387 S Main St · Seymour, CT 06483

$729,900

7 bd · 4.0 ba · 4,362 sqft · MultiFamily public records · 86 Days on market

Built 1770 0.89 ac lot $167/sqft · 13% above area Est $644k · 13% 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 +26.6/30.0
• DSCR +9.1/10.0
• 1% rule +6.9/10.0
• Appreciation +3.8/10.0
• Schools +3.8/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• ARV discount +1.5/15.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 4 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

Excellent investment opportunity in a prime location! This well maintained 4 family property sits on a corner 1acre lot and offers a true turnkey experience for investors. Featuring city water and sewer, separate entrances and utilities, and off street parking, this asset is designed for easy management and long term stability. The building includes four basement storage units plus a walkup attic for additional storage, providing valuable extra space for tenants or owner use. Located on the bus line and just moments from the Sochrin Pond walking trail and dog park, the property offers convenience and lifestyle appeal. Current long term tenants are significantly under market rent, presenting immediate upside potential for the next owner. Initial showings will include Apartment 2 and the basement.

Key facts

• Off street parking
• City water and sewer
• Separate entrances

Tags

• PRIME LOCATION
• CORNER LOT
• CITY WATER AND SEWER
• SEPARATE ENTRANCES
• OFF STREET PARKING
• BASEMENT STORAGE UNITS

What this means for you Summary

Snapshot

• This is a 4 × 2-bed/1.0-bath units multifamily listed at $730k.

Deal economics

• At list price, monthly cash flow is $2k ($23k/yr) — positive. Per door: $490/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($9k rent vs $730k).
• Recommended offer: $686k (6.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Seymour School District (suburban): math 34% / reading 50% proficiency, ranked #93 of 153 in CT (top 61%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 19% free/reduced lunch — higher-income household profile.
• Market conditions: 55 active listings in the ZIP; solid renter incomes; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).
• At $8,661/mo this rent would consume 96% of the median local household income ($108k/yr) (locally 221% 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 (-2.4%/yr); year-one equity from $5k of loan paydown is wiped out by about $18k of value loss. Plan a longer hold.
• At projected returns (-2.4% appreciation + 3.0% rent growth), your $204k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 86 days — a 6% lower offer ($686k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 5y 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 $590k; 24% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1770 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $686,106 (6.0% below list)

Questions for the listing agent

1. It's been on market 86 days. Have you received any prior offers? Is the seller open to a 6% 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 1770 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 1.19% ✓
• Cap rate: 9.51%
• Cash-on-cash: 11.50%
• DSCR: 1.51
• GRM: 7.0

CMA / ARV

• ARV (median comp): $644,034
• List price: $729,900
• Delta: 13.33%
• Verdict: OVERPRICED
• Comps: 4 within 1.0 mi

Projected returns pro-forma

-2.41% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 3.0%
• Equity multiple: 1.12×
• Total profit: $24,560
• Equity at exit: $128,073

10-year hold

• IRR: 11.5%
• Equity multiple: 1.97×
• Total profit: $197,900
• Equity at exit: $96,664

Cash invested: $204,372 (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 06483

• Home prices YoY: -0.8%
• Active inventory: 55
• Price-to-rent: 28.1×

Monthly cashflow live

• Estimated rent: $8,661 high
• Mortgage (P&I): −$3,828
• Tax from tax record: −$752 /mo · $9,027/yr
• Insurance: −$304
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,819
• Net cashflow: $1,958

Break-even live

Break-even rent $6,182

Max offer price $729,900

Occupancy floor 72%

Sensitivity live

Price	-10% $2,371	-5% $2,165	+0% $1,958	+5% $1,752	+10% $1,545
Rent	-10% $1,274	-5% $1,616	+0% $1,958	+5% $2,300	+10% $2,642
Rate	-1.0pp $2,326	-0.5pp $2,144	base $1,958	+0.5pp $1,769	+1.0pp $1,577

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

Units	Beds	Baths	Est. rent
▸ 4× units	2	1	$8,660
Total (4 units)			$8,661

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: $182,475
• Closing costs: $21,897
• Reserves months: —
• Total cash needed: —

