8565 Windypine Ln · Jacksonville, FL 32244

$130,000

2 bd · 2.0 ba · 1,020 sqft · Townhouse public records · 9 Days on market

Built 1984 4,185 sqft lot Est $165k · 21% under $109/mo HOA · 7% of rent

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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 +20.2/30.0
• ARV discount +15.0/15.0
• 1% rule +6.8/10.0
• DSCR +6.4/10.0
• Livability +4.2/5.0
• Schools +3.9/10.0
• Rent growth +3.1/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

One or more photo(s) has been virtually staged. Spacious 1,020 sq ft 2-bedroom, 2-bathroom townhome conveniently located just minutes from NAS Jacksonville, Orange Park Mall, the St. Johns River, and I-295, providing easy access to shopping, dining, and major commuter routes. This property presents excellent value with a super low HOA fee, while exterior maintenance coverage helps provide a more convenient, low-maintenance ownership experience. Interior features carpet throughout and offers a functional layout with generously sized living spaces. Ideal for investors looking to expand a rental portfolio or buyers seeking a property with long-term upside potential. With a little personalization and updating, this home offers an excellent opportunity to build equity and maximize value over time.

Key facts

• $109 HOA
• Built 1984
• Listed 9 days

Property features AI

Finance

• Other: Property type: Residential; Property subtype: Townhouse; Zoning: RMD-D
• Financial info: Total monthly HOA fees $109.80; Total annual HOA fees $1,317.60
• HOA & community: Whispering Pines HOA (monthly fee $109.80; required); Community sidewalks; Pets not allowed

Exterior

• Parking: No parking details provided
• Security: No security details provided
• Utilities: Public water; Public sewer; Electricity connected; Water connected; Sewer connected
• Home design: Residential townhouse; Two levels; Faces southwest; Entry on standard (ground) level
• Construction: Stucco construction; Shingle roof; Slab foundation; Built area information available
• Exterior features: Other exterior features; Asphalt road access; Lot about 0.1 acre

Interior

• Kitchen: Refrigerator
• Bedrooms: 2 bedrooms
• Flooring: Carpet
• Bathrooms: 2 full bathrooms
• Heating & cooling: Central heat; Central air conditioning
• Interior features: Other interior features
• Laundry & utility: Indoor laundry

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath townhouse listed at $130k.

Deal economics

• At list price, monthly cash flow is $163 ($2k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $130k).
• Cap rate 7.8% vs local median 3.9% in Jacksonville — 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 83/100 on livability (#50 in FL, #911 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, housing A+.
• Duval (urban): math 46% / reading 45% proficiency, ranked #48 of 73 in FL (top 66%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Venetia Elementary School (math 52% / reading 47%, grade D, #1,088 of 2,144 statewide, top 53%, 377 students, 48% FRL); Joseph Stilwell Middle School (math 31% / reading 33%, grade F, #448 of 571 statewide, top 79%, 612 students, 68% FRL); Riverside High School (math 24% / reading 39%, grade F, #424 of 667 statewide, top 64%, 1,567 students, 60% FRL).
• Market conditions: Rents rising (+2.2%/yr); 353 active listings in the ZIP; 28 comparable units currently listed for rent nearby; rentals at typical pace (median 16d on market — plan ~3-4 weeks tenant-placement turnaround); 6,503 units permitted in Duval County in 2024 (1,131 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $899 of loan paydown is wiped out by about $4k of value loss. Plan a longer hold.
• Duval County population projected at +19% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• Only 9 days on market — expect competitive offers; lowballing is unlikely to land.
• 3 sale attempts since 20y 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.
• Current owner paid $97k; 34% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $130,000

Questions for the listing agent

1. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
4. 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.
5. 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.
6. 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: 1.18% ✓
• Cap rate: 7.80%
• Cash-on-cash: 5.38%
• DSCR: 1.24
• GRM: 7.1

