5445 Chandler Dr · Winter Haven, FL 33884

$305,000

4 bd · 3.0 ba · 3,010 sqft · SingleFamily public records · 97 Days on market

Built 2006 5,772 sqft lot $47/mo HOA · 2% of rent

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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 +13.1/30.0
• ARV discount +7.5/15.0
• 1% rule +4.3/10.0
• DSCR +3.9/10.0
• Livability +3.7/5.0
• Schools +3.5/10.0
• Rent growth +3.0/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

BRAND NEW 2-STORY HOME IN BENTLEY PLACE. FEATURES; DOWNSTAIRS LARGE OPEN KITCHEN WITH DUAL SINKS & CENTER ISLAND, DUAL OVENS & REFRIGERATORS, DINING & FAMILY ROOM & LARGE BEDROOM WITH BATH. UPSTAIRS; 3 BEDROOMS WITH LARGE MASTER BEDROOM W/ MASTER BATHROOM WITH GARDEN TUB, DUAL WALK-IN CLOSETS, UPSTAIRS ALSO HAS A BONUS ROOM FOR LIVING AREA OR GAME ROOM. GREAT HOME FOR YOUR LARGE FAMILY WITH ROOM FOR EVERYONE.

Key facts

• Brand new roof
• Functional layout
• Large living areas

Tags

• BRAND NEW ROOF
• FRESH INTERIOR PAINT
• FUNCTIONAL LAYOUT
• LARGE LIVING AREAS
• AMPLE SPACE

Property features AI

Finance

• Other: Total lot approximately 0.13 acres; Living area about 3010 square feet
• Financial info: Lease restrictions apply
• HOA & community: HOA managed by Garrison Property Services; Annual association fee of $575 (monthly equivalent about $47.92); Association approval required; Pets allowed (cats and dogs) with breed restrictions

Exterior

• Parking: Attached 2-car garage
• Utilities: Public water; Public sewer; Electricity available; Broadband/High-speed internet available
• Home design: Single family residence; Two stories; Faces southwest; Residential property
• Construction: Block, stucco, and frame construction; Shingle roof; Slab foundation; Built as a two-story home
• Exterior features: Sidewalk; Sliding doors; Asphalt road frontage

Interior

• Kitchen: Built-in oven; Cooktop; Microwave
• Bedrooms: 4 bedrooms
• Flooring: Carpet; Ceramic tile; Laminate
• Bathrooms: 3 full bathrooms
• Heating & cooling: Central heating (electric); Central air conditioning
• Interior features: Eat-in kitchen; High ceilings; Thermostat; Walk-in closets
• Laundry & utility: Inside laundry

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $305k.

Deal economics

• At list price, monthly cash flow is $-13 ($-150/yr) — negative.
• To cash-flow at today's rent, offer at most $303k (0.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $284k (6.8% below list).
• Recommended offer: $278k (9.0% below list) — sets the bar for market timing.

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: Garden Grove Elementary School (math 49% / reading 40%, grade F, #1,288 of 2,144 statewide, top 62%, 723 students, 46% 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 55% FRL track the district average.
• Market conditions: Rents rising (+1.9%/yr); 691 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 10,384 units permitted in Polk County in 2024 (1,716 in 5+ unit buildings).
• At $2,844/mo this rent would consume 48% of the median local household income ($70k/yr) (locally 949% 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 $9k 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 97 days — a 9% lower offer ($278k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 19y ago; this cycle's ask has dropped $20k (6%) 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→25/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $277,550 (9.0% 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 97 days. Have you received any prior offers? Is the seller open to a 9% 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. 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: 0.93% ✗
• Cap rate: 6.24%
• Cash-on-cash: -0.18%
• DSCR: 0.99
• GRM: 8.9

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 1.9% rent growth · sell at horizon

5-year hold

• IRR: -17.9%
• Equity multiple: 0.38×
• Total profit: $-53,199
• Equity at exit: $45,476

10-year hold

• IRR: -12.4%
• Equity multiple: 0.31×
• Total profit: $-59,297
• Equity at exit: $26,371

Cash invested: $85,400 (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 33884

• Home prices YoY: -34.1%
• Rents YoY: 1.9%
• Active inventory: 691
• Price-to-rent: 8.9×

Monthly cashflow live

• Estimated rent: $2,844 medium
• Mortgage (P&I): −$1,599
• Tax from tax record: −$486 /mo · $5,827/yr
• Insurance: −$127
• HOA: −$47
• Vacancy / Maint / Mgmt: −$597
• Net cashflow: $-13

Break-even live

Break-even rent $2,860

Max offer price $302,786

Occupancy floor 95%

Sensitivity live

Price	-10% $160	-5% $74	+0% $-13	+5% $-99	+10% $-185
Rent	-10% $-237	-5% $-125	+0% $-13	+5% $100	+10% $212
Rate	-1.0pp $141	-0.5pp $65	base $-13	+0.5pp $-92	+1.0pp $-172

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: $76,250
• Closing costs: $9,150
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
236 Ruby Lake Ln Winter Haven, FL	3.0	3.0	2266	$4,500	$1.99	26d	1	0.80mi

