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1908 Crossroads Boulevard, Winter Haven
$375,000
4 Beds ⋅ 3 Baths ⋅ Crossroads At Lake Region SubDv. ⋅ 33881 Zip Code
MAJOR PRICE DROP! SELLER MOTIVATED!!! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!

1908 Crossroads Boulevard, Winter Haven

5163 Kinsley Drive, Winter Haven
$339,999
4 Beds ⋅ 3 Baths ⋅ Seasons At Annabelle Estates SubDv. ⋅ 33884 Zip Code
This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the home. Special financing rates and closing cost assistance may be available. Options may vary by community and offers are available on select homes only. Contact builder for more information!

5163 Kinsley Drive, Winter Haven

100 Lakeside Ranch Drive, Winter Haven
$120,000
2 Beds ⋅ 2 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
LAKEFRONT COMMUNITY...Welcome home to Lakeside Ranch, a gated 55+ community with NO LOT RENT! This 2 Bedroom/2 Bath home features a large living room that leads to the lovely Florida room.This open concept home has a tastefully renovated kitchen with lots of counterspace and cabinets, a dining room with built-in cabinetry, a large living room with lighted ceiling fan, luxury vinyl plank flooring throughout. Utility shed all offers additional storage space and includes washer and dryer. Sold Furnished or Vacant, your choice. HOA inscludes water, sewer, lawn service and security. The community features a large clubhouse with a variety of scheduled activities and holiday events, library, meeting space, a boat ramp and fishing dock on Lake Henry, trailer storage area, heated swimming pool, shuffleboard, horseshoe area, and a billiards room. Are you ready for an active lifestyle? Or just relax and fish the day away? This is the place for you either way! Live here year-round or escape the cold winters in sunny Florida!

100 Lakeside Ranch Drive, Winter Haven

2218 Abbey Road, Winter Haven
$179,999
2 Beds ⋅ 2 Baths ⋅ Stonebridge Vls Ph 02 SubDv. ⋅ 33880 Zip Code
Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

2218 Abbey Road, Winter Haven

1505 Dundee Road, Winter Haven
$800,000
Acreage SubDv. ⋅ 33884 Zip Code
Seller has replaced the roof on the building. UP AND COMING NEIGHBORHOOD with lots of shopping, homes and commercial offices. Multi-purpose Commerical/Residential property centrally located on Dundee Rd in Winterhaven. 3 parcels total 10.98 acres. Used to be the home of Boss Hogg Radio. Offers high visibility in a highly traveled intersection with excellent exposure directly on the highway. Building is 2,004 sq ft. with a reception area, bathroom, kitchen and an office, along with a paved parking area. Satellite is currently leased on a monthly basis at $1500, and conveys. The annual average daily traffic for this part of Dundee Road is approximately 16,000 cars/day! This is a great opportunity to either use the existing building or make an addition and build your own. Potential for restaurant, radio stations, professional offices & more. Lot with building is commercial; 2 other lots are deemed residential. Survey shows potential. 40 minutes from Walt Disney World, 20 minutes to Kissimmee, and 52 minutes to Orlando Int'l.

1505 Dundee Road, Winter Haven

Spirit Lake Road, Winter Haven
$175,000
33880 Zip Code
**Prime Commercial Lot for Sale – Spirit Lake Road, Winter Haven, FL** **Location, Location, Location!** This is a rare opportunity to own a prime commercial lot in one of Winter Haven's highest-traffic areas. Located directly on Spirit Lake Road, this vacant parcel is surrounded by thriving businesses, making it an ideal spot for your next commercial venture. With McDonald's as your neighbor, you’ll benefit from the constant flow of foot and vehicle traffic. Additionally, the lot is just a short distance from the Polk Parkway and the world-famous Legoland Florida Resort, bringing millions of visitors to the area each year. **Property Highlights:** - **High Traffic Exposure**: Located in a bustling commercial corridor, providing maximum visibility and easy access for customers. - **Proximity to Major Attractions**: Just minutes from Legoland and the Polk Parkway, ensuring a steady stream of potential customers. - **Neighboring McDonald's**: High-traffic area with established businesses, ensuring you’re in great company. - **Ideal for Retail, Dining, or Office Use**: The flat, spacious lot is versatile and ready for your business ideas. - **Easy Access**: Great road frontage and access to major routes ensure customers will have no trouble finding your location. Whether you're looking to expand your business, open a new restaurant, or develop a retail center, this lot offers an exceptional location to achieve your goals. The combination of high visibility, prime location, and proximity to major attractions makes this an unbeatable investment opportunity. **Don’t miss out on this incredible chance to own a piece of Winter Haven’s commercial future. Contact us today for more information and to schedule a showing!**

Spirit Lake Road, Winter Haven

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

2106 1st Street N, Winter Haven
$265,000
Florence Citrus Growers Assn Sub SubDv. ⋅ 33881 Zip Code
Prime commercial opportunity in a high-visibility location with strong owner-user and investment potential. Freestanding commercial building Just price reduced for you to start your own business. Prime corner lot with a well-established stand alone operating business for over 20 years. This commercial property offers incredible potential and could be converted for other uses with county approval. The roof is only 4 years old, and the AC unit is about 1.5 years old. It has 8 hair stylist chairs, 3 shampoo chairs, 10 waiting chairs and 9 dryers all included in the price. While the property needs some TLC, it’s priced accordingly—making it a fantastic investment. Don’t miss this chance to be your own landlord/boss! Call today for more details. Some photos are staged.

2106 1st Street N, 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

Gerber Dairy Rd, Winter Haven
$49,000
Devonwood SubDv. ⋅ 33880 Zip Code
Take hold of this chance to own a spacious 1.05-acre vacant lot on Gerber Dairy Road in Winter Haven, FL 33880! "Zoning: RC" Located in a tranquil, rural area, this lot providing a blank slate for your custom spot. Buyers should note that parcels in this area typically have dirt road access and require the installation of a well and septic system . This is a perfect opportunity for those seeking a larger, private lot in the growing Polk County, ideal for building the ultimate peaceful Florida retreat.Pin Location: Latitude 27.94750974 , Longitude -81.75258632. Note: buyers I emphasize the importance of conducting thorough due diligence to ensure that the property meets your expectations and requirements.

Gerber Dairy Rd, Winter Haven