101 Highland St · Winchester, TN 37398

$169,000

2 bd · 1.0 ba · 1,770 sqft · SingleFamily public records · 120 Days on market

Built 1950 8,712 sqft lot

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Why this score? — see what drove the C+ 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 +28.9/30.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• 1% rule +6.9/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +1.7/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Charming cottage in the heart of Winchester offering incredible potential and a hard-to-find, large privacy-fenced backyard. This 2-bedroom, 1-bath home features a durable metal roof, newer replacement windows, a new shed, and a recently added driveway. The attic provides impressive space with exciting possibilities for future expansion or storage. While the home needs a little TLC, it's a fantastic opportunity for first-time homebuyers, downsizers, or investors looking to add value. HVAC system is present but currently not operating. With its generous yard and cottage charm, this property is full of promise and ready for its next chapter.

Key facts

• Durable metal roof
• New shed
• 8,712 sq ft lot

Tags

• LARGE PRIVACY-FENCED BACKYARD
• DURABLE METAL ROOF
• NEWER REPLACEMENT WINDOWS
• NEW SHED
• RECENTLY ADDED DRIVEWAY

Property features AI

Finance

• HOA & community: Pets allowed

Exterior

• Parking: Driveway; Gravel parking
• Utilities: Public water; Public sewer; Electricity available; Cable connected
• Home design: Single-family residence; One story
• Construction: Vinyl siding; Metal roof; Block foundation; Year built: existing
• Exterior features: Covered porch; Back yard fencing; Level lot; Storage structure; Satellite dish; Has a view

Interior

• Kitchen: Eat-in kitchen; Electric oven and electric range; Dishwasher; Refrigerator
• Bedrooms: 2 bedrooms (both on the main level)
• Flooring: Laminate flooring
• Bathrooms: 1 full bathroom
• Heating & cooling: Central heating (electric) with dual heating system; Central air (electric); Ceiling fans
• Interior features: Built-in features; Ceiling fans; Electric fireplace in the family room (1 fireplace); Crawl space basement
• Laundry & utility: Washer hookup; Electric dryer hookup

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $169k.

Deal economics

• At list price, monthly cash flow is $571 ($7k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $169k).
• Recommended offer: $154k (9.0% below list) — sets the bar for market timing.
• Cap rate 10.3% vs local median 3.0% in Winchester — 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 65/100 on livability (#149 in TN) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+; Watch: employment C-, crime D, amenities D-.
• Franklin County (town): math 18% / reading 22% proficiency, ranked #111 of 139 in TN (top 80%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Zoned schools: Clark Memorial School (math 14% / reading 27%, grade F, #637 of 952 statewide, top 68%, 489 students, 0% FRL); South Middle School (math 11% / reading 13%, grade F, #242 of 333 statewide, top 74%, 292 students, 0% FRL); Franklin Co High School (math 5% / reading 22%, grade F, #255 of 332 statewide, top 77%, 1,180 students, 0% FRL) — zoned schools average 0% FRL vs 48% district-wide (48 pts lower); this property's tenant base skews higher-income than the district average.
• Market conditions: 324 active listings in the ZIP; 422 units permitted in Franklin County in 2024 (5 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.
• Franklin County population projected at +6% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $47k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 120 days — a 9% lower offer ($154k) is reasonable based on typical stale-listing flexibility.
• 6 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

• Watch-outs: built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 7→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $153,790 (9.0% below list)

Questions for the listing agent

1. It's been on market 120 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Built in 1950 — 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 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?
6. Crime grade is D 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. 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: 1.19% ✓
• Cap rate: 10.35%
• Cash-on-cash: 14.49%
• DSCR: 1.64
• GRM: 7.0

CMA / ARV

• ARV (on-the-fly): $359,310
• Comps found: 7

Show comp detail 7 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
202 8th Ave SE	0.35mi	3/1.5 (+1)	1,736 (-2%)	19mo	$259,900	$150	58
206 Country Club Rd	0.23mi	3/2.0 (+1)	1,710 (-3%)	20mo	$435,000	$254	57
105 Edgewater Dr	0.44mi	3/3.5 (+1)	1,824 (+3%)	5mo	$600,000	$329	55
801 S High St	0.64mi	3/1.5 (+1)	1,697 (-4%)	2mo	$185,000	$109	54
545 Country Club Ln	0.39mi	3/2.5 (+1)	1,932 (+9%)	17mo	$615,000	$318	41
43 Liberty Rd	0.64mi	3/2.0 (+1)	1,525 (-14%)	5mo	$310,000	$203	34
1132 Holders Cove Rd	0.67mi	3/2.0 (+1)	1,667 (-6%)	23mo	$310,000	$186	31

