916 Gillespie St · Englewood, FL 34223

$299,900

3 bd · 2.0 ba · 1,343 sqft · SingleFamily public records · 45 Days on market

Built 1974 9,375 sqft lot $5/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 +16.6/30.0
• ARV discount +7.5/15.0
• Schools +5.4/10.0
• DSCR +5.2/10.0
• Rent growth +4.8/5.0
• 1% rule +4.2/10.0
• Livability +3.7/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Location, location, location! Come see this Old Englewood block 3 bedroom, 2 bathroom home! Fully updated kitchen with granite countertops! This home features a split floor plan and is full of potential! Walk into the large living room which flows into the dinette area. Walk through the well sized galley style kitchen to the master suite right off of the garage. Roof and A/C done in 2018. Great location in Bay Vista and close to Manasota Beach! Conservation and Parks surround this quiet community. Enjoy nature and the outdoors while still being conveniently located to all the amenities, great schools, shopping, parks, restaurants, and beaches that Englewood has to offer.

Key facts

• Refreshed bathrooms
• Large screened lanai
• Updated kitchen

Tags

• UPDATED KITCHEN
• REFRESHED BATHROOMS
• SPLIT-BEDROOM FLOOR PLAN
• LARGE SCREENED LANAI
• PRIVATE PARK-LIKE BACKYARD
• OVERSIZED GARAGE

Property features AI

Finance

• Other: Property type: Residential (Single Family Residence); Zoning: RSF3
• Financial info: Lease restrictions apply
• HOA & community: Has HOA (Bay Vista Blvd. Association) with $60 annual fee ($5/month equivalent); Association fee required; Pets allowed

Exterior

• Parking: Attached garage (1 car)
• Utilities: Public water; Public sewer; Electricity connected; Water connected
• Home design: Single family residence; One story; Faces south
• Construction: Concrete and stucco construction; Shingle roof; Slab foundation; Built on approximately 0.22 acre lot
• Exterior features: Awnings

Interior

• Kitchen: Dishwasher; Range; Microwave; Refrigerator
• Bedrooms: 3 bedrooms
• Flooring: Tile; Vinyl
• Bathrooms: 2 full bathrooms
• Heating & cooling: Electric heating; Central air conditioning
• Interior features: Solid surface counters; Split bedroom floor plan
• Laundry & utility: Washer; Dryer; Laundry located in the garage

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $300k.

Deal economics

• At list price, monthly cash flow is $184 ($2k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $277k (7.6% below list).
• Recommended offer: $277k (7.6% below list) — sets the bar for 1% rule.
• Cap rate 7.0% 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 $2k of loan paydown is wiped out by about $9k 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.
• At projected returns (-3.0% appreciation + 8.0% rent growth), your $84k cash investment doubles in ~10 years — after that, you're playing with house money.

Negotiation context

• It's been on market 45 days — a 3% lower offer ($291k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 12y ago; this cycle's ask has dropped $39k (12%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→31/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $277,209 (7.6% below list)

Questions for the listing agent

1. It's been on market 45 days. Have you received any prior offers? Is the seller open to a 8% concession, seller financing, or rate buy-down credit?
2. Built in 1974 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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?
7. 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.
8. 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.
9. 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: 0.92% ✗
• Cap rate: 7.03%
• Cash-on-cash: 2.62%
• DSCR: 1.12
• GRM: 9.0

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: -6.8%
• Equity multiple: 0.74×
• Total profit: $-22,248
• Equity at exit: $44,716

10-year hold

• IRR: 8.0%
• Equity multiple: 1.74×
• Total profit: $62,372
• Equity at exit: $25,930

Cash invested: $83,972 (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: 9.0×

Monthly cashflow live

• Estimated rent: $2,772 medium
• Mortgage (P&I): −$1,573
• Tax from tax record: −$304 /mo · $3,643/yr
• Insurance: −$125
• HOA: −$5
• Vacancy / Maint / Mgmt: −$582
• Net cashflow: $184

Break-even live

Break-even rent $2,540

Max offer price $299,900

Occupancy floor 88%

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: $74,975
• Closing costs: $8,997
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $5 · $60/yr

Listing history 31 events

1. 2026-06-18
   days on market $299,900 Active 45 DOM
2. 2026-06-17
   days on market $299,900 Active 44 DOM
3. 2026-06-16
   pricedays on market $299,900 Active 43 DOM
4. 2026-06-15
   days on market $309,900 Active 42 DOM
5. 2026-06-13
   days on market $309,900 Active 40 DOM
6. 2026-06-13
   days on market $309,900 Active 39 DOM
7. 2026-06-10
   days on market $309,900 Active 37 DOM
8. 2026-06-09
   days on market $309,900 Active 36 DOM
9. 2026-06-08
   days on market $309,900 Active 35 DOM
10. 2026-06-08
    days on market $309,900 Active 34 DOM
11. 2026-06-05
    pricedays on market $309,900 Active 31 DOM
12. 2026-06-03
    days on market $319,000 Active 30 DOM
13. 2026-06-02
    days on market $319,000 Active 29 DOM
14. 2026-06-01
    days on market $319,000 Active 28 DOM
15. 2026-05-31
    days on market $319,000 Active 27 DOM
16. 2026-05-16
    price $329,000 1367-char remark
17. 2026-05-04
    listed $339,000 Active 1367-char remark
18. 2025-05-16
    historical
19. 2025-05-06
    price $355,000
20. 2025-04-24
    price $360,000
21. 2025-04-23
    listed $390,000 Active
22. 2022-08-08
    price $2,599
23. 2022-06-01
    soldstatus $370,000 Closed