CMA / ARV

• ARV (on-the-fly): $165,240
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
8565 Windypine Ln	0.00mi	2/2.0	1,020 (0%)	1mo	$104,500	$102	99
8547 Pineverde Ln	0.07mi	2/2.0	1,020 (0%)	2mo	$169,900	$167	95
8455 Pineverde Ln	0.10mi	2/2.0	1,020 (0%)	2mo	$168,000	$165	94
8279 Pineverde Ln	0.18mi	2/2.0	1,020 (0%)	5mo	$164,000	$161	87
5450 Pinehaven Ct	0.08mi	2/2.0	1,020 (0%)	16mo	$165,000	$162	83
8378 Pineverde Ln	0.11mi	2/2.0	1,020 (0%)	18mo	$164,000	$161	80
8347 Windypine Ln	0.12mi	2/2.0	1,020 (0%)	18mo	$184,995	$181	79
85 Debarry Ave #1012	0.54mi	2/2.0	1,002 (-2%)	7mo	$120,000	$120	66
85 Debarry Ave #1064	0.54mi	2/2.5	1,050 (+3%)	9mo	$135,000	$129	60
85 Debarry Ave #2023	0.54mi	2/2.0	1,014 (-1%)	18mo	$170,000	$168	59
5025 Fulham Rd S	0.66mi	3/2.0 (+1)	1,050 (+3%)	1mo	$176,500	$168	58
85 Debarry Ave #1055	0.54mi	2/2.5	1,050 (+3%)	15mo	$117,600	$112	55

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 · 2.25% rent growth · sell at horizon

5-year hold

• IRR: -8.8%
• Equity multiple: 0.68×
• Total profit: $-11,695
• Equity at exit: $19,383

10-year hold

• IRR: -0.4%
• Equity multiple: 0.97×
• Total profit: $-957
• Equity at exit: $11,240

Cash invested: $36,400 (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 32244

• Home prices YoY: -17.8%
• Rents YoY: 2.2%
• Active inventory: 353
• Price-to-rent: 7.1×

Monthly cashflow live

• Estimated rent: $1,528 high
• Mortgage (P&I): −$682
• Tax from tax record: −$199 /mo · $2,390/yr
• Insurance: −$54
• HOA: −$109
• Vacancy / Maint / Mgmt: −$321
• Net cashflow: $163

Break-even live

Break-even rent $1,322

Max offer price $130,000

Occupancy floor 84%

Sensitivity live

Price	-10% $237	-5% $200	+0% $163	+5% $127	+10% $90
Rent	-10% $43	-5% $103	+0% $163	+5% $224	+10% $284
Rate	-1.0pp $229	-0.5pp $196	base $163	+0.5pp $130	+1.0pp $95

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: $32,500
• Closing costs: $3,900
• Reserves months: —
• Total cash needed: —

Rent comps 28 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
5524 Greatpine Ln N Jacksonville, FL	3.0	2.0	1450	$1,500	$1.03	18d	1	0.12mi
8326 Windypine Ln Jacksonville, FL	2.0	2.0	1225	$1,325	$1.08	25d	1	0.13mi
5539 Pinebay Cir N Jacksonville, FL	2.0	2.0	1210	$1,350	$1.12	21d	1	0.15mi
8271 Pineverde Ln Jacksonville, FL	2.0	2.0	1182	$1,496	$1.27	6d	1	0.18mi
5258 Collins Preserve Ln Jacksonville, FL	1.0–3.0	1.0–2.0	1002	$1,804	$1.80	5d	49	0.25mi
5620 Collins Rd Jacksonville, FL	1.0–3.0	1.0–2.0	936	$1,050	$1.12	19d	1	0.25mi
5557 Greatpine Ln S Jacksonville, FL	2.0	2.0	1210	$1,495	$1.24	23d	1	0.26mi
5553 Greatpine Ln S Jacksonville, FL	2.0	2.0	1210	$1,495	$1.24	15d	1	0.26mi
5260 Collins Rd Jacksonville, FL	3.0	2.5	1443	$1,575	$1.09	16d	2	0.27mi
8224 Halls Hammock Ct Jacksonville, FL	3.0	2.5	1364	$1,750	$1.28	25d	1	0.27mi
8218 Halls Hammock Ct Jacksonville, FL	3.0	2.5	1364	$1,650	$1.21	25d	1	0.28mi
8155 Pineverde Ln Jacksonville, FL	3.0	2.0	1426	$1,985	$1.39	18d	1	0.34mi
85 Debarry Ave Orange Park, FL	2.0	2.5	1170	$1,295	$1.11	25d	1	0.66mi
4925 Collins Rd Jacksonville, FL	1.0–3.0	1.0–3.0	943	$1,762	$1.87	3d	21	0.66mi
351 Crossing Blvd Orange Park, FL	1.0–3.0	1.0–2.0	1218	$1,584	$1.30	3d	41	0.93mi
330 Canoe Cir Orange Park, FL	3.0	2.0	1299	$1,950	$1.50	9d	1	1.00mi
1747 Papaya Dr N Orange Park, FL	3.0	2.0	1273	$1,895	$1.49	9d	1	1.05mi
8500 Argyle Business Loop Jacksonville, FL	1.0–3.0	1.0–2.0	921	$1,238	$1.34	25d	1	1.29mi
8550 Argyle Business Loop Jacksonville, FL	3.0	2.5	1486	$1,675	$1.13	15d	1	1.40mi
2020 Wells Rd Orange Park, FL	1.0–3.0	1.0–2.0	1167	$1,298	$1.11	23d	8	1.41mi
7610 Blanding Blvd Jacksonville, FL	1.0–3.0	1.0–2.0	880	$1,125	$1.28	16d	1	1.41mi
6024 Du Clay Rd Jacksonville, FL	2.0	2.5	1278	$1,400	$1.10	3d	1	1.42mi
6028 Du Clay Rd Jacksonville, FL	2.0	3.0	1308	$1,500	$1.15	25d	1	1.42mi
8550 Argyle Business Loop Jacksonville, FL	2.0–3.0	2.5–3.0	1331	$1,350	$1.01	4d	2	1.43mi
8550 Argyle Business Loop Jacksonville, FL	3.0	2.5	1486	$1,735	$1.17	18d	3	1.43mi
5900 Townsend Rd Jacksonville, FL	1.0–3.0	1.0–2.0	1177	$1,539	$1.31	4d	12	1.48mi
7350 Blanding Blvd Jacksonville, FL	1.0–3.0	1.0–2.0	872	$1,330	$1.53	4d	23	1.49mi
6500 Lake Gray Blvd Jacksonville, FL	1.0–3.0	1.0–2.0	972	$1,562	$1.61	3d	9	1.50mi

