301 S Osprey Ave · Sarasota, FL 34236

$1,099,000

16 bd · 16.0 ba · 3,320 sqft · MultiFamily · 145 Days on market

Built 1914 Fair condition 6,900 sqft lot

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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 +9.7/30.0
• ARV discount +7.5/15.0
• Appreciation +6.0/10.0
• Schools +5.4/10.0
• Livability +4.0/5.0
• 1% rule +2.9/10.0
• DSCR +2.7/10.0
• Condition / age +2.2/5.0
• Rent growth +1.2/5.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 4 units. confirmed

Listing remarks MLS

Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

Key facts

• High demand location
• Multifamily property
• Historic 4-plex

Tags

• HISTORIC 4-PLEX
• MULTIFAMILY PROPERTY
• HIGH DEMAND LOCATION
• OFF-STREET PARKING
• SHORT-TERM RENTAL
• VACATION-FRIENDLY MARKET

What this means for you Summary

Snapshot

• This is a 4 × 1-bed/1-bath units multifamily listed at $1.10M. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $-731 ($-9k/yr) — negative. Per door: $-183/mo.
• To cash-flow at today's rent, offer at most $993k (9.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $869k (20.9% below list).
• Recommended offer: $869k (20.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 80/100 on livability (#121 in FL, #1,854 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, health & safety A+, commute A; Watch: crime 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 falling (-5.1%/yr); 731 active listings in the ZIP; solid renter incomes; 7,466 units permitted in Sarasota County in 2024 (2,138 in 5+ unit buildings).
• At $8,689/mo this rent would consume 109% of the median local household income ($96k/yr) (locally 927% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $29k of equity ($8k loan paydown + $21k appreciation (1.9% local appreciation)).
• Sarasota County population projected at +20% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 3, paydown + projected appreciation supports a ~$73k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 145 days — a 12% lower offer ($967k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 5y ago; this cycle's ask has dropped $100k (8%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1914 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: 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 $868,900 (20.9% 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 145 days. Have you received any prior offers? Is the seller open to a 21% concession, seller financing, or rate buy-down credit?
3. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
4. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
5. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
6. Built in 1914 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
7. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
8. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
9. 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?
10. Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
11. 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?
12. 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.
13. 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.
14. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 0.79% ✗
• Cap rate: 5.50%
• Cash-on-cash: -2.85%
• DSCR: 0.87
• GRM: 10.5

CMA / ARV

No comps found within radius.

Projected returns pro-forma

1.92% appreciation · 0.0% rent growth · sell at horizon

5-year hold

• IRR: -0.1%
• Equity multiple: 1.00×
• Total profit: $-1,200
• Equity at exit: $428,495

10-year hold

• IRR: 2.8%
• Equity multiple: 1.36×
• Total profit: $111,671
• Equity at exit: $613,236

Cash invested: $307,720 (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 34236

• Home prices YoY: 0.6%
• Rents YoY: -5.1%
• Active inventory: 731
• Price-to-rent: 42.2×

Monthly cashflow live

• Estimated rent: $8,689 medium
• Mortgage (P&I): −$5,763
• Tax est. 1.5%: −$1,374 /mo · $16,485/yr
• Insurance: −$458
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,825
• Net cashflow: $-731

Break-even live

Break-even rent $9,614

Max offer price $993,276

Occupancy floor —

Sensitivity live

Price	-10% $29	-5% $-351	+0% $-731	+5% $-1,110	+10% $-1,490
Rent	-10% $-1,417	-5% $-1,074	+0% $-731	+5% $-387	+10% $-44
Rate	-1.0pp $-177	-0.5pp $-451	base $-731	+0.5pp $-1,015	+1.0pp $-1,305

4-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 4× units	1	1	$8,688
Total (4 units)			$8,689

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: $274,750
• Closing costs: $32,970
• Reserves months: —
• Total cash needed: —

Listing history 39 events

1. 2026-06-21
   days on market $1,099,000 Active 145 DOM
2. 2026-06-18
   days on market $1,099,000 Active 142 DOM
3. 2026-06-17
   days on market $1,099,000 Active 141 DOM
4. 2026-06-16
   days on market $1,099,000 Active 140 DOM
5. 2026-06-15
   days on market $1,099,000 Active 139 DOM
6. 2026-06-13
   days on market $1,099,000 Active 137 DOM
7. 2026-06-13
   days on market $1,099,000 Active 136 DOM
8. 2026-06-10
   days on market $1,099,000 Active 134 DOM
9. 2026-06-09
   days on market $1,099,000 Active 133 DOM
10. 2026-06-08
    days on market $1,099,000 Active 132 DOM
11. 2026-06-08
    days on market $1,099,000 Active 131 DOM
12. 2026-06-05
    days on market $1,099,000 Active 128 DOM
13. 2026-06-03
    days on market $1,099,000 Active 127 DOM
14. 2026-06-02
    days on market $1,099,000 Active 126 DOM
15. 2026-06-01
    days on market $1,099,000 Active 125 DOM
16. 2026-05-31
    days on market $1,099,000 Active 124 DOM
17. 2026-03-24
    price $1,099,000 919-char remark

    Show marketing remark (919 chars)

    Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

18. 2026-01-27
    listed $1,199,000 Active 919-char remark

    Show marketing remark (919 chars)

    Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

19. 2025-09-15
    historical
20. 2025-05-17
    listed $1,299,000 Active
21. 2023-04-05
    soldstatus $1,217,000 Closed
22. 2023-02-27
    status Pending
23. 2023-01-11
    price $1,299,000
24. 2023-01-09
    price $1,299,500
25. 2022-12-26
    price $1,365,000
26. 2022-12-06
    listed $1,395,000 Active
27. 2022-07-29
    historical
28. 2022-06-01
    status Active
29. 2022-05-31
    historical
30. 2022-05-20
    status Active
31. 2022-05-14
    status Pending
32. 2022-04-16
    status Active
33. 2022-04-15
    historical
34. 2022-02-14
    price $1,495,000
35. 2022-01-17
    listed $1,600,000 Active
36. 2021-04-05
    soldstatus $875,000 Closed
37. 2021-03-26
    status Pending
38. 2021-02-24
    status Pending
39. 2021-02-16
    listed $950,000 Active

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 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 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $104,268
• − Mortgage interest: −$61,561
• − Property taxes: −$16,485
• − Insurance: −$5,495
• − Repairs & maintenance: −$8,341
• − Management: −$8,341
• − Depreciation: −$31,971
• Taxable loss: −$27,927
• Est. tax savings @ 24.0%: +$6,702
• After-tax cash flow: $-2,065/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.

Condition & rehab AI · 13 photos

Fair 45/100 Moderate rehab

This 4-unit multifamily property in Laurel Park, Sarasota, FL, requires moderate renovations to improve its condition and appearance. Upgrading the kitchen and bathrooms, along with landscaping, would significantly increase its resale and rental value.

Repairs flagged

• Major kitchen cabinets — The cabinets appear to be outdated and in poor condition.
• Major bathroom fixtures — The fixtures appear to be outdated and in poor condition.
• Minor exterior siding — There is some discoloration and wear visible, but no major damage.
• Minor interior walls — There is some discoloration and wear visible, but no major damage.
• Minor windows — There is some discoloration and wear visible, but no major damage.

Value-add opportunities

• Resale New kitchen cabinets and appliances — Updating the kitchen will significantly improve the home's appearance and functionality, making it more attractive to potential buyers.
• Resale New bathroom fixtures and tiles — Updating the bathrooms will improve the home's appearance and functionality, making it more attractive to potential buyers.
• Both Landscaping and curb appeal — Improving the landscaping and curb appeal will make the home more attractive and increase its overall value.

Renovation cost estimate screening

Repair item	Severity	Est. cost
kitchen cabinets · The cabinets appear to be outdated and in poor condition.	Major	$15,000–50,000
bathroom fixtures · The fixtures appear to be outdated and in poor condition.	Major	$15,000–50,000
exterior siding · There is some discoloration and wear visible, but no major damage.	Minor	$500–3,000
interior walls · There is some discoloration and wear visible, but no major damage.	Minor	$500–3,000
windows · There is some discoloration and wear visible, but no major damage.	Minor	$500–3,000
Total estimated repair cost · 5 items		$31,500–109,000

Value-add ROI direction

• Resale New kitchen cabinets and appliances — Updating the kitchen will significantly improve the home's appearance and functionality, making it more attractive to potential buyers. ↑
• Resale New bathroom fixtures and tiles — Updating the bathrooms will improve the home's appearance and functionality, making it more attractive to potential buyers. ↑
• Both Landscaping and curb appeal — Improving the landscaping and curb appeal will make the home more attractive and increase its overall value. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

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 — Sarasota

• Score: 80/100
• State rank: #121
• US rank: #1854

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Sarasota, FL
• County: Sarasota County · 448,376 people
• City population: 261,896
• Metro: North Port-Sarasota-Bradenton, FL
• Population (ZIP): 14,446
• Household income: $95,881
• Rent vs Own: 41.7% rent · 58.3% own
• Severe rent burden: 927.0

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 (84%)
• Race & ethnicity: White 84% Two or more races 7% Hispanic / Latino 6% Black 4% Asian 3%
• Hispanic origin (detail): Mexican 3% Puerto Rican 1%
• Common ancestry: Lithuanian 3% Slovak 3% Scotch-Irish 3%
• Foreign-born: 12% · Canada, Jamaica
• Languages at home: 90% English-only · Spanish 5% Other Indo-European 2% German/W. Germanic 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: ▲ 1.92%
• Current HPI: 302.9082
• Rent YoY: ▼ -5.12%
• 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

+15.7% since first listed

23 events — show timeline

• 2026-03-24 Price Changed $1,099,000 Stellar MLS as Distributed by MLS Grid
• 2026-01-27 Listed $1,199,000 Stellar MLS as Distributed by MLS Grid
• 2025-09-15 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-05-17 Listed $1,299,000 Stellar MLS as Distributed by MLS Grid
• 2023-04-05 Sold (MLS) $1,217,000 Stellar MLS as Distributed by MLS Grid
• 2023-02-27 Pending — Stellar MLS as Distributed by MLS Grid
• 2023-01-11 Price Changed $1,299,000 Stellar MLS as Distributed by MLS Grid
• 2023-01-09 Price Changed $1,299,500 Stellar MLS as Distributed by MLS Grid
• 2022-12-26 Price Changed $1,365,000 Stellar MLS as Distributed by MLS Grid
• 2022-12-06 Listed $1,395,000 Stellar MLS as Distributed by MLS Grid
• 2022-07-29 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-06-01 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-05-31 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-05-20 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-05-14 Pending — Stellar MLS as Distributed by MLS Grid
• 2022-04-16 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-04-15 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-02-14 Price Changed $1,495,000 Stellar MLS as Distributed by MLS Grid
• 2022-01-17 Listed $1,600,000 Stellar MLS as Distributed by MLS Grid
• 2021-04-05 Sold (MLS) $875,000 Stellar MLS as Distributed by MLS Grid
• 2021-03-26 Pending — Stellar MLS as Distributed by MLS Grid
• 2021-02-24 Pending — Stellar MLS as Distributed by MLS Grid
• 2021-02-16 Listed $950,000 Stellar MLS as Distributed by MLS Grid