14 Cook St · New Preston, CT 06794

$749,000

4 bd · 2.0 ba · 1,792 sqft · SingleFamily public records · 153 Days on market

Built 1900 1.32 ac lot Est $685k · 9% over

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Why this score? — see what drove the B 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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +6.3/10.0
• Appreciation +5.1/10.0
• Livability +3.5/5.0
• ARV discount +3.3/15.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Welcome to 14 Cook Street, a charming circa-1900 Victorian located in the heart of Washington Depot. Rich in history, this home was once known as "Cook's Boarding House, " a local inn that helped shape the character of this picturesque New England village. Offering approximately 1,800 square feet of living space, this 4-bedroom, 2-bath home features a traditional layout with a living room, dining room, den, and kitchen with pantry. Period details blend seamlessly with comfortable living, providing both character and functionality. Set on 1.3+ acres, the property offers a rare combination of in-town convenience and private outdoor space. The level lot is enhanced by mature landscap

Key facts

• 1.32 acre lot
• Garage
• Pool

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $749k.

Deal economics

• At list price, monthly cash flow is $17k ($207k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($28k rent vs $749k).
• Recommended offer: $659k (12.0% below list) — sets the bar for market timing.
• Cap rate 34.0% vs local median 4.0% in New Preston — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 69/100 on livability (#105 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Regional School District 12 (rural): math 64% / reading 77% proficiency, ranked #20 of 153 in CT (top 13%) — strong family-tenant draw, lease renewals of 3-5y typical; only 8% free/reduced lunch — higher-income household profile.
• Zoned schools: Washington Primary School (math 64% / reading 84%, grade A, #44 of 553 statewide, top 10%, 162 students, 25% FRL); Shepaug Valley School (math 61% / reading 76%, grade B, #23 of 194 statewide, top 12%, 494 students, 21% FRL) — zoned schools average 23% FRL vs 8% district-wide (15 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 15 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% of comp listings sitting > 30 days — soft ceiling on asking rent; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).

Forward outlook

• In year one you build about $6k of equity ($5k loan paydown + $1k appreciation (0.2% local appreciation)).
• At projected returns (0.2% appreciation + 3.0% rent growth), your $210k cash investment doubles in ~1 year — after that, you're playing with house money.
• By year 6, paydown + projected appreciation supports a ~$44k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 153 days — a 12% lower offer ($659k) 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: flood insurance adds $56/mo; built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major flood risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $659,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 153 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 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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. 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: 3.69% ✓
• Cap rate: 33.96%
• Cash-on-cash: 98.80%
• DSCR: 5.40
• GRM: 2.3

CMA / ARV

• ARV (on-the-fly): $684,544
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
43 Cook St	0.28mi	3/1.5 (-1)	1,864 (+4%)	13mo	$595,000	$319	63
30 Cook St	0.15mi	3/1.5 (-1)	1,672 (-7%)	17mo	$695,000	$416	61
25 Moody Bridge Rd W	0.45mi	3/2.0 (-1)	1,899 (+6%)	12mo	$725,000	$382	54

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

0.17% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: —
• Equity multiple: 6.15×
• Total profit: $1,080,322
• Equity at exit: $223,863

10-year hold

• IRR: —
• Equity multiple: 12.72×
• Total profit: $2,457,565
• Equity at exit: $274,237

Cash invested: $209,720 (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 06794

• Home prices YoY: 0.1%
• Active inventory: 15
• Price-to-rent: 2.3×

Monthly cashflow live

• Estimated rent: $27,611 medium
• Mortgage (P&I): −$3,928
• Tax from tax record: −$306 /mo · $3,671/yr
• Insurance: −$312
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,798
• Net cashflow: $17,211

