765 Sleepy Hollow Rd · Jamestown, TN 38556

$37,500

2 bd · 1.0 ba · 640 sqft · SingleFamily public records · 36 Days on market

Built 1980 0.49 ac lot $59/sqft · 76% below area

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Appreciation +10.0/10.0
• ARV discount +7.5/15.0
• Livability +3.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +2.1/10.0

Listing remarks MLS

Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

Key facts

• 1/2-acre lot
• Circle drive
• Rustic retreat

Tags

• RUSTIC RETREAT
• 1/2-ACRE LOT
• CIRCLE DRIVE

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $38k.

Deal economics

• At list price, monthly cash flow is $673 ($8k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($1k rent vs $38k).
• Recommended offer: $36k (3.0% below list) — sets the bar for market timing.
• Cap rate 27.8% vs local median 4.6% in Jamestown — 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 61/100 on livability (#250 in TN) — a middle-class / working-renter tenant base. Strengths: cost of living A+, health & safety A+; Watch: housing D, crime F, amenities F.
• Fentress County (rural): math 24% / reading 27% proficiency, ranked #91 of 139 in TN (top 66%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 65% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: South Fentress Elementary School (math 19% / reading 25%, grade F, #601 of 952 statewide, top 66%, 632 students, 0% FRL); Clarkrange High School (math 17% / reading 44%, grade F, #73 of 332 statewide, top 22%, 260 students, 0% FRL) — zoned schools average 0% FRL vs 65% district-wide (65 pts lower); this property's tenant base skews higher-income than the district average.
• Market conditions: 325 active listings in the ZIP.

Forward outlook

• In year one you build about $4k of equity ($259 loan paydown + $4k appreciation (10.0% local appreciation)).
• Fentress County population projected at -19% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $10k cash investment doubles in ~1 year — after that, you're playing with house money.
• By year 8, paydown + projected appreciation supports a ~$35k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 36 days — a 3% lower offer ($36k) is reasonable based on typical stale-listing flexibility.
• 4 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.

Risks & watch-outs

• Climate carrying-cost: major wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $36,375 (3.0% below list)

Questions for the listing agent

1. It's been on market 36 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
4. 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?
5. 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.
6. 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.
7. 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: 3.15% ✓
• Cap rate: 27.84%
• Cash-on-cash: 76.96%
• DSCR: 4.42
• GRM: 2.6

CMA / ARV

• ARV (median comp): $154,425
• List price: $37,500
• Delta: -75.72%
• Verdict: UNDERPRICED
• Comps: 5 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
152 Northwood Dr	0.74mi	2/1.5	730 (+14%)	15mo	$155,000	$212	28

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: 87.2%
• Equity multiple: 7.03×
• Total profit: $63,331
• Equity at exit: $33,783

10-year hold

• IRR: 81.8%
• Equity multiple: 15.55×
• Total profit: $152,807
• Equity at exit: $72,854

Cash invested: $10,500 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Tennessee: 87 Strongly Landlord-Friendly · R+13
• County: — inherits STATE
• City: — inherits STATE

14-day notice (URLTA); generally landlord-favorable; Nashville court paced moderate.

Methodology + full state rankings →

ZIP-level market 38556

• Home prices YoY: 13.5%
• Active inventory: 325
• Price-to-rent: 2.6×

Monthly cashflow live

• Estimated rent: $1,180 medium
• Mortgage (P&I): −$197
• Tax est. 1.5%: −$47 /mo · $562/yr
• Insurance: −$16
• HOA: −$0
• Vacancy / Maint / Mgmt: −$248
• Net cashflow: $673

Break-even live

Break-even rent $328

Max offer price $37,500

Occupancy floor 38%

Sensitivity live

Price	-10% $699	-5% $686	+0% $673	+5% $660	+10% $647
Rent	-10% $580	-5% $627	+0% $673	+5% $720	+10% $767
Rate	-1.0pp $692	-0.5pp $683	base $673	+0.5pp $664	+1.0pp $654

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: $9,375
• Closing costs: $1,125
• Reserves months: —
• Total cash needed: —

Listing history 30 events

1. 2026-06-17
   statusdays on marketlisting id $37,500 Pending 36 DOM

   Show marketing remark (402 chars)

   Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

2. 2026-06-17
   days on market $37,500 Active Under Contract 44 DOM

   Show marketing remark (402 chars)

   Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

3. 2026-06-16
   days on market $37,500 Active Under Contract 43 DOM
4. 2026-06-15
   days on market $37,500 Active Under Contract 42 DOM
5. 2026-06-13
   days on market $37,500 Active Under Contract 40 DOM
6. 2026-06-12
   days on market $37,500 Active Under Contract 39 DOM
7. 2026-06-09
   statusdays on market $37,500 Active Under Contract 36 DOM

   Show marketing remark (402 chars)

   Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

8. 2026-06-08
   days on market $37,500 Active 35 DOM
9. 2026-06-08
   days on market $37,500 Active 34 DOM
10. 2026-06-07
    days on market $37,500 Active 33 DOM
11. 2026-06-03
    days on market $37,500 Active 30 DOM
12. 2026-06-02
    days on market $37,500 Active 29 DOM
13. 2026-06-01
    days on market $37,500 Active 28 DOM
14. 2026-05-31
    days on market $37,500 Active 27 DOM
15. 2026-05-04
    listed $37,500 Active 398-char remark

    Show marketing remark (402 chars)

    Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

16. 2026-05-04
    listed $37,500 Active 402-char remark

    Show marketing remark (402 chars)

    Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

17. 2026-05-04
    listed $37,500 Active

    Show marketing remark (402 chars)

    Handyman Special! This could be made into a nice cabin or rustic retreat. Conveniently located 10 minutes to Jamestown and close to Parks and recreation. The structure is being sold ''AS IS'' there is currently a water meter on the property and electricity is on. Buyer to verify all info. Nice 1/2-acre lot with circle drive. Bring your hammer and make this your next money maker or hideaway.

