21 Overlook Dr

Woodstock, NY 12498

$399,999C

3 bd · 1.0 ba · 1,200 sqft · Built 1956 · SingleFamily · Active · 8 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $3,800/mo
• Mortgage (P&I): −$2,098
• Tax + insurance: −$507
• HOA: −$0
• Vac / Maint / Mgmt: −$798
• Net cashflow: $398/mo
• Annual: $4,770/yr
• Cap rate: 7.49%
• Cash-on-cash: 4.26%
• DSCR: 1.19
• 1% rule: 0.95%
• Cash to close: $112,000

Investor read

• This is a 3-bed/1.0-bath single-family listed at $400k.
• At list price, monthly cash flow is $398 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $380k (5.0% below list).
• Only 8 days on market — expect competitive offers; lowballing is unlikely to land.
• Recommended offer: $380k (5.0% below list) — sets the bar for 1% rule.
• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $12k of value loss. Plan a longer hold.
• Location reads 77/100 on livability (#205 in NY, #3,176 nationally) — a middle-class / working-renter tenant base. Strengths: crime A+, amenities A+, health & safety A+; Watch: employment D, commute F, cost of living F.
• Onteora Central School District (rural): math 58% / reading 59% proficiency, ranked #288 of 755 in NY (top 38%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Watch-outs: built in 1956 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 72 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 464 units permitted in Ulster County in 2024 (170 in 5+ unit buildings).
• Ulster County population projected at -14% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 3 sale attempts since 17y 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 $338k; 19% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Cap rate 7.5% vs local median 2.6% in Woodstock — 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

• Built in 1956 — 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 B-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?
• 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.