HOA detail

• Monthly dues: $109 · $1,308/yr
• Likely covers: exterior maint.

Listing history 9 events

1. 2026-05-20
   status Pending 803-char remark

   Show marketing remark (803 chars)

   One or more photo(s) has been virtually staged. Spacious 1,020 sq ft 2-bedroom, 2-bathroom townhome conveniently located just minutes from NAS Jacksonville, Orange Park Mall, the St. Johns River, and I-295, providing easy access to shopping, dining, and major commuter routes. This property presents excellent value with a super low HOA fee, while exterior maintenance coverage helps provide a more convenient, low-maintenance ownership experience. Interior features carpet throughout and offers a functional layout with generously sized living spaces. Ideal for investors looking to expand a rental portfolio or buyers seeking a property with long-term upside potential. With a little personalization and updating, this home offers an excellent opportunity to build equity and maximize value over time.

2. 2026-05-20
   status Pending

   Show marketing remark (803 chars)

   One or more photo(s) has been virtually staged. Spacious 1,020 sq ft 2-bedroom, 2-bathroom townhome conveniently located just minutes from NAS Jacksonville, Orange Park Mall, the St. Johns River, and I-295, providing easy access to shopping, dining, and major commuter routes. This property presents excellent value with a super low HOA fee, while exterior maintenance coverage helps provide a more convenient, low-maintenance ownership experience. Interior features carpet throughout and offers a functional layout with generously sized living spaces. Ideal for investors looking to expand a rental portfolio or buyers seeking a property with long-term upside potential. With a little personalization and updating, this home offers an excellent opportunity to build equity and maximize value over time.

3. 2026-05-13
   listed $130,000 Active 803-char remark

   Show marketing remark (803 chars)

   One or more photo(s) has been virtually staged. Spacious 1,020 sq ft 2-bedroom, 2-bathroom townhome conveniently located just minutes from NAS Jacksonville, Orange Park Mall, the St. Johns River, and I-295, providing easy access to shopping, dining, and major commuter routes. This property presents excellent value with a super low HOA fee, while exterior maintenance coverage helps provide a more convenient, low-maintenance ownership experience. Interior features carpet throughout and offers a functional layout with generously sized living spaces. Ideal for investors looking to expand a rental portfolio or buyers seeking a property with long-term upside potential. With a little personalization and updating, this home offers an excellent opportunity to build equity and maximize value over time.

4. 2026-05-11
   listed $130,000 Active
5. 2006-06-21
   soldstatus $97,000
6. 2006-06-08
   historical 228-char remark

   Show marketing remark (228 chars)

   GREAT 2BR/2BA CORNER UNIT TOWNHOUSE IN CONVENIENT WHISPERING PINES. FULLY EQUIPPED KITCHEN, SPLIT BEDROOMS, LIVING/DINING COMBO AND FENCED YARD. SALE SUBJECT TO CURRENT LEASE OF $695 PER MONTH. SUPER INVESTMENT OR STARTER HOME.

