37 Church Hill Rd

New Preston, CT 06794

$490,000C+

2 bd · 2.0 ba · 792 sqft · Built 1962 · SingleFamily · Active · 77 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $4,293/mo
• Mortgage (P&I): −$2,570
• Tax + insurance: −$378
• HOA: −$0
• Vac / Maint / Mgmt: −$902
• Net cashflow: $444/mo
• Annual: $5,325/yr
• Cap rate: 7.38%
• Cash-on-cash: 3.88%
• DSCR: 1.17
• 1% rule: 0.88%
• Cash to close: $137,200

Investor read

• This is a 2-bed/2.0-bath single-family listed at $490k.
• At list price, monthly cash flow is $444 ($5k/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 $429k (12.4% below list).
• It's been on market 77 days — a 6% lower offer ($461k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $429k (12.4% below list) — sets the bar for 1% rule.
• In year one you build about $4k of equity ($3k loan paydown + $832 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.
• Market conditions: 15 active listings in the ZIP; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).
• 6 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 $423k; 16% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• At projected returns (0.2% appreciation + 3.0% rent growth), your $137k cash investment doubles in ~9 years — after that, you're playing with house money.
• By year 7, paydown + projected appreciation supports a ~$34k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Cap rate 7.4% 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 77 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1962 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.