4440 S Military Hwy · Chesapeake, VA 23321

$150,000

3 bd · 1.0 ba · 760 sqft · SingleFamily public records · 180 Days on market

Built 1940 9,321 sqft lot

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Why this score? — see what drove the B- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +26.2/30.0
• DSCR +8.9/10.0
• ARV discount +7.5/15.0
• 1% rule +6.7/10.0
• Schools +5.8/10.0
• Rent growth +4.4/5.0
• Livability +3.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Key facts

• 9,321 sq ft lot
• Built 1940
• Listed 180 days

Property features AI

Finance

• HOA & community: No HOA

Exterior

• Parking: Covered carport; Driveway parking spaces
• Utilities: City/County water; City/County sewer; Electric water heater
• Home design: Detached ranch-style home; Single-story
• Construction: Crawl space and slab foundation
• Exterior features: Back yard fully fenced with chain link; Aluminum and vinyl siding; Asphalt shingle roof

Interior

• Kitchen: Range; Refrigerator
• Bedrooms: First-floor master bedroom; Bedroom and full bathroom on first floor; Attic (additional space)
• Flooring: Carpet; Vinyl
• Bathrooms: 1 full bathroom
• Heating & cooling: Electric heating; Central air conditioning
• Interior features: Scuttle access; Window treatments
• Laundry & utility: Utility room

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $150k.

Deal economics

• 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).
• Recommended offer: $132k (12.0% below list) — sets the bar for market timing.

Location & tenants

• 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); Western Branch High (math 71% / reading 84%, grade A-, #83 of 319 statewide, top 28%, 2,121 students, 37% FRL) — zoned schools at 27% FRL track the district average.
• Zoned-school proficiency averages 80% at this address vs 66% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Chesapeake City Public School District average implies; a family-tenant draw the district grade alone would hide.
• 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).

Forward outlook

• 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.
• Chesapeake County population projected at +21% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 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.

Negotiation context

• It's been on market 180 days — a 12% lower offer ($132k) is reasonable based on typical stale-listing flexibility.
• 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.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• 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.

Recommended offer $132,000 (12.0% below list)

Questions for the listing agent

1. 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?
2. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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.
7. 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.
8. 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.

Investment metrics

• 1% rule: 1.17% ✓
• Cap rate: 9.35%
• Cash-on-cash: 10.90%
• DSCR: 1.49
• GRM: 7.1

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 7.59% rent growth · sell at horizon

5-year hold

• IRR: 5.0%
• Equity multiple: 1.20×
• Total profit: $8,525
• Equity at exit: $22,365

10-year hold

• IRR: 18.2%
• Equity multiple: 2.84×
• Total profit: $77,177
• Equity at exit: $12,969

Cash invested: $42,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 55 Moderately Landlord-Leaning
• State Virginia: 55 Moderately Landlord-Leaning · D+2
• County: — inherits STATE
• City: — inherits STATE

VRLTA gives some tenant protections; Northern Virginia courts slower; rural VA landlord-leaning.

Methodology + full state rankings →

ZIP-level market 23321

• Rents YoY: 7.6%
• Active inventory: 234
• Price-to-rent: 7.1×

Monthly cashflow live

• Estimated rent: $1,762 medium
• Mortgage (P&I): −$787
• Tax from tax record: −$161 /mo · $1,932/yr
• Insurance: −$62
• HOA: −$0
• Vacancy / Maint / Mgmt: −$370
• Net cashflow: $382

Break-even live

Break-even rent $1,279

Max offer price $150,000

Occupancy floor 73%

Sensitivity live

Price	-10% $467	-5% $424	+0% $382	+5% $339	+10% $297
Rent	-10% $242	-5% $312	+0% $382	+5% $451	+10% $521
Rate	-1.0pp $457	-0.5pp $420	base $382	+0.5pp $343	+1.0pp $303

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $37,500
• Closing costs: $4,500
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
4100 Sail Ct Unit 4124 Chesapeake, VA	3.0	2.0	1100	$1,595	$1.45	16d	1	1.17mi
4100 Sail Ct Unit 4105 Chesapeake, VA	3.0	2.0	1100	$1,495	$1.36	18d	1	1.17mi
4100 Sail Ct Unit 4118 Chesapeake, VA	3.0	2.0	1100	$1,500	$1.36	8d	1	1.17mi

