14108 Chesswood Ln · Rotonda, FL 33981

$329,900

4 bd · 2.0 ba · 1,666 sqft · Land public records · 204 Days on market

Built 2024 10,000 sqft lot

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Why this score? — see what drove the F 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 +8.2/30.0
• ARV discount +7.5/15.0
• Schools +4.6/10.0
• Rent growth +3.8/5.0
• Livability +3.4/5.0
• 1% rule +2.6/10.0
• Condition / age +2.5/5.0
• DSCR +2.2/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Great building lot in South Gulf Cove. New large homes on street. Good lot for investment or home site.

Key facts

• Gardening space
• Creek views
• Waterfront living

Tags

• WATERFRONT LIVING
• CREEK VIEWS
• OUTDOOR LIVING
• WATER ACCESS
• GARDENING SPACE
• QUIET NEIGHBORHOOD

Property features AI

Finance

• Other: Zoned RSF3.5; Lot is approximately 0.23 acres with asphalt road access; Water view: creek; Unfurnished
• HOA & community: Pets allowed

Exterior

• Parking: Attached 2-car garage
• Utilities: Public water; Public sewer; Electricity connected; Cable available; Broadband/high-speed internet available; Water connected; Sewer connected
• Home design: Single-family residence; New construction (completed); One-story; Southwest facing
• Construction: Block construction; Shingle roof; Stem wall foundation; Built as new construction
• Exterior features: Dog run; Sliding doors; Private mailbox; Additional exterior features noted

Interior

• Kitchen: Dishwasher; Disposal; Microwave; Range; Refrigerator; Electric water heater
• Bedrooms: 4 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Central heating; Central air conditioning
• Interior features: Ceiling fans; High ceilings; Open floor plan; Aluminum-frame windows with blinds
• Laundry & utility: Dedicated laundry room; Washer/dryer accessibility (accessible washer/dryer noted)

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath land listed at $330k.

Deal economics

• At list price, monthly cash flow is $-732 ($-9k/yr) — negative.
• To cash-flow at today's rent, offer at most $201k (39.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $250k (24.4% below list).
• Recommended offer: $201k (39.2% below list) — sets the bar for cash-flow.
• Cap rate 5.2% vs local median 3.1% in Rotonda — 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 67/100 on livability (#548 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A-, cost of living B+; Watch: schools D, amenities F, commute F.
• Charlotte (suburban): math 54% / reading 54% proficiency, ranked #22 of 73 in FL (top 30%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents rising fast (+5.3%/yr); 2188 active listings in the ZIP; 26 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 4,585 units permitted in Charlotte County in 2024 (703 in 5+ unit buildings).
• This rent runs 36% of the median local income ($84k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.
• Charlotte County population projected at +24% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 204 days — a 12% lower offer ($290k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 20y ago; this cycle's ask is 14250% above the opening price — seller raised mid-cycle; expect resistance to lowballs.
• Current owner paid $17k; list at $330k implies a 1841% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→28/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $200,611 (39.2% 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 204 days. Have you received any prior offers? Is the seller open to a 39% concession, seller financing, or rate buy-down credit?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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?
8. 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.
9. 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.
10. 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: 0.76% ✗
• Cap rate: 5.18%
• Cash-on-cash: -3.97%
• DSCR: 0.82
• GRM: 11.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 5.29% rent growth · sell at horizon

5-year hold

• IRR: -30.0%
• Equity multiple: -0.02×
• Total profit: $-93,893
• Equity at exit: $49,189

10-year hold

• IRR: -21.6%
• Equity multiple: -0.25×
• Total profit: $-115,284
• Equity at exit: $28,524

Cash invested: $92,372 (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 33981

• Home prices YoY: -7.5%
• Rents YoY: 5.3%
• Active inventory: 2188
• Price-to-rent: 11.0×

Monthly cashflow live

• Estimated rent: $2,495 high
• Mortgage (P&I): −$1,730
• Tax from tax record: −$409 /mo · $4,909/yr
• Insurance: −$137
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$524
• Net cashflow: $-732

