30 Upland Rd · Winchester, CT 06098

$220,000

4 bd · 2.0 ba · 1,844 sqft · SingleFamily public records · 33 Days on market

Built 1869 7,405 sqft lot Est $326k · 33% under

---

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 +14.4/30.0
• Schools +4.6/10.0
• DSCR +4.4/10.0
• 1% rule +3.9/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Well kept in town colonial featuring 4 spacious bedrooms, 2 full baths, upper level den and sunroom. Beautiful hardwood floors throughout the upper level with built-ins. Vinyl sided with a metal roof. Walk up attic for extra storage. Seller is motivated!

Key facts

• Large walk up attic
• Nearby highland lake
• Tree lined backyard

Tags

• TREE LINED BACKYARD
• LARGE WALK UP ATTIC
• NEARBY HIGHLAND LAKE

Property features AI

Exterior

• Parking: Driveway parking for 1 vehicle
• Utilities: Public water connected; Public sewer connected (metered); Electric hot water; Electric power
• Home design: Single-family home; Frame construction; White exterior; Paved driveway; Driveway parking
• Construction: Metal roof; Vinyl siding; Stone foundation
• Exterior features: Porch; Level to sloping lot

Interior

• Kitchen: Oven/Range; Refrigerator
• Bedrooms: 4 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Hot air heating; Oil-fired heat; fuel tank located in basement; Electric 40-gallon hot water tank
• Interior features: 8 total rooms; Full, unfinished basement; Walk-up attic; Bonus room
• Laundry & utility: Washer and Dryer included; Laundry located in hallway on the main level

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $220k.

Deal economics

• At list price, monthly cash flow is $44 ($530/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $197k (10.6% below list).
• Recommended offer: $197k (10.6% 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.
• 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.
• Zoned schools: Pearson School (math 42% / reading 47%, grade F, #272 of 553 statewide, top 50%, 294 students, 60% FRL) — zoned schools average 60% FRL vs 41% district-wide (19 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 63 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).
• This rent runs 36% of the median local income ($66k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

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 ($213k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 8y 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 $110k; list at $220k implies a 100% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1869 — 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 $196,645 (10.6% below list)

Questions for the listing agent

1. It's been on market 33 days. Have you received any prior offers? Is the seller open to a 11% concession, seller financing, or rate buy-down credit?
2. Built in 1869 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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 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: 0.89% ✗
• Cap rate: 6.53%
• Cash-on-cash: 0.86%
• DSCR: 1.04
• GRM: 9.3

CMA / ARV

• ARV (on-the-fly): $326,388
• Comps found: 9

Show comp detail 9 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
38 Upland Rd	0.00mi	3/1.5 (-1)	1,736 (-6%)	3mo	$240,000	$138	80
9 Loomis St	0.26mi	3/2.0 (-1)	1,768 (-4%)	13mo	$144,000	$81	65
150 Meadow St	0.11mi	4/2.0	2,094 (+14%)	13mo	$250,000	$119	62
47 Orchard St	0.75mi	4/2.0	1,818 (-1%)	14mo	$395,000	$217	51
17 Adams St	0.57mi	3/1.5 (-1)	1,747 (-5%)	9mo	$315,000	$180	50
17 Woodland Ave	0.35mi	3/2.0 (-1)	2,105 (+14%)	11mo	$410,000	$195	46
29 Manchester Hts	0.31mi	3/1.5 (-1)	2,066 (+12%)	20mo	$365,000	$177	42
31 Cottage St	0.64mi	4/1.5	1,966 (+7%)	22mo	$273,000	$139	39
150 E Lake St	0.58mi	3/2.5 (-1)	1,659 (-10%)	22mo	$378,000	$228	31

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: -14.9%
• Equity multiple: 0.47×
• Total profit: $-32,811
• Equity at exit: $32,803

10-year hold

• IRR: -6.3%
• Equity multiple: 0.60×
• Total profit: $-24,853
• Equity at exit: $19,022

Cash invested: $61,600 (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: 63
• Price-to-rent: 9.3×

Monthly cashflow live

• Estimated rent: $1,966 medium
• Mortgage (P&I): −$1,154
• Tax from tax record: −$264 /mo · $3,167/yr
• Insurance: −$92
• HOA: −$0
• Vacancy / Maint / Mgmt: −$413
• Net cashflow: $44