Listing history 28 events

1. 2026-06-18
   days on market $729,900 Active 86 DOM
2. 2026-06-17
   days on market $729,900 Active 85 DOM
3. 2026-06-16
   days on market $729,900 Active 84 DOM
4. 2026-06-15
   days on market $729,900 Active 83 DOM
5. 2026-06-14
   days on market $729,900 Active 81 DOM
6. 2026-06-13
   days on market $729,900 Active 80 DOM
7. 2026-06-10
   days on market $729,900 Active 78 DOM
8. 2026-06-09
   days on market $729,900 Active 77 DOM
9. 2026-06-08
   days on market $729,900 Active 76 DOM
10. 2026-06-07
    days on market $729,900 Active 75 DOM
11. 2026-06-05
    days on market $729,900 Active 72 DOM
12. 2026-06-03
    days on market $729,900 Active 71 DOM
13. 2026-06-03
    days on market $729,900 Active 70 DOM
14. 2026-06-01
    days on market $729,900 Active 69 DOM
15. 2026-05-31
    days on market $729,900 Active 68 DOM
16. 2026-03-24
    listed $729,900 Active 806-char remark

    Show marketing remark (806 chars)

    Excellent investment opportunity in a prime location! This well maintained 4 family property sits on a corner 1acre lot and offers a true turnkey experience for investors. Featuring city water and sewer, separate entrances and utilities, and off street parking, this asset is designed for easy management and long term stability. The building includes four basement storage units plus a walkup attic for additional storage, providing valuable extra space for tenants or owner use. Located on the bus line and just moments from the Sochrin Pond walking trail and dog park, the property offers convenience and lifestyle appeal. Current long term tenants are significantly under market rent, presenting immediate upside potential for the next owner. Initial showings will include Apartment 2 and the basement.

17. 2023-07-18
    soldstatus $590,000 Closed 684-char remark

    Show marketing remark (684 chars)

    Excellent Investment! Great Condition! Superior Location! +/- 1 Acre, Corner Lot, 4+ Family Investment, Turn Key, City Water/Sewer, Separate Entrances, Utilities, Off-Street Parking, Bus Line, Additional Income Coin-Op Laundry, 4 Bsmt Storage Units & Walk-Up Attic Storage (Possible 5th Apt.), Great Neighborhood! Nearby Sochrin Pond Walking Trail & Dog Park! Apts Leased Thru June 30, 2024. Long Term Tenants Receive Below Market Rental Benefit, Initial Appointments Can Show Apts #1, 2, Attic & Bsmt, Upon Further Interest Rest Of Property. 48 Hour Notice. Seller can hold $200k paper, first position only. NOTE: PROOF OF FUNDS REQUIRED BEFORE APPOINTMENT IS CONFIRMED.

18. 2023-07-17
    status Under Contract 684-char remark

    Show marketing remark (684 chars)

    Excellent Investment! Great Condition! Superior Location! +/- 1 Acre, Corner Lot, 4+ Family Investment, Turn Key, City Water/Sewer, Separate Entrances, Utilities, Off-Street Parking, Bus Line, Additional Income Coin-Op Laundry, 4 Bsmt Storage Units & Walk-Up Attic Storage (Possible 5th Apt.), Great Neighborhood! Nearby Sochrin Pond Walking Trail & Dog Park! Apts Leased Thru June 30, 2024. Long Term Tenants Receive Below Market Rental Benefit, Initial Appointments Can Show Apts #1, 2, Attic & Bsmt, Upon Further Interest Rest Of Property. 48 Hour Notice. Seller can hold $200k paper, first position only. NOTE: PROOF OF FUNDS REQUIRED BEFORE APPOINTMENT IS CONFIRMED.

19. 2023-06-11
    historical Under Contract - Continue to Show 684-char remark

    Show marketing remark (684 chars)

    Excellent Investment! Great Condition! Superior Location! +/- 1 Acre, Corner Lot, 4+ Family Investment, Turn Key, City Water/Sewer, Separate Entrances, Utilities, Off-Street Parking, Bus Line, Additional Income Coin-Op Laundry, 4 Bsmt Storage Units & Walk-Up Attic Storage (Possible 5th Apt.), Great Neighborhood! Nearby Sochrin Pond Walking Trail & Dog Park! Apts Leased Thru June 30, 2024. Long Term Tenants Receive Below Market Rental Benefit, Initial Appointments Can Show Apts #1, 2, Attic & Bsmt, Upon Further Interest Rest Of Property. 48 Hour Notice. Seller can hold $200k paper, first position only. NOTE: PROOF OF FUNDS REQUIRED BEFORE APPOINTMENT IS CONFIRMED.