HOA detail

• Monthly dues: $47 · $564/yr

Listing history 25 events

1. 2026-06-23
   days on market $305,000 Active 97 DOM
2. 2026-06-22
   days on market $305,000 Active 96 DOM
3. 2026-06-18
   days on market $305,000 Active 93 DOM
4. 2026-06-17
   days on market $305,000 Active 92 DOM
5. 2026-06-16
   days on market $305,000 Active 91 DOM
6. 2026-06-15
   days on market $305,000 Active 90 DOM
7. 2026-06-13
   pricedays on market $305,000 Active 88 DOM
8. 2026-06-10
   days on market $314,500 Active 85 DOM
9. 2026-06-09
   days on market $314,500 Active 84 DOM
10. 2026-06-08
    days on market $314,500 Active 83 DOM
11. 2026-06-07
    days on market $314,500 Active 82 DOM
12. 2026-06-05
    days on market $314,500 Active 79 DOM
13. 2026-06-03
    days on market $314,500 Active 78 DOM
14. 2026-06-03
    days on market $314,500 Active 77 DOM
15. 2026-06-01
    days on market $314,500 Active 76 DOM
16. 2026-05-31
    days on market $314,500 Active 75 DOM
17. 2026-05-21
    price $314,500
18. 2026-04-20
    price $319,500
19. 2026-03-17
    listed $325,000 Active
20. 2024-08-15
    historical $2,675
21. 2024-08-14
    historical
22. 2024-02-15
    listed $2,675
23. 2024-02-14
    listed $375,000 Active
24. 2021-04-30
    historical 436-char remark

    Show marketing remark (436 chars)

    BRAND NEW 2-STORY HOME IN BENTLEY PLACE. FEATURES; DOWNSTAIRS LARGE OPEN KITCHEN WITH DUAL SINKS & CENTER ISLAND, DUAL OVENS & REFRIGERATORS, DINING & FAMILY ROOM & LARGE BEDROOM WITH BATH. UPSTAIRS; 3 BEDROOMS WITH LARGE MASTER BEDROOM W/ MASTER BATHROOM WITH GARDEN TUB, DUAL WALK-IN CLOSETS, UPSTAIRS ALSO HAS A BONUS ROOM FOR LIVING AREA OR GAME ROOM. GREAT HOME FOR YOUR LARGE FAMILY WITH ROOM FOR EVERYONE.

25. 2007-01-29
    listed $299,900 436-char remark

    Show marketing remark (436 chars)

    BRAND NEW 2-STORY HOME IN BENTLEY PLACE. FEATURES; DOWNSTAIRS LARGE OPEN KITCHEN WITH DUAL SINKS & CENTER ISLAND, DUAL OVENS & REFRIGERATORS, DINING & FAMILY ROOM & LARGE BEDROOM WITH BATH. UPSTAIRS; 3 BEDROOMS WITH LARGE MASTER BEDROOM W/ MASTER BATHROOM WITH GARDEN TUB, DUAL WALK-IN CLOSETS, UPSTAIRS ALSO HAS A BONUS ROOM FOR LIVING AREA OR GAME ROOM. GREAT HOME FOR YOUR LARGE FAMILY WITH ROOM FOR EVERYONE.

ⓘ 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: $5,827 · $486/mo
• Projected year-2 tax: $5,827 · $486/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 4/10 Moderate
• 🌡 Heat 8/10 Severe 7 d/yr ≥108°F today · 25 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: $34,125
• − Mortgage interest: −$17,085
• − Property taxes: −$5,827
• − Insurance: −$1,525
• − Repairs & maintenance: −$2,730
• − Management: −$2,730
• − HOA: −$564
• − Depreciation: −$8,873
• Taxable loss: −$5,208
• Est. tax savings @ 24.0%: +$1,250
• After-tax cash flow: $1,100/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): 37,561
• Household income: $70,443
• Rent vs Own: 25.7% rent · 74.3% own
• Severe rent burden: 949.0

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 0.55)
• Race & ethnicity: White 63% Hispanic / Latino 19% Black 14% Two or more races 7% Asian 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 10% Cuban 2%
• Common ancestry: Romanian 2% Lithuanian 2% Hispanic 2%
• Foreign-born: 7% · Canada, Jamaica
• Languages at home: 84% English-only · Spanish 12% French/Haitian/Cajun 1% Other Indo-European 1%

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: ▼ -134.69%
• Current HPI: 260.1421
• Rent YoY: ▲ 1.90%
• 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

+4.9% since first listed

9 events — show timeline

• 2026-05-21 Price Changed $314,500 Stellar MLS as Distributed by MLS Grid
• 2026-04-20 Price Changed $319,500 Stellar MLS as Distributed by MLS Grid
• 2026-03-17 Listed $325,000 Stellar MLS as Distributed by MLS Grid
• 2024-08-15 Rental Removed $2,675 STELLARMLS
• 2024-08-14 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2024-02-15 Listed for Rent $2,675 STELLARMLS
• 2024-02-14 Listed $375,000 Stellar MLS as Distributed by MLS Grid
• 2021-04-30 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2007-01-29 Listed $299,900 Stellar MLS as Distributed by MLS Grid

Property tax history

+8.1%/yr

Latest (2025): $5,827 · +4.8% YoY. Source: county tax records.