53 High St

Middlebury, VT 05753

$275,000C

3 bd · 3.0 ba · 1,740 sqft · Built 1920 · SingleFamily · Pending · 315 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,800/mo
• Mortgage (P&I): −$1,442
• Tax + insurance: −$458
• HOA: −$0
• Vac / Maint / Mgmt: −$588
• Net cashflow: $312/mo
• Annual: $3,738/yr
• Cap rate: 7.65%
• Cash-on-cash: 4.86%
• DSCR: 1.22
• 1% rule: 1.02%
• Cash to close: $77,000

Investor read

• This is a 3-bed/3.0-bath single-family listed at $275k.
• At list price, monthly cash flow is $312 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $275k).
• It's been on market 315 days — a 12% lower offer ($242k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $242k (12.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $8k of value loss. Plan a longer hold.
• Location reads 81/100 on livability (#7 in VT, #1,594 nationally) — a professional / high-income tenant draw. Strengths: schools A+, health & safety A+, amenities A; Watch: cost of living D+, commute F.
• Watch-outs: built in 1920 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 41 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 104 units permitted in Addison County in 2024 (6 in 5+ unit buildings).
• Addison County population projected at -12% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 2 sale attempts; this cycle's ask has dropped $75k (21%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Cap rate 7.7% vs local median 2.3% in Middlebury — 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

• It's been on market 315 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1920 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.
• Schools are A-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.