14 Cook St

New Preston, CT 06794

$749,000B

4 bd · 2.0 ba · 1,792 sqft · Built 1900 · SingleFamily · Active · 153 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $27,611/mo
• Mortgage (P&I): −$3,928
• Tax + insurance: −$674
• HOA: −$0
• Vac / Maint / Mgmt: −$5,798
• Net cashflow: $17,211/mo
• Annual: $206,531/yr
• Cap rate: 33.96%
• Cash-on-cash: 98.80%
• DSCR: 5.40
• 1% rule: 3.69%
• Cash to close: $209,720

Investor read

• This is a 4-bed/2.0-bath single-family listed at $749k.
• 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).
• It's been on market 153 days — a 12% lower offer ($659k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $659k (12.0% below list) — sets the bar for market timing.
• In year one you build about $6k of equity ($5k loan paydown + $1k appreciation (0.2% local appreciation)).
• 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.
• Watch-outs: flood insurance adds $56/mo; built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• 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).
• 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.
• 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.
• Climate carrying-cost: major flood risk — expect insurance premiums to compound above CPI over the hold.
• 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.

Questions for listing agent

• 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?
• Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
• Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• 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.
• 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.
• 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.