28 Old Orchard Dr

Weston, CT 06883

$1,779,000F

4 bd · 4.5 ba · 4,079 sqft · Built 1986 · SingleFamily · Active · 424 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $4,881/mo
• Mortgage (P&I): −$9,329
• Tax + insurance: −$2,519
• HOA: −$0
• Vac / Maint / Mgmt: −$1,025
• Net cashflow: $-7,992/mo
• Annual: $-95,909/yr
• Cap rate: 0.90%
• Cash-on-cash: -19.25%
• DSCR: 0.14
• 1% rule: 0.27%
• Cash to close: $498,120

Investor read

• This is a 4-bed/4.5-bath single-family listed at $1.78M.
• At list price, monthly cash flow is $-8k ($-96k/yr) — negative.
• To cash-flow at today's rent, offer at most $427k (76.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $488k (72.6% below list).
• It's been on market 424 days — a 12% lower offer ($1.57M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $427k (76.0% below list) — sets the bar for cash-flow.
• Local home prices are declining (-3.0%/yr); year-one equity from $12k of loan paydown is wiped out by about $53k of value loss. Plan a longer hold.
• Location reads: area grade F — affects rentability + tenant quality, not the cash-flow math above.
• Weston School District (suburban): math 68% / reading 77% proficiency, ranked #4 of 153 in CT (top 3%) — strong family-tenant draw, lease renewals of 3-5y typical; only 1% free/reduced lunch — higher-income household profile.
• Market conditions: 73 active listings in the ZIP; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 2 sale attempts since 32y 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 $620k; list at $1.78M implies a 187% gain — meaningful room to come down on a strong offer.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 0.9% vs local median 2.9% in Weston — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

Questions for listing agent

• What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
• It's been on market 424 days. Have you received any prior offers? Is the seller open to a 76% concession, seller financing, or rate buy-down credit?
• 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.
• 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.