Cypresswood Homes with Golf Course Amenities

Welcome to Cypresswood, a hidden gem nestled in the heart of Winter Haven, Florida. This enchanting subdivision offers a unique blend of serene living and active lifestyle, making it the perfect choice for families, retirees, and golf enthusiasts alike. With its lush landscapes and picturesque surroundings, Cypresswood embodies the essence of Florida living.

One of the standout features of this community is its exceptional golf course amenities. Imagine waking up to breathtaking views of meticulously manicured greens right from your window. Whether you're an avid golfer or simply enjoy the tranquility of the fairways, Cypresswood provides a lifestyle that revolves around outdoor leisure and recreation. Residents can take full advantage of the championship golf course, complete with a pro shop and practice facilities, ensuring that both seasoned players and newcomers can enjoy the sport.

The homes in Cypresswood are designed with comfort and elegance in mind, offering a variety of floor plans to suit diverse needs. From cozy single-family homes to spacious villas, each residence is crafted with quality materials and modern finishes. Many properties feature expansive patios and outdoor spaces, perfect for entertaining friends or simply soaking up the Florida sunshine.

With its prime location in Polk County, residents of Cypresswood enjoy easy access to Winter Haven's vibrant downtown, shopping, dining, and recreational activities. The community's friendly atmosphere fosters a strong sense of belonging, making it easy to connect with neighbors and create lasting friendships.

Discover the charm of Cypresswood, where golf course living meets the warmth of community. 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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