16 Hickory Hill Rd

Windham, NY 12496

$599,000D-

2 bd · 2.0 ba · 2,250 sqft · Built 2001 · SingleFamily · Active · 129 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,339/mo
• Mortgage (P&I): −$3,141
• Tax + insurance: −$635
• HOA: −$0
• Vac / Maint / Mgmt: −$491
• Net cashflow: $-1,928/mo
• Annual: $-23,139/yr
• Cap rate: 2.43%
• Cash-on-cash: -13.80%
• DSCR: 0.39
• 1% rule: 0.39%
• Cash to close: $167,720

Investor read

• This is a 2-bed/2.0-bath single-family listed at $599k.
• At list price, monthly cash flow is $-2k ($-23k/yr) — negative.
• To cash-flow at today's rent, offer at most $258k (56.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $234k (61.0% below list).
• It's been on market 129 days — a 12% lower offer ($527k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $234k (61.0% below list) — sets the bar for 1% rule.
• In year one you build about $34k of equity ($4k loan paydown + $30k appreciation (5.1% local appreciation)).
• Location reads 60/100 on livability (#964 in NY) — a middle-class / working-renter tenant base. Strengths: housing A+, employment B+; Watch: schools C-, crime D+, cost of living D+.
• Windham-Ashland-Jewett Central School District (rural): math 55% / reading 40% proficiency, ranked #517 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 143 active listings in the ZIP; 97 units permitted in Greene County in 2024 (0 in 5+ unit buildings).
• Greene County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 5 sale attempts since 5y 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 $470k; 27% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• By year 2, paydown + projected appreciation supports a ~$55k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Cap rate 2.4% vs local median 3.2% in Windham — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

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 129 days. Have you received any prior offers? Is the seller open to a 61% concession, seller financing, or rate buy-down credit?
• 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.
• Crime grade is D in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
• 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.