4099 ISLAND LAKES DRIVE, WINTER HAVEN, FL, 33881
Active491 days on marketListed Apr 1, 2025MLS #P4934266
About this home
4099 ISLAND LAKES DRIVE
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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,603
Sqft
0.4 ac
Lot size
2
Garage
2006
Year built
One
Levels
$236
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$3,009 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,009/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+24.7%
$/sqft vs Winter Haven actives
$236 vs $170
Days on market
491 vs 48 typical
Where $236/sqft sits among the 400 Winter Haven actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Winter Haven
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
WINTER HAVEN 33881 — neighborhood snapshot
Population
39,189
Median age
43.6
Median income
$53,867
Median home value
$177,400
Avg household
2.61
Households w/ children
3,730
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Haven market
$283K → $280K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
197 of 400
Winter Haven actives have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 55% above the WINTER HAVEN 33881 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 4099 ISLAND LAKES DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$254,000
4108 ISLAND LAKES DRIVE · same community
3 bd · 2 ba · 1,507 sqft · $169/sqft · 157 DOM
Sold · Oct ’25$400,000
4027 ISLAND LAKES DRIVE · same community
4 bd · 2 ba · 1,855 sqft · $216/sqft · 63 DOM
Sold · Dec ’25$273,000
4070 ISLAND LAKES DRIVE · same community
4 bd · 2 ba · 1,860 sqft · $147/sqft · 336 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 4099 ISLAND LAKES DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4099 ISLAND LAKES DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
4099 ISLAND LAKES DRIVE FAQs
What would the monthly payment be for 4099 ISLAND LAKES DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,009/mo — principal and interest, the actual property-tax bill, the $17/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 4099 ISLAND LAKES DRIVE?+
The association fee works out to $17 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4099 ISLAND LAKES DRIVE?+
The most recent tax bill on record (2024) was $5,194. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 4099 ISLAND LAKES DRIVE?+
The listing reports pets: Cats OK, Dogs OK, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Haven?+
At $379,000, this home is listed about 33% above the Winter Haven median of $285,000. The market section on this page shows how the area is trending.
Which schools are assigned to 4099 ISLAND LAKES DRIVE?+
Lake Alfred Polytech Academy (middle), Fred G. Garner Academy (elementary), Winter Haven Senior High School (high) — Polk County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$379,000 runs 55% above the WINTER HAVEN 33881 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
491 days on market against a Winter Haven median of 48 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $439,000, now $379,000 — a $60K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY SMART 1 · Don Jerue. MLS #P4934266.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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