341 High St Ext · Thomaston, CT 06787

$800,000

6 bd · 6.5 ba · 5,729 sqft · MultiFamily public records · 48 Days on market

Built 2001 3.69 ac lot $140/sqft · 22% above area Est $655k · 22% over ↓ 20% since listing

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Why this score? — see what drove the D+ 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 +20.9/30.0
• DSCR +6.7/10.0
• 1% rule +6.1/10.0
• Schools +3.6/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks

Hidden Estate at High Street: A private Litchfield County retreat offering relaxed country living with exceptional versatility. This secluded country estate features fantastic outdoor spaces, 5 bedrooms, 6 baths, 12x24 salt water fountained pool, pool house and 2 studio apartments. Boasting 4,291 sq ft on 3.69 acres, this secluded oasis is the perfect hideaway to relax and refresh. The heart of the home is the oversized sunlit kitchen complete with granite breakfast bar, 6 burner stove, wall oven, dishwasher and double refrigerators. Kitchen is open to dining room and huge family room with sliders to pool area. There is also a formal living room w/ granite fireplace. Upstairs consists of 4

Key facts

• Pool house
• Private retreat
• 3.69 acre lot

Tags

• PRIVATE RETREAT
• FANTASTIC OUTDOOR SPACES
• SALT WATER FOUNTAINED POOL
• POOL HOUSE
• OVERSIZED SUNLIT KITCHEN
• GRANITE BREAKFAST BAR

Property features AI

Exterior

• Parking: Detached/attached garage with automatic opener (garage access to basement)
• Utilities: Private well (private water system); Septic system; Electric power; Propane available (in-ground fuel tank)
• Home design: Single-family home; Yellow exterior with vinyl siding; Asphalt shingle roof
• Construction: Frame construction; Concrete foundation
• Exterior features: Balcony; Awnings; Fruit trees and garden area; Cabana; Outdoor lighting; Hot tub; French doors; Pool house; Gunite in-ground heated saltwater pool

Interior

• Kitchen: Gas cooktop; Wall oven; Microwave; Refrigerator; Dishwasher
• Bedrooms: 4 bedrooms
• Bathrooms: 4 full bathrooms; 1 half bathroom
• Heating & cooling: Central air with ceiling fans and zoned cooling; Hot air and hot water heating with zoning; Electric and propane fuel
• Interior features: Auto garage door opener; Cable pre-wired; In-law apartment with separate first-floor entry; One fireplace; Has attic (access via hatch); Full finished, heated basement with garage access, interior access and walk-out; includes apartment
• Laundry & utility: Upper level laundry room; Washer; Electric dryer

What this means for you Summary

Snapshot

• This is a 6-bed/6.5-bath multifamily listed at $800k.

Deal economics

• At list price, monthly cash flow is $1k ($13k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($9k rent vs $800k).
• Recommended offer: $776k (3.0% below list) — sets the bar for market timing.
• Cap rate 8.0% vs local median 4.5% in Thomaston — 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 64/100 on livability (#127 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A-, cost of living B+; Watch: amenities F, commute F, employment D-.
• Thomaston School District (suburban): math 31% / reading 48% proficiency, ranked #101 of 153 in CT (top 66%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 15% free/reduced lunch — higher-income household profile.
• Zoned schools: Black Rock School (math 54% / reading 44%, grade D, #237 of 553 statewide, top 45%, 292 students, 37% FRL); Thomaston High School (math 32% / reading 57%, grade F, #94 of 194 statewide, top 49%, 317 students, 33% FRL) — zoned schools average 35% FRL vs 15% district-wide (20 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 16 active listings in the ZIP; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $6k of loan paydown is wiped out by about $24k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 48 days — a 3% lower offer ($776k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 6y 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.

