21018 Chestnut Cv · San Antonio, TX 78266

$399,900

4 bd · 3.0 ba · 2,233 sqft · SingleFamily public records · 156 Days on market

Built 2018 6,316 sqft lot $179/sqft · 13% below area Est $458k · 13% under $92/mo HOA · 4% of rent

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Why this score? — see what drove the D 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).

• ARV discount +13.2/15.0
• Appreciation +10.0/10.0
• Cash flow +4.0/30.0
• Livability +4.0/5.0
• Schools +3.8/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +1.4/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Looking for the perfect blend of modern style and functional design? Welcome home to your 4-bedroom, 3-bathroom gem in the gated Winding Oaks community & ready for its new owners. Skip the wait for new construction and move right into this beautifully finished home today! Secondary bedroom and full bath on the main floor-ideal for guests or a home office. Kitchen features gas cooking, stainless steel appliances, a large island, a walk-in pantry, and ample cabinetry for storage. In addition to the open-concept main floor, the second level features a spacious loft perfect for a media room, playroom, or secondary lounge. Ideally situated for easy commutes via Loop 1604, Hwy 281, and I-35. Just minutes from major shopping, dining, and military installations including Fort Sam Houston/BAMC and Randolph AFB & located in the highly-regarded North East ISD schools.

Key facts

• Gated community
• Ample cabinetry
• Gas cooking

Tags

• GATED COMMUNITY
• GAS COOKING
• STAINLESS STEEL APPLIANCES
• LARGE ISLAND
• WALK-IN PANTRY
• AMPLE CABINETRY

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $400k.

Deal economics

• At list price, monthly cash flow is $-1k ($-13k/yr) — negative.
• To cash-flow at today's rent, offer at most $201k (49.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $255k (36.3% below list).
• Recommended offer: $201k (49.7% below list) — sets the bar for cash-flow.
• Cap rate 2.9% vs local median 3.8% in San Antonio — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

Location & tenants

• Location reads 80/100 on livability (#31 in TX, #1,616 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, cost of living A+; Watch: crime F.
• North East ISD (urban): math 38% / reading 49% proficiency, ranked #276 of 826 in TX (top 33%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Bulverde Creek (math 51% / reading 58%, grade C, #621 of 4,322 statewide, top 15%, 1,003 students, 39% FRL); Hill Middle (math 51% / reading 64%, grade B, #206 of 1,662 statewide, top 13%, 1,044 students, 28% FRL); Johnson H S (math 69% / reading 80%, grade B+, #82 of 1,632 statewide, top 6%, 3,202 students, 24% FRL).
• Zoned-school proficiency averages 62% at this address vs 44% district-wide (+19 pts) — the actual schools serving this property are materially stronger than the North East ISD average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 230 active listings in the ZIP; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 20d on market — plan ~3-4 weeks tenant-placement turnaround); 8,308 units permitted in Bexar County in 2024 (2,506 in 5+ unit buildings).

Forward outlook

• In year one you build about $43k of equity ($3k loan paydown + $40k appreciation (10.0% local appreciation)).
• Bexar County population projected at +50% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 2, paydown + projected appreciation supports a ~$69k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 156 days — a 12% lower offer ($352k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 7y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 70% chance of damaging wind over 30y; extreme-heat days projected 7→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $201,256 (49.7% below list)

Questions for the listing agent

1. 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?
2. It's been on market 156 days. Have you received any prior offers? Is the seller open to a 50% concession, seller financing, or rate buy-down credit?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
7. 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?
8. 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.
9. 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.
10. 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: 0.64% ✗
• Cap rate: 2.92%
• Cash-on-cash: -12.05%
• DSCR: 0.46
• GRM: 13.1

CMA / ARV

• ARV (median comp): $458,206
• List price: $399,900
• Delta: -12.72%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
21158 Boulder Flts	0.47mi	4/3.0	2,257 (+1%)	1mo	$417,950	$185	76
21106 Boulder Flts	0.52mi	4/3.0	2,257 (+1%)	0mo	$419,950	$186	74
21165 Boulder Flts	0.50mi	4/3.0	2,257 (+1%)	2mo	$420,950	$187	74
5216 Beck Path	0.55mi	4/3.0	2,257 (+1%)	0mo	$444,045	$197	72
21114 Boulder Flts	0.52mi	4/2.5	2,257 (+1%)	1mo	$392,950	$174	71
21010 Gravel Keep	0.56mi	4/3.0	2,257 (+1%)	2mo	$417,950	$185	70
20922 Gravel Keep	0.59mi	4/3.0	2,257 (+1%)	1mo	$438,000	$194	70
21133 Boulder Flts	0.52mi	4/2.5	2,171 (-3%)	2mo	$390,950	$180	68
21146 Boulder Flts	0.48mi	4/2.5	2,336 (+5%)	1mo	$428,950	$184	67
5602 Southern Oaks	0.40mi	4/2.5	2,481 (+11%)	1mo	$389,000	$157	60
21726 Seminole Oaks	0.62mi	3/2.5 (-1)	2,152 (-4%)	0mo	$330,000	$153	58
20931 Stonework Spur	0.75mi	4/2.0	2,031 (-9%)	1mo	$425,950	$210	45

