265 South St · Thomaston, CT 06782

$239,900

3 bd · 1.0 ba · 1,072 sqft · SingleFamily public records · 42 Days on market

Built 1966 8,276 sqft lot $224/sqft · 30% below area Est $341k · 30% under

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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).

• ARV discount +15.0/15.0
• Cash flow +8.2/30.0
• Schools +4.5/10.0
• Livability +3.2/5.0
• 1% rule +3.0/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.2/10.0
• Appreciation +0.0/10.0

Listing remarks

A rare offering in this area, you can own a piece of the lakeside lifestyle! This charming one-level ranch is the ultimate "diamond in the rough" for a first-time buyer ready to build sweat equity. The bones are all there: a cozy fireplace for chilly nights, an open kitchen perfect for hosting your first housewarming, and a covered deck for all-weather entertaining. The real "bonus feature" is the massive walkout basement-with its high ceilings, it's a blank canvas just waiting to become your future game room, home office, or guest suite. Best of all? You're just a short walk away from the lake! Plus, its location on a main route means you'll have some of the best-mainta

Key facts

• Covered deck
• Cozy fireplace
• High ceilings

Tags

• COZY FIREPLACE
• OPEN KITCHEN
• COVERED DECK
• MASSIVE WALKOUT BASEMENT
• HIGH CEILINGS
• SHORT WALK TO THE LAKE

Property features AI

Exterior

• Parking: Paved driveway and off-street parking; Approximately 4 parking spaces
• Utilities: Private well water; Public sewer connection; Oil tank located in basement; Electric service (standard)
• Home design: Single-family home
• Construction: Concrete foundation; Frame and brick construction; Clapboard and brick siding; Asphalt shingle roof; Red exterior color
• Exterior features: Awnings; Covered deck; Level to rolling lot; Walkable to water and in a water community; Private paved asphalt driveway

Interior

• Bedrooms: 3 bedrooms
• Bathrooms: 1 full bathroom
• Heating & cooling: Hot air heating; Oil-fired heat; 30-gallon oil hot water tank
• Interior features: One fireplace; Full walk-out basement; Full basement; Attic with hatch access; Total of 5 rooms; Central air conditioning
• Laundry & utility: Laundry in basement (lower level)

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $240k.

Deal economics

• At list price, monthly cash flow is $-222 ($-3k/yr) — negative.
• To cash-flow at today's rent, offer at most $201k (16.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $193k (19.7% below list).
• Recommended offer: $193k (19.7% below list) — sets the bar for 1% rule.
• Cap rate 5.2% vs local median 4.3% in Thomaston — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.

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-.
• Plymouth School District (suburban): math 42% / reading 58% proficiency, ranked #78 of 153 in CT (top 51%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Plymouth Center School (math 47% / reading 67%, grade C+, #177 of 553 statewide, top 34%, 342 students, 48% FRL); Eli Terry Jr. Middle School (math 44% / reading 63%, grade C+, #70 of 175 statewide, top 40%, 279 students, 48% FRL); Terryville High School (math 44% / reading 64%, grade C-, #63 of 194 statewide, top 39%, 367 students, 43% FRL) — zoned schools average 46% FRL vs 22% district-wide (24 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 18 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 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 $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 42 days — a 3% lower offer ($233k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $192,574 (19.7% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 42 days. Have you received any prior offers? Is the seller open to a 20% concession, seller financing, or rate buy-down credit?
3. Built in 1966 — 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. 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?
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 for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.80% ✗
• Cap rate: 5.18%
• Cash-on-cash: -3.97%
• DSCR: 0.82
• GRM: 10.4

