1339 Keyway Rd · Englewood, FL 34223

$365,000

3 bd · 2.0 ba · 1,514 sqft · SingleFamily public records · 64 Days on market

Built 2006 10,875 sqft lot $8/mo HOA

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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 +5.4/10.0
• Rent growth +4.8/5.0
• Livability +3.7/5.0
• DSCR +3.1/10.0
• 1% rule +2.7/10.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Nestled in the desirable Overbrook Gardens neighborhood of Englewood, 1339 Keyway Road is a beautifully maintained 3-bedroom, 2-bathroom home offering 1,514 square feet of thoughtfully designed living space. Built in 2006, this residence blends comfort and style with an open-concept great room featuring soaring vaulted ceilings, creating an inviting atmosphere that flows seamlessly from living to dining to kitchen. The kitchen is a true standout, boasting generous granite countertops and gleaming stainless steel appliances — perfect for everyday meals and effortless entertaining. Elegant 18-inch tile flooring spans the common areas while warm wood flooring adds character to each bedroom. Ceiling fans throughout keep the coastal breeze circulating in every room. A wall of sliding glass doors off the dining area opens to a generous screened lanai, ideal for morning coffee or evening relaxation. Out front, a second screened lanai welcomes you home in style. The fully fenced backyard provides privacy & security for room to roam, while the two-car garage offers ample storage. Retreat to a spacious primary suite complete with an ensuite bathroom and walk-in closet. Major updates include a new roof in late 2022 and a brand-new HVAC system in 2026, delivering true peace of mind. The low annual HOA supports community parks and a private boat ramp — a rare perk for water enthusiasts. Just minutes from Manasota Key Beach, Lemon Bay Park, and charming Dearborn Street, this home delivers the quintessential Florida lifestyle.

Key facts

• Wood flooring
• Screened lanai
• Granite countertops

Tags

• OPEN-CONCEPT GREAT ROOM
• GRANITE COUNTERTOPS
• STAINLESS STEEL APPLIANCES
• 18-INCH TILE FLOORING
• WOOD FLOORING
• SCREENED LANAI

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $365k.

Deal economics

• At list price, monthly cash flow is $-168 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $335k (8.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $281k (23.1% below list).
• Recommended offer: $281k (23.1% below list) — sets the bar for 1% rule.
• Cap rate 5.7% vs local median 3.8% in Englewood — 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 73/100 on livability (#321 in FL) — a middle-class / working-renter tenant base. Strengths: housing A+, cost of living A, health & safety A; Watch: employment C-, amenities F, commute F.
• Sarasota (urban): math 63% / reading 63% proficiency, ranked #7 of 73 in FL (top 10%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents rising fast (+9.0%/yr); 717 active listings in the ZIP; solid renter incomes; 7,466 units permitted in Sarasota County in 2024 (2,138 in 5+ unit buildings).
• This rent runs 44% of the median local income ($76k/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 $3k of loan paydown is wiped out by about $11k of value loss. Plan a longer hold.
• Sarasota County population projected at +20% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 64 days — a 6% lower offer ($343k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 11y 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 $212k; list at $365k implies a 73% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

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

Recommended offer $280,728 (23.1% 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 64 days. Have you received any prior offers? Is the seller open to a 23% 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 A-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?
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: 0.77% ✗
• Cap rate: 5.74%
• Cash-on-cash: -1.97%
• DSCR: 0.91
• GRM: 10.8

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 8.0% rent growth · sell at horizon

5-year hold

• IRR: -14.4%
• Equity multiple: 0.46×
• Total profit: $-55,024
• Equity at exit: $54,423

10-year hold

• IRR: 0.7%
• Equity multiple: 1.06×
• Total profit: $5,698
• Equity at exit: $31,559

Cash invested: $102,200 (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 34223

• Home prices YoY: -34.2%
• Rents YoY: 9.0%
• Active inventory: 717
• Price-to-rent: 10.8×

Monthly cashflow live

• Estimated rent: $2,807 medium
• Mortgage (P&I): −$1,914
• Tax from tax record: −$311 /mo · $3,734/yr
• Insurance: −$152
• HOA: −$8
• Vacancy / Maint / Mgmt: −$590
• Net cashflow: $-168

Break-even live

Break-even rent $3,019

Max offer price $335,400

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: $91,250
• Closing costs: $10,950
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $8 · $96/yr
• Likely covers: watersecurity

Listing history 26 events

1. 2026-06-18
   days on market $365,000 Active 64 DOM
2. 2026-06-17
   days on market $365,000 Active 63 DOM
3. 2026-06-16
   days on market $365,000 Active 62 DOM
4. 2026-06-15
   days on market $365,000 Active 61 DOM
5. 2026-06-13
   days on market $365,000 Active 59 DOM
6. 2026-06-13
   days on market $365,000 Active 58 DOM
7. 2026-06-10
   days on market $365,000 Active 56 DOM
8. 2026-06-09
   days on market $365,000 Active 55 DOM
9. 2026-06-08
   days on market $365,000 Active 54 DOM
10. 2026-06-08
    days on market $365,000 Active 53 DOM
11. 2026-06-05
    days on market $365,000 Active 50 DOM
12. 2026-06-03
    days on market $365,000 Active 49 DOM
13. 2026-06-02
    days on market $365,000 Active 48 DOM
14. 2026-06-01
    days on market $365,000 Active 47 DOM
15. 2026-05-31
    days on market $365,000 Active 46 DOM
16. 2026-04-15
    listed $365,000 Active 1555-char remark

