14168 Hemingway Oaks Trl · Olga, FL 33905

$299,999

4 bd · 2.0 ba · 1,499 sqft · Land · 143 Days on market

Built 2025 5,662 sqft lot $109/mo HOA · 5% of rent ↓ 7% since listing

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Why this score? — see what drove the D- 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 +10.8/30.0
• ARV discount +7.5/15.0
• Schools +4.1/10.0
• Livability +3.2/5.0
• DSCR +3.1/10.0
• Condition / age +2.5/5.0
• 1% rule +2.3/10.0
• Rent growth +1.8/5.0
• Appreciation +0.0/10.0

Listing remarks

Fort Myers, known for its sunny beaches and lively neighborhoods, has recently introduced a new gated community, offering an exclusive living experience with only 104 home sites. This limited number of homes ensures a community feel amidst a private and serene environment. The surrounding area is rich with amenities, offering residents easy access to shopping centers, parks, and schools, making it an ideal location to settle down in a picturesque, sunny setting. The homes within this community are thoughtfully designed with a focus on both comfort and functionality. The Freeport II plan includes four bedrooms and two bathrooms, providing ample space for family and guests. Enjoy the Large op

Key facts

• Gated community
• Private environment
• Large back yard

Tags

• GATED COMMUNITY
• PRIVATE ENVIRONMENT
• EASY ACCESS TO PARKS
• EASY ACCESS TO SCHOOLS
• LARGE OPEN GREAT ROOM
• LARGE BACK YARD

Property features AI

Finance

• Other: Architectural restrictions; Developer-provided lot dimensions
• HOA & community: Mandatory HOA (gated community); Monthly HOA fee; Professional management; HOA maintains irrigation water and street lights; Community amenities include streetlights and underground utilities; One-time fee applicable

Exterior

• Parking: Attached 2-car garage; Paved driveway
• Security: Gated community
• Utilities: Central water; Central sewer; Electric service (central)
• Home design: Single-family residence; One story / ranch; South rear exposure; Located in Hemingway Pointe (gated community)
• Construction: Concrete block construction; Stucco exterior; Shingle roof; Single-hung windows; Manual shutters for storm protection; Built in 2025
• Exterior features: Decorative shutters; Patio; Room for a pool; Automatic sprinkler system; Private road access

Interior

• Kitchen: Kitchen island; Walk-in pantry; Breakfast bar / dining (family); Dishwasher; Disposal; Microwave; Range / oven (self-cleaning); Refrigerator / freezer with icemaker
• Bedrooms: 4 bedrooms; First-floor bedroom; Ground-level master bedroom; Split bedroom arrangement
• Flooring: Carpet; Laminate
• Bathrooms: 2 full bathrooms; Master bath with dual sinks and shower (no tub)
• Heating & cooling: Central electric heat; Central electric cooling
• Interior features: Foyer; High-speed internet available; Pantry; Smoke detectors; Open porch / lanai; Great room floor plan; Split bedroom layout; 7 total rooms
• Laundry & utility: Laundry in residence; Washer/dryer hookup; Auto garage door; Home automation

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath land listed at $300k.

Deal economics

• At list price, monthly cash flow is $-136 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $276k (8.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $218k (27.3% below list).
• Recommended offer: $218k (27.3% below list) — sets the bar for 1% rule.
• Cap rate 5.7% vs local median 3.5% in Olga — 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 63/100 on livability (#707 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B; Watch: amenities F, commute F, health & safety D-.
• Lee (suburban): math 47% / reading 50% proficiency, ranked #42 of 73 in FL (top 58%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: East Lee County High School (math 18% / reading 29%, grade F, #533 of 667 statewide, top 80%, 1,896 students, 61% FRL) — zoned schools at 61% FRL track the district average.
• Zoned-school proficiency averages 24% at this address vs 48% district-wide (-25 pts) — the specific schools serving this property underperform the Lee average; the district grade overstates school quality for this exact location.
• Market conditions: Rents soft (-3.0%/yr); 763 active listings in the ZIP; 28 comparable units currently listed for rent nearby; rentals at typical pace (median 23d on market — plan ~3-4 weeks tenant-placement turnaround); 15,411 units permitted in Lee County in 2024 (4,686 in 5+ unit buildings).
• This rent runs 36% of the median local income ($72k/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 $9k of value loss. Plan a longer hold.
• Lee County population projected at +44% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 143 days — a 12% lower offer ($264k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $22k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Recommended offer $218,051 (27.3% 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 143 days. Have you received any prior offers? Is the seller open to a 27% concession, seller financing, or rate buy-down credit?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
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 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?
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: 0.73% ✗
• Cap rate: 5.75%
• Cash-on-cash: -1.94%
• DSCR: 0.91
• GRM: 11.5

