86 Carpenter Rd

Middletown, NY 10958

$379,900C-

4 bd · 1.0 ba · 1,620 sqft · Built 1872 · SingleFamily · Pending · 19 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $3,300/mo
• Mortgage (P&I): −$1,992
• Tax + insurance: −$681
• HOA: −$0
• Vac / Maint / Mgmt: −$693
• Net cashflow: $-66/mo
• Annual: $-796/yr
• Cap rate: 6.08%
• Cash-on-cash: -0.75%
• DSCR: 0.97
• 1% rule: 0.87%
• Cash to close: $106,372

Investor read

• This is a 4-bed/1.0-bath single-family listed at $380k.
• At list price, monthly cash flow is $-66 ($-796/yr) — negative.
• To cash-flow at today's rent, offer at most $368k (3.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $330k (13.1% below list).
• It's been on market 19 days — a 2% lower offer ($374k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $330k (13.1% below list) — sets the bar for 1% rule.
• In year one you build about $41k of equity ($3k loan paydown + $38k appreciation (10.0% local appreciation)).
• Location reads 82/100 on livability (#79 in NY, #1,219 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, housing A+, health & safety A+; Watch: commute C-.
• Minisink Valley Central School District (rural): math 51% / reading 59% proficiency, ranked #254 of 590 in NY (top 43%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 17% free/reduced lunch — higher-income household profile.
• Zoned schools: Minisink Valley Intermediate School (math 32% / reading 58%, grade D-, #1,274 of 2,108 statewide, top 61%, 444 students, 26% FRL); Minisink Valley Middle School (math 27% / reading 58%, grade D-, #373 of 729 statewide, top 52%, 775 students, 28% FRL); Minisink Valley High School (math 94% / reading 75%, grade A, #379 of 1,100 statewide, top 36%, 1,172 students, 28% FRL).
• Watch-outs: built in 1872 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 31 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,746 units permitted in Orange County in 2024 (1,265 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 $160k; list at $380k implies a 137% gain — meaningful room to come down on a strong offer.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $106k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$65k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Cap rate 6.1% vs local median 3.3% in Middletown — 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?
• Built in 1872 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
• This sits on a lake — are riparian / water-frontage rights deeded with the parcel? Any dock permits, shoreline easements, or HOA water-use restrictions?
• What's the documented flood / surge / shoreline-erosion history here (FEMA AND non-FEMA — e.g., storm surge, creek backup, septic-field saturation)?
• Any water-quality or seasonal algae-bloom issues that affect tenant satisfaction or short-term-rental demand?
• 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.