20. 2023-05-13
    listed $579,900 Active 684-char remark

    Show marketing remark (684 chars)

    Excellent Investment! Great Condition! Superior Location! +/- 1 Acre, Corner Lot, 4+ Family Investment, Turn Key, City Water/Sewer, Separate Entrances, Utilities, Off-Street Parking, Bus Line, Additional Income Coin-Op Laundry, 4 Bsmt Storage Units & Walk-Up Attic Storage (Possible 5th Apt.), Great Neighborhood! Nearby Sochrin Pond Walking Trail & Dog Park! Apts Leased Thru June 30, 2024. Long Term Tenants Receive Below Market Rental Benefit, Initial Appointments Can Show Apts #1, 2, Attic & Bsmt, Upon Further Interest Rest Of Property. 48 Hour Notice. Seller can hold $200k paper, first position only. NOTE: PROOF OF FUNDS REQUIRED BEFORE APPOINTMENT IS CONFIRMED.

21. 2022-11-30
    historical
22. 2022-10-21
    price $579,900
23. 2022-06-22
    listed $640,000 Active
24. 2022-05-31
    historical
25. 2021-12-20
    status Active
26. 2021-12-19
    historical
27. 2021-03-24
    listed $640,000 Active
28. 1992-12-01
    soldstatus $132,500

ⓘ 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: $9,027 · $752/mo
• Projected year-2 tax: $12,323 · $1,027/mo
• Expected delta: +$3,296/yr (+$275/mo · 36.5%)

ⓘ 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 5/10 Major 7 d/yr ≥97°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $103,932
• − Mortgage interest: −$40,886
• − Property taxes: −$9,027
• − Insurance: −$3,650
• − Repairs & maintenance: −$8,315
• − Management: −$8,315
• − Depreciation: −$21,233
• Taxable income: $12,507
• Est. tax owed @ 24.0%: −$3,002
• After-tax cash flow: $20,496/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: Seymour School District
• NCES district ID: 0903990
• Math proficiency: 34% ▼ -13.00%
• Reading proficiency: 50% ▼ -5.00%
• Median HH income: $71,700
• Composite: 38.17/100
• National rank: #4263
• State rank: #93 of 153 in CT

Livability — Seymour

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

Census & demographics

• County: New Haven County · 688,236 people
• City population: 16,889
• Metro: New Haven-Milford, CT
• Population (ZIP): 16,889
• Household income: $107,708
• Rent vs Own: 25.8% rent · 74.2% own
• Severe rent burden: 221.0

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (67%)
• Race & ethnicity: White 67% Hispanic / Latino 19% Two or more races 16% Black 7% Asian 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 12%
• Common ancestry: Romanian 9% Scotch-Irish 3% Lithuanian 2%
• Foreign-born: 11% · Canada, Dominican Republic
• Languages at home: 83% English-only · Spanish 10% Russian/Polish/Slavic 3% Other Indo-European 3%

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: ▼ -2.41%
• Current HPI: 294.2705
• 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

+450.9% since first listed

13 events — show timeline

• 2026-03-24 Listed $729,900 Smart MLS
• 2023-07-18 Sold (MLS) $590,000 Smart MLS
• 2023-07-17 Pending — Smart MLS
• 2023-06-11 Contingent — Smart MLS
• 2023-05-13 Listed $579,900 Smart MLS
• 2022-11-30 Listing Removed — Smart MLS
• 2022-10-21 Price Changed $579,900 Smart MLS
• 2022-06-22 Listed $640,000 Smart MLS
• 2022-05-31 Listing Removed — Smart MLS
• 2021-12-20 Relisted — Smart MLS
• 2021-12-19 Listing Removed — Smart MLS
• 2021-03-24 Listed $640,000 Smart MLS
• 1992-12-01 Sold (Public Records) $132,500 Public Records

Property tax history

+1.5%/yr

Latest (2023): $9,027 · +1.1% YoY. Source: county tax records.