100 Hillsdale Rd

Great Barrington, MA 01230

$225,000C-

3 bd · 1.0 ba · 2,073 sqft · Built 1950 · SingleFamily · Pending · 6 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,355/mo
• Mortgage (P&I): −$1,180
• Tax + insurance: −$375
• HOA: −$0
• Vac / Maint / Mgmt: −$495
• Net cashflow: $306/mo
• Annual: $3,670/yr
• Cap rate: 7.92%
• Cash-on-cash: 5.82%
• DSCR: 1.26
• 1% rule: 1.05%
• Cash to close: $63,000

Investor read

• This is a 3-bed/1.0-bath single-family listed at $225k. Condition is rated fair.
• At list price, monthly cash flow is $306 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $225k).
• Only 6 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Location reads 78/100 on livability (#50 in MA, #2,550 nationally) — a middle-class / working-renter tenant base. Strengths: health & safety A+, crime A-, commute A-; Watch: schools C-, employment C-, cost of living F.
• Southern Berkshire (rural): math 22% / reading 44% proficiency, ranked #243 of 302 in MA (top 80%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Watch-outs: built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 121 active listings in the ZIP; 130 units permitted in Berkshire County in 2024 (10 in 5+ unit buildings).
• Berkshire County population projected at -24% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 3 sale attempts since 3y 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.
• Cap rate 7.9% vs local median 1.0% in Great Barrington — 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

• Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
• Built in 1950 — 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.
• 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.

Repairs flagged (vision-AI assessment)

• Major: kitchen cabinets — severely outdated and in poor condition
• Major: bathroom fixtures — outdated and in poor condition
• Major: roof — visible moss and potential leak
• Major: exterior siding — poor condition
• Major: HVAC system — outdated and likely inefficient