19 Urban St · New Canaan, CT 06840

$1,950,000

4 bd · 9.0 ba · 2,534 sqft · MultiFamily public records · 17 Days on market

Built 1941 9,147 sqft lot

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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 +20.2/30.0
• Schools +8.1/10.0
• ARV discount +7.5/15.0
• DSCR +6.4/10.0
• 1% rule +4.3/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 3 units. estimate disagrees with records

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks MLS

A unique opportunity to own a multi-family property in highly sought-after New Canaan. This well-maintained three-family home is fully turn-key, with each unit offering in-unit laundry and comfortable, functional layouts that are equally appealing for tenants or extended family living. The property includes four attached garages plus a two-car detached garage with storage, providing flexibility for additional rental income, personal use, or future customization. Whether you're an investor looking for a strong income-producing asset in Fairfield County or a buyer seeking multi-generational living with built-in value, this property delivers the perfect balance of lifestyle and opportunity-all within one of Connecticut's most desirable communities.

Key facts

• Fully leased
• Garage
• Income producing

Tags

• FULLY LEASED
• INCOME PRODUCING
• IN UNIT LAUNDRY
• GARAGE
• FUNCTIONAL LAYOUTS
• 6 GARAGE SPACES

Property features AI

Exterior

• Parking: Attached garage; Detached garage; Under-house garage; 6 total garage spaces
• Utilities: Public water connected; Public sewer connected; Domestic hot water (oil and propane)
• Home design: Multi-family property (3-family)
• Construction: Built with stone and masonry; White exterior; Stucco siding; Concrete foundation; Asphalt shingle roof
• Exterior features: Balcony; Garden area; Level lot

Interior

• Bedrooms: 5 bedrooms total
• Bathrooms: 3 full bathrooms
• Heating & cooling: Hot water heating; Oil and propane fuel with above-ground fuel tank
• Interior features: 12 total rooms; Full walk-out basement with garage access; One fireplace; Split system and window unit cooling
• Laundry & utility: Washer and dryer in each unit (W/D in each unit)

What this means for you Summary

Snapshot

• This is a 3 × 3-bed/3-bath units multifamily listed at $1.95M.

Deal economics

• At list price, monthly cash flow is $2k ($30k/yr) — positive. Per door: $820/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 $1.81M (7.2% below list).
• Recommended offer: $1.81M (7.2% below list) — sets the bar for 1% rule.
• Cap rate 7.8% vs local median 1.5% in New Canaan — 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: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• New Canaan School District (suburban): math 81% / reading 86% proficiency, ranked #1 of 153 in CT (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 6% free/reduced lunch — higher-income household profile.
• Zoned schools: East School (math 84% / reading 84%, grade A+, #7 of 553 statewide, top 1%, 550 students, 0% FRL); New Canaan High School (math 77% / reading 92%, grade A, #1 of 194 statewide, top 1%, 1,294 students, 0% FRL).
• Market conditions: 165 active listings in the ZIP; 7 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 57% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• At $18,088/mo this rent would consume 87% of the median local household income ($250k/yr) (locally 261% 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 $13k of loan paydown is wiped out by about $58k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 17 days — a 2% lower offer ($1.92M) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 17y 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 $1.28M; list at $1.95M implies a 52% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1941 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 59% 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 $1,808,800 (7.2% 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 1941 — 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. 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.
6. 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.
7. 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: 0.93% ✗
• Cap rate: 7.81%
• Cash-on-cash: 5.41%
• DSCR: 1.24
• GRM: 9.0

CMA / ARV

• ARV (on-the-fly): $1,279,670
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
19 Urban St	0.00mi	5/3.0 (+1)	2,534 (0%)	8mo	$1,280,000	$505	73
15 Brook St	0.06mi	5/3.0 (+1)	2,802 (+11%)	20mo	$1,275,000	$455	43
14 Richmond Hill Rd	0.70mi	5/6.0 (+1)	2,756 (+9%)	19mo	$1,625,000	$590	20

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -8.0%
• Equity multiple: 0.71×
• Total profit: $-159,970
• Equity at exit: $290,751

10-year hold

• IRR: 1.5%
• Equity multiple: 1.11×
• Total profit: $59,542
• Equity at exit: $168,600

Cash invested: $546,000 (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 06840

• Active inventory: 165
• Price-to-rent: 27.0×

Monthly cashflow live

• Estimated rent: $18,088 medium
• Mortgage (P&I): −$10,226
• Tax from tax record: −$790 /mo · $9,478/yr
• Insurance: −$812
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,798
• Net cashflow: $2,461