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 0.0% rent growth · sell at horizon

5-year hold

• IRR: -22.6%
• Equity multiple: 0.24×
• Total profit: $-63,768
• Equity at exit: $44,731

10-year hold

• IRR: -25.6%
• Equity multiple: -0.09×
• Total profit: $-91,785
• Equity at exit: $25,938

Cash invested: $84,000 (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 33905

• Home prices YoY: -31.4%
• Rents YoY: -3.0%
• Active inventory: 763
• Price-to-rent: 11.5×

Monthly cashflow live

• Estimated rent: $2,181 high
• Mortgage (P&I): −$1,573
• Tax from tax record: −$51 /mo · $617/yr
• Insurance: −$125
• HOA: −$109
• Vacancy / Maint / Mgmt: −$458
• Net cashflow: $-136

Break-even live

Break-even rent $2,353

Max offer price $275,962

Occupancy floor —

Sensitivity live

Price	-10% $34	-5% $-51	+0% $-136	+5% $-563	+10% $-667
Rent	-10% $-308	-5% $-222	+0% $-136	+5% $-50	+10% $36
Rate	-1.0pp $15	-0.5pp $-60	base $-136	+0.5pp $-214	+1.0pp $-293

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: $75,000
• Closing costs: $9,000
• Reserves months: —
• Total cash needed: —

Rent comps 28 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
14093 Oviedo Pl Fort Myers, FL	3.0	2.0	1378	$1,850	$1.34	17d	1	0.09mi
14018 Aledo Ct Unit 14018 Fort Myers, FL	3.0	3.0	1852	$2,450	$1.32	16d	1	0.12mi
14236 Oviedo Pl Fort Myers, FL	3.0	2.5	1378	$1,895	$1.38	25d	1	0.28mi
14297 Oviedo Pl Fort Myers, FL	3.0	2.5	1378	$1,795	$1.30	4d	1	0.29mi
15624 Sunny Crest Ln Fort Myers, FL	3.0	2.0	1290	$1,776	$1.38	13d	1	0.41mi
15688 Spring Line Ln Fort Myers, FL	3.0	2.0	1474	$1,840	$1.25	25d	1	0.50mi
14060 Vindel Cir Fort Myers, FL	3.0	3.0	1852	$2,700	$1.46	25d	1	0.52mi
14060 Vindel Cir Fort Myers, FL	3.0	3.0	1852	$2,700	$1.46	17d	1	0.52mi
15603 Spring Line Ln Fort Myers, FL	3.0	2.0	1619	$1,900	$1.17	4d	1	0.56mi
14980 Coopers Hawk Way Fort Myers, FL	3.0	2.0	1605	$2,100	$1.31	25d	1	0.63mi
13926 1st St Fort Myers, FL	3.0	1.0	982	$1,550	$1.58	17d	1	0.74mi
3850 Treasure Oak Way Fort Myers, FL	4.0	2.0	1812	$2,195	$1.21	25d	1	0.74mi
13832 1st St Fort Myers, FL	3.0	2.0	1164	$1,900	$1.63	16d	1	0.78mi
13802 2nd St Fort Myers, FL	3.0	2.0	1802	$1,900	$1.05	25d	1	0.87mi
13802 2nd St Fort Myers, FL	3.0	2.0	1802	$1,900	$1.05	17d	1	0.87mi
2510 Barcelona Ave Fort Myers, FL	4.0	2.0	1257	$1,870	$1.49	4d	1	0.89mi
2431 Hawks Preserve Dr Fort Myers, FL	3.0	2.0	1595	$1,995	$1.25	25d	1	0.91mi
13650 Caribbean Blvd Fort Myers, FL	3.0	1.0	1040	$1,700	$1.63	22d	1	1.01mi
13606 River Forest Dr Fort Myers, FL	3.0	2.0	1733	$1,860	$1.07	25d	1	1.06mi
3460 Lakeview Isle Ct Fort Myers, FL	3.0	2.0	1637	$5,500	$3.36	25d	1	1.15mi
13214 1st St Fort Myers, FL	4.0	2.0	1405	$2,000	$1.42	4d	1	1.16mi
2143 W Tobago Cir Fort Myers, FL	3.0	2.0	1326	$1,800	$1.36	25d	1	1.23mi
13208 Fourth St Fort Myers, FL	3.0	1.0	1103	$1,500	$1.36	4d	1	1.26mi
14638 Cantabria Dr Fort Myers, FL	3.0	3.0	1849	$2,200	$1.19	25d	1	1.41mi
14570 Palamos Cir Fort Myers, FL	3.0	3.0	1852	$2,100	$1.13	15d	1	1.47mi
14570 Palamos Cir Fort Myers, FL	3.0	3.0	1852	$2,100	$1.13	15d	1	1.47mi
14680 Portico Blvd Fort Myers, FL	3.0	3.0	1850	$6,000	$3.24	25d	1	1.47mi
13320 Marquette Blvd Fort Myers, FL	3.0	2.0	1798	$5,500	$3.06	25d	1	1.50mi

