355 Route 111 #6

Smithtown, NY 11787

$249,000F

1 bd · 1.0 ba · 750 sqft · Built 1964 · Condo · Pending · 40 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,696/mo
• Mortgage (P&I): −$1,306
• Tax + insurance: −$415
• HOA: −$1,075
• Vac / Maint / Mgmt: −$566
• Net cashflow: $-666/mo
• Annual: $-7,996/yr
• Cap rate: 3.08%
• Cash-on-cash: -11.47%
• DSCR: 0.49
• 1% rule: 1.08%
• Cash to close: $69,720

Investor read

• This is a 1-bed/1.0-bath condo listed at $249k.
• At list price, monthly cash flow is $-666 ($-8k/yr) — negative.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $249k).
• It's been on market 40 days — a 3% lower offer ($242k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $242k (3.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Location reads 68/100 on livability (#550 in NY) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety A+; Watch: amenities F, commute F, cost of living F.
• Smithtown Central School District (suburban): math 71% / reading 70% proficiency, ranked #86 of 590 in NY (top 15%) — strong family-tenant draw, lease renewals of 3-5y typical; only 5% free/reduced lunch — higher-income household profile.
• Zoned schools: Smithtown Elementary School (math 72% / reading 72%, grade A-, #378 of 2,108 statewide, top 20%, 514 students, 14% FRL); Great Hollow Middle School (math 57% / reading 74%, grade A-, #119 of 729 statewide, top 16%, 828 students, 11% FRL); Smithtown High School-West (math 97% / reading 87%, grade A+, #171 of 1,100 statewide, top 18%, 1,270 students, 13% FRL).
• Watch-outs: HOA is 40% of rent.
• Market conditions: 172 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); 40% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• 2 sale attempts since 4y 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 $200k; 24% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Climate carrying-cost: severe wind risk, 80% 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 3.1% vs local median 1.9% in Smithtown — 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?
• It's been on market 40 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Built in 1964 — 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.
• 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?