Email: | Brokerage: HR Moon Homes
    1. Home
    2. Property Search
    3. Search results
    4. 4099 Island Lakes Drive, WINTER HAVEN, FL 33881
    Contact HR Moon Homes
    Contacting HR Moon Homes
    • All fields are required.
    Schedule A Showing
    Schedule a Showing.
    • All fields are required.
    Check this box to Register with us:
    Submit an Offer Now!
    Submit an Offer Now!
    All fields are required.
    Print Flyer
    Active
    Property Photos
    4099 Island Lakes Drive
    1. Image 1 of 37 For 4099 Island Lakes Drive
    2. Image 2 of 37 For 4099 Island Lakes Drive
    3. Image 3 of 37 For 4099 Island Lakes Drive
    4. Image 4 of 37 For 4099 Island Lakes Drive
    5. Image 5 of 37 For 4099 Island Lakes Drive
    6. Image 6 of 37 For 4099 Island Lakes Drive
    7. Image 7 of 37 For 4099 Island Lakes Drive
    8. Image 8 of 37 For 4099 Island Lakes Drive
    9. Image 9 of 37 For 4099 Island Lakes Drive
    10. Image 10 of 37 For 4099 Island Lakes Drive
    11. Image 11 of 37 For 4099 Island Lakes Drive
    12. Image 12 of 37 For 4099 Island Lakes Drive
    13. Image 13 of 37 For 4099 Island Lakes Drive
    14. Image 14 of 37 For 4099 Island Lakes Drive
    15. Image 15 of 37 For 4099 Island Lakes Drive
    16. Image 16 of 37 For 4099 Island Lakes Drive
    17. Image 17 of 37 For 4099 Island Lakes Drive
    18. Image 18 of 37 For 4099 Island Lakes Drive
    19. Image 19 of 37 For 4099 Island Lakes Drive
    20. Image 20 of 37 For 4099 Island Lakes Drive
    21. Image 21 of 37 For 4099 Island Lakes Drive
    22. Image 22 of 37 For 4099 Island Lakes Drive
    23. Image 23 of 37 For 4099 Island Lakes Drive
    24. Image 24 of 37 For 4099 Island Lakes Drive
    25. Image 25 of 37 For 4099 Island Lakes Drive
    26. Image 26 of 37 For 4099 Island Lakes Drive
    27. Image 27 of 37 For 4099 Island Lakes Drive
    28. Image 28 of 37 For 4099 Island Lakes Drive
    29. Image 29 of 37 For 4099 Island Lakes Drive
    30. Image 30 of 37 For 4099 Island Lakes Drive
    31. Image 31 of 37 For 4099 Island Lakes Drive
    32. Image 32 of 37 For 4099 Island Lakes Drive
    33. Image 33 of 37 For 4099 Island Lakes Drive
    34. Image 34 of 37 For 4099 Island Lakes Drive
    35. Image 35 of 37 For 4099 Island Lakes Drive
    36. Image 36 of 37 For 4099 Island Lakes Drive
    37. Image 37 of 37 For 4099 Island Lakes Drive
    Image Gallery

    PRICED AT ONLY: $394,000

    Address: 4099 Island Lakes Drive, WINTER HAVEN, FL 33881

    Description

    One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $45,000 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 todays market. Inside, youll 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.

