5359 Main St Unit 2h.

Windham, NY 12496

$289,000D-

2 bd · 1.0 ba · 838 sqft · Built 2008 · Townhouse · Active · 91 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,000/mo
• Mortgage (P&I): −$1,516
• Tax + insurance: −$254
• HOA: −$0
• Vac / Maint / Mgmt: −$420
• Net cashflow: $-190/mo
• Annual: $-2,280/yr
• Cap rate: 5.50%
• Cash-on-cash: -2.82%
• DSCR: 0.87
• 1% rule: 0.69%
• Cash to close: $80,920

Investor read

• This is a 2-bed/1.0-bath townhouse listed at $289k.
• At list price, monthly cash flow is $-190 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $255k (11.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $200k (30.8% below list).
• It's been on market 91 days — a 9% lower offer ($263k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $200k (30.8% below list) — sets the bar for 1% rule.
• In year one you build about $17k of equity ($2k loan paydown + $15k 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: 145 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 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.
• 2 sale attempts since 6y 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 $250k; 16% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• By year 3, paydown + projected appreciation supports a ~$41k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Cap rate 5.5% vs local median 3.4% in Windham — 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 91 days. Have you received any prior offers? Is the seller open to a 31% 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.