Break-even live

Break-even rent $5,825

Max offer price $749,000

Occupancy floor 33%

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: $187,250
• Closing costs: $22,470
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
47 Calhoun St Washington Depot, CT	4.0	2.0	1720	$26,900	$15.64	43d	1	0.55mi
115 River Rd Washington Depot, CT	4.0	3.5	2538	$8,500	$3.35	43d	1	1.04mi
114 Bee Brook Rd Washington Depot, CT	3.0	1.0	1450	$3,950	$2.72	43d	1	1.04mi
126 River Rd Washington Depot, CT	4.0	2.5	2360	$29,500	$12.50	43d	1	1.16mi

Listing history 22 events

1. 2026-06-19
   days on market $749,000 Active 153 DOM
2. 2026-06-18
   days on market $749,000 Active 152 DOM
3. 2026-06-17
   days on market $749,000 Active 151 DOM
4. 2026-06-16
   days on market $749,000 Active 150 DOM
5. 2026-06-15
   days on market $749,000 Active 149 DOM
6. 2026-06-14
   days on market $749,000 Active 147 DOM
7. 2026-06-13
   days on market $749,000 Active 146 DOM
8. 2026-06-10
   days on market $749,000 Active 144 DOM
9. 2026-06-09
   days on market $749,000 Active 143 DOM
10. 2026-06-08
    days on market $749,000 Active 142 DOM
11. 2026-06-07
    days on market $749,000 Active 141 DOM
12. 2026-06-05
    days on market $749,000 Active 138 DOM
13. 2026-06-03
    days on market $749,000 Active 137 DOM
14. 2026-06-02
    days on market $749,000 Active 136 DOM
15. 2026-06-01
    days on market $749,000 Active 135 DOM
16. 2026-05-31
    status $749,000 Active 134 DOM
17. 2026-04-12
    status Under Contract
18. 2026-03-24
    historical Under Contract - Continue to Show
19. 2026-03-19
    status Active
20. 2025-10-29
    historical
21. 2025-07-12
    listed $749,000 Active
22. 2025-06-29
    historical $749,000

ⓘ 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: $3,671 · $306/mo
• Projected year-2 tax: $9,850 · $821/mo
• Expected delta: +$6,179/yr (+$515/mo · 168.3%)

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

Climate risk First Street

• 🌊 Flood 7/10 Severe FEMA zone X · 98% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥95°F today · 17 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 22% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $331,327
• − Mortgage interest: −$41,956
• − Property taxes: −$3,671
• − Insurance: −$4,412
• − Repairs & maintenance: −$26,506
• − Management: −$26,506
• − Depreciation: −$21,789
• Taxable income: $206,487
• Est. tax owed @ 24.0%: −$49,557
• After-tax cash flow: $156,975/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 12
• NCES district ID: 0903530
• Math proficiency: 64% ▼ -9.00%
• Reading proficiency: 77% ▬ 0.00%
• Median HH income: $86,065
• Composite: 63.18/100
• National rank: #638
• State rank: #20 of 153 in CT

Livability — New Preston

• Score: 69/100
• State rank: #105
• US rank: #9031

Category grades

Amenities F Commute F Cost of living F Crime A+ Employment A+ Housing A+ Health & safety D- User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 1,802
• Population (ZIP): 953

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (75%)
• Race & ethnicity: White 75% Hispanic / Latino 23% Two or more races 14%
• Hispanic origin (detail): Dominican 10%
• Common ancestry: Lithuanian 7% Romanian 6% Iranian 3%
• Foreign-born: 20% · Canada
• Languages at home: 69% English-only · Spanish 26% French/Haitian/Cajun 2% German/W. Germanic 2%

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: ▲ 0.17%
• Current HPI: 215.191
• 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

+0.0% since first listed

6 events — show timeline

• 2026-04-12 Pending — Smart MLS
• 2026-03-24 Contingent — Smart MLS
• 2026-03-19 Relisted — Smart MLS
• 2025-10-29 Listing Removed — Smart MLS
• 2025-07-12 Listed $749,000 Smart MLS
• 2025-06-29 Coming Soon $749,000 Smart MLS

Property tax history

+0.1%/yr

Latest (2023): $3,671 · +0.0% YoY. Source: county tax records.