Risks & watch-outs

• 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 $776,000 (3.0% below list)

Questions for the listing agent

1. It's been on market 48 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
4. 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.
5. 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.
6. 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: 1.11% ✓
• Cap rate: 7.97%
• Cash-on-cash: 5.97%
• DSCR: 1.27
• GRM: 7.5

CMA / ARV

• ARV (median comp): $654,675
• List price: $800,000
• Delta: 22.20%
• Verdict: OVERPRICED
• Comps: 1 within 2.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: -7.0%
• Equity multiple: 0.74×
• Total profit: $-58,271
• Equity at exit: $119,283

10-year hold

• IRR: 2.6%
• Equity multiple: 1.19×
• Total profit: $42,161
• Equity at exit: $69,169

Cash invested: $224,000 (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 06787

• Home prices YoY: -27.1%
• Active inventory: 16
• Price-to-rent: 45.0×

Monthly cashflow live

• Estimated rent: $8,884 medium
• Mortgage (P&I): −$4,195
• Tax from tax record: −$1,375 /mo · $16,500/yr
• Insurance: −$333
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,866
• Net cashflow: $1,115

Break-even live

Break-even rent $7,473

Max offer price $800,000

Occupancy floor 82%

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

Units	Beds	Baths	Est. rent
▸ 6× units	2	1	$8,886
Total (6 units)			$8,884

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: $200,000
• Closing costs: $24,000
• Reserves months: —
• Total cash needed: —

Listing history 19 events

1. 2026-06-18
   days on market $800,000 Active 48 DOM
2. 2026-06-17
   days on market $800,000 Active 47 DOM
3. 2026-06-16
   days on market $800,000 Active 46 DOM
4. 2026-06-15
   days on market $800,000 Active 45 DOM
5. 2026-06-14
   days on market $800,000 Active 43 DOM
6. 2026-06-13
   days on market $800,000 Active 42 DOM
7. 2026-06-10
   days on market $800,000 Active 40 DOM
8. 2026-06-09
   days on market $800,000 Active 39 DOM
9. 2026-06-08
   days on market $800,000 Active 38 DOM
10. 2026-06-07
    days on market $800,000 Active 37 DOM
11. 2026-06-03
    days on market $800,000 Active 33 DOM
12. 2026-06-03
    days on market $800,000 Active 32 DOM
13. 2026-06-01
    days on market $800,000 Active 31 DOM
14. 2026-05-31
    days on market $800,000 Active 30 DOM
15. 2026-05-01
    listed $800,000 Active 1210-char remark
16. 2021-09-01
    historical
17. 2021-05-15
    listed $995,000 Active
18. 2021-04-28
    historical
19. 2020-07-31
    listed $995,000 Active

ⓘ 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: $16,500 · $1,375/mo
• Projected year-2 tax: $16,810 · $1,401/mo
• Expected delta: +$310/yr (+$26/mo · 1.9%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥96°F today · 16 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: $106,608
• − Mortgage interest: −$44,812
• − Property taxes: −$16,500
• − Insurance: −$4,000
• − Repairs & maintenance: −$8,529
• − Management: −$8,529
• − Depreciation: −$23,273
• Taxable income: $966
• Est. tax owed @ 24.0%: −$232
• After-tax cash flow: $13,145/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: Thomaston School District
• NCES district ID: 0904500
• Math proficiency: 31% ▼ -10.00%
• Reading proficiency: 48% ▼ -8.00%
• Median HH income: $65,757
• Composite: 35.52/100
• National rank: #4909
• State rank: #101 of 153 in CT

Livability — Thomaston

• Score: 64/100
• State rank: #127
• US rank: #14400

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Thomaston, CT
• City population: 7,493
• Population (ZIP): 7,493

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (80%)
• Race & ethnicity: White 80% Hispanic / Latino 9% Two or more races 8% Black 2% Asian 2%
• Hispanic origin (detail): Puerto Rican 7%
• Common ancestry: Romanian 7% Lithuanian 7% Russian 4%
• Foreign-born: 5% · Canada, Vietnam
• Languages at home: 96% English-only · Spanish 2% Other Indo-European 1% Korean 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: ▼ -71.78%
• Current HPI: 192.8437
• Rent YoY: —
• Metro: —
• 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

-19.6% since first listed

5 events — show timeline

• 2026-05-01 Listed $800,000 Smart MLS
• 2021-09-01 Listing Removed — Smart MLS
• 2021-05-15 Listed $995,000 Smart MLS
• 2021-04-28 Listing Removed — Smart MLS
• 2020-07-31 Listed $995,000 Smart MLS

Property tax history

+3.7%/yr

Latest (2023): $16,500 · +4.7% YoY. Source: county tax records.