568 Wellesley St

Wellesley, MA 02493

$4,388,000D

5 bd · 6.0 ba · 8,152 sqft · Built 1988 · SingleFamily · Active · 132 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $25,000/mo
• Mortgage (P&I): −$23,011
• Tax + insurance: −$4,717
• HOA: −$0
• Vac / Maint / Mgmt: −$5,250
• Net cashflow: $-7,978/mo
• Annual: $-95,734/yr
• Cap rate: 4.11%
• Cash-on-cash: -7.79%
• DSCR: 0.65
• 1% rule: 0.57%
• Cash to close: $1,228,640

Investor read

• This is a 5-bed/6.0-bath single-family listed at $4.39M.
• At list price, monthly cash flow is $-8k ($-96k/yr) — negative.
• To cash-flow at today's rent, offer at most $2.98M (32.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $2.50M (43.0% below list).
• It's been on market 132 days — a 12% lower offer ($3.86M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $2.50M (43.0% below list) — sets the bar for 1% rule.
• In year one you build about $97k of equity ($30k loan paydown + $66k appreciation (1.5% local appreciation)).
• Location reads 85/100 on livability (#13 in MA, #568 nationally) — a professional / high-income tenant draw. Strengths: crime A+, commute A+, employment A+; Watch: amenities C-, cost of living F.
• Weston (suburban): math 71% / reading 77% proficiency, ranked #7 of 302 in MA (top 2%) — strong family-tenant draw, lease renewals of 3-5y typical; only 4% free/reduced lunch — higher-income household profile.
• Zoned schools: Country (math 44% / reading 74%, grade B-, #167 of 938 statewide, top 21%, 331 students, 0% FRL); Weston Middle (math 72% / reading 76%, grade A, #5 of 305 statewide, top 2%, 444 students, 0% FRL); Weston High (math 87% / reading 82%, grade A, #22 of 343 statewide, top 8%, 639 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Market conditions: 54 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 3,670 units permitted in Middlesex County in 2024 (2,611 in 5+ unit buildings).
• Middlesex County population projected at +20% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 7 sale attempts since 19y ago; this cycle's ask has dropped $300k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $635k; list at $4.39M implies a 591% gain — meaningful room to come down on a strong offer.
• By year 3, paydown + projected appreciation supports a ~$249k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: major wind risk, 50% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 4.1% vs local median 1.6% in Wellesley — 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

• 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 132 days. Have you received any prior offers? Is the seller open to a 43% concession, seller financing, or rate buy-down credit?
• 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?
• 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.