27-31 Pleasant St

Pittsfield, MA 01201

$300,000D-

5 bd · 3.0 ba · 2,118 sqft · Built 1880 · MultiFamily · Pending · 39 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $15,249/mo
• Mortgage (P&I): −$1,573
• Tax + insurance: −$345
• HOA: −$0
• Vac / Maint / Mgmt: −$3,202
• Net cashflow: $10,129/mo
• Annual: $121,546/yr
• Cap rate: 46.81%
• Cash-on-cash: 144.70%
• DSCR: 7.44
• 1% rule: 5.08%
• Cash to close: $84,000

Investor read

• This is a 11 × 1-bed/?-bath units multifamily listed at $300k.
• At list price, monthly cash flow is $10k ($122k/yr) — positive. Per door: $921/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($15k rent vs $300k).
• It's been on market 39 days — a 3% lower offer ($291k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $291k (3.0% 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 $9k of value loss. Plan a longer hold.
• Location reads 75/100 on livability (#70 in MA, #3,820 nationally) — a middle-class / working-renter tenant base. Strengths: commute A+, housing A+, health & safety A+; Watch: employment C-, amenities D+, crime D.
• Pittsfield (urban): math 19% / reading 34% proficiency, ranked #272 of 302 in MA (top 90%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Zoned schools: Morningside Community School (math 8% / reading 22%, grade F, #854 of 938 statewide, top 93%, 355 students, 0% FRL); John T Reid Middle (math 7% / reading 17%, grade F, #283 of 305 statewide, top 93%, 450 students, 0% FRL); Pittsfield High (math 32% / reading 57%, grade F, #203 of 343 statewide, top 60%, 651 students, 0% FRL) — zoned schools average 0% FRL vs 50% district-wide (50 pts lower); this property's tenant base skews higher-income than the district average.
• Watch-outs: built in 1880 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+7.7%/yr); 276 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 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.
• 2 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.
• Current owner paid $240k; 25% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• At projected returns (-3.0% appreciation + 7.7% rent growth), your $84k cash investment doubles in ~1 year — after that, you're playing with house money.
• Cap rate 46.8% vs local median 3.6% in Pittsfield — 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.
• At $15,249/mo this rent would consume 257% of the median local household income ($71k/yr) (locally 1580% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• It's been on market 39 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
• What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
• Built in 1880 — 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 D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
• 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?