343 W Main St · Waterbury, CT 06702

$2,625,000

3 bd · 1.0 ba · 20,428 sqft · MultiFamily · 61 Days on market

Built 1900 Good condition 7,840 sqft lot $129/sqft · 13% above area Est $2321k · 13% over ↓ 5% since listing

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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 +21.9/30.0
• DSCR +7.0/10.0
• 1% rule +5.7/10.0
• Appreciation +5.0/10.0
• Livability +4.0/5.0
• Condition / age +4.0/5.0
• Rent growth +2.5/5.0
• ARV discount +1.6/15.0
• Schools +1.5/10.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 1 unit. 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

Exceptional mixed-use investment opportunity Downtown featuring three contiguous parcels totaling 0.42 acres with 26,948 SF of GLA. The offering includes two mixed-use buildings (343-367 West Main St & 495 Meadow St, Waterbury) plus a 31-car parking lot (367 West Main St), providing strong infrastructure for both residential and commercial tenancy. The property consists of 6 ground-level commercial units with stable, long-term tenants, and 21 residential apartments with a unit mix of (3) one-bedroom, (16) two-bedroom, and (2) three-bedroom units. Residential occupancy has historically remained high, reflecting consistent rental demand. Many units have been updated with modern flooring

Key facts

• Renovated kitchens
• 7,840 sq ft lot
• 31 parking spots

Tags

• THREE CONTIGUOUS PARCELS
• GROUND-LEVEL COMMERCIAL UNITS
• RESIDENTIAL APARTMENTS
• UPDATED MODERN FLOORING
• RENOVATED KITCHENS
• NEWER FLAT RUBBER ROOF

Property features AI

Exterior

• Parking: Off-street parking; 31 total parking spaces
• Utilities: Public water connected; Public sewer connected; Natural gas hot water
• Home design: Multi-family property (5+ units)
• Construction: Masonry and stone foundation; Brick construction; Flat roof
• Exterior features: Brick exterior; Sidewalk; Porch; Exterior lighting; Corner lot; Level lot

Interior

• Bedrooms: 3 bedrooms
• Bathrooms: 1 full bathroom
• Heating & cooling: Hot air heating; Natural gas heating
• Interior features: Window air conditioning units; Full unfinished basement

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath multifamily listed at $2.62M. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $4k ($49k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($28k rent vs $2.62M).
• Recommended offer: $2.47M (6.0% below list) — sets the bar for market timing.
• Cap rate 8.2% vs local median 3.5% in Waterbury — 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 (#32 in CT, #2,205 nationally) — a middle-class / working-renter tenant base. Strengths: commute A+, cost of living A+, housing A+; Watch: crime D, employment D.
• Waterbury School District (suburban): math 12% / reading 23% proficiency, ranked #148 of 153 in CT (top 97%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 73% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: Bunker Hill School (math 8% / reading 17%, grade F, #490 of 553 statewide, top 90%, 468 students, 76% FRL); West Side Middle School (math 8% / reading 23%, grade F, #165 of 175 statewide, top 94%, 817 students, 81% FRL); John F. Kennedy High School (math 17% / reading 37%, grade F, #147 of 194 statewide, top 78%, 1,297 students, 79% FRL).
• Market conditions: 5 active listings in the ZIP; lower-income renter base — watch delinquency; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).
• At $28,164/mo this rent would consume 2335% of the median local household income ($14k/yr) (locally 729% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $97k of equity ($18k loan paydown + $79k appreciation (3.0% local appreciation)).
• At projected returns (3.0% appreciation + 3.0% rent growth), your $735k cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$158k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 61 days — a 6% lower offer ($2.47M) 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.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $2,467,500 (6.0% below list)

Questions for the listing agent

1. It's been on market 61 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
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 D 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: 1.07% ✓
• Cap rate: 8.17%
• Cash-on-cash: 6.71%
• DSCR: 1.30
• GRM: 7.8

CMA / ARV

• ARV (median comp): $2,320,504
• List price: $2,625,000
• Delta: 13.12%
• Verdict: OVERPRICED
• Comps: 2 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 13.8%
• Equity multiple: 1.79×
• Total profit: $578,335
• Equity at exit: $1,180,314

10-year hold

• IRR: 15.6%
• Equity multiple: 3.30×
• Total profit: $1,693,061
• Equity at exit: $1,819,004

Cash invested: $735,000 (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 06702

• Active inventory: 5
• Price-to-rent: 175.9×

Monthly cashflow live

• Estimated rent: $28,164 high
• Mortgage (P&I): −$13,766
• Tax est. 1.5%: −$3,281 /mo · $39,375/yr
• Insurance: −$1,094
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,914
• Net cashflow: $4,109

Break-even live

Break-even rent $22,963

Max offer price $2,625,000

Occupancy floor 80%

Sensitivity live

Price	-10% $5,923	-5% $5,016	+0% $4,109	+5% $3,202	+10% $2,295
Rent	-10% $1,884	-5% $2,996	+0% $4,109	+5% $5,221	+10% $6,334
Rate	-1.0pp $5,431	-0.5pp $4,776	base $4,109	+0.5pp $3,429	+1.0pp $2,737

