150 Oak St · Winsted, CT 06098

$579,000

9 bd · 5.0 ba · 5,233 sqft · MultiFamily public records · 50 Days on market

Built 1924 8,276 sqft lot $111/sqft · 7% above area Est $544k · 6% over

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Why this score? — see what drove the B- 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 +30.0/30.0
• DSCR +10.0/10.0
• 1% rule +9.1/10.0
• ARV discount +4.6/15.0
• Schools +4.6/10.0
• Livability +4.0/5.0
• Rent growth +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: 5 units. confirmed

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

150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

Key facts

• 8,276 sq ft lot
• 4 garage spots
• Built 1924

What this means for you Summary

Snapshot

• This is a 4×2bd/1.6ba + 1×3bd/1.5ba units multifamily listed at $579k.

Deal economics

• At list price, monthly cash flow is $3k ($32k/yr) — positive. Per door: $540/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($8k rent vs $579k).
• Recommended offer: $562k (3.0% below list) — sets the bar for market timing.
• Cap rate 11.9% vs local median 4.1% in Winsted — 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 80/100 on livability (#25 in CT, #1,955 nationally) — a professional / high-income tenant draw. Strengths: housing A+, health & safety A+, cost of living A; Watch: amenities F, employment D-.
• Winchester School District (town): math 53% / reading 49% proficiency, ranked #131 of 192 in CT (top 68%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 61 active listings in the ZIP; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).
• At $8,179/mo this rent would consume 148% of the median local household income ($66k/yr) (locally 576% 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 $4k of loan paydown is wiped out by about $17k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $162k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• It's been on market 50 days — a 3% lower offer ($562k) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 19y 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 $341k; list at $579k implies a 70% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1924 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $561,630 (3.0% below list)

Questions for the listing agent

1. It's been on market 50 days. Have you received any prior offers? Is the seller open to a 3% 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 1924 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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.
7. 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.
8. 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: 1.41% ✓
• Cap rate: 11.89%
• Cash-on-cash: 19.99%
• DSCR: 1.89
• GRM: 5.9

CMA / ARV

• ARV (median comp): $543,671
• List price: $579,000
• Delta: 6.50%
• Verdict: FAIR
• Comps: 5 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
247 N Main St	0.27mi	8/5.0 (-1)	5,093 (-3%)	18mo	$470,000	$92	63

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: 12.1%
• Equity multiple: 1.48×
• Total profit: $78,164
• Equity at exit: $86,331

10-year hold

• IRR: 21.1%
• Equity multiple: 2.79×
• Total profit: $289,457
• Equity at exit: $50,061

Cash invested: $162,120 (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 06098

• Home prices YoY: -19.2%
• Active inventory: 61
• Price-to-rent: 30.0×

Monthly cashflow live

• Estimated rent: $8,179 medium
• Mortgage (P&I): −$3,036
• Tax from tax record: −$483 /mo · $5,797/yr
• Insurance: −$241
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,718
• Net cashflow: $2,701

Break-even live

Break-even rent $4,760

Max offer price $579,000

Occupancy floor 62%

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

Units	Beds	Baths	Est. rent
▸ 4× units	2	1.6	$6,428
1× unit	3	1.5	$1,752
Total (5 units)			$8,179

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: $144,750
• Closing costs: $17,370
• Reserves months: —
• Total cash needed: —

Listing history 36 events

1. 2026-06-19
   days on market $579,000 Active 50 DOM
2. 2026-06-18
   days on market $579,000 Active 49 DOM
3. 2026-06-17
   days on market $579,000 Active 48 DOM
4. 2026-06-16
   days on market $579,000 Active 47 DOM
5. 2026-06-15
   days on market $579,000 Active 46 DOM
6. 2026-06-14
   days on market $579,000 Active 44 DOM
7. 2026-06-13
   days on market $579,000 Active 43 DOM
8. 2026-06-10
   days on market $579,000 Active 41 DOM
9. 2026-06-09
   days on market $579,000 Active 40 DOM
10. 2026-06-08
    days on market $579,000 Active 39 DOM
11. 2026-06-07
    days on market $579,000 Active 38 DOM
12. 2026-06-03
    days on market $579,000 Active 34 DOM
13. 2026-06-02
    days on market $579,000 Active 33 DOM
14. 2026-06-01
    days on market $579,000 Active 32 DOM
15. 2026-05-31
    days on market $579,000 Active 31 DOM
16. 2026-05-30
    days on market $579,000 Active 30 DOM
17. 2026-05-01
    listed $579,000 Active 943-char remark

    Show marketing remark (943 chars)

    150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

18. 2026-04-20
    historical $579,000 943-char remark

    Show marketing remark (943 chars)

    150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

19. 2021-08-19
    soldstatus $341,000
20. 2021-08-16
    soldstatus $341,000
21. 2021-08-13
    soldstatus $341,000 Closed 355-char remark

    Show marketing remark (355 chars)

    High income property, $36,000.00 net income approx. 5 family fully rented with long term tenants all tenants are current on rent. All units have separate utilities. Four units are natural gas and the third floor unit is electric. Four units are 2 bedroom 1 bath, and the third floor is 3 bedrooms and 1-1/2 baths. Four car detached garage produces income.

