33 Halsey Dr

Old Greenwich, CT 06870

$1,465,000F

3 bd · 2.0 ba · 1,481 sqft · Built 1948 · SingleFamily · Under Contract · 259 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $8,497/mo
• Mortgage (P&I): −$7,683
• Tax + insurance: −$1,140
• HOA: −$0
• Vac / Maint / Mgmt: −$1,784
• Net cashflow: $-2,110/mo
• Annual: $-25,325/yr
• Cap rate: 4.56%
• Cash-on-cash: -6.17%
• DSCR: 0.73
• 1% rule: 0.58%
• Cash to close: $410,200

Investor read

• This is a 3-bed/2.0-bath single-family listed at $1.47M.
• At list price, monthly cash flow is $-2k ($-25k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.09M (25.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $850k (42.0% below list).
• It's been on market 259 days — a 12% lower offer ($1.29M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $850k (42.0% below list) — sets the bar for 1% rule.
• In year one you build about $148k of equity ($10k loan paydown + $138k appreciation (9.4% local appreciation)).
• Location reads 68/100 on livability (#108 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, commute F, 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 Mianus School (math 83% / reading 81%, grade A+, #11 of 553 statewide, top 3%, 492 students, 3% FRL); Greenwich High School (math 59% / reading 78%, grade B, #23 of 194 statewide, top 12%, 2,668 students, 20% FRL) — zoned schools at 11% FRL track the district average.
• Watch-outs: built in 1948 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 49 active listings in the ZIP; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 5 sale attempts since 7y 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 $675k; list at $1.47M implies a 117% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$237k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: major wind risk, 70% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• This rent runs 41% of the median local income ($250k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

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 259 days. Have you received any prior offers? Is the seller open to a 42% concession, seller financing, or rate buy-down credit?
• Built in 1948 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.
• 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.