33 E Hills Dr #33

New Canaan, CT 06840

$699,990D

3 bd · 1.5 ba · 1,554 sqft · Built 1968 · Condo · Under Contract · 15 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $6,411/mo
• Mortgage (P&I): −$3,671
• Tax + insurance: −$1,167
• HOA: −$320
• Vac / Maint / Mgmt: −$1,346
• Net cashflow: $-93/mo
• Annual: $-1,115/yr
• Cap rate: 6.13%
• Cash-on-cash: -0.57%
• DSCR: 0.97
• 1% rule: 0.92%
• Cash to close: $195,997

Investor read

• This is a 3-bed/1.5-bath condo listed at $700k.
• At list price, monthly cash flow is $-93 ($-1k/yr) — negative.
• To cash-flow at today's rent, offer at most $687k (1.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $641k (8.4% below list).
• It's been on market 15 days — a 2% lower offer ($689k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $641k (8.4% below list) — sets the bar for 1% rule.
• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $21k of value loss. Plan a longer hold.
• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• New Canaan School District (suburban): math 81% / reading 86% proficiency, ranked #1 of 153 in CT (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 6% free/reduced lunch — higher-income household profile.
• Zoned schools: East School (math 84% / reading 84%, grade A+, #7 of 553 statewide, top 1%, 550 students, 0% FRL); Saxe Middle School (math 79% / reading 85%, grade A+, #1 of 175 statewide, top 0%, 1,315 students, 0% FRL); New Canaan High School (math 77% / reading 92%, grade A, #1 of 194 statewide, top 1%, 1,294 students, 0% FRL).
• Market conditions: 165 active listings in the ZIP; 12 comparable units currently listed for rent nearby; rentals at typical pace (median 26d on market — plan ~3-4 weeks tenant-placement turnaround); 42% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• 4 sale attempts since 11y 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 $430k; list at $700k implies a 63% gain — meaningful room to come down on a strong offer.
• Climate carrying-cost: major wind risk, 59% 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.
• Cap rate 6.1% vs local median 1.5% in New Canaan — 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.
• This rent runs 31% 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?
• Built in 1968 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• 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.