Break-even live

Break-even rent $1,910

Max offer price $220,000

Occupancy floor 93%

Sensitivity live

Price	-10% $169	-5% $106	+0% $44	+5% $-18	+10% $-80
Rent	-10% $-111	-5% $-33	+0% $44	+5% $122	+10% $200
Rate	-1.0pp $155	-0.5pp $100	base $44	+0.5pp $-13	+1.0pp $-71

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: $55,000
• Closing costs: $6,600
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
17 Union St Unit 2 Winsted, CT	3.0	1.0	1300	$1,700	$1.31	23d	1	0.57mi

Listing history 21 events

1. 2026-06-21
   days on market $220,000 Active 33 DOM
2. 2026-06-19
   days on market $220,000 Active 31 DOM
3. 2026-06-18
   days on market $220,000 Active 30 DOM
4. 2026-06-17
   days on market $220,000 Active 29 DOM
5. 2026-06-16
   days on market $220,000 Active 28 DOM
6. 2026-06-15
   days on market $220,000 Active 27 DOM
7. 2026-06-14
   days on market $220,000 Active 25 DOM
8. 2026-06-13
   days on market $220,000 Active 24 DOM
9. 2026-06-10
   days on market $220,000 Active 22 DOM
10. 2026-06-09
    days on market $220,000 Active 21 DOM
11. 2026-06-08
    days on market $220,000 Active 20 DOM
12. 2026-06-07
    statusdays on market $220,000 Active 19 DOM
13. 2026-06-03
    days on market $220,000 Under Contract - Continue to Show 15 DOM
14. 2026-06-02
    days on market $220,000 Under Contract - Continue to Show 14 DOM
15. 2026-06-01
    days on market $220,000 Under Contract - Continue to Show 13 DOM
16. 2026-05-31
    days on market $220,000 Under Contract - Continue to Show 12 DOM
17. 2026-05-30
    days on market $220,000 Under Contract - Continue to Show 11 DOM
18. 2026-05-19
    listed $220,000 Active
19. 2018-09-28
    soldstatus $110,000 Closed 254-char remark

    Show marketing remark (254 chars)

    Well kept in town colonial featuring 4 spacious bedrooms, 2 full baths, upper level den and sunroom. Beautiful hardwood floors throughout the upper level with built-ins. Vinyl sided with a metal roof. Walk up attic for extra storage. Seller is motivated!

20. 2018-08-04
    historical Under Contract - Continue to Show 254-char remark

    Show marketing remark (254 chars)

    Well kept in town colonial featuring 4 spacious bedrooms, 2 full baths, upper level den and sunroom. Beautiful hardwood floors throughout the upper level with built-ins. Vinyl sided with a metal roof. Walk up attic for extra storage. Seller is motivated!

21. 2018-06-01
    listed $115,000 Active 254-char remark

    Show marketing remark (254 chars)

    Well kept in town colonial featuring 4 spacious bedrooms, 2 full baths, upper level den and sunroom. Beautiful hardwood floors throughout the upper level with built-ins. Vinyl sided with a metal roof. Walk up attic for extra storage. Seller is motivated!

ⓘ 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: $3,167 · $264/mo
• Projected year-2 tax: $3,938 · $328/mo
• Expected delta: +$770/yr (+$64/mo · 24.3%)

ⓘ 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 3/10 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: $23,597
• − Mortgage interest: −$12,323
• − Property taxes: −$3,167
• − Insurance: −$1,100
• − Repairs & maintenance: −$1,888
• − Management: −$1,888
• − Depreciation: −$6,400
• Taxable loss: −$3,169
• Est. tax savings @ 24.0%: +$760
• After-tax cash flow: $1,291/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 — Winchester

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

Census & demographics

• Census place: Winsted, CT
• County: Litchfield County · 81,203 people
• 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

+91.3% since first listed

6 events — show timeline

• 2026-06-05 Relisted — Smart MLS
• 2026-05-29 Contingent — Smart MLS
• 2026-05-19 Listed $220,000 Smart MLS
• 2018-09-28 Sold (MLS) $110,000 Smart MLS
• 2018-08-04 Contingent — Smart MLS
• 2018-06-01 Listed $115,000 Smart MLS

Property tax history

+1.3%/yr

Latest (2022): $3,167 · +0.0% YoY. Source: county tax records.