    Property Location and Similar Properties

    All
    Similar
    Payment Calculator
    •   Principal & Interest -
    •   Property Tax $
    •   Home Insurance $
    •   HOA Fees $
    •   Mortgage Insurance-
    •   Monthly -
    Virtual Tour
    Reduced
    More Like This
    • MLS#: P4934266 ( Residential )
    • Street Address: 4099 Island Lakes Drive
    • Viewed: 187
    • Price: $394,000
    • Price sqft: $175
    • Waterfront: Yes
    • Wateraccess: Yes
    • Waterfront Type: Lake Privileges
    • Year Built: 2006
    • Bldg sqft: 2252
    • Bedrooms: 3
    • Total Baths: 2
    • Full Baths: 2
    • Garage / Parking Spaces: 2
    • Days On Market: 403
    Request More Information
    • All fields are required.
    Features
    Building and Construction
    • Covered Spaces: 0.00
    • Exterior Features: Lighting
    • Flooring: Laminate
    • Living Area: 1603.00
    • Roof: Shingle
    Land Information
    • Lot Features: City Limits, Paved
    Garage and Parking
    • Garage Spaces: 2.00
    • Open Parking Spaces: 0.00
    Eco-Communities
    • Water Source: Public
    Utilities
    • Carport Spaces: 0.00
    • Cooling: Central Air
    • Heating: Central
    • Pets Allowed: Cats OK, Dogs OK, Yes
    • Sewer: Public Sewer
    • Utilities: Electricity Connected, Water Connected
    Finance and Tax Information
    • Home Owners Association Fee: 50.00
    • Insurance Expense: 0.00
    • Net Operating Income: 0.00
    • Other Expense: 0.00
    • Tax Year: 2024
    Other Features
    • Appliances: Dishwasher, Microwave, Range, Refrigerator
    • Association Name: Highland Community
    • Association Phone: 863-940-2863
    • Country: US
    • Interior Features: 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)
    • Legal Description: ISLAND LAKES PLAT BOOK 134 PGS 4 & 5 LOT 43
    • Levels: One
    • Area Major: 33881 - Winter Haven / Florence Villa
    • Occupant Type: Vacant
    • Parcel Number: 26-28-09-530005-000430
    • Possession: Close Of Escrow
    • Views: 187
    Nearby Subdivisions
    Biltmore Shores   Brenton Manor   Buckeye Hills   Buckeye Pointe   Buckeye Rdg   Buckeye Ridge   Buckeye Trace   Campbell Henry Sub   Carefree Cove   Chestnut Creek   Chestnut Crk   Chris Brown Cemetery Replat   Coker A B Add   Country Club Estates   Country Walkwinter Haven Ph 2   Crossroads At Lake Region   Deerwood Or Harriben Investmen   Dundee Station   Eagle Crest   East View Parkway Pb 13 Pg 4   East View Pkwy   Eastwood Sub   Elbert Acres   Elbert Landings   Elbert Park   Eula Vista Sub   Florence Village   Forest Ridge   Gates Lake Region   Gates Of Lake Region   Hamilton Pointe   Hamilton Ridge   Hamilton West Ph 01   Hampton Cove   Hampton Cove Pb 147 Pg 1618 Lo   Harbor At Lake Henry   Harmony On Lake Eloise Phase 4   Harrington A B Sub   Hartridge Hills   Hartridge Manor   Haven Shores   Hutchinson Add   Hutton Rep   Ida Lake Sub   Idylwild Heights   Inman Groves   Inman Grvs Ph 1   Inman Grvs Ph 2   Inwood   Inwood No 3 Pb 9 Pgs 7a 7c   Inwood 1   Inwood No 4 Pb 9 Pgs 35a 35b   Island Lakes   Jace Landings   Jace Lndg   Jarvis Heights   Jewett Mary B   Kenilworth Park   Krenson Bay   Lake Elbert Heights   Lake Idyll Estates   Lake Lucerne Ii   Lake Lucerne Ph 5   Lake Lucurne   Lake Silver Terrace   Lake Smart Estates   Lake Smart Pointe   Lake View Sub   Lake View Sub Pb 3 Pg 80   Lakeridge Estates   Lakes At Lucerne Park Ph 02   Lakeside Landings Ph 01   Lakeside Lndgs Ph 3   Lakeslucerne Park Ph 4   Lucerne Park   Lucerne Park Reserve   Lucerne Shores   Magnolia Shores   Maud Meadows   North Gate Village   North Lake Elbert Heights   Orange Shores   Revised Map Of Fernwood Add   Robinson Sub   Rochelle Gardens   Rosewood Manor   Royal Hills   Sanctuary By The Lake Ph 2   Sanctuary By The Lake Ph One   Sanctuary By The Lake Phase On   Savannah Lake   Saxonmyers Rep Ph 02   Smith Ida M Sub 2nd Replat Pb    South Lake Elbert Heights   St James Xing   Stately Oaks   Swan Lake Estates   The Shores   Van Duyne Shores   Villa Manor   West Cannon Heights   West Cannon Terrace   Willowbrook   Willowbrook North   Willowbrook South   Winter Haven Heights  
    Similar Properties

    Active
    Details for 814 Turner Lane, WINTER HAVEN, FL 33881
    $369,000.00 ($116.18 / sqft )

    814 Turner Lane Virtual Tour More Like This

    Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two story home offers 5 bedrooms, 3 full bathrooms, and over 2,500

    1. Request Information
    1. Bedrooms: 5
    2. Baths: 3
    3. Approx. 3176 sqft
    1. MLSID: S5134153
    2. Provided by KELLER WILLIAMS LEGACY REALTY
    3. Contact Rafael Ortiz Pena
    4. mfrmls
    5. DMCA Notice
    24 Pictures and Information
    Active
    Details for 592 Lake Smart Boulevard, WINTER HAVEN, FL 33881
    $415,000.00 ($138.33 / sqft )

    592 Lake Smart Boulevard Virtual Tour More Like This

    Welcome to a home that offers more than just space it delivers lifestyle, efficiency, and long term value. Situated on a premium oversized corner lot, this 5 bedroom, 3 bathroom residence in Winte

    1. Request Information
    1. Bedrooms: 5
    2. Baths: 3
    3. Approx. 3000 sqft
    1. MLSID: S5148989
    2. Provided by MY REALTY GROUP, LLC.
    3. Contact Oscar Allende Melendez
    4. mfrmls
    5. DMCA Notice
    72 Pictures and Information
    Active
    Details for 344 Alexzander Way, WINTER HAVEN, FL 33881
    $390,000.00 ($120.07 / sqft )

    344 Alexzander Way Virtual Tour More Like This

    Welcome to this stunning 5 bedroom, 3 bath home located in the Jace Landing community of Winter Haven. Built in 2021, this modern two story residence provides nearly 2,700 square feet of living space