CMA / ARV

• ARV (median comp): $341,438
• List price: $239,900
• Delta: -29.74%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
105 Lake Plymouth Blvd	0.27mi	2/1.0 (-1)	1,024 (-4%)	1mo	$330,000	$322	74
349 Lake Plymouth Blvd	0.38mi	2/1.0 (-1)	950 (-11%)	4mo	$75,000	$79	54
265 Lake Plymouth Blvd	0.50mi	3/1.0	1,232 (+15%)	3mo	$300,000	$244	49
271 Lake Plymouth Blvd	0.49mi	2/1.0 (-1)	1,120 (+4%)	21mo	$275,000	$246	47
47 Hosier Rd	0.50mi	3/1.0	954 (-11%)	16mo	$220,000	$231	45

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: -22.9%
• Equity multiple: 0.21×
• Total profit: $-52,959
• Equity at exit: $35,770

10-year hold

• IRR: -17.3%
• Equity multiple: 0.05×
• Total profit: $-64,026
• Equity at exit: $20,742

Cash invested: $67,172 (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 06782

• Home prices YoY: -10.9%
• Active inventory: 18
• Price-to-rent: 10.4×

Monthly cashflow live

• Estimated rent: $1,926 medium
• Mortgage (P&I): −$1,258
• Tax from tax record: −$386 /mo · $4,629/yr
• Insurance: −$100
• HOA: −$0
• Vacancy / Maint / Mgmt: −$404
• Net cashflow: $-222

Break-even live

Break-even rent $2,207

Max offer price $200,606

Occupancy floor —

Sensitivity live

Price	-10% $-87	-5% $-155	+0% $-222	+5% $-290	+10% $-358
Rent	-10% $-375	-5% $-299	+0% $-222	+5% $-146	+10% $-70
Rate	-1.0pp $-102	-0.5pp $-161	base $-222	+0.5pp $-285	+1.0pp $-348

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: $59,975
• Closing costs: $7,197
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
8 Maple Ave Plymouth, CT	2.0	1.0	834	$1,500	$1.80	45d	1	1.04mi
720 Main St Unit 1ST Plymouth, CT	4.0	1.0	1120	$2,300	$2.05	4d	1	1.12mi

Listing history 5 events

1. 2026-06-02
   status $239,900 Under Contract 42 DOM
2. 2026-06-01
   days on market $239,900 Under Contract - Continue to Show 42 DOM
3. 2026-05-31
   days on market $239,900 Under Contract - Continue to Show 41 DOM
4. 2026-05-06
   historical Under Contract - Continue to Show 891-char remark
5. 2026-04-20
   listed $239,900 Active 891-char remark

ⓘ 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: $4,629 · $386/mo
• Projected year-2 tax: $4,881 · $407/mo
• Expected delta: +$252/yr (+$21/mo · 5.5%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥95°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% 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: $23,109
• − Mortgage interest: −$13,438
• − Property taxes: −$4,629
• − Insurance: −$1,200
• − Repairs & maintenance: −$1,849
• − Management: −$1,849
• − Depreciation: −$6,979
• Taxable loss: −$6,834
• Est. tax savings @ 24.0%: +$1,640
• After-tax cash flow: $-1,029/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: Plymouth School District
• NCES district ID: 0903330
• Math proficiency: 42% ▼ -10.00%
• Reading proficiency: 58% ▼ -2.00%
• Median HH income: $71,517
• Composite: 44.78/100
• National rank: #2743
• State rank: #78 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

• City population: 7,493
• Population (ZIP): 2,098

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (85%)
• Race & ethnicity: White 85% Black 6% Hispanic / Latino 5% Asian 4% Two or more races 1%
• Hispanic origin (detail): Puerto Rican 2%
• Common ancestry: Lithuanian 7% Slovak 3% Romanian 3%
• Foreign-born: 8% · China, Canada
• Languages at home: 95% English-only · Chinese 2% Spanish 1% 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: ▼ -24.38%
• Current HPI: 199.1652
• 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

3 events — show timeline

• 2026-06-01 Pending — Smart MLS
• 2026-05-06 Contingent — Smart MLS
• 2026-04-20 Listed $239,900 Smart MLS

Property tax history

+1.8%/yr

Latest (2023): $4,629 · +3.8% YoY. Source: county tax records.