165 Main St · Plymouth, CT 06786

$239,900

3 bd · 2.0 ba · 1,366 sqft · SingleFamily public records · 33 Days on market

Built 1910 0.40 ac lot $176/sqft · 17% below area Est $291k · 17% under ↓ 4% 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).

• ARV discount +15.0/15.0
• Cash flow +9.2/30.0
• Schools +4.5/10.0
• 1% rule +3.0/10.0
• DSCR +2.6/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Victorian colonial that has been in the family for decades. It may need cosmetic work but well worth the effort to bring back to sparkling condition. The first floor features an eat in kitchen, formal dining room, living room and full bath. Upstairs you find three bedrooms, full bath and a walk up attic. Step outside and enjoy the large private yard with a two car garage. Take a look!

Key facts

• 0.4 acre lot
• 2 garage spots
• Pool

Property features AI

Exterior

• Parking: Detached 2-car garage
• Utilities: Public water connected; Public sewer connected
• Home design: Single-family home
• Construction: Frame construction; Masonry foundation; Asphalt shingle roof
• Exterior features: Above-ground swimming pool; Lightly wooded, level lot; Vinyl siding

Interior

• Kitchen: Oven/Range; Microwave; Range hood; Refrigerator; Dishwasher
• Bedrooms: 3 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Hot air heating fueled by natural gas; Window AC unit(s)
• Interior features: 6 total rooms; Full basement; Walk-up attic
• Laundry & utility: Washer; Dryer; Natural gas domestic hot water

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $240k.

Deal economics

• At list price, monthly cash flow is $-179 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $208k (13.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $192k (20.0% below list).
• Recommended offer: $192k (20.0% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• 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: Terryville High School (math 44% / reading 64%, grade C-, #63 of 194 statewide, top 39%, 367 students, 43% FRL) — zoned schools average 43% FRL vs 22% district-wide (20 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 55 active listings in the ZIP; 7 comparable units currently listed for rent nearby; rentals leasing fast (median 3d on market — plan ~1-2 weeks tenant-placement turnaround); 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 33 days — a 3% lower offer ($233k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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

• Watch-outs: built in 1910 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate flood risk; major wind risk, 27% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $191,851 (20.0% 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 33 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 1910 — 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: 5.40%
• Cash-on-cash: -3.20%
• DSCR: 0.86
• GRM: 10.4

CMA / ARV

• ARV (median comp): $290,722
• List price: $239,900
• Delta: -17.48%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
19 Beach Ave	0.18mi	3/2.0	1,338 (-2%)	16mo	$240,000	$179	74
5 Union St	0.10mi	3/1.5	1,470 (+8%)	9mo	$315,000	$214	73
45 S Main St	0.20mi	3/2.0	1,224 (-10%)	1mo	$335,000	$274	73
20 High St	0.39mi	3/1.5	1,398 (+2%)	6mo	$342,500	$245	71
75 S Eagle St	0.56mi	3/1.5	1,364 (-0%)	8mo	$320,000	$235	65
10 Diamond St	0.38mi	4/2.0 (+1)	1,428 (+4%)	6mo	$370,000	$259	65
43 (A) Hillside Ave	0.37mi	4/3.0 (+1)	1,284 (-6%)	6mo	$385,000	$300	58
52 High St	0.47mi	3/1.0	1,378 (+1%)	18mo	$250,000	$181	58
45 S Eagle St	0.42mi	3/2.0	1,497 (+10%)	9mo	$359,900	$240	57
14 Church St	0.52mi	3/1.5	1,236 (-10%)	6mo	$350,000	$283	53
19 Benedict St	0.48mi	2/1.5 (-1)	1,560 (+14%)	10mo	$300,500	$193	38
17 Adams Dr	0.73mi	4/2.0 (+1)	1,544 (+13%)	14mo	$315,000	$204	28

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: -21.6%
• Equity multiple: 0.25×
• Total profit: $-50,217
• Equity at exit: $35,770

10-year hold

• IRR: -15.3%
• Equity multiple: 0.13×
• Total profit: $-58,190
• 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 06786

