585 Trailwoods Dr · Brownsville, KY 42754

$169,000

2 bd · 2.0 ba · 812 sqft · Other · 107 Days on market

Built 2018 1.90 ac lot ↓ 6% since listing

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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).

• Cash flow +12.9/30.0
• ARV discount +7.5/15.0
• DSCR +3.9/10.0
• Livability +3.3/5.0
• Appreciation +3.1/10.0
• Schools +2.8/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +2.4/10.0

Listing remarks

Cute and functional lake place in Ambassador Shores! This place is perfect for weekends with friends and family, or to use as a short-term rental for extra income. It's a 2 bedroom with an alcove for a third bed, with 2 full bathrooms, an open living and kitchen area, and a cool covered porch with lighting and tv hookup. Outside there is nearly 2 acres for space and privacy, as well as a 12x20 garage, and a dock down the street! The dock will transfer with COE approval.

Key facts

• Covered porch
• Short term rental
• Dock

Tags

• SHORT TERM RENTAL
• OPEN LIVING AND KITCHEN AREA
• COVERED PORCH
• DOCK

Property features AI

Finance

• Other: Lot is approximately 1.9 acres, cleared and wooded; Property listed as residential — single family residence; Ranch architectural style; Rental allowed
• HOA & community: No association fee; Pets allowed subject to restrictions; Subdivision: Ambassador Shores

Exterior

• Parking: Detached garage (1 car); Driveway parking
• Utilities: Electricity connected
• Home design: Single-family ranch home; 1 story; Built in 2018
• Construction: Vinyl siding; Metal roof; Built in 2018
• Exterior features: Boat slip

Interior

• Kitchen: Kitchen (first floor)
• Bedrooms: 2 bedrooms (both on the first floor)
• Bathrooms: 2 full bathrooms
• Heating & cooling: Mini-split / ductless heating (electric); Wall/window cooling units
• Interior features: 5 total rooms; 2 closets; No basement; First-floor laundry
• Laundry & utility: Laundry on the first floor

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath other listed at $169k.

Deal economics

• At list price, monthly cash flow is $-13 ($-155/yr) — negative.
• To cash-flow at today's rent, offer at most $167k (1.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $125k (26.3% below list).
• Recommended offer: $125k (26.3% below list) — sets the bar for 1% rule.
• Cap rate 6.2% vs local median 3.2% in Brownsville — 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.

Location & tenants

• Location reads 66/100 on livability (#234 in KY) — a middle-class / working-renter tenant base. Strengths: crime A+, cost of living A+, housing A+; Watch: amenities F, commute F, employment F.
• Grayson County (rural): math 27% / reading 40% proficiency, ranked #84 of 165 in KY (top 51%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Clarkson Elementary School (math 33% / reading 44%, grade F, #234 of 676 statewide, top 36%, 609 students, 65% FRL); Grayson County Middle School (math 23% / reading 38%, grade F, #143 of 217 statewide, top 67%, 839 students, 63% FRL); Grayson County High School (math 24% / reading 38%, grade F, #118 of 254 statewide, top 47%, 1,252 students, 61% FRL).
• Market conditions: 186 active listings in the ZIP; 23 units permitted in Grayson County in 2024 (12 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 $5k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 107 days — a 9% lower offer ($154k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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.

Recommended offer $124,508 (26.3% 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 107 days. Have you received any prior offers? Is the seller open to a 26% concession, seller financing, or rate buy-down credit?
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 D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
6. 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?
7. 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.
8. 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.
9. 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: 0.74% ✗
• Cap rate: 6.20%
• Cash-on-cash: -0.33%
• DSCR: 0.99
• GRM: 11.3

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: -16.9%
• Equity multiple: 0.40×
• Total profit: $-28,295
• Equity at exit: $25,198

10-year hold

• IRR: -8.9%
• Equity multiple: 0.45×
• Total profit: $-26,050
• Equity at exit: $14,612

Cash invested: $47,320 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 83 Strongly Landlord-Friendly
• State Kentucky: 83 Strongly Landlord-Friendly · R+16
• County: — inherits STATE
• City: — inherits STATE

7-day pay-or-quit (URLTA cities); generally landlord-friendly.

