30 Chestnut Hill Rd · Killingworth, CT 06419

$340,000

4 bd · 1.0 ba · 1,756 sqft · SingleFamily public records · 399 Days on market

Built 1890 2.10 ac lot $194/sqft · 31% below area Est $493k · 31% under

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Why this score? — see what drove the C+ 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 +22.2/30.0
• ARV discount +15.0/15.0
• DSCR +7.1/10.0
• Schools +5.8/10.0
• 1% rule +5.4/10.0
• 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

** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of transformation. Exterior work-including masonry, roof detailing, windows, and finish-is underway. Current renovation plans envision a spacious 3-bedroom, 2.5-bath layout featuring a dedicated office, library, and over 3,000 square feet of living space. When completed, the home-along with a barn/garage addition and refreshed landscaping-is projected to be valued between $800,000 and $925,000. An optional larger barn built on the existing foundation at the rear of the property could add approximately $248,000 in additional value. The seller is now seeking a new steward for this exceptional property. There's also the option to retain the current owner as architect and contractor to help bring the vision to life. This is a rare chance to be part of a meaningful restoration-combining history, craftsmanship, and future potential.

Key facts

• Masonry work
• Watertight roof
• Roof detailing

Tags

• WATERTIGHT ROOF
• MASONRY WORK
• ROOF DETAILING
• WINDOWS FINISH
• DEDICATED OFFICE
• LIBRARY

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $340k.

Deal economics

• At list price, monthly cash flow is $554 ($7k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $340k).
• Recommended offer: $299k (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Regional School District 17 (rural): math 55% / reading 72% proficiency, ranked #29 of 153 in CT (top 19%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 6% free/reduced lunch — higher-income household profile.
• Market conditions: 25 active listings in the ZIP; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 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 $10k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 399 days — a 12% lower offer ($299k) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 2y 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 $130k; list at $340k implies a 162% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1890 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 67% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $299,200 (12.0% below list)

Questions for the listing agent

1. It's been on market 399 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1890 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 1.04% ✓
• Cap rate: 8.25%
• Cash-on-cash: 6.98%
• DSCR: 1.31
• GRM: 8.0

CMA / ARV

• ARV (median comp): $492,990
• List price: $340,000
• Delta: -31.03%
• Verdict: UNDERPRICED
• Comps: 3 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: -5.6%
• Equity multiple: 0.79×
• Total profit: $-19,855
• Equity at exit: $50,695

10-year hold

• IRR: 4.0%
• Equity multiple: 1.29×
• Total profit: $28,033
• Equity at exit: $29,397

Cash invested: $95,200 (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 06419

• Active inventory: 25
• Price-to-rent: 8.0×

Monthly cashflow live

• Estimated rent: $3,525 medium
• Mortgage (P&I): −$1,783
• Tax from tax record: −$306 /mo · $3,678/yr
• Insurance: −$142
• HOA: −$0
• Vacancy / Maint / Mgmt: −$740
• Net cashflow: $554

Break-even live

Break-even rent $2,824

Max offer price $340,000

Occupancy floor 79%

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: $85,000
• Closing costs: $10,200
• Reserves months: —
• Total cash needed: —

Listing history 32 events

1. 2026-06-18
   days on market $340,000 Active 399 DOM
2. 2026-06-17
   days on market $340,000 Active 398 DOM
3. 2026-06-16
   days on market $340,000 Active 397 DOM
4. 2026-06-15
   days on market $340,000 Active 396 DOM
5. 2026-06-13
   days on market $340,000 Active 394 DOM
6. 2026-06-13
   days on market $340,000 Active 393 DOM
7. 2026-06-10
   days on market $340,000 Active 391 DOM
8. 2026-06-09
   days on market $340,000 Active 390 DOM
9. 2026-06-08
   days on market $340,000 Active 389 DOM
10. 2026-06-07
    days on market $340,000 Active 388 DOM
11. 2026-06-03
    days on market $340,000 Active 384 DOM
12. 2026-06-02
    days on market $340,000 Active 383 DOM
13. 2026-06-01
    days on market $340,000 Active 382 DOM
14. 2026-05-31
    days on market $340,000 Active 381 DOM
15. 2025-05-14
    listed $340,000 Active 1232-char remark

