340 S Waukeenah St · Monticello, FL 32344

$100,000

3 bd · 1.0 ba · 2,008 sqft · SingleFamily public records · 33 Days on market

Built 1900 0.48 ac lot

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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
• ARV discount +7.5/15.0
• Livability +3.6/5.0
• Rent growth +2.5/5.0
• Schools +2.5/10.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious 3-bedroom floor plan with an updated kitchen and bathroom already in place. While the home has solid bones and endless potential, it will require significant renovations including electrical updates, roof replacement, plumbing updates, and HVAC installation. A rare opportunity to bring new life to a

Key facts

• Beadboard walls
• Half-acre lot
• 9 foot ceilings

Tags

• HISTORIC HOME
• DOWNTOWN MONTICELLO
• HALF-ACRE LOT
• ORIGINAL HARDWOOD FLOORS
• BEADBOARD WALLS
• 9 FOOT CEILINGS

Property features AI

Finance

• Financial info: Offered for sale

Exterior

• Parking: Driveway; On-street parking
• Utilities: Public sewer
• Home design: Single-family property
• Exterior features: Patio; Paved road access

Interior

• Kitchen: Refrigerator; Stove; Microwave; Dishwasher
• Bedrooms: Bedroom 2 — 16 x 16; Bedroom 3 — 14 x 16
• Flooring: Hardwood
• Bathrooms: 1 full bathroom
• Heating & cooling: Space heater; Ceiling fans; Wall/window AC unit(s)
• Interior features: High ceilings; Split bedroom layout; Fireplace
• Laundry & utility: Washer; Dryer; Utility room — 16 x 16

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $100k.

Deal economics

• At list price, monthly cash flow is $554 ($7k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $100k).
• Recommended offer: $97k (3.0% below list) — sets the bar for market timing.
• Cap rate 12.9% vs local median 2.6% in Monticello — 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 72/100 on livability (#356 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, cost of living A+, health & safety A+; Watch: amenities D-, commute F, employment D-.
• Jefferson (rural): math 28% / reading 30% proficiency, ranked #71 of 73 in FL (top 97%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 74% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: Jefferson Schools K-12 (math 32% / reading 32%, 715 students, 58% FRL) — zoned schools average 58% FRL vs 74% district-wide (16 pts lower); this property's tenant base skews higher-income than the district average.
• Market conditions: 65 active listings in the ZIP; 64 units permitted in Jefferson County in 2024 (0 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $691 of loan paydown is wiped out by about $3k of value loss. Plan a longer hold.
• Jefferson County population projected at -34% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $28k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 33 days — a 3% lower offer ($97k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $30k; list at $100k implies a 233% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; moderate wildfire risk; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $97,000 (3.0% below list)

Questions for the listing agent

1. It's been on market 33 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 1.59% ✓
• Cap rate: 12.94%
• Cash-on-cash: 23.75%
• DSCR: 2.06
• GRM: 5.2

CMA / ARV

• ARV (on-the-fly): $295,176
• Comps found: 9

Show comp detail 9 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
480 W Washington St	0.34mi	3/2.0	1,985 (-1%)	8mo	$360,000	$181	72
300 Cedar St	0.53mi	3/2.0	2,044 (+2%)	5mo	$263,000	$129	64
685 E Washington St	0.19mi	4/2.0 (+1)	1,812 (-10%)	3mo	$266,000	$147	64
375 Maple St	0.07mi	3/2.0	1,716 (-14%)	7mo	$168,100	$98	63
950 E Pearl St	0.44mi	3/1.5	1,855 (-8%)	3mo	$300,000	$162	62
575 W Madison St	0.48mi	3/1.5	1,834 (-9%)	2mo	$277,500	$151	60
395 W Palmer Mill Rd	0.26mi	3/1.5	1,772 (-12%)	10mo	$315,000	$178	58
265 W Seminole Ave	0.47mi	2/1.0 (-1)	1,741 (-13%)	2mo	$180,000	$103	49
955 E Pearl St	0.44mi	4/2.0 (+1)	2,152 (+7%)	12mo	$110,000	$51	48

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: 16.9%
• Equity multiple: 1.68×
• Total profit: $19,122
• Equity at exit: $14,910

10-year hold

• IRR: 25.5%
• Equity multiple: 3.22×
• Total profit: $62,226
• Equity at exit: $8,646

Cash invested: $28,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Florida: 87 Strongly Landlord-Friendly · R+3
• County: — inherits STATE
• City: — inherits STATE

3-day pay-or-quit; preempts local rent control; landlord-friendly statutes. Court speed varies by county.

