37 Prospect St

Greenwich, CT 06830

$1,699,000D

7 bd · 3.5 ba · 2,592 sqft · Built 1908 · MultiFamily · Active · 26 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $10,018/mo
• Mortgage (P&I): −$8,910
• Tax + insurance: −$1,376
• HOA: −$0
• Vac / Maint / Mgmt: −$2,104
• Net cashflow: $-2,372/mo
• Annual: $-28,460/yr
• Cap rate: 4.66%
• Cash-on-cash: -5.84%
• DSCR: 0.74
• 1% rule: 0.59%
• Cash to close: $475,720

Investor read

• This is a 2 × 3-bed/1.5-bath units multifamily listed at $1.70M.
• At list price, monthly cash flow is $-2k ($-28k/yr) — negative. Per door: $-1k/mo.
• To cash-flow at today's rent, offer at most $1.28M (24.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.00M (41.0% below list).
• It's been on market 26 days — a 2% lower offer ($1.67M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.00M (41.0% below list) — sets the bar for 1% rule.
• In year one you build about $129k of equity ($12k loan paydown + $117k 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: Hamilton Avenue School (math 32% / reading 47%, grade F, #298 of 553 statewide, top 56%, 294 students, 56% FRL); Western Middle School (math 50% / reading 59%, grade B-, #67 of 175 statewide, top 39%, 617 students, 38% FRL); Greenwich High School (math 59% / reading 78%, grade B, #23 of 194 statewide, top 12%, 2,668 students, 20% FRL) — zoned schools average 38% FRL vs 11% district-wide (27 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Zoned-school proficiency averages 54% at this address vs 68% district-wide (-14 pts) — the specific schools serving this property underperform the Greenwich School District average; the district grade overstates school quality for this exact location.
• Watch-outs: flood insurance adds $56/mo; built in 1908 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising (+3.4%/yr); 128 active listings in the ZIP; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 7 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 $695k; list at $1.70M implies a 144% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$206k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: severe flood risk; major wind risk, 60% 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 4.7% vs local median 1.1% in Greenwich — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

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?
• Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
• What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
• Built in 1908 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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?