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 15.9%
• Equity multiple: 2.31×
• Total profit: $146,445
• Equity at exit: $360,262

10-year hold

• IRR: 15.3%
• Equity multiple: 5.36×
• Total profit: $488,110
• Equity at exit: $776,918

Cash invested: $111,972 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Texas: 87 Strongly Landlord-Friendly · R+5
• County: — inherits STATE
• City: — inherits STATE

3-day notice; statewide preemption; one of the fastest eviction climates; Travis County (Austin) slightly slower.

Methodology + full state rankings →

ZIP-level market 78266

• Home prices YoY: 3.9%
• Active inventory: 230
• Price-to-rent: 13.1×

Monthly cashflow live

• Estimated rent: $2,547 high
• Mortgage (P&I): −$2,097
• Tax from tax record: −$781 /mo · $9,370/yr
• Insurance: −$167
• HOA: −$92
• Vacancy / Maint / Mgmt: −$535
• Net cashflow: $-1,124

Break-even live

Break-even rent $3,970

Max offer price $201,256

Occupancy floor —

Sensitivity live

Price	-10% $-898	-5% $-1,011	+0% $-1,124	+5% $-1,238	+10% $-1,351
Rent	-10% $-1,326	-5% $-1,225	+0% $-1,124	+5% $-1,024	+10% $-923
Rate	-1.0pp $-923	-0.5pp $-1,023	base $-1,124	+0.5pp $-1,228	+1.0pp $-1,334

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: $99,975
• Closing costs: $11,997
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
5603 Chestnut Xing Unit 1545924P San Antonio, TX	5.0	3.0	2992	$4,214	$1.41	9d	1	0.13mi
5603 Chestnut Xing San Antonio, TX	5.0	3.0	2995	$2,800	$0.93	12d	1	0.13mi
5602 Chestnut Xing San Antonio, TX	3.0	2.5	1958	$2,250	$1.15	25d	1	0.15mi
5714 Pin Pt San Antonio, TX	4.0	2.5	2146	$2,400	$1.12	0d	1	0.19mi
5526 Pin Pt San Antonio, TX	5.0	3.0	2995	$2,800	$0.93	4d	1	0.25mi
5536 Jewel Curv San Antonio, TX	4.0	2.0	1750	$2,500	$1.43	45d	1	0.28mi
21514 Thunder Basin San Antonio, TX	3.0	2.5	1928	$2,100	$1.09	19d	1	0.31mi
5518 Stormie Keep San Antonio, TX	4.0	2.0	1778	$2,250	$1.27	3d	1	0.35mi
5518 Stormie Keep San Antonio, TX	4.0	2.0	1779	$2,250	$1.26	4d	1	0.35mi
5515 Stormie Keep San Antonio, TX	4.0	3.0	2257	$2,450	$1.09	23d	1	0.37mi
21223 Cobbles Loop San Antonio, TX	4.0	3.0	2464	$2,850	$1.16	0d	1	0.40mi
21735 Thunder Basin San Antonio, TX	4.0	2.5	2363	$2,150	$0.91	45d	1	0.43mi
21066 Gravel Keep San Antonio, TX	4.0	2.5	2257	$2,400	$1.06	0d	1	0.49mi
5951 Southern Knl San Antonio, TX	3.0	2.0	1648	$2,500	$1.52	0d	1	0.57mi
5103 Gully Way San Antonio, TX	4.0	2.0	1778	$2,200	$1.24	14d	1	0.74mi
21266 Watercourse Way San Antonio, TX	4.0	3.0	2257	$2,400	$1.06	45d	1	0.81mi
5015 Gully Way San Antonio, TX	4.0	2.5	2023	$2,400	$1.19	0d	1	0.81mi
10822 Rindle Ln San Antonio, TX	3.0	2.5	2320	$1,949	$0.84	45d	1	0.84mi
6015 Akin Stroll San Antonio, TX	3.0	2.0	1534	$2,100	$1.37	45d	1	0.88mi
20859 Rindle Ln San Antonio, TX	4.0	3.0	2032	$2,500	$1.23	21d	1	0.88mi
21339 Watercourse Way San Antonio, TX	4.0	2.5	2171	$2,300	$1.06	46d	1	0.90mi
22419 Carriage Bush San Antonio, TX	4.0	3.0	2340	$2,395	$1.02	45d	1	0.91mi
21027 Watercourse Way San Antonio, TX	4.0	2.5	1823	$2,195	$1.20	22d	1	0.91mi
22414 Akin Hts San Antonio, TX	4.0	2.5	2827	$2,550	$0.90	45d	1	0.95mi
22219 Esperanza Way San Antonio, TX	3.0	2.0	2428	$2,350	$0.97	4d	1	1.02mi
5819 Akin Pl San Antonio, TX	4.0	2.0	1648	$1,800	$1.09	25d	1	1.03mi
22224 Backspin San Antonio, TX	4.0	2.5	2323	$2,290	$0.99	12d	1	1.06mi
6035 Akin Pl San Antonio, TX	3.0	2.0	1690	$2,100	$1.24	6d	1	1.10mi
6022 Akin Quay San Antonio, TX	4.0	2.0	1739	$2,200	$1.27	6d	1	1.11mi
6050 Akin Cir San Antonio, TX	4.0	2.0	2054	$2,450	$1.19	4d	1	1.18mi
6074 Akin Cir San Antonio, TX	4.0	2.5	2092	$2,300	$1.10	45d	1	1.20mi
5714 Agave Spine San Antonio, TX	4.0	3.0	2011	$2,600	$1.29	45d	1	1.20mi
6048 Akin Song San Antonio, TX	5.0	3.0	2734	$2,650	$0.97	5d	1	1.23mi
22618 Double Bogey San Antonio, TX	4.0	2.0	1720	$1,950	$1.13	5d	1	1.25mi
22626 Double Bogey San Antonio, TX	4.0	2.5	2309	$2,500	$1.08	45d	1	1.26mi
22507 Green Jacket San Antonio, TX	3.0	2.0	1535	$2,100	$1.37	45d	1	1.27mi
5131 Blind Shot San Antonio, TX	4.0	2.0	1572	$2,100	$1.34	45d	1	1.29mi
5040 Pitch San Antonio, TX	4.0	3.0	2473	$2,600	$1.05	0d	1	1.38mi
4610 Sebastian Oak San Antonio, TX	3.0	2.0	2094	$2,095	$1.00	19d	1	1.39mi
5106 Blind Shot San Antonio, TX	5.0	2.5	1950	$2,400	$1.23	45d	1	1.47mi