Break-even live

Break-even rent $3,422

Max offer price $200,611

Occupancy floor —

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: $82,475
• Closing costs: $9,897
• Reserves months: —
• Total cash needed: —

Rent comps 26 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
8362 Santa Cruz Dr Port Charlotte, FL	3.0	2.5	2016	$3,500	$1.74	21d	1	0.21mi
14295 Overlook Ave Port Charlotte, FL	3.0	2.0	1450	$1,700	$1.17	21d	1	0.36mi
14073 Naylor Ave Port Charlotte, FL	3.0	2.0	1818	$2,250	$1.24	21d	1	0.47mi
8373 Agate St Unit 8375 Port Charlotte, FL	3.0	2.0	1379	$1,747	$1.27	21d	1	0.50mi
8249 Dimstead St Port Charlotte, FL	3.0	2.0	1202	$1,675	$1.39	21d	1	0.52mi
9108 Santa Lucia Dr Port Charlotte, FL	4.0	2.0	1917	$3,100	$1.62	13d	1	0.52mi
13376 Yager Ln Port Charlotte, FL	3.0	2.0	2002	$3,500	$1.75	13d	1	0.54mi
8479 Agate St Port Charlotte, FL	3.0	2.0	1379	$2,495	$1.81	21d	1	0.62mi
8519 Agate St Unit 8521 Port Charlotte, FL	3.0	2.0	1379	$1,697	$1.23	21d	1	0.67mi
9116 Agate St #9118 Port Charlotte, FL	3.0	2.0	1429	$1,750	$1.22	21d	1	0.94mi
7415 Beckley St Port Charlotte, FL	3.0	2.0	1405	$1,400	$1.00	21d	1	0.97mi
9156 Agate St Unit 9156 Port Charlotte, FL	3.0	2.0	1379	$1,747	$1.27	21d	1	1.02mi
15077 Acorn Cir Port Charlotte, FL	3.0	2.0	2044	$2,000	$0.98	13d	1	1.02mi
9163 Agate St Unit 9165 Port Charlotte, FL	3.0	2.0	1379	$1,697	$1.23	21d	1	1.05mi
9163 Agate St Unit 9163 Port Charlotte, FL	3.0	2.0	1379	$1,747	$1.27	21d	1	1.05mi
9379 Snapper Cir Port Charlotte, FL	4.0	2.0	2013	$2,690	$1.34	13d	1	1.07mi
9195 Agate St Port Charlotte, FL	3.0	2.0	1200	$1,650	$1.38	13d	1	1.10mi
203 Wright Dr Rotonda West, FL	4.0	3.0	2092	$2,400	$1.15	21d	1	1.11mi
9251 Agate St Port Charlotte, FL	3.0	2.0	1237	$1,565	$1.27	21d	1	1.19mi
15153 Spanish Point Dr Port Charlotte, FL	4.0	3.0	2006	$3,575	$1.78	21d	1	1.25mi
9317 Agate St Unit 9317 Port Charlotte, FL	3.0	2.0	1379	$1,747	$1.27	21d	1	1.29mi
13180 Amaryllis Cir Port Charlotte, FL	3.0	2.0	1704	$2,950	$1.73	13d	1	1.32mi
9458 Modesto Cir Port Charlotte, FL	3.0	2.0	2153	$2,750	$1.28	21d	1	1.35mi
9400 Agate St Pt Charlotte, FL	3.0	2.0	1429	$1,795	$1.26	21d	1	1.39mi
9425 Agate St Unit 9425 Port Charlotte, FL	3.0	2.0	1379	$1,700	$1.23	21d	1	1.44mi
10047 Greetings St Port Charlotte, FL	4.0	2.0	2238	$3,200	$1.43	21d	1	1.47mi

