Cypresswood Homes with Golf Course Amenities

Welcome to Cypresswood, a serene and picturesque subdivision nestled in the heart of Winter Haven, Florida. This charming community, located in Polk County, boasts a unique blend of natural beauty and modern living, making it an ideal place for families, retirees, and golf enthusiasts alike.

Cypresswood is renowned for its stunning homes that offer golf course amenities, providing residents with an unmatched lifestyle. Picture waking up to panoramic views of lush fairways and meticulously maintained greens right from your backyard. Whether you're an avid golfer or simply enjoy the tranquility of the landscape, living in Cypresswood means you’ll have direct access to a beautifully designed golf course that challenges players of all skill levels.

The homes in this community are crafted with care, featuring spacious layouts, modern finishes, and outdoor living spaces perfect for entertaining. Many properties come equipped with private pools, gourmet kitchens, and expansive patios, allowing you to fully embrace the Florida lifestyle. The community itself is well-maintained, with tree-lined streets, parks, and recreational areas that encourage outdoor activities and foster a strong sense of community.

Beyond the golf course, Cypresswood offers a variety of amenities, including clubhouses, swimming pools, and walking trails, ensuring that residents have everything they need for a fulfilling lifestyle. With its prime location in Winter Haven, you're just a short drive away from shopping, dining, and the stunning lakes that make this area so special.

Discover the charm of Cypresswood, where every day feels like a vacation, and your dream home awaits!

Newest Cypresswood Homes with Golf Course Amenities

$249,900

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

$462,000

4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

Here is your opportunity to own an immaculate home in the sought after community of Cypresswood Golf and Country Club. Consistently voted the Number 1 Golf Course in the area. This vibrant community has it all. Aside from the fantastic course right out your door, enjoy everything else it has to offer. A wonderful restaurant and Club House where they host live music 3 nights a week and top notch food offerings. An Olympic size pool that was just recently redone along with newly redone tennis courts and pickle ball courts. There is even a fitness center. Take a drive in your golf cart in the evenings and enjoy the natural elements and animals that Central Florida is famous for. Bald Eagles, wild turkey, Sand Cranes are just some of the sights you are likely to see on your ride. Then, come home to your beautifully maintained home that allows for easy entertaining, or peaceful times out on the back screened in patio where you can watch golfers and animals alike. The combination kitchen and family room is second to none. Stainless steel appliances including a new dishwasher for the experienced chef or novice. You can't help enjoying cooking in this home. Second bedroom with it's own ensuite full bath, and two other bedrooms that share a Jack and Jill full bath. You will find storage gallore everywhere you look. Peaceful yard offers privacy and views for days. Come and tour this home today, and you will know that you have found The One!

1814 Sandhill Lane, Winter Haven

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