30 Upland Rd

Winchester, CT 06098

$220,000D+

4 bd · 2.0 ba · 1,844 sqft · Built 1869 · SingleFamily · Active · 33 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,966/mo
• Mortgage (P&I): −$1,154
• Tax + insurance: −$356
• HOA: −$0
• Vac / Maint / Mgmt: −$413
• Net cashflow: $44/mo
• Annual: $530/yr
• Cap rate: 6.53%
• Cash-on-cash: 0.86%
• DSCR: 1.04
• 1% rule: 0.89%
• Cash to close: $61,600

Investor read

• This is a 4-bed/2.0-bath single-family listed at $220k.
• At list price, monthly cash flow is $44 ($530/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 $197k (10.6% below list).
• It's been on market 33 days — a 3% lower offer ($213k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $197k (10.6% below list) — sets the bar for 1% rule.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• Winchester School District (town): math 53% / reading 49% proficiency, ranked #131 of 192 in CT (top 68%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Pearson School (math 42% / reading 47%, grade F, #272 of 553 statewide, top 50%, 294 students, 60% FRL) — zoned schools average 60% FRL vs 41% district-wide (19 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Watch-outs: built in 1869 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 63 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).
• 3 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 $110k; list at $220k implies a 100% gain — meaningful room to come down on a strong offer.
• Climate carrying-cost: moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.
• This rent runs 36% of the median local income ($66k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• It's been on market 33 days. Have you received any prior offers? Is the seller open to a 11% concession, seller financing, or rate buy-down credit?
• Built in 1869 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
• 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.