    Show marketing remark (679 chars)

    Location, location, location! Come see this Old Englewood block 3 bedroom, 2 bathroom home! Fully updated kitchen with granite countertops! This home features a split floor plan and is full of potential! Walk into the large living room which flows into the dinette area. Walk through the well sized galley style kitchen to the master suite right off of the garage. Roof and A/C done in 2018. Great location in Bay Vista and close to Manasota Beach! Conservation and Parks surround this quiet community. Enjoy nature and the outdoors while still being conveniently located to all the amenities, great schools, shopping, parks, restaurants, and beaches that Englewood has to offer.

24. 2022-06-01
    soldstatus $370,000

    Show marketing remark (679 chars)

    Location, location, location! Come see this Old Englewood block 3 bedroom, 2 bathroom home! Fully updated kitchen with granite countertops! This home features a split floor plan and is full of potential! Walk into the large living room which flows into the dinette area. Walk through the well sized galley style kitchen to the master suite right off of the garage. Roof and A/C done in 2018. Great location in Bay Vista and close to Manasota Beach! Conservation and Parks surround this quiet community. Enjoy nature and the outdoors while still being conveniently located to all the amenities, great schools, shopping, parks, restaurants, and beaches that Englewood has to offer.

25. 2022-05-11
    status Pending

    Show marketing remark (679 chars)

    Location, location, location! Come see this Old Englewood block 3 bedroom, 2 bathroom home! Fully updated kitchen with granite countertops! This home features a split floor plan and is full of potential! Walk into the large living room which flows into the dinette area. Walk through the well sized galley style kitchen to the master suite right off of the garage. Roof and A/C done in 2018. Great location in Bay Vista and close to Manasota Beach! Conservation and Parks surround this quiet community. Enjoy nature and the outdoors while still being conveniently located to all the amenities, great schools, shopping, parks, restaurants, and beaches that Englewood has to offer.

26. 2022-04-28
    listed $369,000 Active

    Show marketing remark (679 chars)

    Location, location, location! Come see this Old Englewood block 3 bedroom, 2 bathroom home! Fully updated kitchen with granite countertops! This home features a split floor plan and is full of potential! Walk into the large living room which flows into the dinette area. Walk through the well sized galley style kitchen to the master suite right off of the garage. Roof and A/C done in 2018. Great location in Bay Vista and close to Manasota Beach! Conservation and Parks surround this quiet community. Enjoy nature and the outdoors while still being conveniently located to all the amenities, great schools, shopping, parks, restaurants, and beaches that Englewood has to offer.

27. 2018-05-16
    soldstatus $94,900
28. 2014-10-30
    historical
29. 2014-09-06
    listed $134,900 Active
30. 2002-09-10
    soldstatus $94,000
31. 1975-12-01
    soldstatus $32,500

ⓘ 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: $3,643 · $304/mo
• Projected year-2 tax: $3,643 · $304/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 4/10 Moderate FEMA zone X (unshaded) · 22% chance over 30 yrs
• 🔥 Wildfire 2/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥107°F today · 31 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: $33,265
• − Mortgage interest: −$16,799
• − Property taxes: −$3,643
• − Insurance: −$1,500
• − Repairs & maintenance: −$2,661
• − Management: −$2,661
• − HOA: −$60
• − Depreciation: −$8,724
• Taxable loss: −$2,784
• Est. tax savings @ 24.0%: +$668
• After-tax cash flow: $2,872/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

+822.8% since first listed

19 events — show timeline

• 2026-06-16 Price Changed $299,900 Stellar MLS as Distributed by MLS Grid
• 2026-06-04 Price Changed $309,900 Stellar MLS as Distributed by MLS Grid
• 2026-05-20 Price Changed $319,000 Stellar MLS as Distributed by MLS Grid
• 2026-05-16 Price Changed $329,000 Stellar MLS as Distributed by MLS Grid
• 2026-05-04 Listed $339,000 Stellar MLS as Distributed by MLS Grid
• 2025-05-16 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-05-06 Price Changed $355,000 Stellar MLS as Distributed by MLS Grid
• 2025-04-24 Price Changed $360,000 Stellar MLS as Distributed by MLS Grid
• 2025-04-23 Listed $390,000 Stellar MLS as Distributed by MLS Grid
• 2022-08-08 Price Changed $2,599 RENT.
• 2022-06-01 Sold (Public Records) $370,000 Public Records
• 2022-06-01 Sold (MLS) $370,000 Stellar MLS as Distributed by MLS Grid
• 2022-05-11 Pending — Stellar MLS as Distributed by MLS Grid
• 2022-04-28 Listed $369,000 Stellar MLS as Distributed by MLS Grid
• 2018-05-16 Sold (Public Records) $94,900 Public Records
• 2014-10-30 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2014-09-06 Listed $134,900 Stellar MLS as Distributed by MLS Grid
• 2002-09-10 Sold (Public Records) $94,000 Public Records
• 1975-12-01 Sold (Public Records) $32,500 Public Records

Property tax history

+9.2%/yr

Latest (2025): $3,643 · -3.8% YoY. Source: county tax records.