7786 S Main St

Pine Plains, NY 12567

$499,000A-

4 bd · 1.5 ba · 3,072 sqft · Built 1903 · SingleFamily · Active · 36 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $12,000/mo
• Mortgage (P&I): −$2,617
• Tax + insurance: −$824
• HOA: −$0
• Vac / Maint / Mgmt: −$2,520
• Net cashflow: $6,039/mo
• Annual: $72,474/yr
• Cap rate: 20.82%
• Cash-on-cash: 51.87%
• DSCR: 3.31
• 1% rule: 2.40%
• Cash to close: $139,720

Investor read

• This is a 4-bed/1.5-bath single-family listed at $499k.
• At list price, monthly cash flow is $6k ($72k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($12k rent vs $499k).
• It's been on market 36 days — a 3% lower offer ($484k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $484k (3.0% below list) — sets the bar for market timing.
• In year one you build about $53k of equity ($3k loan paydown + $50k appreciation (10.0% local appreciation)).
• Location reads 64/100 on livability (#746 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B+; Watch: cost of living D+, amenities F, commute F.
• Pine Plains Central School District (rural): math 55% / reading 50% proficiency, ranked #372 of 755 in NY (top 49%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Seymour Smith Intermediate Learning Center (math 24% / reading 75%, grade D+, #1,057 of 2,108 statewide, top 51%, 201 students, 40% FRL); Stissing Mountain Junior/Senior High School (math 92% / reading 75%, grade A, #409 of 1,100 statewide, top 39%, 460 students, 36% FRL).
• Zoned-school proficiency averages 67% at this address vs 52% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Pine Plains Central School District average implies; a family-tenant draw the district grade alone would hide.
• Watch-outs: built in 1903 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 39 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 3 sale attempts since 2y 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 $110k; list at $499k implies a 354% gain — meaningful room to come down on a strong offer.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $140k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$86k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Questions for listing agent

• It's been on market 36 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Built in 1903 — 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.
• 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.
• How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.