140 Dudley St

Brookline, MA 02445

$2,698,000D

5 bd · 3.5 ba · 3,648 sqft · Built 1925 · SingleFamily · Active · 84 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $7,995/mo
• Mortgage (P&I): −$14,149
• Tax + insurance: −$3,203
• HOA: −$0
• Vac / Maint / Mgmt: −$1,679
• Net cashflow: $-11,036/mo
• Annual: $-132,432/yr
• Cap rate: 1.41%
• Cash-on-cash: -17.44%
• DSCR: 0.22
• 1% rule: 0.30%
• Cash to close: $755,440

Investor read

• This is a 5-bed/3.5-bath single-family listed at $2.70M.
• At list price, monthly cash flow is $-11k ($-132k/yr) — negative.
• To cash-flow at today's rent, offer at most $748k (72.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $799k (70.4% below list).
• It's been on market 84 days — a 6% lower offer ($2.54M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $748k (72.3% below list) — sets the bar for cash-flow.
• In year one you build about $288k of equity ($19k loan paydown + $270k appreciation (10.0% local appreciation)).
• Location reads 84/100 on livability (#16 in MA, #704 nationally) — a professional / high-income tenant draw. Strengths: schools A+, crime A+, commute A+; Watch: amenities D+, cost of living F.
• Brookline (suburban): math 66% / reading 73% proficiency, ranked #29 of 302 in MA (top 10%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 10% free/reduced lunch — higher-income household profile.
• Watch-outs: flood insurance adds $56/mo; built in 1925 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising (+1.5%/yr); 83 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 958 units permitted in Norfolk County in 2024 (305 in 5+ unit buildings).
• Norfolk County population projected at +10% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• 2 sale attempts since 19y ago; this cycle's ask has dropped $242k (8%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $1.56M; list at $2.70M implies a 73% gain — meaningful room to come down on a strong offer.
• By year 2, paydown + projected appreciation supports a ~$464k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: severe flood risk; major wind risk, 61% chance of damaging wind over 30y; extreme-heat days projected 7→14/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• At $7,995/mo this rent would consume 69% of the median local household income ($140k/yr) (locally 1138% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

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?
• It's been on market 84 days. Have you received any prior offers? Is the seller open to a 72% concession, seller financing, or rate buy-down credit?
• Built in 1925 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
• 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?
• 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?