16 Doubling Rd

Greenwich, CT 06830

$19,950,000D-

6 bd · 9.5 ba · 11,323 sqft · Built 2026 · SingleFamily · Active · 51 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,972/mo
• Mortgage (P&I): −$104,620
• Tax + insurance: −$12,311
• HOA: −$0
• Vac / Maint / Mgmt: −$1,254
• Net cashflow: $-112,213/mo
• Annual: $-1,346,561/yr
• Cap rate: -0.46%
• Cash-on-cash: -24.11%
• DSCR: -0.07
• 1% rule: 0.03%
• Cash to close: $5,586,000

Investor read

• This is a 6-bed/9.5-bath single-family listed at $19.95M.
• At list price, monthly cash flow is $-112k ($-1.35M/yr) — negative.
• To cash-flow at today's rent, offer at most $683k (96.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $597k (97.0% below list).
• It's been on market 51 days — a 3% lower offer ($19.35M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $597k (97.0% below list) — sets the bar for 1% rule.
• In year one you build about $1.51M of equity ($138k loan paydown + $1.38M appreciation (6.9% local appreciation)).
• Location reads 80/100 on livability (#23 in CT, #1,655 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, health & safety A+; Watch: amenities D, cost of living 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: North Street School (math 72% / reading 82%, grade A, #28 of 553 statewide, top 7%, 387 students, 4% FRL); Central Middle School (math 60% / reading 71%, grade A-, #26 of 175 statewide, top 16%, 506 students, 18% FRL); Greenwich High School (math 59% / reading 78%, grade B, #23 of 194 statewide, top 12%, 2,668 students, 20% FRL) — zoned schools at 14% FRL track the district average.
• Market conditions: Rents rising (+3.4%/yr); 128 active listings in the ZIP; 2 comparable units currently listed for rent nearby; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 4 sale attempts since 8y ago; this cycle's ask has dropped $4.55M (19%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $8.35M; list at $19.95M implies a 139% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$2.42M cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: 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.
• Cap rate -0.5% vs local median 1.1% in Greenwich — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.
• At $5,972/mo this rent would consume 49% of the median local household income ($147k/yr) (locally 1088% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

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 51 days. Have you received any prior offers? Is the seller open to a 97% concession, seller financing, or rate buy-down credit?
• 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.