Listing history 50 events

1. 2026-06-18
   days on market $329,900 Active 204 DOM
2. 2026-06-17
   days on market $329,900 Active 203 DOM
3. 2026-06-16
   days on market $329,900 Active 202 DOM
4. 2026-06-15
   days on market $329,900 Active 201 DOM
5. 2026-06-14
   days on market $329,900 Active 199 DOM
6. 2026-06-13
   days on market $329,900 Active 198 DOM
7. 2026-06-10
   days on market $329,900 Active 196 DOM
8. 2026-06-09
   days on market $329,900 Active 195 DOM
9. 2026-06-08
   days on market $329,900 Active 194 DOM
10. 2026-06-05
    days on market $329,900 Active 190 DOM
11. 2026-06-03
    price $329,900 Active 188 DOM
12. 2026-06-02
    days on market $332,900 Active 188 DOM
13. 2026-06-01
    days on market $332,900 Active 187 DOM
14. 2026-06-01
    price $332,900 Active 186 DOM
15. 2026-05-31
    days on market $329,900 Active 186 DOM
16. 2026-05-30
    days on market $329,900 Active 185 DOM
17. 2026-05-15
    price $299,900
18. 2026-03-24
    status Active
19. 2026-03-24
    price $305,000
20. 2026-03-02
    historical $2,200
21. 2026-02-17
    price $310,000
22. 2026-02-15
    status Active
23. 2026-02-03
    price $315,000
24. 2026-01-25
    price $349,900
25. 2026-01-21
    price $310,000
26. 2026-01-14
    price $2,200
27. 2026-01-13
    price $315,000
28. 2026-01-13
    status Active
29. 2026-01-06
    listed $2,299
30. 2026-01-05
    historical
31. 2025-12-24
    status Active
32. 2025-11-20
    status Pending
33. 2025-11-18
    price $320,000
34. 2025-11-15
    price $314,900
35. 2025-10-30
    price $319,900
36. 2025-10-27
    price $325,000
37. 2025-10-22
    price $336,800
38. 2025-10-22
    price $338,900
39. 2025-10-21
    price $349,900
40. 2025-10-21
    price $358,000
41. 2025-10-19
    price $338,000
42. 2025-09-05
    listed $348,000 Active
43. 2025-09-05
    historical $1,995
44. 2025-08-09
    price $1,995
45. 2025-08-09
    price $2,195
46. 2025-08-07
    price $1,995
47. 2025-07-10
    price $2,195
48. 2025-06-21
    listed $2,349
49. 2021-08-09
    soldstatus $17,000
50. 2007-06-06
    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 FL · Resets to sale price

• Current annual tax: $4,909 · $409/mo
• Projected year-2 tax: $4,909 · $409/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 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥107°F today · 28 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $29,943
• − Mortgage interest: −$18,480
• − Property taxes: −$4,909
• − Insurance: −$6,768
• − Repairs & maintenance: −$2,395
• − Management: −$2,395
• − Depreciation: −$9,597
• Taxable loss: −$14,602
• Est. tax savings @ 24.0%: +$3,504
• After-tax cash flow: $-5,278/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: Charlotte
• NCES district ID: 1200240
• Math proficiency: 54% ▼ -6.00%
• Reading proficiency: 54% ▼ -1.00%
• Median HH income: $44,864
• Composite: 45.62/100
• National rank: #2586
• State rank: #22 of 73 in FL

Livability — Rotonda

• Score: 67/100
• State rank: #548
• US rank: #10359

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Charlotte County · 196,994 people
• City population: 10,490
• Metro: Punta Gorda, FL
• Population (ZIP): 15,622
• Household income: $84,098
• Rent vs Own: 9.3% rent · 90.7% own
• Severe rent burden: 105.0

Population outlook (Charlotte County) Hauer SSP2

• Today (2025): 198,646 people
• By 2030: 210,507 · +6.0%
• By 2040: 230,857 · +16.2%
• By 2050: 247,148 · +24.4%
• By 2075: 281,777 · +41.8%
• By 2100: 293,609 · +47.8%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (89%)
• Race & ethnicity: White 89% Two or more races 4% Hispanic / Latino 4% Black 2% Asian 1%
• Common ancestry: Romanian 4% Lithuanian 3% Italian 2%
• Foreign-born: 6% · Canada
• Languages at home: 96% English-only · Spanish 1% German/W. Germanic 1% Tagalog/Filipino 1%

