106 Orchard St

Cos Cob, CT 06807

$2,450,000D-

5 bd · 4.5 ba · 2,939 sqft · Built 2008 · SingleFamily · Pending · 11 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $13,108/mo
• Mortgage (P&I): −$12,848
• Tax + insurance: −$2,170
• HOA: −$0
• Vac / Maint / Mgmt: −$2,753
• Net cashflow: $-4,663/mo
• Annual: $-55,950/yr
• Cap rate: 4.04%
• Cash-on-cash: -8.06%
• DSCR: 0.64
• 1% rule: 0.54%
• Cash to close: $686,000

Investor read

• This is a 5-bed/4.5-bath single-family listed at $2.45M.
• At list price, monthly cash flow is $-5k ($-56k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.63M (33.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.31M (46.5% below list).
• Only 11 days on market — expect competitive offers; lowballing is unlikely to land.
• Recommended offer: $1.31M (46.5% below list) — sets the bar for 1% rule.
• In year one you build about $211k of equity ($17k loan paydown + $194k appreciation (7.9% local appreciation)).
• Location reads 73/100 on livability (#72 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety B; Watch: housing D+, amenities F, commute F.
• Greenwich School District (suburban): math 64% / reading 73% proficiency, ranked #12 of 153 in CT (top 8%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 11% free/reduced lunch — higher-income household profile.
• Zoned schools: Cos Cob School (math 62% / reading 67%, grade B, #118 of 553 statewide, top 23%, 337 students, 13% FRL); Central Middle School (math 60% / reading 71%, grade A-, #26 of 175 statewide, top 16%, 506 students, 18% FRL).
• Watch-outs: flood insurance adds $56/mo.
• Market conditions: 31 active listings in the ZIP; 20 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 12 sale attempts since 20y 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 $750k; list at $2.45M implies a 227% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$337k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: severe flood risk; major wind risk, 67% 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.

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?
• What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
• 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.