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

Units	Beds	Baths	Est. rent
▸ 3× units	1	1	$3,732
▸ 16× units	2	1	$21,408
▸ 2× units	3	1	$3,022
Total (21 units)			$28,164

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: $656,250
• Closing costs: $78,750
• Reserves months: —
• Total cash needed: —

Listing history 22 events

1. 2026-06-21
   days on market $2,625,000 Active 61 DOM
2. 2026-06-18
   days on market $2,625,000 Active 58 DOM
3. 2026-06-17
   days on market $2,625,000 Active 57 DOM
4. 2026-06-16
   days on market $2,625,000 Active 56 DOM
5. 2026-06-15
   days on market $2,625,000 Active 55 DOM
6. 2026-06-14
   days on market $2,625,000 Active 53 DOM
7. 2026-06-13
   days on market $2,625,000 Active 52 DOM
8. 2026-06-10
   days on market $2,625,000 Active 50 DOM
9. 2026-06-09
   days on market $2,625,000 Active 49 DOM
10. 2026-06-08
    days on market $2,625,000 Active 48 DOM
11. 2026-06-07
    days on market $2,625,000 Active 47 DOM
12. 2026-06-05
    days on market $2,625,000 Active 44 DOM
13. 2026-06-03
    days on market $2,625,000 Active 43 DOM
14. 2026-06-03
    days on market $2,625,000 Active 42 DOM
15. 2026-06-01
    days on market $2,625,000 Active 41 DOM
16. 2026-05-31
    days on market $2,625,000 Active 40 DOM
17. 2026-04-21
    historical
18. 2026-04-21
    listed $2,650,000 Active 1462-char remark
19. 2026-03-08
    price $2,700,000
20. 2026-03-08
    price $2,750,000
21. 2026-03-07
    price $2,650,000
22. 2026-01-28
    listed $2,750,000 Active

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

Taxation est. · year 1

• Rental income: $337,968
• − Mortgage interest: −$147,041
• − Property taxes: −$39,375
• − Insurance: −$13,125
• − Repairs & maintenance: −$27,037
• − Management: −$27,037
• − Depreciation: −$76,364
• Taxable income: $7,989
• Est. tax owed @ 24.0%: −$1,917
• After-tax cash flow: $47,388/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.

Condition & rehab AI · 12 photos

Good 80/100 Cosmetic rehab

This mixed-use property offers a good investment opportunity with minimal repairs and maintenance needed. The property is well-maintained and ready for immediate rental or resale.

Value-add opportunities

• Both Paint exterior walls — Enhances curb appeal and property value.
• Both Clean gutters — Improves drainage and property value.
• Both Install energy-efficient windows — Reduces energy costs and enhances property value.
• Resale Update kitchen appliances — Modernizes the kitchen and attracts buyers.
• Rental Install smart home features — Attracts tech-savvy renters and enhances property value.

Renovation cost estimate screening

Value-add ROI direction

• Both Paint exterior walls — Enhances curb appeal and property value. ↑
• Both Clean gutters — Improves drainage and property value. ↑
• Both Install energy-efficient windows — Reduces energy costs and enhances property value. ↑
• Resale Update kitchen appliances — Modernizes the kitchen and attracts buyers. ↑
• Rental Install smart home features — Attracts tech-savvy renters and enhances property value. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Waterbury School District
• NCES district ID: 0904830
• Math proficiency: 12% ▼ -7.00%
• Reading proficiency: 23% ▼ -8.00%
• Median HH income: $40,040
• Composite: 14.85/100
• National rank: #9380
• State rank: #148 of 153 in CT

Livability — Waterbury

• Score: 79/100
• State rank: #32
• US rank: #2205

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Waterbury, CT
• County: New Haven County · 688,236 people
• City population: 115,012
• Metro: New Haven-Milford, CT
• Population (ZIP): 2,946
• Household income: $14,474
• Rent vs Own: 92.0% rent · 8.0% own
• Severe rent burden: 729.0

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.68)
• Race & ethnicity: Black 37% Hispanic / Latino 36% White 24% Two or more races 7%
• Hispanic origin (detail): Mexican 2% Puerto Rican 20% Cuban 3% Dominican 9%
• Common ancestry: Russian 1% Subsaharan African 1% Romanian 1%
• Foreign-born: 10% · Canada
• Languages at home: 68% English-only · Spanish 30% Other Indo-European 1%

Political lean MEDSL · Naugatuck Valley

• 2024 margin: Lean R (+7.4) · D 45.6% · R 53.0% · Other 1.4%
• All cycles: 2024: R+7.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: —
• Current HPI: —
• Rent YoY: —
• 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

-4.5% since first listed

7 events — show timeline

• 2026-05-23 Price Changed $2,625,000 Smart MLS
• 2026-04-21 Listing Removed — Smart MLS
• 2026-04-21 Listed $2,650,000 Smart MLS
• 2026-03-08 Price Changed $2,700,000 Smart MLS
• 2026-03-08 Price Changed $2,750,000 Smart MLS
• 2026-03-07 Price Changed $2,650,000 Smart MLS
• 2026-01-28 Listed $2,750,000 Smart MLS