    1. Request Information
    1. Bedrooms: 5
    2. Baths: 3
    3. Approx. 3248 sqft
    1. MLSID: P4936876
    2. Provided by DALTON WADE INC
    3. Contact Andres Ramirez
    4. mfrmls
    5. DMCA Notice
    36 Pictures and Information
    Active
    Details for 920 Gotthard Pass Drive, WINTER HAVEN, FL 33881
    $394,999.00 ($125.00 / sqft )

    920 Gotthard Pass Drive Virtual Tour More Like This

    Spacious single family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private offi

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 3
    3. Approx. 3160 sqft
    1. MLSID: S5142092
    2. Provided by LA ROSA REALTY LLC
    3. Contact Maria Chavez
    4. mfrmls
    5. DMCA Notice
    55 Pictures and Information
    Active
    Details for 108 Lake Region Boulevard N, WINTER HAVEN, FL 33881
    $425,000.00 ($127.02 / sqft )

    108 Lake Region Boulevard N Virtual Tour More Like This

    Gated custom home in the Gates of Lake Region! This quiet and highly desirable neighborhood has the look, feel and privacy of an age restricted community, but it is open to all ages. This property was

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 3
    3. Approx. 3346 sqft
    1. MLSID: L4957549
    2. Provided by THE STONES REAL ESTATE FIRM
    3. Contact Michael Stone
    4. mfrmls
    5. DMCA Notice
    52 Pictures and Information
    Active
    Details for 1215 26th Street Nw, WINTER HAVEN, FL 33881
    $374,000.00 ($153.59 / sqft )

    1215 26th Street Nw Virtual Tour Reduced More Like This

    Unique and spacious property offering flexibility and great outdoor living! This home features multiple living areas with beautiful exposed wood beam ceilings, updated flooring throughout, and plenty

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 4
    3. Approx. 2435 sqft
    1. MLSID: S5145609
    2. Provided by LIFESTYLE INTERNATIONAL REALTY
    3. Contact Talitha Lastre
    4. mfrmls
    5. DMCA Notice
    40 Pictures and Information
    Active
    Details for 652 Grove Street, WINTER HAVEN, FL 33881
    $370,000.00 ($131.95 / sqft )

    652 Grove Street Virtual Tour More Like This

    Welcome to 652 Grove St, a versatile and spacious 'Freedom' model home in the heart of Winter Haven! This unique property has a main residence featuring 3 bedrooms, 2 bathrooms, a dedicated office spa

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 3
    3. Approx. 2804 sqft
    1. MLSID: O6387580
    2. Provided by MY REALTY GROUP, LLC.
    3. Contact Lizandra Troisi Passos
    4. mfrmls
    5. DMCA Notice
    42 Pictures and Information
    Active
    Details for 225 Franklin Court, WINTER HAVEN, FL 33881
    $427,500.00 ($139.48 / sqft )

    225 Franklin Court Green Listing Reduced More Like This

    ***PRICE REDUCTION*** Refined luxury meets modern efficiency in this stunning 4 bedroom, 3 bath home located in the private gated community of Hampton Cove, tucked away on a peaceful cul de sac, accen

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 3
    3. Approx. 3065 sqft
    1. MLSID: L4958723
    2. Provided by THE STONES REAL ESTATE FIRM
    3. Contact Jessica Willaford
    4. mfrmls
    5. DMCA Notice
    57 Pictures and Information
    Active
    Details for 1280 Denali Drive, WINTER HAVEN, FL 33881
    $409,000.00 ($124.62 / sqft )

    1280 Denali Drive Virtual Tour More Like This

    One or more photo(s) has been virtually staged. Move In Incentive Available! Qualified buyers who finance with our affiliated lender may choose one of the following: a 4.5 interest rate or $5,000 towa

    1. Request Information
    1. Bedrooms: 3
    2. Baths: 3
    3. Approx. 3282 sqft
    1. MLSID: G5107453
    2. Provided by LPT REALTY, LLC
    3. Contact Luisa Hurtado
    4. mfrmls
    5. DMCA Notice
    32 Pictures and Information
    Active
    Details for 280 Lake Smart Circle, WINTER HAVEN, FL 33881
    $425,000.00 ($144.46 / sqft )

    280 Lake Smart Circle Virtual Tour More Like This

    Welcome to your 4 bedroom, 2.5 bathroom 2 story home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. Arriving at the home, youll appreciate the tastefull

    1. Request Information
    1. Bedrooms: 4
    2. Baths: 3
    3. Approx. 2942 sqft
    1. MLSID: L4959205
    2. Provided by KELLER WILLIAMS REALTY SMART
    3. Contact Casandra Vann
    4. mfrmls
    5. DMCA Notice
    64 Pictures and Information

    Contact Info

    Skip to Main Content
    1. We are the World
    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 9, 2026 @ 12:00 am
    ©2006-2026 brokerIDXsites.com - https://brokerIDXsites.com
    We believe in accessibility for all
    Your Privacy Is Important
    XML Sitemap
    Manage Your Account