44 Chester St

Milford city (balance), CT 06460

$250,000C+

3 bd · 1.0 ba · 936 sqft · Built 1960 · SingleFamily · Under Contract · 7 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,898/mo
• Mortgage (P&I): −$1,311
• Tax + insurance: −$539
• HOA: −$0
• Vac / Maint / Mgmt: −$609
• Net cashflow: $440/mo
• Annual: $5,277/yr
• Cap rate: 8.40%
• Cash-on-cash: 7.54%
• DSCR: 1.34
• 1% rule: 1.16%
• Cash to close: $70,000

Investor read

• This is a 3-bed/1.0-bath single-family listed at $250k.
• At list price, monthly cash flow is $440 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $250k).
• Only 7 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 $8k of value loss. Plan a longer hold.
• Location reads: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Milford School District (urban): math 44% / reading 58% proficiency, ranked #73 of 153 in CT (top 48%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 15% free/reduced lunch — higher-income household profile.
• Zoned schools: Calf Pen Meadow School (math 47% / reading 52%, grade D, #237 of 553 statewide, top 45%, 265 students, 23% FRL); Joseph A. Foran High School (math 47% / reading 67%, grade C, #52 of 194 statewide, top 31%, 765 students, 26% FRL).
• Market conditions: Rents rising (+2.2%/yr); 180 active listings in the ZIP; 7 comparable units currently listed for rent nearby; rentals leasing fast (median 4d on market — plan ~1-2 weeks tenant-placement turnaround); solid renter incomes; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• Climate carrying-cost: major flood risk; major wind risk, 61% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 8.4% vs local median 3.3% in Milford city (balance) — 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.
• This rent runs 33% of the median local income ($104k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• Built in 1960 — 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.