439 Washington Rd · Woodbury, CT 06798

$289,000

2 bd · 1.5 ba · 1,920 sqft · SingleFamily · 468 Days on market

Built 1955 9.88 ac lot $151/sqft · 44% below area Est $517k · 44% under ↓ 10% 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 +8.4/30.0
• Schools +4.6/10.0
• 1% rule +2.6/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.3/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

Key facts

• Rural woodbury land
• Basement workshop
• Road frontage

Tags

• RURAL WOODBURY LAND
• BABBLING SPRAIN BROOK
• ROAD FRONTAGE
• DRY LEVEL BUILDING LOT
• BASEMENT WORKSHOP

What this means for you Summary

Snapshot

• This is a 2-bed/1.5-bath single-family listed at $289k.

Deal economics

• At list price, monthly cash flow is $-259 ($-3k/yr) — negative.
• To cash-flow at today's rent, offer at most $252k (13.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $220k (23.9% below list).
• Recommended offer: $220k (23.9% 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.
• Regional School District 14 (rural): math 43% / reading 59% proficiency, ranked #74 of 153 in CT (top 48%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Market conditions: 61 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 $2k of loan paydown is wiped out by about $9k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 468 days — a 12% lower offer ($254k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts; this cycle's ask has dropped $61k (17%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1955 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $220,058 (23.9% 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 468 days. Have you received any prior offers? Is the seller open to a 24% concession, seller financing, or rate buy-down credit?
3. Built in 1955 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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.
8. 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.
9. 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: 0.76% ✗
• Cap rate: 5.22%
• Cash-on-cash: -3.84%
• DSCR: 0.83
• GRM: 10.9

CMA / ARV

• ARV (median comp): $517,447
• List price: $289,000
• Delta: -44.15%
• Verdict: UNDERPRICED
• Comps: 9 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
35 Weekeepeemee Rd	0.67mi	3/1.5 (+1)	1,959 (+2%)	17mo	$399,000	$204	46

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: -22.7%
• Equity multiple: 0.22×
• Total profit: $-63,278
• Equity at exit: $43,091

10-year hold

• IRR: -17.0%
• Equity multiple: 0.06×
• Total profit: $-76,187
• Equity at exit: $24,987

Cash invested: $80,920 (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 06798

• Home prices YoY: -29.7%
• Active inventory: 61
• Price-to-rent: 10.9×

Monthly cashflow live

• Estimated rent: $2,201 medium
• Mortgage (P&I): −$1,516
• Tax est. 1.5%: −$361 /mo · $4,335/yr
• Insurance: −$120
• HOA: −$0
• Vacancy / Maint / Mgmt: −$462
• Net cashflow: $-259

Break-even live

Break-even rent $2,528

Max offer price $251,558

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: $72,250
• Closing costs: $8,670
• Reserves months: —
• Total cash needed: —

Listing history 21 events

1. 2026-06-18
   days on market $289,000 Active 468 DOM
2. 2026-06-17
   days on market $289,000 Active 467 DOM
3. 2026-06-16
   days on market $289,000 Active 466 DOM
4. 2026-06-15
   days on market $289,000 Active 465 DOM
5. 2026-06-13
   days on market $289,000 Active 463 DOM
6. 2026-06-12
   days on market $289,000 Active 462 DOM
7. 2026-06-09
   days on market $289,000 Active 459 DOM
8. 2026-06-08
   days on market $289,000 Active 458 DOM
9. 2026-06-07
   days on market $289,000 Active 457 DOM
10. 2026-06-05
    days on market $289,000 Active 455 DOM
11. 2026-06-04
    pricedays on market $289,000 Active 453 DOM
12. 2026-06-02
    days on market $314,900 Active 452 DOM
13. 2026-06-01
    days on market $314,900 Active 451 DOM
14. 2026-05-31
    days on market $314,900 Active 450 DOM
15. 2026-05-31
    days on market $314,900 Active 449 DOM
16. 2026-05-10
    status Active 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

17. 2026-04-30
    historical Under Contract - Continue to Show 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

18. 2025-12-13
    status Active 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

19. 2025-11-21
    historical Under Contract - Continue to Show 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

20. 2025-07-11
    price $314,900 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

21. 2025-03-03
    listed $349,900 Active 644-char remark

    Show marketing remark (644 chars)

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $26,407
• − Mortgage interest: −$16,188
• − Property taxes: −$4,335
• − Insurance: −$1,445
• − Repairs & maintenance: −$2,113
• − Management: −$2,113
• − Depreciation: −$8,407
• Taxable loss: −$8,194
• Est. tax savings @ 24.0%: +$1,967
• After-tax cash flow: $-1,139/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: Regional School District 14
• NCES district ID: 0903536
• Math proficiency: 43% ▼ -7.00%
• Reading proficiency: 59% ▼ -4.00%
• Median HH income: $80,016
• Composite: 46.42/100
• National rank: #2453
• State rank: #74 of 153 in CT

Livability — Woodbury

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

Census & demographics

• Population (ZIP): 9,787

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (87%)
• Race & ethnicity: White 87% Two or more races 5% Hispanic / Latino 4% Asian 3% Black 2%
• Common ancestry: Romanian 11% Lithuanian 4% Scotch-Irish 2%
• Foreign-born: 10% · Canada, China
• Languages at home: 88% English-only · Spanish 3% Russian/Polish/Slavic 2% Arabic 2%

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: ▼ -73.81%
• Current HPI: 174.592
• 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

-10.0% since first listed

6 events — show timeline

• 2026-05-10 Relisted — Smart MLS
• 2026-04-30 Contingent — Smart MLS
• 2025-12-13 Relisted — Smart MLS
• 2025-11-21 Contingent — Smart MLS
• 2025-07-11 Price Changed $314,900 Smart MLS
• 2025-03-03 Listed $349,900 Smart MLS