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4099 Island Lakes Drive, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code
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.

4099 Island Lakes Drive, Winter Haven

1787 White Elephant Loop, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code
NO CDD fees! Welcome to Peach Crossings, Winter Haven’s newest community! This brand-new three-bedroom, two-bathroom home is designed for both comfort and style. The kitchen is the heart of the home, offering ample counter space—perfect for meal prep and entertaining. It comes fully equipped with Whirlpool stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! Granite countertops and modern cabinetry provide a classic, elegant touch. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy the outdoors year-round with the covered patio, a great spot for dining, relaxing, and taking in the fresh air—made even better by the privacy of having no rear neighbors and a beautiful pond view. This home is packed with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom off the garage offers the perfect drop zone for shoes, bags, and coats, making daily routines easier. Located next to the laundry room, this space helps keep everything organized and clutter-free. Situated in Polk County, Peach Crossings offers a balance of peaceful lake life and easy access to shopping, dining, and major attractions. Families will love the top-rated Polk County schools, and the community features a playground and picnic area for all to enjoy. Don’t miss out on this incredible opportunity—schedule your tour today!

1787 White Elephant Loop, Winter Haven

5713 Lucerne Park Road, Winter Haven
$950,000
33881 Zip Code
Under contract-accepting backup offers. Nestled on just under 10 acres of picturesque grounds, this property offers an unparalleled blend of rustic charm and modern convenience, making it an ideal location for weddings, parties, corporate events, and more. Formerly part of a sprawling ranch, this stunning property has been meticulously transformed into a fully equipped, multi-functional venue that combines serene country appeal with thoughtful, functional spaces. Boasting a spacious layout, the venue includes a lofted area, private rooms, dressing spaces, and a full bathroom with a shower, all designed for comfort and style. The prep kitchen and catering area, alongside separate bathrooms and versatile indoor and outdoor entertaining spaces, make this venue not only visually striking but practical for large-scale events. Additional amenities include a charming barn with horse stalls, an office, and a fenced riding arena—perfect for equestrian enthusiasts or those seeking to bring a unique touch to events. The property is fully fenced and offers ample parking and space for customization to suit your vision. Located with frontage on Lake Lucerne Rd and just minutes from US-27, this property is not only a stunning venue but also a prime, easily accessible location for events of all kinds. For those seeking to expand, an additional +/- 10 acres adjoining the property is available, offering further potential for development. This property is an exceptional opportunity for anyone looking to create a standout venue or bring their own vision to life. The possibilities here are as boundless as the property itself. For those looking for a full-package investment, an additional 9.75-acre parcel with a 2,000 sq ft custom home, which backs directly to the venue, is also available for purchase. Don’t miss your chance to own a piece of one of the most stunning properties in the area.

5713 Lucerne Park Road, Winter Haven

304 Avenue E  Sw, Winter Haven
$3,000,000
Overstreets Sub SubDv. ⋅ 33880 Zip Code
We are pleased to present this Reputable TURNKEY Well Established Tire Center & Auto Repair Shop business, available for sale in Polk County, FL. Located near Downtown Winter Haven. Valuable Real Estate included in the sales price. First-class facility in a great location with tons of visibility. Includes: business land, building, major equipment & Inventory. Profitable equipped Tire Center & Auto Repair Business plus free-standing commercial building. Operating Since 2016 at the same location. The facility includes a large industrial building - 7440 sq ft, with high vaulted ceilings, 7 overhead doors & deep bays with 4 auto lifts. Includes storage to accommodate Motor Home or Bus. Fully Equipped with all tools & diagnostic equipment. All equipment is currently in 1st class condition. The interior has a waiting room/reception/Lobby, Showroom & Space for tire accessories and wheels., unisex restroom plus an office. The Exterior Secured Entire Fenced Side Yard Space has plenty of storage area. “Chain Link Fence’. PLENTY OF SPACE FOR PARKING VEHICLES IN FRONT OF PROPERTY. Full-Service Business. High Traffic Area with Great Road Frontage, busy, corner lot, busy prime location, sits on 0.39 acres of land. Road Front Footage 542 -2 sides. US HWY 17, Avenue E SW with access from both. This is a very well-established operation with many years of experience. Great Reputation. Highly confidential, and no financial information will be released without proof of ability. A detailed list of tire inventory & tools/equipment would be given upon receiving the buyers/ability to purchase. There will continue to be demand for good local auto repair shops. This tire center & automotive repair company is perfect for someone looking to capitalize on Polk County, Central Florida's growing population. A detailed confidential summary package is available for this Winter Haven POLK COUNTY company for sale. FULLY EQUIPPED TIRE CENTER & AUTO REPAIR BUSINESS READY FOR A NEW BUYER Services include OIL CHANGE, ALIGNMENT, BRAKES, SHOCKS & TIRES. Seller is willing to entertain any and all requests you put in your offer.

304 Avenue E Sw, Winter Haven

1101 Cypress Gardens Boulevard, Winter Haven
$850,000
Royonne Place Resub SubDv. ⋅ 33884 Zip Code
“Extraordinary Commercial Property” - This 5.33-acre commercial vacant land site is a rare opportunity to own a prime piece of real estate on busy Cypress Gardens Boulevard. With 550 feet of road frontage, this property is made up of 4 separate parcels & includes a small lake of about 1.5 acres (Lake Rey) (Lake Rey is classified as a Lake in Polk County, Florida). with 2 access points on either side of the lake off Cypress Gardens Blvd. The utilities available include city water, electric, gas-LP, and public sewer. The land use designation of CR (Commercial Retail) by The City of Winter Haven is within the city limits. It allows commercial development with any retail, including but Not Limited to retail strip centers, restaurants, stand-alone retail stores, etc. This property is on the primary east/west commercial corridor in this part of Winter Haven & is minutes away from LEGOLAND Florida. Don’t miss out on this outstanding opportunity to develop and clear this land with commercial improvements. Easy access to Us Hwy 27, and Downtown Winter Haven. There Is Little to No Remaining Vacant Commercial Development Parcels Alone, this is a Highly Traveled Roadway Great traffic and potential exposure. Close to The Chain of Lakes Complex Redevelopment - (This is a major development that will occur in Winter Haven over the next several years). The listing price includes all four parcels and is set at $999,000. Parcel A has the physical address of 1101 Cypress Gardens Boulevard. Outstanding location for many prospective uses. The property was formerly known as Slocum Water Gardens.” Seller is willing to entertain any and all requests you put in your offer.

1101 Cypress Gardens Boulevard, Winter Haven

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