8 Windy Hill Rd

Topstone, CT 06896

$1,195,000B-

4 bd · 3.0 ba · 3,007 sqft · Built 1998 · SingleFamily · Under Contract · 14 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $20,000/mo
• Mortgage (P&I): −$6,267
• Tax + insurance: −$1,914
• HOA: −$0
• Vac / Maint / Mgmt: −$4,200
• Net cashflow: $7,619/mo
• Annual: $91,433/yr
• Cap rate: 13.94%
• Cash-on-cash: 27.33%
• DSCR: 2.22
• 1% rule: 1.67%
• Cash to close: $334,600

Investor read

• This is a 4-bed/3.0-bath single-family listed at $1.20M.
• At list price, monthly cash flow is $8k ($91k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.20M).
• Only 14 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-3.0%/yr); year-one equity from $8k of loan paydown is wiped out by about $36k of value loss. Plan a longer hold.
• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Regional School District 09 (rural): math 75% / reading 90% proficiency, ranked #7 of 192 in CT (top 4%) — strong family-tenant draw, lease renewals of 3-5y typical.
• Zoned schools: Redding Elementary School (math 67% / reading 72%, grade A-, #78 of 553 statewide, top 17%, 479 students, 9% FRL); John Read Middle School (math 69% / reading 76%, grade A, #6 of 175 statewide, top 3%, 350 students, 9% FRL); Joel Barlow High School (math 57% / reading 82%, grade B, #18 of 194 statewide, top 10%, 768 students, 12% FRL).
• Zoned-school proficiency averages 70% at this address vs 82% district-wide (-12 pts) — the specific schools serving this property underperform the Regional School District 09 average; the district grade overstates school quality for this exact location.
• Market conditions: 62 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 8 sale attempts since 30y 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 $1.02M; 17% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $335k cash investment doubles in ~5 years — after that, you're playing with house money.
• Climate carrying-cost: moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Questions for listing agent

• 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.