4099 ISLAND LAKES DRIVE Winter Haven, FL $ 399,000
4099 ISLAND LAKES DRIVE
$ 399,000
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4099 ISLAND LAKES DRIVE

Winter Haven, FL, 33881
$ 399,000
Bedrooms3 Baths2.0 Sq 1,603

Monthly Estimate*

$ 2,457

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Single Family Home for sale in Winter Haven, FL

for $399,000 with 3 bedrooms and 2 full baths. This 1,603 square foot home was built in 2006 on a lot size of 0.4.

NEW ROOF 2/9/2026 + $40,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.

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Single Family Active

Price

$ 399,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 5,193

Style

Single Family Residence

Lot Size

0.4

Year Built

2006

Town/City

Winter Haven

County/Region

Polk

MLS | Web ID

P4934266

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Connected Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Microwave Range Refrigerator
HOA Fee 50
Garage Spaces 2
Patio/Porch Features Covered Front Porch Rear Porch Screened
Construction Materials Block Stucco
Pets Allowed Cats OK Dogs OK Yes
Year Built 2006
Levels One
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Lake - Chain of Lakes
Assoc Fee Paid Per Quarterly
County Polk
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name ISLAND LAKES
Facing Direction South
Garage Y/N true
Total Rooms 5
Full Baths 2
Status Active
Directions From Hwy 27 head west on Hwy 544 right on Conine Dr East over the bridge right at the fork in the road house is on the right.
City WINTER HAVEN
Body of Water LAKE ROCHELLE
Association Name Highland Community
Senior Community Y/N false
MLS Area 33881 - Winter Haven / Florence Villa
Lot Size Units Square Feet
Lot Size Square Feet 17529
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Land Lease Y/N false
Tax Annual Amount 5193.87
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/P4934266
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 43
Legal Description ISLAND LAKES PLAT BOOK 134 PGS 4 & 5 LOT 43
Water View Lake - Chain of Lakes
Water Access Type Lake - Chain of Lakes
Minimum Lease 1-2 Years
Water Access Y/N true
Monthly HOA Amount 16.67
Water View Y/N true
Flood Zone Code X
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Interior
Interior Amenities Cathedral Ceiling(s) Ceiling Fan(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)
Flooring Laminate
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Inside
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Lighting
Lot Features City Lot
Water Source Public
Lot Size Area 17529
Foundation Details Slab
Building Area Total 2252
Lot Size Acres 0.4
Road Surface Type Paved
Private Pool false
Waterfront Y/N true
Covered Spaces 2
Road Frontage Type Street Paved
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* Excluded Features
List By
Keller Williams Realty Smart 1

Broker

donjerue11@gmail.com

Email

Affordability Calculator

$2,889
Per Month
85%
15%
0%
Monthly Principal & Interest
$2,457
Monthly Property Taxes
$433
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$399,000 Listed Price

Map


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4099 ISLAND LAKES DRIVE, Winter Haven, FL, 33881 is a Single Family Home for sale at $399,000 with 1,603 sqft and a lot size of 0.4. 4099 ISLAND LAKES DRIVE has 3 bedrooms, 2.0 baths, and was built in 2006. The property's zip code is 33881 which is in Winter Haven, FL