• Home prices YoY: -23.7%
• Active inventory: 55
• Price-to-rent: 10.4×

Monthly cashflow live

• Estimated rent: $1,919 high
• Mortgage (P&I): −$1,258
• Tax from tax record: −$336 /mo · $4,038/yr
• Insurance: −$100
• HOA: −$0
• Vacancy / Maint / Mgmt: −$403
• Net cashflow: $-179

Break-even live

Break-even rent $2,145

Max offer price $208,297

Occupancy floor —

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 7 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
3 Pearl St Unit 3 Terryville, CT	2.0	1.0	930	$1,450	$1.56	24d	1	0.20mi
34 S Main St Unit 3 Terryville, CT	2.0	1.0	1000	$1,600	$1.60	3d	1	0.26mi
8 Burnham St Unit 2A Terryville, CT	3.0	1.0	1100	$2,495	$2.27	2d	1	0.26mi
282 Main St Terryville, CT	2.0	1.0	900	$1,650	$1.83	2d	1	0.55mi
75 High St Terryville, CT	2.0	1.5	1593	$2,500	$1.57	2d	1	0.59mi
78 Kearney St Terryville, CT	4.0	2.0	1747	$1,650	$0.94	15d	1	0.68mi
389 Main St Terryville, CT	4.0	1.5	1204	$2,500	$2.08	2d	1	0.97mi

Listing history 18 events

1. 2026-06-18
   days on market $239,900 Active 33 DOM
2. 2026-06-17
   days on market $239,900 Active 32 DOM
3. 2026-06-16
   days on market $239,900 Active 31 DOM
4. 2026-06-15
   days on market $239,900 Active 30 DOM
5. 2026-06-13
   days on market $239,900 Active 28 DOM
6. 2026-06-13
   days on market $239,900 Active 27 DOM
7. 2026-06-10
   days on market $239,900 Active 25 DOM
8. 2026-06-09
   days on market $239,900 Active 24 DOM
9. 2026-06-08
   days on market $239,900 Active 23 DOM
10. 2026-06-07
    days on market $239,900 Active 22 DOM
11. 2026-06-05
    days on market $239,900 Active 19 DOM
12. 2026-06-03
    days on market $239,900 Active 18 DOM
13. 2026-06-02
    days on market $239,900 Active 17 DOM
14. 2026-06-01
    days on market $239,900 Active 16 DOM
15. 2026-05-31
    days on market $239,900 Active 15 DOM
16. 2026-05-15
    status Under Contract 387-char remark
17. 2026-05-05
    listed $239,900 Active 387-char remark
18. 1989-05-01
    soldstatus $250,000

ⓘ 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: $4,038 · $336/mo
• Projected year-2 tax: $4,586 · $382/mo
• Expected delta: +$548/yr (+$46/mo · 13.6%)

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

Climate risk First Street

• 🌊 Flood 5/10 Major 49% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥94°F today · 16 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: $23,022
• − Mortgage interest: −$13,438
• − Property taxes: −$4,038
• − Insurance: −$1,200
• − Repairs & maintenance: −$1,842
• − Management: −$1,842
• − Depreciation: −$6,979
• Taxable loss: −$6,316
• Est. tax savings @ 24.0%: +$1,516
• After-tax cash flow: $-631/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 — Plymouth

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

Census & demographics

• Census place: Terryville, CT
• Population (ZIP): 9,617

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (86%)
• Race & ethnicity: White 86% Hispanic / Latino 8% Two or more races 7%
• Hispanic origin (detail): Puerto Rican 4% Dominican 1%
• Common ancestry: Romanian 13% Lithuanian 11% Russian 4%
• Foreign-born: 3% · Canada, Jamaica
• Languages at home: 92% English-only · Spanish 5% Other Indo-European 1% French/Haitian/Cajun 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: ▼ -62.57%
• Current HPI: 201.83
• 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

-4.0% since first listed

4 events — show timeline

• 2026-05-26 Relisted — Smart MLS
• 2026-05-15 Pending — Smart MLS
• 2026-05-05 Listed $239,900 Smart MLS
• 1989-05-01 Sold (Public Records) $250,000 Public Records

Property tax history

+2.5%/yr

Latest (2023): $4,038 · +3.8% YoY. Source: county tax records.