Methodology + full state rankings →

ZIP-level market 42754

• Home prices YoY: -1.3%
• Active inventory: 186
• Price-to-rent: 11.3×

Monthly cashflow live

• Estimated rent: $1,245 medium
• Mortgage (P&I): −$886
• Tax from tax record: −$40 /mo · $478/yr
• Insurance: −$70
• HOA: −$0
• Vacancy / Maint / Mgmt: −$261
• Net cashflow: $-13

Break-even live

Break-even rent $1,261

Max offer price $166,717

Occupancy floor 96%

Sensitivity live

Price	-10% $83	-5% $35	+0% $-13	+5% $-61	+10% $-109
Rent	-10% $-111	-5% $-62	+0% $-13	+5% $36	+10% $85
Rate	-1.0pp $72	-0.5pp $30	base $-13	+0.5pp $-57	+1.0pp $-101

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: $42,250
• Closing costs: $5,070
• Reserves months: —
• Total cash needed: —

Listing history 23 events

1. 2026-06-22
   days on market $169,000 Active 107 DOM
2. 2026-06-21
   days on market $169,000 Active 106 DOM
3. 2026-06-21
   days on market $169,000 Active 105 DOM
4. 2026-06-18
   days on market $169,000 Active 103 DOM
5. 2026-06-17
   days on market $169,000 Active 102 DOM
6. 2026-06-16
   days on market $169,000 Active 101 DOM
7. 2026-06-15
   days on market $169,000 Active 100 DOM
8. 2026-06-13
   days on market $169,000 Active 98 DOM
9. 2026-06-12
   days on market $169,000 Active 97 DOM
10. 2026-06-09
    days on market $169,000 Active 94 DOM
11. 2026-06-08
    days on market $169,000 Active 93 DOM
12. 2026-06-07
    days on market $169,000 Active 92 DOM
13. 2026-06-07
    days on market $169,000 Active 91 DOM
14. 2026-06-04
    days on market $169,000 Active 88 DOM
15. 2026-06-02
    days on market $169,000 Active 87 DOM
16. 2026-06-01
    days on market $169,000 Active 86 DOM
17. 2026-05-31
    days on market $169,000 Active 85 DOM
18. 2026-05-31
    days on market $169,000 Active 84 DOM
19. 2026-05-07
    price $169,000
20. 2026-04-17
    price $172,500
21. 2026-03-07
    listed $175,000 Active
22. 2025-12-17
    historical
23. 2025-08-30
    listed $179,500 Active

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

Tax reassessment forecast KY · Resets to sale price

• Current annual tax: $478 · $40/mo
• Projected year-2 tax: $1,453 · $121/mo
• Expected delta: +$975/yr (+$81/mo · 203.8%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥107°F today · 18 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 3% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $14,941
• − Mortgage interest: −$9,467
• − Property taxes: −$478
• − Insurance: −$845
• − Repairs & maintenance: −$1,195
• − Management: −$1,195
• − Depreciation: −$4,916
• Taxable loss: −$3,156
• Est. tax savings @ 24.0%: +$757
• After-tax cash flow: $602/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: Grayson County
• NCES district ID: 2102300
• Math proficiency: 27% ▼ -23.00%
• Reading proficiency: 40% ▼ -17.00%
• Median HH income: $34,256
• Composite: 27.55/100
• National rank: #6944
• State rank: #84 of 165 in KY

Livability — Brownsville

• Score: 66/100
• State rank: #234
• US rank: #11426

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 15,817

Population outlook (Grayson County) Hauer SSP2

• Today (2025): 26,840 people
• By 2030: 27,032 · +0.7%
• By 2040: 27,236 · +1.5%
• By 2050: 27,076 · +0.9%
• By 2075: 26,565 · -1.0%
• By 2100: 24,007 · -10.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (95%)
• Race & ethnicity: White 95% Two or more races 3% Black 2%
• Common ancestry: Slovak 4% Lithuanian 2% Romanian 1%
• Foreign-born: 1%
• Languages at home: 99% English-only · Spanish 1%

Political lean MEDSL · Grayson

• 2024 margin: Solid R (+61.8) · D 18.5% · R 80.3% · Other 1.2%
• 2008→2024 swing: -26.9pp toward R · 2008: -34.9pp · 2024: -61.8pp
• All cycles: 2024: R+61.8 2020: R+58.8 2016: R+59.3 2012: R+39.5 2008: R+34.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -3.82%
• Current HPI: 283.0264
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 1.81%
• F500 in state: 4

Industry mix (Fortune 500 HQ in KY)

Industry	F500 HQs	Revenue
▸Healthcare	1	$118B
▸Food / Beverage	1	$7B

Price history

-5.8% since first listed

5 events — show timeline

• 2026-05-07 Price Changed $169,000 Metro Search MLS
• 2026-04-17 Price Changed $172,500 Metro Search MLS
• 2026-03-07 Listed $175,000 Metro Search MLS
• 2025-12-17 Listing Removed — Metro Search MLS
• 2025-08-30 Listed $179,500 Metro Search MLS

Property tax history

+23.0%/yr

Latest (2024): $478 · -2.4% YoY. Source: county tax records.