Break-even live

Break-even rent $14,973

Max offer price $1,950,000

Occupancy floor 81%

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

Units	Beds	Baths	Est. rent
▸ 3× units	3	3	$18,087
Total (3 units)			$18,088

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: $487,500
• Closing costs: $58,500
• Reserves months: —
• Total cash needed: —

Rent comps 7 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
112 East Ave New Canaan, CT	4.0	2.5	2800	$6,950	$2.48	3d	1	0.22mi
126 East Ave New Canaan, CT	3.0	1.5	2124	$4,500	$2.12	43d	1	0.23mi
42 Forest St #4 New Canaan, CT	3.0	3.5	3290	$16,000	$4.86	11d	1	0.36mi
138 Millport Ave New Canaan, CT	3.0	1.5	1750	$5,300	$3.03	43d	1	0.55mi
129 Park St New Canaan, CT	3.0	3.0	3058	$6,950	$2.27	3d	1	0.65mi
136 Harrison Ave New Canaan, CT	4.0	3.5	3455	$16,000	$4.63	43d	1	0.66mi
70 Seminary St Unit 1 New Canaan, CT	3.0	4.0	2100	$9,500	$4.52	43d	1	0.72mi

Listing history 13 events

1. 2026-06-18
   days on market $1,950,000 Active 17 DOM
2. 2026-06-17
   days on market $1,950,000 Active 16 DOM
3. 2026-06-16
   days on market $1,950,000 Active 15 DOM
4. 2026-06-15
   days on market $1,950,000 Active 14 DOM
5. 2026-06-13
   days on market $1,950,000 Active 12 DOM
6. 2026-06-10
   days on market $1,950,000 Active 9 DOM
7. 2026-06-09
   days on market $1,950,000 Active 8 DOM
8. 2026-06-08
   days on market $1,950,000 Active 7 DOM
9. 2026-06-07
   days on market $1,950,000 Active 6 DOM
10. 2026-06-05
    days on market $1,950,000 Active 3 DOM
11. 2026-06-03
    days on market $1,950,000 Active 2 DOM
12. 2026-06-02
    remarks 699-char remark
13. 2026-06-02
    listed $1,950,000 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: $9,478 · $790/mo
• Projected year-2 tax: $25,604 · $2,134/mo
• Expected delta: +$16,126/yr (+$1,344/mo · 170.1%)

ⓘ 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 5/10 Major 7 d/yr ≥99°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 59% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 3 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $217,056
• − Mortgage interest: −$109,230
• − Property taxes: −$9,478
• − Insurance: −$9,750
• − Repairs & maintenance: −$17,364
• − Management: −$17,364
• − Depreciation: −$56,727
• Taxable loss: −$2,859
• Est. tax savings @ 24.0%: +$686
• After-tax cash flow: $30,220/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 Canaan School District
• NCES district ID: 0902700
• Math proficiency: 81% ▼ -6.00%
• Reading proficiency: 86% ▼ -4.00%
• Median HH income: $164,303
• Composite: 81.47/100
• National rank: #38
• State rank: #1 of 153 in CT

Livability — New Canaan

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Census place: New Canaan, CT
• County: Fairfield County · 765,532 people
• City population: 20,870
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 20,870
• Household income: $250,001
• Rent vs Own: 16.3% rent · 83.7% own
• Severe rent burden: 261.0

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (83%)
• Race & ethnicity: White 83% Two or more races 7% Asian 6% Hispanic / Latino 5% Black 2%
• Common ancestry: Romanian 5% Lithuanian 4% Italian 2%
• Foreign-born: 14% · Canada, China, South Korea
• Languages at home: 85% English-only · Other Indo-European 6% Chinese 2% Spanish 2%

Political lean MEDSL · Western Connecticut

• 2024 margin: D (+19.1) · D 58.8% · R 39.7% · Other 1.6%
• All cycles: 2024: D+19.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -480.93%
• Current HPI: 232.5667
• Rent YoY: —
• Metro: Bridgeport-Stamford-Norwalk, 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

+278.6% since first listed

9 events — show timeline

• 2026-05-31 Listed $1,950,000 Smart MLS
• 2025-10-14 Sold (MLS) $1,280,000 Smart MLS
• 2025-10-03 Pending — Smart MLS
• 2025-09-26 Contingent — Smart MLS
• 2025-09-18 Listed $1,150,000 Smart MLS
• 2025-09-12 Coming Soon $1,150,000 Smart MLS
• 2011-04-26 Sold (MLS) $450,000 Smart MLS
• 2011-04-21 Sold (Public Records) $450,000 Public Records
• 2009-09-25 Listed $515,000 Smart MLS

Property tax history

+2.2%/yr

Latest (2023): $9,478 · +3.1% YoY. Source: county tax records.