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

Projected returns pro-forma

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

5-year hold

• IRR: 4.9%
• Equity multiple: 1.19×
• Total profit: $8,929
• Equity at exit: $25,198

10-year hold

• IRR: 14.3%
• Equity multiple: 2.15×
• Total profit: $54,356
• Equity at exit: $14,612

Cash invested: $47,320 (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 37398

• Home prices YoY: -21.1%
• Active inventory: 324
• Price-to-rent: 7.0×

Monthly cashflow live

• Estimated rent: $2,005 medium
• Mortgage (P&I): −$886
• Tax from tax record: −$56 /mo · $675/yr
• Insurance: −$70
• HOA: −$0
• Vacancy / Maint / Mgmt: −$421
• Net cashflow: $571

Break-even live

Break-even rent $1,282

Max offer price $169,000

Occupancy floor 67%

Sensitivity live

Price	-10% $667	-5% $619	+0% $571	+5% $523	+10% $476
Rent	-10% $413	-5% $492	+0% $571	+5% $650	+10% $730
Rate	-1.0pp $656	-0.5pp $614	base $571	+0.5pp $527	+1.0pp $483

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 29 events

1. 2026-06-09
   days on market $169,000 Active 120 DOM
2. 2026-06-09
   days on marketlisting id $169,000 Active 119 DOM
3. 2026-06-08
   days on market $169,000 Active 121 DOM
4. 2026-06-07
   days on market $169,000 Active 120 DOM
5. 2026-06-05
   days on market $169,000 Active 117 DOM
6. 2026-06-03
   days on market $169,000 Active 116 DOM
7. 2026-06-02
   days on market $169,000 Active 115 DOM
8. 2026-06-01
   days on market $169,000 Active 114 DOM
9. 2026-05-31
   days on market $169,000 Active 113 DOM
10. 2026-05-30
    days on market $169,000 Active 112 DOM
11. 2026-02-10
    listed $169,000 Active 647-char remark

    Show marketing remark (647 chars)

    Charming cottage in the heart of Winchester offering incredible potential and a hard-to-find, large privacy-fenced backyard. This 2-bedroom, 1-bath home features a durable metal roof, newer replacement windows, a new shed, and a recently added driveway. The attic provides impressive space with exciting possibilities for future expansion or storage. While the home needs a little TLC, it's a fantastic opportunity for first-time homebuyers, downsizers, or investors looking to add value. HVAC system is present but currently not operating. With its generous yard and cottage charm, this property is full of promise and ready for its next chapter.

12. 2026-02-08
    listed $169,000 Active
13. 2023-08-24
    soldstatus $162,000 Closed 144-char remark

    Show marketing remark (144 chars)

    This Charming Cottage with the large fenced yard is absolutely perfect for first time home buyers, down sizing, or a clean, investment property.

14. 2023-08-24
    soldstatus $162,000

    Show marketing remark (144 chars)

    This Charming Cottage with the large fenced yard is absolutely perfect for first time home buyers, down sizing, or a clean, investment property.

15. 2023-07-24
    status Pending 144-char remark

    Show marketing remark (144 chars)

    This Charming Cottage with the large fenced yard is absolutely perfect for first time home buyers, down sizing, or a clean, investment property.

16. 2023-07-24
    listed $145,000 Active 144-char remark

    Show marketing remark (144 chars)

    This Charming Cottage with the large fenced yard is absolutely perfect for first time home buyers, down sizing, or a clean, investment property.

