765 Sleepy Hollow Rd

Jamestown, TN 38556

$37,500B+

2 bd · 1.0 ba · 640 sqft · Built 1980 · SingleFamily · Pending · 36 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,180/mo
• Mortgage (P&I): −$197
• Tax + insurance: −$62
• HOA: −$0
• Vac / Maint / Mgmt: −$248
• Net cashflow: $673/mo
• Annual: $8,081/yr
• Cap rate: 27.84%
• Cash-on-cash: 76.96%
• DSCR: 4.42
• 1% rule: 3.15%
• Cash to close: $10,500

Investor read

• This is a 2-bed/1.0-bath single-family listed at $38k.
• 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).
• It's been on market 36 days — a 3% lower offer ($36k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $36k (3.0% below list) — sets the bar for market timing.
• In year one you build about $4k of equity ($259 loan paydown + $4k appreciation (10.0% local appreciation)).
• 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.
• Fentress County population projected at -19% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 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.
• 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.
• Climate carrying-cost: major wildfire risk — expect insurance premiums to compound above CPI over the hold.
• 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.

Questions for listing agent

• 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?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• 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?
• 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?
• 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.