Methodology + full state rankings →

ZIP-level market 32344

• Home prices YoY: -18.6%
• Active inventory: 65
• Price-to-rent: 5.2×

Monthly cashflow live

• Estimated rent: $1,591 medium
• Mortgage (P&I): −$524
• Tax from tax record: −$137 /mo · $1,638/yr
• Insurance: −$42
• HOA: −$0
• Vacancy / Maint / Mgmt: −$334
• Net cashflow: $554

Break-even live

Break-even rent $889

Max offer price $100,000

Occupancy floor 60%

Sensitivity live

Price	-10% $611	-5% $582	+0% $554	+5% $526	+10% $498
Rent	-10% $428	-5% $491	+0% $554	+5% $617	+10% $680
Rate	-1.0pp $605	-0.5pp $580	base $554	+0.5pp $528	+1.0pp $502

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: $25,000
• Closing costs: $3,000
• Reserves months: —
• Total cash needed: —

Listing history 19 events

1. 2026-06-21
   days on market $100,000 Active 33 DOM
2. 2026-06-18
   days on market $100,000 Active 30 DOM
3. 2026-06-17
   days on market $100,000 Active 29 DOM
4. 2026-06-16
   days on market $100,000 Active 28 DOM
5. 2026-06-15
   days on market $100,000 Active 27 DOM
6. 2026-06-14
   days on market $100,000 Active 25 DOM
7. 2026-06-13
   days on market $100,000 Active 24 DOM
8. 2026-06-10
   days on market $100,000 Active 22 DOM
9. 2026-06-09
   days on market $100,000 Active 21 DOM
10. 2026-06-08
    days on market $100,000 Active 20 DOM
11. 2026-06-07
    days on market $100,000 Active 19 DOM
12. 2026-06-03
    days on market $100,000 Active 15 DOM
13. 2026-06-02
    days on market $100,000 Active 14 DOM
14. 2026-06-01
    days on market $100,000 Active 13 DOM
15. 2026-05-31
    days on market $100,000 Active 12 DOM
16. 2026-05-30
    days on market $100,000 Active 11 DOM
17. 2026-05-19
    listed $100,000 Active
18. 1993-04-01
    soldstatus $30,000
19. 1993-03-23
    soldstatus $30,000

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

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $1,638 · $137/mo
• Projected year-2 tax: $1,638 · $137/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 5/10 Major
• 🌡 Heat 8/10 Severe 7 d/yr ≥107°F today · 19 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 7 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $19,090
• − Mortgage interest: −$5,602
• − Property taxes: −$1,638
• − Insurance: −$500
• − Repairs & maintenance: −$1,527
• − Management: −$1,527
• − Depreciation: −$2,909
• Taxable income: $5,387
• Est. tax owed @ 24.0%: −$1,293
• After-tax cash flow: $5,357/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: Jefferson
• NCES district ID: 1200990
• Math proficiency: 28% ▼ -10.00%
• Reading proficiency: 30% ▼ -3.00%
• Median HH income: $43,356
• Composite: 24.74/100
• National rank: #7605
• State rank: #71 of 73 in FL

Livability — Monticello

• Score: 72/100
• State rank: #356
• US rank: #6199

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Monticello, FL
• Population (ZIP): 12,879

Population outlook (Jefferson County) Hauer SSP2

• Today (2025): 12,681 people
• By 2030: 11,811 · -6.9%
• By 2040: 9,968 · -21.4%
• By 2050: 8,319 · -34.4%
• By 2075: 5,406 · -57.4%
• By 2100: 3,278 · -74.2%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.56)
• Race & ethnicity: White 59% Black 30% Hispanic / Latino 5% Two or more races 5%
• Hispanic origin (detail): Mexican 3%
• Common ancestry: Slovak 2% Lithuanian 1% Portuguese 1%
• Foreign-born: 3% · Canada
• Languages at home: 95% English-only · Spanish 3% Tagalog/Filipino 1%

Political lean MEDSL · Jefferson

• 2024 margin: R (+18.6) · D 40.3% · R 58.9%
• 2008→2024 swing: -22.3pp toward R · 2008: 3.7pp · 2024: -18.6pp
• All cycles: 2024: R+18.6 2020: R+6.9 2016: R+5.1 2012: D+1.8 2008: D+3.7

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -41.71%
• Current HPI: 182.5741
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 3.28%
• F500 in state: 36

Industry mix (Fortune 500 HQ in FL)

Industry	F500 HQs	Revenue
▸Industrial Technology	2	$29B
▸Insurance	2	$17B
▸Retail	1	$60B
▸Technology Distribution	1	$58B
▸Homebuilding	1	$35B
▸Technology Manufacturing	1	$35B

Price history

+233.3% since first listed

3 events — show timeline

• 2026-05-19 Listed $100,000 CATRS
• 1993-04-01 Sold (Public Records) $30,000 Public Records
• 1993-03-23 Sold (Public Records) $30,000 Public Records

Property tax history

+9.4%/yr

Latest (2025): $1,638 · +1.8% YoY. Source: county tax records.