17. 2022-04-29
    soldstatus $133,000 Closed
18. 2022-04-29
    soldstatus $133,000
19. 2022-03-24
    historical Active Under Contract
20. 2022-03-22
    listed $129,900 Active
21. 2022-03-21
    historical $129,900
22. 2020-07-30
    soldstatus $87,350
23. 2020-06-22
    price $96,399
24. 2020-06-03
    listed $99,450 Active
25. 2019-08-23
    soldstatus $27,500 Closed
26. 2019-08-20
    status Pending
27. 2019-08-07
    listed $33,900 Active
28. 2008-09-10
    soldstatus $48,000
29. 2001-05-04
    soldstatus $20,000

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

Tax reassessment forecast TN · Resets to sale price

• Current annual tax: $675 · $56/mo
• Projected year-2 tax: $1,200 · $100/mo
• Expected delta: +$525/yr (+$44/mo · 77.8%)

ⓘ 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 2/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥104°F today · 20 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 12% 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: $24,063
• − Mortgage interest: −$9,467
• − Property taxes: −$675
• − Insurance: −$845
• − Repairs & maintenance: −$1,925
• − Management: −$1,925
• − Depreciation: −$4,916
• Taxable income: $4,310
• Est. tax owed @ 24.0%: −$1,034
• After-tax cash flow: $5,820/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: Franklin County
• NCES district ID: 4701290
• Math proficiency: 18% ▼ -9.00%
• Reading proficiency: 22% ▼ -8.00%
• Median HH income: $43,108
• Composite: 17.24/100
• National rank: #9094
• State rank: #111 of 139 in TN

Livability — Winchester

• Score: 65/100
• State rank: #149
• US rank: #13341

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winchester, TN
• Population (ZIP): 15,712

Population outlook (Franklin County) Hauer SSP2

• Today (2025): 42,858 people
• By 2030: 43,540 · +1.6%
• By 2040: 44,623 · +4.1%
• By 2050: 45,523 · +6.2%
• By 2075: 48,954 · +14.2%
• By 2100: 50,170 · +17.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (81%)
• Race & ethnicity: White 81% Hispanic / Latino 7% Black 7% Two or more races 6% Asian 1%
• Hispanic origin (detail): Mexican 4%
• Common ancestry: Serbian 2% Lithuanian 2% Slovak 1%
• Foreign-born: 4% · Canada
• Languages at home: 93% English-only · Spanish 5% Other Indo-European 1% German/W. Germanic 1%

Political lean MEDSL · Franklin

• 2024 margin: Solid R (+53.2) · D 23.0% · R 76.1%
• 2008→2024 swing: -30.6pp toward R · 2008: -22.5pp · 2024: -53.2pp
• All cycles: 2024: R+53.2 2020: R+47.7 2016: R+43.7 2012: R+28.9 2008: R+22.5

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -89.03%
• Current HPI: 333.839
• 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

+745.0% since first listed

19 events — show timeline

• 2026-02-10 Listed $169,000 GCAR
• 2026-02-08 Listed $169,000 REALTRACS as Distributed by MLS Grid
• 2023-08-24 Sold (Public Records) $162,000 Public Records
• 2023-08-24 Sold (MLS) $162,000 REALTRACS as Distributed by MLS Grid
• 2023-07-24 Pending — REALTRACS as Distributed by MLS Grid
• 2023-07-24 Listed $145,000 REALTRACS as Distributed by MLS Grid
• 2022-04-29 Sold (Public Records) $133,000 Public Records
• 2022-04-29 Sold (MLS) $133,000 REALTRACS as Distributed by MLS Grid
• 2022-03-24 Contingent — REALTRACS as Distributed by MLS Grid
• 2022-03-22 Listed $129,900 REALTRACS as Distributed by MLS Grid
• 2022-03-21 Coming Soon $129,900 REALTRACS as Distributed by MLS Grid
• 2020-07-30 Sold (Public Records) $87,350 Public Records
• 2020-06-22 Price Changed $96,399 REALTRACS as Distributed by MLS Grid
• 2020-06-03 Listed $99,450 REALTRACS as Distributed by MLS Grid
• 2019-08-23 Sold (MLS) $27,500 REALTRACS as Distributed by MLS Grid
• 2019-08-20 Pending — REALTRACS as Distributed by MLS Grid
• 2019-08-07 Listed $33,900 REALTRACS as Distributed by MLS Grid
• 2008-09-10 Sold (Public Records) $48,000 Public Records
• 2001-05-04 Sold (Public Records) $20,000 Public Records

Property tax history

+9.1%/yr

Latest (2025): $675 · +0.0% YoY. Source: county tax records.