4440 S Military Hwy

Chesapeake, VA 23321

$150,000B-

3 bd · 1.0 ba · 760 sqft · Built 1940 · SingleFamily · Under Contract · 180 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,762/mo
• Mortgage (P&I): −$787
• Tax + insurance: −$224
• HOA: −$0
• Vac / Maint / Mgmt: −$370
• Net cashflow: $382/mo
• Annual: $4,580/yr
• Cap rate: 9.35%
• Cash-on-cash: 10.90%
• DSCR: 1.49
• 1% rule: 1.17%
• Cash to close: $42,000

Investor read

• This is a 3-bed/1.0-bath single-family listed at $150k.
• At list price, monthly cash flow is $382 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $150k).
• It's been on market 180 days — a 12% lower offer ($132k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $132k (12.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $1k of loan paydown is wiped out by about $4k of value loss. Plan a longer hold.
• Location reads 70/100 on livability (#236 in VA) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+; Watch: crime C-, cost of living C-, amenities F.
• Chesapeake City Public School District (suburban): math 58% / reading 74% proficiency, ranked #31 of 131 in VA (top 24%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Southeastern Elementary (math 80% / reading 83%, grade A+, #120 of 1,108 statewide, top 11%, 837 students, 17% FRL); Jolliff Middle (math 40% / reading 69%, grade B-, #194 of 342 statewide, top 60%, 702 students, 43% FRL); Western Branch High (math 71% / reading 84%, grade A-, #83 of 319 statewide, top 28%, 2,121 students, 37% FRL) — zoned schools at 32% FRL track the district average.
• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+7.6%/yr); 234 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 16d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 597 units permitted in Chesapeake city in 2024 (0 in 5+ unit buildings).
• Chesapeake County population projected at +21% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 3 sale attempts since 4y ago; this cycle's ask has dropped $35k (19%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $59k; list at $150k implies a 155% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 7.6% rent growth), your $42k cash investment doubles in ~8 years — after that, you're playing with house money.
• Climate carrying-cost: severe wind risk, 80% 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 9.3% vs local median 3.7% in Chesapeake — 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

• It's been on market 180 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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?
• 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.