HOA detail

• Monthly dues: $92 · $1,104/yr
• Likely covers: gassecurity

Listing history 30 events

1. 2026-06-21
   days on market $399,900 Active 156 DOM
2. 2026-06-18
   days on market $399,900 Active 153 DOM
3. 2026-06-17
   days on market $399,900 Active 152 DOM
4. 2026-06-16
   days on market $399,900 Active 151 DOM
5. 2026-06-13
   days on market $399,900 Active 148 DOM
6. 2026-06-13
   days on market $399,900 Active 147 DOM
7. 2026-06-09
   days on market $399,900 Active 144 DOM
8. 2026-06-08
   days on market $399,900 Active 143 DOM
9. 2026-06-07
   days on market $399,900 Active 142 DOM
10. 2026-06-04
    days on market $399,900 Active 139 DOM
11. 2026-06-03
    days on market $399,900 Active 138 DOM
12. 2026-06-02
    days on market $399,900 Active 137 DOM
13. 2026-06-01
    days on market $399,900 Active 136 DOM
14. 2026-05-31
    days on market $399,900 Active 135 DOM
15. 2026-04-06
    price $399,900 878-char remark

    Show marketing remark (878 chars)

    Looking for the perfect blend of modern style and functional design? Welcome home to your 4-bedroom, 3-bathroom gem in the gated Winding Oaks community & ready for its new owners. Skip the wait for new construction and move right into this beautifully finished home today! Secondary bedroom and full bath on the main floor-ideal for guests or a home office. Kitchen features gas cooking, stainless steel appliances, a large island, a walk-in pantry, and ample cabinetry for storage. In addition to the open-concept main floor, the second level features a spacious loft perfect for a media room, playroom, or secondary lounge. Ideally situated for easy commutes via Loop 1604, Hwy 281, and I-35. Just minutes from major shopping, dining, and military installations including Fort Sam Houston/BAMC and Randolph AFB & located in the highly-regarded North East ISD schools.