    Show marketing remark (1555 chars)

    Nestled in the desirable Overbrook Gardens neighborhood of Englewood, 1339 Keyway Road is a beautifully maintained 3-bedroom, 2-bathroom home offering 1,514 square feet of thoughtfully designed living space. Built in 2006, this residence blends comfort and style with an open-concept great room featuring soaring vaulted ceilings, creating an inviting atmosphere that flows seamlessly from living to dining to kitchen. The kitchen is a true standout, boasting generous granite countertops and gleaming stainless steel appliances — perfect for everyday meals and effortless entertaining. Elegant 18-inch tile flooring spans the common areas while warm wood flooring adds character to each bedroom. Ceiling fans throughout keep the coastal breeze circulating in every room. A wall of sliding glass doors off the dining area opens to a generous screened lanai, ideal for morning coffee or evening relaxation. Out front, a second screened lanai welcomes you home in style. The fully fenced backyard provides privacy & security for room to roam, while the two-car garage offers ample storage. Retreat to a spacious primary suite complete with an ensuite bathroom and walk-in closet. Major updates include a new roof in late 2022 and a brand-new HVAC system in 2026, delivering true peace of mind. The low annual HOA supports community parks and a private boat ramp — a rare perk for water enthusiasts. Just minutes from Manasota Key Beach, Lemon Bay Park, and charming Dearborn Street, this home delivers the quintessential Florida lifestyle.

17. 2023-10-12
    historical
18. 2023-09-14
    price $430,000
19. 2023-08-25
    status Active
20. 2023-04-11
    price $435,000
21. 2023-01-27
    listed $450,000 Active
22. 2015-08-31
    soldstatus $211,500
23. 2015-08-27
    soldstatus $211,500 Sold
24. 2015-06-30
    status Pending
25. 2015-06-10
    listed $235,000 Active
26. 2002-10-07
    soldstatus $9,000

ⓘ 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: $3,734 · $311/mo
• Projected year-2 tax: $3,734 · $311/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 6/10 Major FEMA zone X (shaded) · 54% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 10/10 Extreme 7 d/yr ≥107°F today · 30 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $33,687
• − Mortgage interest: −$20,446
• − Property taxes: −$3,734
• − Insurance: −$1,825
• − Repairs & maintenance: −$2,695
• − Management: −$2,695
• − HOA: −$96
• − Depreciation: −$10,618
• Taxable loss: −$8,421
• Est. tax savings @ 24.0%: +$2,021
• After-tax cash flow: $10/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: Sarasota
• NCES district ID: 1201680
• Math proficiency: 63% ▼ -8.00%
• Reading proficiency: 63% ▼ -3.00%
• Median HH income: $51,167
• Composite: 53.68/100
• National rank: #1428
• State rank: #7 of 73 in FL

Livability — Englewood

• Score: 73/100
• State rank: #321
• US rank: #5655

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Englewood, FL
• County: Sarasota County · 448,376 people
• City population: 35,420
• Metro: North Port-Sarasota-Bradenton, FL
• Population (ZIP): 19,884
• Household income: $76,016
• Rent vs Own: 12.5% rent · 87.5% own
• Severe rent burden: 290.0

Population outlook (Sarasota County) Hauer SSP2

• Today (2025): 452,380 people
• By 2030: 474,175 · +4.8%
• By 2040: 511,577 · +13.1%
• By 2050: 541,467 · +19.7%
• By 2075: 604,947 · +33.7%
• By 2100: 621,965 · +37.5%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (94%)
• Race & ethnicity: White 94% Two or more races 3% Hispanic / Latino 3% Asian 1%
• Common ancestry: Romanian 7% Lithuanian 4% Iranian 2%
• Foreign-born: 9% · Canada
• Languages at home: 94% English-only · German/W. Germanic 2% Spanish 1% Other Indo-European 1%

Political lean MEDSL · Sarasota

• 2024 margin: R (+18.2) · D 40.5% · R 58.7%
• 2008→2024 swing: -18.1pp toward R · 2008: -0.1pp · 2024: -18.2pp
• All cycles: 2024: R+18.2 2020: R+10.4 2016: R+11.6 2012: R+7.4 2008: R+0.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -146.26%
• Current HPI: 281.0529
• Rent YoY: ▲ 9.02%
• Metro: North Port-Sarasota-Bradenton, 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

+3955.6% since first listed

11 events — show timeline

• 2026-04-15 Listed $365,000 Stellar MLS as Distributed by MLS Grid
• 2023-10-12 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2023-09-14 Price Changed $430,000 Stellar MLS as Distributed by MLS Grid
• 2023-08-25 Relisted — Stellar MLS as Distributed by MLS Grid
• 2023-04-11 Price Changed $435,000 Stellar MLS as Distributed by MLS Grid
• 2023-01-27 Listed $450,000 Stellar MLS as Distributed by MLS Grid
• 2015-08-31 Sold (Public Records) $211,500 Public Records
• 2015-08-27 Sold (MLS) $211,500 Stellar MLS as Distributed by MLS Grid
• 2015-06-30 Pending — Stellar MLS as Distributed by MLS Grid
• 2015-06-10 Listed $235,000 Stellar MLS as Distributed by MLS Grid
• 2002-10-07 Sold (Public Records) $9,000 Public Records

Property tax history

+8.7%/yr

Latest (2025): $3,734 · -7.6% YoY. Source: county tax records.