner. The first floor unit has five rooms. The living room has a high ceiling, fantastic cast iron moldings and pocket doors. There is a spacious dining room, updated kitchen with good work and storage space, two bedrooms and a bath. The apartment has gas heat and central air conditioning. The second floor offers two good condition apartments, a three room one bedroom unit and a two room one bedroom apartment. Each unit has its own heat and electric. There is one hot water heater and the owner pays the cost of this. The yard has a garden area plus a two car garage. This Wooster Square neighborhood is close to Yale, YNHH, the train station, a weekly farmer's market, downtown New Haven and is part of the Yale Homebuyer area. Ideal for an investor or an owner occupant.

3. 2025-11-19
   historical
4. 2025-09-09
   listed $749,500 Active
5. 1988-07-21
   soldstatus $240,000

ⓘ 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: $12,067 · $1,006/mo
• Projected year-2 tax: $14,053 · $1,171/mo
• Expected delta: +$1,986/yr (+$166/mo · 16.5%)

ⓘ 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 60% 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: $110,376
• − Mortgage interest: −$41,984
• − Property taxes: −$12,067
• − Insurance: −$3,748
• − Repairs & maintenance: −$8,830
• − Management: −$8,830
• − Depreciation: −$21,804
• Taxable income: $13,114
• Est. tax owed @ 24.0%: −$3,147
• After-tax cash flow: $21,070/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): 54,730
• Household income: $59,969
• Rent vs Own: 80.3% rent · 19.7% own
• Severe rent burden: 4999.0

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Highly diverse neighborhood (Simpson 0.73)
• Race & ethnicity: Black 34% White 32% Hispanic / Latino 21% Two or more races 8% Asian 7%
• Hispanic origin (detail): Mexican 4% Puerto Rican 10% Dominican 2%
• Common ancestry: Romanian 2% Lithuanian 1% Russian 1%
• Foreign-born: 17% · Canada, China, South Korea
• Languages at home: 74% English-only · Spanish 15% Chinese 3% Other Indo-European 2%

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: ▼ -86.05%
• Current HPI: 328.1353
• Rent YoY: ▲ 2.60%
• 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

+212.3% since first listed

5 events — show timeline

• 2026-04-02 Pending — Smart MLS
• 2026-03-12 Listed $749,500 Smart MLS
• 2025-11-19 Listing Removed — Smart MLS
• 2025-09-09 Listed $749,500 Smart MLS
• 1988-07-21 Sold (Public Records) $240,000 Public Records

Property tax history

+3.6%/yr

Latest (2023): $12,067 · -6.4% YoY. Source: county tax records.