69 Prospect St · Winsted, CT 06098

$274,900

4 bd · 3.0 ba · 2,204 sqft · MultiFamily public records · 5 Days on market

Built 1900 0.27 ac lot $125/sqft · at area comps Est $287k · at est.

---

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
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +9.4/15.0
• 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 (2-4 Unit). Listing-text estimate: 3 units. confirmed

Listing remarks MLS

Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

Key facts

• Off street parking
• Newer roof
• Near highland lake

Tags

• OFF STREET PARKING
• IN UNIT LAUNDRY HOOKUPS
• NEWER ROOF
• CLOSE PROXIMITY TO RESTAURANTS
• NEAR HIGHLAND LAKE
• EASY ACCESS TO ROUTE 8

Property features AI

Exterior

• Utilities: Public water connected; Public sewer connected
• Home design: Multi-family property (3-family)
• Construction: Frame construction; Stone foundation; Asphalt shingle roof; Built as a multi-family dwelling
• Exterior features: Gutters; Lightly wooded lot; Vinyl siding; Yellow exterior color

Interior

• Bedrooms: 7 bedrooms
• Bathrooms: 3 full bathrooms
• Heating & cooling: Baseboard heat; Electric and natural gas utilities for heating; Wall cooling units; Window cooling units
• Interior features: 13 total rooms; Full, unfinished basement with hatchway
• Laundry & utility: Basement laundry hook-ups; In-unit laundry hook-up in one unit

What this means for you Summary

Snapshot

• This is a 3 × 2-bed/1.0-bath units multifamily listed at $275k.

Deal economics

• At list price, monthly cash flow is $2k ($22k/yr) — positive. Per door: $613/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $275k).
• Cap rate 14.3% 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 $4,614/mo this rent would consume 84% 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 $2k of loan paydown is wiped out by about $8k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $77k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• 4 sale attempts since 10y 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 $198k; 39% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $274,900

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. 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: 1.68% ✓
• Cap rate: 14.32%
• Cash-on-cash: 28.67%
• DSCR: 2.28
• GRM: 5.0

CMA / ARV

• ARV (median comp): $286,834
• List price: $274,900
• Delta: -4.16%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 8 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
30 Rock St	0.20mi	4/2.0	2,299 (+4%)	7mo	$235,000	$102	74
49 Walnut St	0.61mi	5/2.0 (+1)	2,344 (+6%)	6mo	$305,000	$130	47
10 Crescent St	0.57mi	4/2.0	2,444 (+11%)	5mo	$280,000	$115	47
41 Lovely St	0.29mi	5/2.0 (+1)	2,531 (+15%)	9mo	$383,000	$151	45
18 Upland Rd	0.63mi	5/2.0 (+1)	2,338 (+6%)	14mo	$290,000	$124	40
50-52 Cottage St	0.73mi	5/— (+1)	2,016 (-8%)	14mo	$70,000	$35	35
44 Wetmore Ave	0.59mi	4/3.0	1,945 (-12%)	23mo	$250,600	$129	34
17 Chestnut St	0.45mi	5/2.0 (+1)	1,932 (-12%)	23mo	$243,000	$126	30

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: 23.0%
• Equity multiple: 1.94×
• Total profit: $72,609
• Equity at exit: $40,988

10-year hold

• IRR: 30.9%
• Equity multiple: 3.78×
• Total profit: $214,115
• Equity at exit: $23,768

Cash invested: $76,972 (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: 14.9×

Monthly cashflow live

• Estimated rent: $4,614 medium
• Mortgage (P&I): −$1,442
• Tax from tax record: −$250 /mo · $2,996/yr
• Insurance: −$115
• HOA: −$0
• Vacancy / Maint / Mgmt: −$969
• Net cashflow: $1,839

Break-even live

Break-even rent $2,286

Max offer price $274,900

Occupancy floor 55%

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

Units	Beds	Baths	Est. rent
▸ 3× units	2	1	$4,614
Total (3 units)			$4,614

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: $68,725
• Closing costs: $8,247
• Reserves months: —
• Total cash needed: —