    Show marketing remark (1232 chars)

    ** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of transformation. Exterior work-including masonry, roof detailing, windows, and finish-is underway. Current renovation plans envision a spacious 3-bedroom, 2.5-bath layout featuring a dedicated office, library, and over 3,000 square feet of living space. When completed, the home-along with a barn/garage addition and refreshed landscaping-is projected to be valued between $800,000 and $925,000. An optional larger barn built on the existing foundation at the rear of the property could add approximately $248,000 in additional value. The seller is now seeking a new steward for this exceptional property. There's also the option to retain the current owner as architect and contractor to help bring the vision to life. This is a rare chance to be part of a meaningful restoration-combining history, craftsmanship, and future potential.

16. 2025-03-14
    historical
17. 2025-02-24
    price $324,925
18. 2025-02-20
    price $319,925
19. 2025-01-22
    historical
20. 2025-01-22
    listed $324,925 Active
21. 2025-01-20
    price $324,925
22. 2024-12-14
    listed $359,925 Active
23. 2024-12-04
    historical
24. 2024-12-04
    historical
25. 2024-09-26
    listed $925,000 Active
26. 2024-08-19
    listed $360,000 Active
27. 2024-03-21
    soldstatus $130,000 Closed
28. 2024-03-07
    status Under Contract
29. 2024-03-06
    status Active
30. 2024-02-28
    historical
31. 2024-02-06
    status Under Contract
32. 2024-02-04
    listed $130,000 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: $3,678 · $306/mo
• Projected year-2 tax: $5,477 · $456/mo
• Expected delta: +$1,799/yr (+$150/mo · 48.9%)

ⓘ 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 (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥93°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 67% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $42,300
• − Mortgage interest: −$19,045
• − Property taxes: −$3,678
• − Insurance: −$1,700
• − Repairs & maintenance: −$3,384
• − Management: −$3,384
• − Depreciation: −$9,891
• Taxable income: $1,218
• Est. tax owed @ 24.0%: −$292
• After-tax cash flow: $6,351/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 17
• NCES district ID: 0903539
• Math proficiency: 55% ▼ -6.00%
• Reading proficiency: 72% ▼ -1.00%
• Median HH income: $97,473
• Composite: 58.45/100
• National rank: #1003
• State rank: #29 of 153 in CT

Livability — Killingworth

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

Census & demographics

• Population (ZIP): 6,219

Population outlook (Lower Connecticut River Valley County) Hauer SSP2

• By 2040: 188,651

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Two or more races 9% Hispanic / Latino 3%
• Common ancestry: Romanian 16% Lithuanian 3% Slovak 3%
• Foreign-born: 2% · Canada, China
• Languages at home: 98% English-only · French/Haitian/Cajun 1% Chinese 1%

Political lean MEDSL · Lower Connecticut River Valley

• 2024 margin: D (+13.4) · D 55.9% · R 42.4% · Other 1.7%
• All cycles: 2024: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -111.43%
• Current HPI: 182.4072
• 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

+161.5% since first listed

18 events — show timeline

• 2025-05-14 Listed $340,000 Smart MLS
• 2025-03-14 Listing Removed — Smart MLS
• 2025-02-24 Price Changed $324,925 Smart MLS
• 2025-02-20 Price Changed $319,925 Smart MLS
• 2025-01-22 Listing Removed — Smart MLS
• 2025-01-22 Listed $324,925 Smart MLS
• 2025-01-20 Price Changed $324,925 Smart MLS
• 2024-12-14 Listed $359,925 Smart MLS
• 2024-12-04 Listing Removed — Smart MLS
• 2024-12-04 Listing Removed — Smart MLS
• 2024-09-26 Listed $925,000 Smart MLS
• 2024-08-19 Listed $360,000 Smart MLS
• 2024-03-21 Sold (MLS) $130,000 Smart MLS
• 2024-03-07 Pending — Smart MLS
• 2024-03-06 Relisted — Smart MLS
• 2024-02-28 Listing Removed — Smart MLS
• 2024-02-06 Pending — Smart MLS
• 2024-02-04 Listed $130,000 Smart MLS

Property tax history

-0.7%/yr

Latest (2023): $3,678 · +1.1% YoY. Source: county tax records.