18. 2025-03-24
    historical
19. 2025-03-24
    historical
20. 2025-02-27
    price $39,900
21. 2025-02-27
    price $39,900
22. 2025-02-27
    price $39,900
23. 2025-02-10
    price $45,000
24. 2025-02-10
    price $45,000
25. 2025-02-10
    price $45,000
26. 2025-01-30
    listed $49,000 Active
27. 2025-01-30
    listed $49,000 Active
28. 2020-05-22
    soldstatus $25,000
29. 2013-12-05
    soldstatus $18,561
30. 1995-03-28
    soldstatus $9,000

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 7/10 Severe
• 🌡 Heat 3/10 Moderate 7 d/yr ≥100°F today · 19 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 5% 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: $14,166
• − Mortgage interest: −$2,101
• − Property taxes: −$562
• − Insurance: −$188
• − Repairs & maintenance: −$1,133
• − Management: −$1,133
• − Depreciation: −$1,091
• Taxable income: $7,958
• Est. tax owed @ 24.0%: −$1,910
• After-tax cash flow: $6,171/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: Fentress County
• NCES district ID: 4701230
• Math proficiency: 24% ▼ -13.00%
• Reading proficiency: 27% ▼ -8.00%
• Median HH income: $30,419
• Composite: 20.6/100
• National rank: #8552
• State rank: #91 of 139 in TN

Livability — Jamestown

• Score: 61/100
• State rank: #250
• US rank: #17976

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 12,531

Population outlook (Fentress County) Hauer SSP2

• Today (2025): 17,295 people
• By 2030: 16,749 · -3.2%
• By 2040: 15,443 · -10.7%
• By 2050: 14,077 · -18.6%
• By 2075: 11,482 · -33.6%
• By 2100: 9,658 · -44.2%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (96%)
• Race & ethnicity: White 96% Two or more races 3% Hispanic / Latino 1%
• Common ancestry: Serbian 3% Lithuanian 2% Iranian 1%
• Foreign-born: 1% · Canada
• Languages at home: 99% English-only · Spanish 1%

Political lean MEDSL · Fentress

• 2024 margin: Solid R (+75.8) · D 11.8% · R 87.6%
• 2008→2024 swing: -31.9pp toward R · 2008: -43.9pp · 2024: -75.8pp
• All cycles: 2024: R+75.8 2020: R+71.3 2016: R+67.5 2012: R+53.4 2008: R+43.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 44.31%
• Current HPI: 372.5676
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.78%
• F500 in state: 22

Industry mix (Fortune 500 HQ in TN)

Industry	F500 HQs	Revenue
▸Healthcare	3	$91B
▸Retail	3	$72B
▸Transportation / Logistics	1	$88B
▸Paper / Packaging	1	$19B
▸Insurance	1	$13B
▸Energy	1	$12B

Price history

+316.7% since first listed

19 events — show timeline

• 2026-06-17 Sold (MLS) $37,500 Knoxville MLS
• 2026-06-17 Sold (MLS) $37,500 REALTRACS as Distributed by MLS Grid
• 2026-06-09 Contingent — REALTRACS as Distributed by MLS Grid
• 2026-06-09 Contingent — Knoxville MLS
• 2026-05-04 Listed $37,500 REALTRACS as Distributed by MLS Grid
• 2026-05-04 Listed $37,500 Knoxville MLS
• 2025-03-24 Listing Removed — Knoxville MLS
• 2025-03-24 Listing Removed — REALTRACS as Distributed by MLS Grid
• 2025-02-27 Price Changed $39,900 UCMLS
• 2025-02-27 Price Changed $39,900 Knoxville MLS
• 2025-02-27 Price Changed $39,900 REALTRACS as Distributed by MLS Grid
• 2025-02-10 Price Changed $45,000 Knoxville MLS
• 2025-02-10 Price Changed $45,000 UCMLS
• 2025-02-10 Price Changed $45,000 REALTRACS as Distributed by MLS Grid
• 2025-01-30 Listed $49,000 Knoxville MLS
• 2025-01-30 Listed $49,000 REALTRACS as Distributed by MLS Grid
• 2020-05-22 Sold (Public Records) $25,000 Public Records
• 2013-12-05 Sold (Public Records) $18,561 Public Records
• 1995-03-28 Sold (Public Records) $9,000 Public Records

Property tax history

-1.8%/yr

Latest (2025): $45 · +0.0% YoY. Source: county tax records.