Listing history 16 events

1. 2026-05-18
   status Under Contract 1325-char remark
2. 2026-05-13
   listed $274,900 Active 1325-char remark
3. 2021-07-26
   soldstatus $197,500
4. 2021-07-19
   historical 382-char remark

   Show marketing remark (382 chars)

   Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

5. 2021-07-19
   soldstatus $197,500 Closed 382-char remark

   Show marketing remark (382 chars)

   Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

6. 2021-05-14
   historical Under Contract - Continue to Show 382-char remark

   Show marketing remark (382 chars)

   Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

7. 2021-04-23
   price $194,900 382-char remark

   Show marketing remark (382 chars)

   Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

8. 2021-03-11
   listed $199,900 Active 382-char remark

   Show marketing remark (382 chars)

   Great Investment Opportunity! All three units are rented with separate utilities. Two of the units offer a washer/dryer hook ups and long term tenants. The second floor features 3 bedrooms, kitchen, living room and dining room. First floor has two units, one with 2 bedrooms and the other is a large one bedroom. All units have newer hot water heaters. Plenty of off street parking.

9. 2018-03-28
   soldstatus $51,700 Closed

   Show marketing remark (120 chars)

   SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

10. 2018-02-27
    status Under Contract

    Show marketing remark (120 chars)

    SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

11. 2018-02-21
    price $59,900

    Show marketing remark (120 chars)

    SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

12. 2018-01-30
    price $74,900

    Show marketing remark (120 chars)

    SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

13. 2018-01-10
    price $84,900

    Show marketing remark (120 chars)

    SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

14. 2017-10-06
    listed $99,900 Active

    Show marketing remark (120 chars)

    SEE THE POTENTIAL IN THIS VINYL SIDED 3 FAMILY, SEPARATE ENTRANCES, SEPARATE UTILITIES. CLOSE TO TOWN, LIBRARY, SCHOOLS.

15. 2016-09-26
    historical
16. 2016-02-09
    listed $72,000

ⓘ 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: $2,996 · $250/mo
• Projected year-2 tax: $4,439 · $370/mo
• Expected delta: +$1,443/yr (+$120/mo · 48.2%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 4/10 Moderate 8 d/yr ≥93°F today · 18 d/yr by 30 yrs out
• 💨 Wind 5/10 Major 26% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $55,368
• − Mortgage interest: −$15,399
• − Property taxes: −$2,996
• − Insurance: −$1,374
• − Repairs & maintenance: −$4,429
• − Management: −$4,429
• − Depreciation: −$7,997
• Taxable income: $18,743
• Est. tax owed @ 24.0%: −$4,498
• After-tax cash flow: $17,573/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

+281.8% since first listed

16 events — show timeline

• 2026-05-18 Pending — Smart MLS
• 2026-05-13 Listed $274,900 Smart MLS
• 2021-07-26 Sold (Public Records) $197,500 Public Records
• 2021-07-19 Listing Removed — Smart MLS
• 2021-07-19 Sold (MLS) $197,500 Smart MLS
• 2021-05-14 Contingent — Smart MLS
• 2021-04-23 Price Changed $194,900 Smart MLS
• 2021-03-11 Listed $199,900 Smart MLS
• 2018-03-28 Sold (MLS) $51,700 Smart MLS
• 2018-02-27 Pending — Smart MLS
• 2018-02-21 Price Changed $59,900 Smart MLS
• 2018-01-30 Price Changed $74,900 Smart MLS
• 2018-01-10 Price Changed $84,900 Smart MLS
• 2017-10-06 Listed $99,900 Smart MLS
• 2016-09-26 Listing Removed — Smart MLS
• 2016-02-09 Listed $72,000 Smart MLS

Property tax history

+0.5%/yr

Latest (2022): $2,996 · +0.0% YoY. Source: county tax records.