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5445 Chandler Dr, Winter Haven, FL, 33884

$96/sqft·Bentley Place

4 bd3 ba3,010 sqft2 car garageSingle Family
Listed by TRANSCEND REALTY· Last updated · MLS# S5146003

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Est. monthly payment
$2,190/mo
Down payment (20%)
$58,000
Property taxes
$486/mo
HOA
$575/yr
Rate assumed
6.8% · 30 yr
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At a glance

Single family
Built 2006
2 car garage
5,772 sqft lot
Lot size
3,010 sqft
Living area

About this home

Eat-in KitchenHigh CeilingsThermostatWalk-in Closet(s)SidewalkBuilt-in OvenCooktopMicrowave

5445 Chandler Dr is a 2006-built home in Bentley Place, Winter Haven. Inside you'll find 4 bedrooms, 3 bathrooms, and 3,010 square feet of living space. Listed at $290,000 (about $96/sqft), 171 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $575 annually.

From the listing

Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!

The essentials

Built
2006
Price / sqft
$96
On market
180 days
Annual tax
$5,827
HOA
$575/yr
Flood zone
X · Low risk
Lot
5,772 sqft
Type
Single Family Residence

Location

5445 Chandler Dr
Winter Haven, FL, 33884·33884 - Winter Haven / Cypress Gardens
Type
Single Family Residence
Year Built
2006
Lot
5,772 sqft
Cooling
Central Air
Heating
Central, Electric
Parking
-
Days on Market
180
Eat-in Kitchen
High Ceilings
Thermostat
Walk-in Closet(s)
Sidewalk
Built-in Oven
Cooktop
Microwave
Flood Zone X

Annual Tax (2025)

$5,827

Parcel #

26-29-01-663574-000330

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Bentley Place

County

Polk

MLS Area

33884 - Winter Haven / Cypress Gardens

Lot Size

5,772 sqft

HOA
$575/yr
Garrison Property Services
Date
Event
Price
9/4/2026
Price change
Source: Stellar MLS #S5146003
$290,000-3.3%
$96/sqft
Price change
Source: Stellar MLS #S5146003
$299,900-7.7%
$100/sqft
3/17/2026
Listed for sale
Source: Stellar MLS #S5146003
$325,000
$108/sqft
Est. monthly payment$2,191/mo
Principal & interest$1,512
Property taxes$486
Insurance$145
HOA$48
Down payment20% · $58,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

Choose an offer strength

List price: $290,000
$287,500 – $290,000
99.5% – 100% of listTops out right at the list price
80% of listList price
163 of the last 255 home closings in 33884 landed at this number or higher (64%). The median one sat 39 days before it went under contract, and this one is on day 180 after a $35,000 cut.

Sample: 255 closed home sales in 33884 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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