22. 2021-06-01
    historical Under Contract - Continue to Show 355-char remark

    Show marketing remark (355 chars)

    High income property, $36,000.00 net income approx. 5 family fully rented with long term tenants all tenants are current on rent. All units have separate utilities. Four units are natural gas and the third floor unit is electric. Four units are 2 bedroom 1 bath, and the third floor is 3 bedrooms and 1-1/2 baths. Four car detached garage produces income.

23. 2021-03-26
    listed $399,000 Active 355-char remark

    Show marketing remark (355 chars)

    High income property, $36,000.00 net income approx. 5 family fully rented with long term tenants all tenants are current on rent. All units have separate utilities. Four units are natural gas and the third floor unit is electric. Four units are 2 bedroom 1 bath, and the third floor is 3 bedrooms and 1-1/2 baths. Four car detached garage produces income.

24. 2020-08-12
    historical Under Contract - Continue to Show
25. 2020-07-30
    soldstatus $8,000 Closed
26. 2020-01-22
    listed $10,000 Active
27. 2018-11-25
    historical
28. 2018-10-12
    price $13,888
29. 2018-07-24
    listed $19,500 Active
30. 2009-01-27
    historical
31. 2008-07-01
    listed $29,500
32. 2008-06-28
    historical
33. 2008-05-13
    listed $29,500
34. 2007-07-02
    soldstatus $230,000
35. 2007-06-28
    soldstatus $230,000
36. 2007-04-17
    listed $259,900

ⓘ 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: $5,797 · $483/mo
• Projected year-2 tax: $9,094 · $758/mo
• Expected delta: +$3,297/yr (+$275/mo · 56.9%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Taxation est. · year 1

• Rental income: $98,148
• − Mortgage interest: −$32,433
• − Property taxes: −$5,797
• − Insurance: −$2,895
• − Repairs & maintenance: −$7,852
• − Management: −$7,852
• − Depreciation: −$16,844
• Taxable income: $24,476
• Est. tax owed @ 24.0%: −$5,874
• After-tax cash flow: $26,535/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: Winchester School District
• NCES district ID: 0905160
• Math proficiency: 53% ▲ 5.00%
• Reading proficiency: 49% ▲ 2.00%
• Median HH income: $58,334
• Composite: 46.4/100
• National rank: #5353
• State rank: #131 of 192 in CT

Livability — Winsted

• Score: 80/100
• State rank: #25
• US rank: #1955

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winsted, CT
• County: Litchfield County · 81,203 people
• City population: 10,263
• Metro: Torrington, CT
• Population (ZIP): 10,263
• Household income: $66,269
• Rent vs Own: 34.3% rent · 65.7% own
• Severe rent burden: 576.0

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (87%)
• Race & ethnicity: White 87% Hispanic / Latino 9% Two or more races 8% Black 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1% Dominican 4%
• Common ancestry: Romanian 6% Lithuanian 5% Slovak 3%
• Foreign-born: 7% · Canada, Jamaica
• Languages at home: 90% English-only · Spanish 5% Other Indo-European 2% French/Haitian/Cajun 1%

Political lean MEDSL · Northwest Hills

• 2024 margin: Toss-up / Even · D 48.6% · R 49.9% · Other 1.6%
• All cycles: 2024: R+1.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -62.68%
• Current HPI: 263.2141
• Rent YoY: —
• Metro: Torrington, 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

+122.8% since first listed

20 events — show timeline

• 2026-05-01 Listed $579,000 Smart MLS
• 2026-04-20 Coming Soon $579,000 Smart MLS
• 2021-08-19 Sold (Public Records) $341,000 Public Records
• 2021-08-16 Sold (Public Records) $341,000 Public Records
• 2021-08-13 Sold (MLS) $341,000 Smart MLS
• 2021-06-01 Contingent — Smart MLS
• 2021-03-26 Listed $399,000 Smart MLS
• 2020-08-12 Contingent — Smart MLS
• 2020-07-30 Sold (MLS) $8,000 Smart MLS
• 2020-01-22 Listed $10,000 Smart MLS
• 2018-11-25 Listing Removed — Smart MLS
• 2018-10-12 Price Changed $13,888 Smart MLS
• 2018-07-24 Listed $19,500 Smart MLS
• 2009-01-27 Listing Removed — Smart MLS
• 2008-07-01 Listed $29,500 Smart MLS
• 2008-06-28 Listing Removed — Smart MLS
• 2008-05-13 Listed $29,500 Smart MLS
• 2007-07-02 Sold (Public Records) $230,000 Public Records
• 2007-06-28 Sold (MLS) $230,000 Smart MLS
• 2007-04-17 Listed $259,900 Smart MLS

Property tax history

+2.0%/yr

Latest (2022): $5,797 · +0.0% YoY. Source: county tax records.