880 Oleander Dr SE · Winter Haven, FL 33880

$279,900

3 bd · 2.0 ba · 1,860 sqft · SingleFamily public records · 217 Days on market

Built 1958 0.31 ac 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 +14.1/30.0
• ARV discount +7.5/15.0
• DSCR +4.3/10.0
• Livability +3.7/5.0
• Schools +3.5/10.0
• Rent growth +3.1/5.0
• 1% rule +2.8/10.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Under contract-accepting backup offers. Welcome to this inviting 3 bedroom, 2 bath home in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious Florida Room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a decorative fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all

Key facts

• Sought-after area
• Large glass windows
• Outdoor living

Tags

• SPACIOUS FAMILY ROOM
• LARGE GLASS WINDOWS
• FULLY FENCED BACKYARD
• OUTDOOR LIVING
• SOUGHT-AFTER AREA

Property features AI

Finance

• Other: Homestead exempt; Zoned R-1A; No CDD; No lease restrictions

Exterior

• Parking: Carport with 2 spaces
• Utilities: Public water; Public sewer; Electricity connected; High-speed internet available; Water connected; Sewer connected
• Home design: Single-family residence; One story; Faces north
• Construction: Block construction; Shingle roof; Slab foundation; Living area ~2,172 (estimated); total building area ~2,830 (estimated)
• Exterior features: Exterior lighting; Private mailbox; Paved road access; Lot approximately 0.31 acres (100 x 135)

Interior

• Kitchen: Dishwasher; Disposal; Range
• Bedrooms: 3 bedrooms
• Flooring: Carpet; Ceramic tile; Laminate; Parquet
• Bathrooms: 2 full bathrooms
• Heating & cooling: Central electric heating; Central air conditioning
• Interior features: Built-in features; Decorative living room fireplace
• Laundry & utility: Dedicated laundry room; Exterior laundry access

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $280k.

Deal economics

• At list price, monthly cash flow is $42 ($509/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 $219k (21.9% below list).
• Recommended offer: $219k (21.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 74/100 on livability (#291 in FL, #4,898 nationally) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+, health & safety A; Watch: employment C-, amenities F, commute F.
• Polk (suburban): math 39% / reading 43% proficiency, ranked #62 of 73 in FL (top 85%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Elbert Elementary School (math 35% / reading 37%, grade F, #1,670 of 2,144 statewide, top 78%, 601 students, 62% FRL); Denison Middle School (math 24% / reading 25%, grade F, #522 of 571 statewide, top 93%, 738 students, 69% FRL); Winter Haven Senior High School (math 26% / reading 38%, grade F, #415 of 667 statewide, top 63%, 2,467 students, 50% FRL) — zoned schools at 60% FRL track the district average.
• Market conditions: Rents rising (+2.5%/yr); 345 active listings in the ZIP; 9 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); 10,384 units permitted in Polk County in 2024 (1,716 in 5+ unit buildings).
• At $2,186/mo this rent would consume 47% of the median local household income ($56k/yr) (locally 1412% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $8k of value loss. Plan a longer hold.
• Polk County population projected at +33% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 217 days — a 12% lower offer ($246k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts; this cycle's ask has dropped $50k (15%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $85k; list at $280k implies a 229% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1958 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→24/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $218,579 (21.9% below list)

Questions for the listing agent

1. It's been on market 217 days. Have you received any prior offers? Is the seller open to a 22% concession, seller financing, or rate buy-down credit?
2. Built in 1958 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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.
7. 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.
8. 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: 0.78% ✗
• Cap rate: 6.47%
• Cash-on-cash: 0.65%
• DSCR: 1.03
• GRM: 10.7

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 2.47% rent growth · sell at horizon

5-year hold

• IRR: -15.8%
• Equity multiple: 0.44×
• Total profit: $-43,936
• Equity at exit: $41,734

10-year hold

• IRR: -8.3%
• Equity multiple: 0.49×
• Total profit: $-39,980
• Equity at exit: $24,201

Cash invested: $78,372 (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 33880

• Home prices YoY: -16.2%
• Rents YoY: 2.5%
• Active inventory: 345
• Price-to-rent: 10.7×

Monthly cashflow live

• Estimated rent: $2,186 high
• Mortgage (P&I): −$1,468
• Tax from tax record: −$100 /mo · $1,199/yr
• Insurance: −$117
• HOA: −$0
• Vacancy / Maint / Mgmt: −$459
• Net cashflow: $42

Break-even live

Break-even rent $2,132

Max offer price $279,900

Occupancy floor 93%

Sensitivity live

Price	-10% $201	-5% $122	+0% $42	+5% $-37	+10% $-116
Rent	-10% $-130	-5% $-44	+0% $42	+5% $129	+10% $215
Rate	-1.0pp $183	-0.5pp $114	base $42	+0.5pp $-30	+1.0pp $-104

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: $69,975
• Closing costs: $8,397
• Reserves months: —
• Total cash needed: —