Listing history 18 events

1. 2026-06-21
   statusdays on market $150,000 Under Contract 180 DOM
2. 2026-06-18
   days on market $150,000 Active 178 DOM
3. 2026-06-17
   days on market $150,000 Active 177 DOM
4. 2026-06-16
   days on market $150,000 Active 176 DOM
5. 2026-06-15
   days on market $150,000 Active 175 DOM
6. 2026-06-13
   status $150,000 Active 173 DOM
7. 2026-06-02
   statusdays on market $150,000 Under Contract 173 DOM
8. 2026-06-01
   days on market $150,000 Active Under Contract 172 DOM
9. 2026-05-31
   days on market $150,000 Active Under Contract 171 DOM
10. 2026-05-22
    historical Active Under Contract
11. 2026-05-11
    status Active
12. 2026-03-13
    historical Active Under Contract
13. 2026-01-13
    price $150,000
14. 2025-12-11
    listed $185,000 Active
15. 2022-02-07
    status Under Contract
16. 2022-02-04
    listed $105,000 Active
17. 2001-08-08
    soldstatus $58,900
18. 1988-05-27
    soldstatus $21,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast VA · Resets to sale price

• Current annual tax: $1,932 · $161/mo
• Projected year-2 tax: $1,932 · $161/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 3/10 Moderate FEMA zone X (unshaded) · 10% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 9/10 Extreme 7 d/yr ≥106°F today · 16 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $21,141
• − Mortgage interest: −$8,402
• − Property taxes: −$1,932
• − Insurance: −$750
• − Repairs & maintenance: −$1,691
• − Management: −$1,691
• − Depreciation: −$4,364
• Taxable income: $2,310
• Est. tax owed @ 24.0%: −$555
• After-tax cash flow: $4,025/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Chesapeake City Public School District
• NCES district ID: 5100810
• Math proficiency: 58% ▼ -29.00%
• Reading proficiency: 74% ▼ -7.00%
• Median HH income: $69,356
• Composite: 57.84/100
• National rank: #1047
• State rank: #31 of 131 in VA

Livability — Chesapeake

• Score: 70/100
• State rank: #236
• US rank: #7942

Category grades

Amenities F Commute F Cost of living C- Crime C- Employment A+ Housing A+ Health & safety F User ratings A+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Chesapeake, VA
• County: Chesapeake City · 253,091 people
• City population: 253,091
• Metro: Virginia Beach-Norfolk-Newport News, VA-NC
• Population (ZIP): 40,176
• Household income: $101,568
• Rent vs Own: 20.3% rent · 79.7% own
• Severe rent burden: 839.0

Population outlook (Chesapeake County) Hauer SSP2

• Today (2025): 263,804 people
• By 2030: 276,798 · +4.9%
• By 2040: 299,906 · +13.7%
• By 2050: 318,284 · +20.7%
• By 2075: 362,137 · +37.3%
• By 2100: 372,225 · +41.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.63)
• Race & ethnicity: White 49% Black 37% Two or more races 8% Hispanic / Latino 5% Asian 3%
• Common ancestry: Romanian 3% Italian 2% Lithuanian 2%
• Foreign-born: 6% · Canada, Vietnam, South Korea
• Languages at home: 92% English-only · Spanish 4% Vietnamese 1% Korean 1%

Political lean MEDSL · Chesapeake

• 2024 margin: Toss-up / Even · D 51.3% · R 47.5% · Other 1.2%
• 2008→2024 swing: +2.5pp toward D · 2008: 1.3pp · 2024: 3.8pp
• All cycles: 2024: D+3.8 2020: D+6.5 2016: R+1.3 2012: D+1.1 2008: D+1.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -256.23%
• Current HPI: 295.6473
• Rent YoY: ▲ 7.59%
• Metro: Virginia Beach-Norfolk-Newport News, VA-NC
• State GDP YoY: ▲ 2.40%
• F500 in state: 50

Industry mix (Fortune 500 HQ in VA)

Industry	F500 HQs	Revenue
▸Aerospace / Defense	4	$236B
▸Technology / Defense	3	$32B
▸Financial Services	2	$176B
▸Utilities	2	$27B
▸Insurance	2	$25B
▸Technology	2	$15B

Price history

+614.3% since first listed

9 events — show timeline

• 2026-05-22 Contingent — REINMLS
• 2026-05-11 Relisted — REINMLS
• 2026-03-13 Contingent — REINMLS
• 2026-01-13 Price Changed $150,000 REINMLS
• 2025-12-11 Listed $185,000 REINMLS
• 2022-02-07 Pending — REINMLS
• 2022-02-04 Listed $105,000 REINMLS
• 2001-08-08 Sold (Public Records) $58,900 Public Records
• 1988-05-27 Sold (Public Records) $21,000 Public Records

Property tax history

+6.5%/yr

Latest (2025): $1,932 · +13.0% YoY. Source: county tax records.