Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 2 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 3 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 4 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 5 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 6 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 7 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 8 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 9 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 10 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 11 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 12 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 13 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 14 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 15 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 16 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 17 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 18 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 19 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 20 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 21 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 22 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 23 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 24 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 25 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 26 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 27 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 28 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 29 of 40
virtually staged - 4099 ISLAND LAKES DR, WINTER HAVEN
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 31 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 32 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 33 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 34 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 35 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 36 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 37 of 40
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 38 of 40
virtually staged - 4099 ISLAND LAKES DR, WINTER HAVEN
Single Family Residence at 4099 ISLAND LAKES DR, WINTER HAVEN, photo 40 of 40
40 photos

$379,000

4099 ISLAND LAKES DR
WINTER HAVEN, FL 33881
Listed by Don Jerue · KELLER WILLIAMS REALTY SMART 1
Bedrooms
3
Bathrooms
2
Living area
1,603 sqft
Year built
2006

About this home

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.

Highlights

Waterfront

Property details

MLS #
MFRP4934266
Property type
Single Family Residence
Subdivision
ISLAND LAKES
Status
Active
Days on market
548
On market date
April 1, 2025
Stories
N/A
Total bathrooms
2
Garage spaces
2
Parking spaces
N/A
Lot size
0.4 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

ElementaryCharter
HARTRIDGE ACADEMY
1.28 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
201
Student:teacher ratio
16.8:1
District
POLK
Middle
JEWETT MIDDLE ACADEMY MAGNET
1.61 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
554
Student:teacher ratio
17.9:1
District
POLK
HighCharter
NEW BEGINNINGS HIGH SCHOOL
0.82 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
671
Student:teacher ratio
39.5:1
District
POLK

Walkability

Blended score for WINTER HAVEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

79
Walkable
out of 100
EPA National Walkability Index
12.8 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes12
Grocery stores5
Parks4
Schools3
Transit stops18
Pharmacies4

Market position

How this listing compares to current activity in WINTER HAVEN, from live MLS data.

On the market 548 days -- 454 more days than WINTER HAVEN's current average of 94 days.
For reference, the median list price across 1,269 active listings in WINTER HAVEN right now is $247,500.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$2,432/mo
$75,800 down
$303,200 loan
Principal & interest$1,967
Property tax (est.)$316
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 5 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.