35 Timber Trail Ln

Medford, NY 11763

$499,900D-

4 bd · 3.0 ba · 1,577 sqft · Built 1977 · SingleFamily · Pending · 29 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $3,915/mo
• Mortgage (P&I): −$2,622
• Tax + insurance: −$1,205
• HOA: −$0
• Vac / Maint / Mgmt: −$822
• Net cashflow: $-734/mo
• Annual: $-8,810/yr
• Cap rate: 4.53%
• Cash-on-cash: -6.29%
• DSCR: 0.72
• 1% rule: 0.78%
• Cash to close: $139,972

Investor read

• This is a 4-bed/3.0-bath single-family listed at $500k.
• At list price, monthly cash flow is $-734 ($-9k/yr) — negative.
• To cash-flow at today's rent, offer at most $370k (25.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $391k (21.7% below list).
• It's been on market 29 days — a 2% lower offer ($492k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $370k (25.9% below list) — sets the bar for cash-flow.
• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $15k of value loss. Plan a longer hold.
• Location reads 69/100 on livability (#502 in NY) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety B; Watch: schools C-, amenities F, commute F.
• Longwood Central School District (rural): math 61% / reading 55% proficiency, ranked #235 of 590 in NY (top 40%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 186 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• 3 sale attempts 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.
• Climate carrying-cost: major wind risk, 78% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.
• Cap rate 4.5% vs local median 3.5% in Medford — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.
• This rent runs 39% of the median local income ($121k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

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 1977 — 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.
• 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.
• 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.