Political lean MEDSL · Charlotte

• 2024 margin: Solid R (+34.0) · D 32.7% · R 66.7%
• 2008→2024 swing: -26.7pp toward R · 2008: -7.2pp · 2024: -34.0pp
• All cycles: 2024: R+34.0 2020: R+26.6 2016: R+27.8 2012: R+14.3 2008: R+7.2

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -28.09%
• Current HPI: 346.5247
• Rent YoY: ▲ 5.29%
• Metro: Punta Gorda, FL
• 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

+21321.4% since first listed

37 events — show timeline

• 2026-05-15 Price Changed $299,900 Stellar MLS as Distributed by MLS Grid
• 2026-03-24 Relisted — Stellar MLS as Distributed by MLS Grid
• 2026-03-24 Price Changed $305,000 Stellar MLS as Distributed by MLS Grid
• 2026-03-02 Rental Removed $2,200 STELLARMLS
• 2026-02-17 Price Changed $310,000 Stellar MLS as Distributed by MLS Grid
• 2026-02-15 Relisted — Stellar MLS as Distributed by MLS Grid
• 2026-02-03 Price Changed $315,000 Stellar MLS as Distributed by MLS Grid
• 2026-01-25 Price Changed $349,900 Stellar MLS as Distributed by MLS Grid
• 2026-01-21 Price Changed $310,000 Stellar MLS as Distributed by MLS Grid
• 2026-01-14 Price Changed $2,200 STELLARMLS
• 2026-01-13 Price Changed $315,000 Stellar MLS as Distributed by MLS Grid
• 2026-01-13 Relisted — Stellar MLS as Distributed by MLS Grid
• 2026-01-06 Listed for Rent $2,299 STELLARMLS
• 2026-01-05 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-12-24 Relisted — Stellar MLS as Distributed by MLS Grid
• 2025-11-20 Pending — Stellar MLS as Distributed by MLS Grid
• 2025-11-18 Price Changed $320,000 Stellar MLS as Distributed by MLS Grid
• 2025-11-15 Price Changed $314,900 Stellar MLS as Distributed by MLS Grid
• 2025-10-30 Price Changed $319,900 Stellar MLS as Distributed by MLS Grid
• 2025-10-27 Price Changed $325,000 Stellar MLS as Distributed by MLS Grid
• 2025-10-22 Price Changed $336,800 Stellar MLS as Distributed by MLS Grid
• 2025-10-22 Price Changed $338,900 Stellar MLS as Distributed by MLS Grid
• 2025-10-21 Price Changed $349,900 Stellar MLS as Distributed by MLS Grid
• 2025-10-21 Price Changed $358,000 Stellar MLS as Distributed by MLS Grid
• 2025-10-19 Price Changed $338,000 Stellar MLS as Distributed by MLS Grid
• 2025-09-05 Listed $348,000 Stellar MLS as Distributed by MLS Grid
• 2025-09-05 Rental Removed $1,995 TENANTTURNER2
• 2025-08-09 Price Changed $1,995 TENANTTURNER2
• 2025-08-09 Price Changed $2,195 TENANTTURNER2
• 2025-08-07 Price Changed $1,995 TENANTTURNER2
• 2025-07-10 Price Changed $2,195 TENANTTURNER2
• 2025-06-21 Listed for Rent $2,349 TENANTTURNER2
• 2021-08-09 Sold (Public Records) $17,000 Public Records
• 2007-06-06 Sold (Public Records) $20,000 Public Records
• 2007-06-01 Sold (MLS) $20,000 Stellar MLS as Distributed by MLS Grid
• 2006-11-14 Listed $29,900 Stellar MLS as Distributed by MLS Grid
• 2001-06-25 Sold (Public Records) $1,400 Public Records

Property tax history

+23.2%/yr

Latest (2025): $4,909 · +691.1% YoY. Source: county tax records.