Rent comps 9 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
919 S AVE SE Unit 1325030P Eloise, FL	3.0	2.0	1722	$2,954	$1.72	4d	1	0.31mi
200 Avenue K SE Winter Haven, FL	1.0–3.0	1.0–2.0	1095	$1,735	$1.58	4d	45	0.71mi
2249 9th St SE Winter Haven, FL	3.0	2.0	1520	$1,449	$0.95	20d	1	0.72mi
2312 Isle Royale Ct SE Winter Haven, FL	2.0	2.5	1280	$1,499	$1.17	5d	1	0.82mi
2374 Isle Royale Ct SE Winter Haven, FL	2.0	1.5	1320	$1,700	$1.29	25d	1	0.89mi
227 W Lake Ina Dr Winter Haven, FL	3.0	2.0	1764	$2,500	$1.42	25d	1	0.92mi
123 Tremont Dr Winter Haven, FL	4.0	3.0	1260	$2,350	$1.87	25d	1	0.98mi
2005 N Lake Eloise Dr Winter Haven, FL	3.0	2.0	1513	$1,950	$1.29	5d	1	1.04mi
240 2nd St SW #201 Winter Haven, FL	2.0	2.0	1241	$1,725	$1.39	25d	1	1.33mi

Listing history 12 events

1. 2026-05-15
   status Pending
2. 2026-04-20
   status Active
3. 2026-04-06
   status Pending
4. 2026-04-02
   status Active
5. 2026-03-26
   status Pending
6. 2026-03-10
   price $279,900
7. 2026-02-10
   price $289,000
8. 2026-01-10
   price $294,900
9. 2025-10-15
   price $299,900
10. 2025-09-19
    listed $329,900 Active
11. 1993-02-26
    soldstatus $85,000
12. 1976-06-01
    soldstatus $45,000

ⓘ 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: $1,199 · $100/mo
• Projected year-2 tax: $2,323 · $194/mo
• Expected delta: +$1,124/yr (+$94/mo · 93.7%)

ⓘ 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 8/10 Severe 7 d/yr ≥107°F today · 24 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $26,229
• − Mortgage interest: −$15,679
• − Property taxes: −$1,199
• − Insurance: −$1,400
• − Repairs & maintenance: −$2,098
• − Management: −$2,098
• − Depreciation: −$8,143
• Taxable loss: −$4,387
• Est. tax savings @ 24.0%: +$1,053
• After-tax cash flow: $1,562/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: Polk
• NCES district ID: 1201590
• Math proficiency: 39% ▼ -11.00%
• Reading proficiency: 43% ▼ -4.00%
• Median HH income: $43,979
• Composite: 34.74/100
• National rank: #5132
• State rank: #62 of 73 in FL

Livability — Winter Haven

• Score: 74/100
• State rank: #291
• US rank: #4898

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winter Haven, FL
• County: Polk County · 740,051 people
• City population: 121,740
• Metro: Lakeland-Winter Haven, FL
• Population (ZIP): 43,371
• Household income: $56,390
• Rent vs Own: 33.4% rent · 66.6% own
• Severe rent burden: 1412.0

Population outlook (Polk County) Hauer SSP2

• Today (2025): 752,975 people
• By 2030: 804,621 · +6.9%
• By 2040: 906,117 · +20.3%
• By 2050: 1,000,476 · +32.9%
• By 2075: 1,197,520 · +59.0%
• By 2100: 1,271,518 · +68.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.65)
• Race & ethnicity: White 49% Hispanic / Latino 27% Black 17% Two or more races 14% Asian 1%
• Hispanic origin (detail): Mexican 11% Puerto Rican 10% Cuban 2%
• Common ancestry: Hispanic 2% Lithuanian 1% Italian 1%
• Foreign-born: 9% · Canada, Jamaica
• Languages at home: 74% English-only · Spanish 21% French/Haitian/Cajun 4%

Political lean MEDSL · Polk

• 2024 margin: Strong R (+20.7) · D 39.2% · R 59.9%
• 2008→2024 swing: -14.6pp toward R · 2008: -6.1pp · 2024: -20.7pp
• All cycles: 2024: R+20.7 2020: R+14.4 2016: R+14.1 2012: R+6.8 2008: R+6.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -61.41%
• Current HPI: 317.8788
• Rent YoY: ▲ 2.47%
• Metro: Lakeland-Winter Haven, 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

+522.0% since first listed

12 events — show timeline

• 2026-05-15 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-04-20 Relisted — Stellar MLS as Distributed by MLS Grid
• 2026-04-06 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-04-02 Relisted — Stellar MLS as Distributed by MLS Grid
• 2026-03-26 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-03-10 Price Changed $279,900 Stellar MLS as Distributed by MLS Grid
• 2026-02-10 Price Changed $289,000 Stellar MLS as Distributed by MLS Grid
• 2026-01-10 Price Changed $294,900 Stellar MLS as Distributed by MLS Grid
• 2025-10-15 Price Changed $299,900 Stellar MLS as Distributed by MLS Grid
• 2025-09-19 Listed $329,900 Stellar MLS as Distributed by MLS Grid
• 1993-02-26 Sold (Public Records) $85,000 Public Records
• 1976-06-01 Sold (Public Records) $45,000 Public Records

Property tax history

+2.6%/yr

Latest (2025): $1,199 · +3.9% YoY. Source: county tax records.