7. 2006-05-31
   soldstatus $97,000 228-char remark

   Show marketing remark (228 chars)

   GREAT 2BR/2BA CORNER UNIT TOWNHOUSE IN CONVENIENT WHISPERING PINES. FULLY EQUIPPED KITCHEN, SPLIT BEDROOMS, LIVING/DINING COMBO AND FENCED YARD. SALE SUBJECT TO CURRENT LEASE OF $695 PER MONTH. SUPER INVESTMENT OR STARTER HOME.

8. 2006-04-05
   listed $99,900 228-char remark

   Show marketing remark (228 chars)

   GREAT 2BR/2BA CORNER UNIT TOWNHOUSE IN CONVENIENT WHISPERING PINES. FULLY EQUIPPED KITCHEN, SPLIT BEDROOMS, LIVING/DINING COMBO AND FENCED YARD. SALE SUBJECT TO CURRENT LEASE OF $695 PER MONTH. SUPER INVESTMENT OR STARTER HOME.

9. 1984-07-01
   soldstatus $43,500

ⓘ 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: $2,390 · $199/mo
• Projected year-2 tax: $2,390 · $199/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 3/10 Moderate
• 🌡 Heat 9/10 Extreme 7 d/yr ≥107°F today · 20 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $18,341
• − Mortgage interest: −$7,282
• − Property taxes: −$2,390
• − Insurance: −$650
• − Repairs & maintenance: −$1,467
• − Management: −$1,467
• − HOA: −$1,308
• − Depreciation: −$3,782
• Taxable loss: −$6
• Est. tax savings @ 24.0%: +$1
• After-tax cash flow: $1,962/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: Duval
• NCES district ID: 1200480
• Math proficiency: 46% ▼ -11.00%
• Reading proficiency: 45% ▼ -4.00%
• Median HH income: $48,987
• Composite: 38.97/100
• National rank: #4076
• State rank: #48 of 73 in FL

Livability — Jacksonville

• Score: 83/100
• State rank: #50
• US rank: #911

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Jacksonville, FL
• County: Duval County · 1,015,274 people
• City population: 979,034
• Metro: Jacksonville, FL
• Population (ZIP): 63,592
• Household income: $62,204
• Rent vs Own: 43.7% rent · 56.3% own
• Severe rent burden: 2799.0

Population outlook (Duval County) Hauer SSP2

• Today (2025): 1,013,010 people
• By 2030: 1,059,228 · +4.6%
• By 2040: 1,141,439 · +12.7%
• By 2050: 1,205,258 · +19.0%
• By 2075: 1,324,282 · +30.7%
• By 2100: 1,319,620 · +30.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Highly diverse neighborhood (Simpson 0.70)
• Race & ethnicity: White 39% Black 35% Hispanic / Latino 15% Two or more races 10% Asian 6%
• Hispanic origin (detail): Mexican 3% Puerto Rican 6% Cuban 3%
• Common ancestry: Hispanic 1% Lithuanian 1% Romanian 1%
• Foreign-born: 12% · Canada, Vietnam, China
• Languages at home: 83% English-only · Spanish 9% Tagalog/Filipino 3% French/Haitian/Cajun 2%

Political lean MEDSL · Duval

• 2024 margin: Toss-up / Even · D 48.7% · R 50.1% · Other 1.2%
• 2008→2024 swing: +0.4pp no change · 2008: -1.9pp · 2024: -1.5pp
• All cycles: 2024: R+1.5 2020: D+3.8 2016: R+1.5 2012: R+3.6 2008: R+1.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -64.22%
• Current HPI: 296.5375
• Rent YoY: ▲ 2.25%
• Metro: Jacksonville, 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

+198.9% since first listed

9 events — show timeline

• 2026-05-20 Pending — realMLS
• 2026-05-20 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-05-13 Listed $130,000 realMLS
• 2026-05-11 Listed $130,000 Stellar MLS as Distributed by MLS Grid
• 2006-06-21 Sold (Public Records) $97,000 Public Records
• 2006-06-08 Listing Removed — realMLS
• 2006-05-31 Sold (MLS) $97,000 realMLS
• 2006-04-05 Listed $99,900 realMLS
• 1984-07-01 Sold (Public Records) $43,500 Public Records

Property tax history

+27.0%/yr

Latest (2025): $2,390 · +14.4% YoY. Source: county tax records.