16. 2026-01-16
    listed $409,900 New 878-char remark

    Show marketing remark (878 chars)

    Looking for the perfect blend of modern style and functional design? Welcome home to your 4-bedroom, 3-bathroom gem in the gated Winding Oaks community & ready for its new owners. Skip the wait for new construction and move right into this beautifully finished home today! Secondary bedroom and full bath on the main floor-ideal for guests or a home office. Kitchen features gas cooking, stainless steel appliances, a large island, a walk-in pantry, and ample cabinetry for storage. In addition to the open-concept main floor, the second level features a spacious loft perfect for a media room, playroom, or secondary lounge. Ideally situated for easy commutes via Loop 1604, Hwy 281, and I-35. Just minutes from major shopping, dining, and military installations including Fort Sam Houston/BAMC and Randolph AFB & located in the highly-regarded North East ISD schools.

17. 2025-12-23
    historical
18. 2025-10-30
    price $412,500
19. 2025-09-05
    price $415,000
20. 2025-07-25
    listed $419,999 New
21. 2023-08-30
    soldstatus
22. 2023-08-29
    soldstatus Sold
23. 2023-08-16
    status Pending
24. 2023-08-08
    historical Active Option
25. 2023-08-05
    price $407,000
26. 2023-05-24
    listed $410,000 New
27. 2019-10-17
    soldstatus Sold
28. 2019-09-17
    status Pending
29. 2019-09-04
    price $276,999
30. 2019-08-12
    listed $295,635 New

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

Tax reassessment forecast TX · Resets to sale price

• Current annual tax: $9,370 · $781/mo
• Projected year-2 tax: $9,370 · $781/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 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 7/10 Severe 7 d/yr ≥107°F today · 20 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 70% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $30,563
• − Mortgage interest: −$22,401
• − Property taxes: −$9,370
• − Insurance: −$2,000
• − Repairs & maintenance: −$2,445
• − Management: −$2,445
• − HOA: −$1,104
• − Depreciation: −$11,633
• Taxable loss: −$20,834
• Est. tax savings @ 24.0%: +$5,000
• After-tax cash flow: $-8,494/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: North East ISD
• NCES district ID: 4832940
• Math proficiency: 38% ▼ -14.00%
• Reading proficiency: 49% ▼ -4.00%
• Median HH income: $57,715
• Composite: 38.1/100
• National rank: #4276
• State rank: #276 of 826 in TX

Livability — San Antonio

• Score: 80/100
• State rank: #31
• US rank: #1616

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: San Antonio, TX
• City population: 1,806,925
• Population (ZIP): 7,274

Population outlook (Bexar County) Hauer SSP2

• Today (2025): 2,336,851 people
• By 2030: 2,560,728 · +9.6%
• By 2040: 3,020,569 · +29.3%
• By 2050: 3,493,522 · +49.5%
• By 2075: 4,668,459 · +99.8%
• By 2100: 5,533,242 · +136.8%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.65)
• Race & ethnicity: White 44% Hispanic / Latino 36% Two or more races 25% Black 14%
• Hispanic origin (detail): Mexican 30%
• Common ancestry: Romanian 3% Serbian 2% Lithuanian 1%
• Foreign-born: 6% · Canada, South Korea
• Languages at home: 85% English-only · Spanish 11% German/W. Germanic 2% Korean 1%

Political lean MEDSL · Bexar

• 2024 margin: Lean D (+9.8) · D 54.3% · R 44.6% · Other 1.1%
• 2008→2024 swing: +4.2pp toward D · 2008: 5.6pp · 2024: 9.8pp
• All cycles: 2024: D+9.8 2020: D+18.2 2016: D+13.5 2012: D+4.6 2008: D+5.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 13.56%
• Current HPI: 361.01
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 3.95%
• F500 in state: 110

Industry mix (Fortune 500 HQ in TX)

Industry	F500 HQs	Revenue
▸Energy	16	$1,198B
▸Technology	5	$198B
▸Engineering / Construction	4	$72B
▸Energy Services	3	$60B
▸Utilities	3	$41B
▸Healthcare	2	$330B

Price history

+35.3% since first listed

16 events — show timeline

• 2026-04-06 Price Changed $399,900 LERA
• 2026-01-16 Listed $409,900 LERA
• 2025-12-23 Listing Removed — LERA
• 2025-10-30 Price Changed $412,500 LERA
• 2025-09-05 Price Changed $415,000 LERA
• 2025-07-25 Listed $419,999 LERA
• 2023-08-30 Sold (Public Records) — Public Records
• 2023-08-29 Sold (MLS) — LERA
• 2023-08-16 Pending — LERA
• 2023-08-08 Contingent — LERA
• 2023-08-05 Price Changed $407,000 LERA
• 2023-05-24 Listed $410,000 LERA
• 2019-10-17 Sold (MLS) — LERA
• 2019-09-17 Pending — LERA
• 2019-09-04 Price Changed $276,999 LERA
• 2019-08-12 Listed $295,635 LERA

Property tax history

+36.7%/yr

Latest (2025): $9,370 · -2.2% YoY. Source: county tax records.