4099 Island Lakes Dr, photo 1
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Overview

3 bd2 ba1,603 sqft2 car garageSingle Family
TypeSingle Family
HOA$50/qtr
Built2006
Lot17,529 sqft
Living area1,603 sqft
Price / sqft$236
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Cathedral Ceiling(s)Ceiling Fans(s)IN Wall Pest SystemKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanSplit BedroomVaulted Ceiling(s)

4099 Island Lakes Dr is a 2006-built home in Island Lakes, Winter Haven. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,603 square feet of living space. Listed at $379,000 (about $236/sqft), 562 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $50 quarterly.

From the listing

One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $10K PRICE IMPROVEMENT on 7/24! Now offered at another improved price, this waterfront home on Lake Rochelle delivers the best value currently available on the Winter Haven Chain of Lakes. Located in the desirable Island Lakes community, this well-maintained 3-bedroom, 2-bath home combines lakefront living, major recent updates, and everyday functionality. A brand new roof was installed in February 2026, offering added peace of mind and potential insurance advantages for the next owner. Fresh landscaping and new sod create excellent curb appeal, while the open split-bedroom floorplan provides comfortable living with beautiful natural light throughout. The spacious primary suite overlooks the water and includes a private bath and walk-in closet. The living and dining areas flow easily into the kitchen, making the home ideal for entertaining, weekend guests, or simply enjoying the lake lifestyle. Step outside and enjoy direct access to the Chain of Lakes with boating, fishing, kayaking, and sunset views right from your backyard. Conveniently located near shopping, dining, medical facilities, and major roadways while still offering a peaceful waterfront setting. Whether you’re looking for a primary residence, winter retreat, or investment opportunity, this property checks all the boxes for Florida lakefront living. Schedule your private showing today.

The essentials

Built
2006
Price / sqft
$236
On market
562 days
Annual tax
$5,194
HOA
$50/qtr
Flood zone
X · Low risk
Lot
17,529 sqft
Type
Single Family Residence

At a glance

Single family
Built 2006
Waterfront
Lake Privileges
2 car garage
0.40 acres
Lot size
1,603 sqft
Living area

Payment

Est. monthly payment
$2,616/mo
Down payment (20%)
$75,800
Property taxes
$433/mo
HOA
$50/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
2006
Lot
17,529 sqft
Cooling
Central Air
Heating
Central
Parking
-
Waterfront
Lake Privileges
Days on Market
562
Cathedral Ceiling(s)
Ceiling Fans(s)
IN Wall Pest System
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Open Floorplan
Split Bedroom
Vaulted Ceiling(s)
Walk-in Closet(s)
Lighting
Dishwasher
Microwave
Range
Refrigerator
Flood Zone X
Annual Tax (2024)
$5,194
Parcel #
26-28-09-530005-000430

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
Island Lakes
County
Polk
MLS Area
33881 - Winter Haven / Florence Villa
Lot Size
17,529 sqft
City LimitsPaved
HOA
$50/qtr
Highland Community

Price history

Date
Event
Price
7/24/2026
Price change
Source: Stellar MLS #P4934266
$379,000-2.6%
$236/sqft
-
Price change
Source: Stellar MLS #P4934266
$389,000-11.4%
$243/sqft
4/1/2025
Listed for sale
Source: Stellar MLS #P4934266
$439,000
$274/sqft

Neighborhood

4099 Island Lakes Dr
Winter Haven, FL, 33881 · 33881 - Winter Haven / Florence Villa

Market insights

Offer Insights

Choose an offer strength

List price: $379,000
$377,500 – $379,000
99.5% – 100% of listTops out right at the list price
80% of listList price
169 of the last 272 home closings in 33881 landed at this number or higher (62%). The median one sat 42 days before it went under contract, and this one is on day 562 after a $60,000 cut.

Sample: 272 closed home sales in 33881 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$2,616/mo
Principal & interest$1,977
Property taxes$433
Insurance$190
HOA$17
Down payment20% · $75,800
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 includes any condo dues 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.

Quick answers.

Price

$379,000

$236 per sq ft

Beds and baths

3 beds, 2 baths

Size

1,603 sq ft

Time on market

562 days

Year built

2006

Monthly payment

About $2,616/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,194 annual tax bill, insurance, and the $50/qtr HOA fee.

HOA fee

$50/qtr

Managed by Highland Community.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byKELLER WILLIAMS REALTY SMART 1Listing agent: Don JerueListing data from Stellar MLS, MLS# P4934266.

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