HOA detail

• Monthly dues: $109 · $1,308/yr
• Likely covers: security

Listing history 9 events

1. 2026-05-15
   status Pending
2. 2026-05-11
   status Active
3. 2026-04-02
   status Pending
4. 2026-03-19
   price $299,999
5. 2026-03-19
   price $302,999
6. 2025-12-31
   price $299,999
7. 2025-12-18
   price $309,999
8. 2025-12-12
   price $316,999
9. 2025-11-14
   listed $321,999 Active

ⓘ 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: $617 · $51/mo
• Projected year-2 tax: $2,490 · $207/mo
• Expected delta: +$1,873/yr (+$156/mo · 303.3%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Taxation est. · year 1

• Rental income: $26,166
• − Mortgage interest: −$16,805
• − Property taxes: −$617
• − Insurance: −$1,500
• − Repairs & maintenance: −$2,093
• − Management: −$2,093
• − HOA: −$1,308
• − Depreciation: −$8,727
• Taxable loss: −$6,978
• Est. tax savings @ 24.0%: +$1,675
• After-tax cash flow: $42/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: Lee
• NCES district ID: 1201080
• Math proficiency: 47% ▼ -11.00%
• Reading proficiency: 50% ▼ -4.00%
• Median HH income: $49,518
• Composite: 41.49/100
• National rank: #3458
• State rank: #42 of 73 in FL

Livability — Olga

• Score: 63/100
• State rank: #707
• US rank: #15011

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Lee County · 788,662 people
• Metro: Cape Coral-Fort Myers, FL
• Population (ZIP): 41,381
• Household income: $71,987
• Rent vs Own: 37.2% rent · 62.8% own
• Severe rent burden: 1358.0

Population outlook (Lee County) Hauer SSP2

• Today (2025): 871,946 people
• By 2030: 955,468 · +9.6%
• By 2040: 1,113,587 · +27.7%
• By 2050: 1,256,891 · +44.1%
• By 2075: 1,560,270 · +78.9%
• By 2100: 1,726,848 · +98.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.59)
• Race & ethnicity: White 53% Hispanic / Latino 34% Two or more races 17% Black 9% Native American 4% Asian 2%
• Hispanic origin (detail): Mexican 11% Puerto Rican 5% Cuban 2%
• Common ancestry: Romanian 2% Slovak 2% Lithuanian 2%
• Foreign-born: 20% · Canada, Jamaica
• Languages at home: 68% English-only · Spanish 29% Other Indo-European 1% German/W. Germanic 1%

Political lean MEDSL · Lee

• 2024 margin: Strong R (+28.4) · D 35.5% · R 63.9%
• 2008→2024 swing: -18.0pp toward R · 2008: -10.4pp · 2024: -28.4pp
• All cycles: 2024: R+28.4 2020: R+19.2 2016: R+20.4 2012: R+16.6 2008: R+10.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -122.89%
• Current HPI: 268.4598
• Rent YoY: ▼ -2.97%
• Metro: Cape Coral-Fort Myers, 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

-6.8% since first listed

9 events — show timeline

• 2026-05-15 Pending — NAPLESMLS
• 2026-05-11 Relisted — NAPLESMLS
• 2026-04-02 Pending — NAPLESMLS
• 2026-03-19 Price Changed $299,999 NAPLESMLS
• 2026-03-19 Price Changed $302,999 NAPLESMLS
• 2025-12-31 Price Changed $299,999 NAPLESMLS
• 2025-12-18 Price Changed $309,999 NAPLESMLS
• 2025-12-12 Price Changed $316,999 NAPLESMLS
• 2025-11-14 Listed $321,999 NAPLESMLS

Property tax history

+85.0%/yr

Latest (2025): $617 · +85.0% YoY. Source: county tax records.