Cypresswood Homes with Golf Course Amenities

Welcome to Cypresswood, a hidden gem nestled in the heart of Winter Haven, Florida, within the picturesque Polk County. This charming subdivision offers a unique blend of tranquility and active living, making it a perfect choice for families, retirees, and golf enthusiasts alike.

Cypresswood is renowned for its stunning homes that boast golf course amenities, providing residents with a lifestyle that is both luxurious and leisurely. Imagine waking up to breathtaking views of meticulously manicured fairways and lush landscapes right in your backyard. Each home is designed with comfort and style in mind, featuring spacious layouts, modern finishes, and outdoor spaces perfect for entertaining or simply enjoying the serene surroundings.

The community itself is a haven for those who appreciate an active lifestyle. With the Cypresswood Golf and Country Club at your doorstep, you can indulge in a round of golf or partake in various social events throughout the year. The club offers a welcoming atmosphere, making it easy to forge friendships and create lasting memories with neighbors who share your passion for the game.

In addition to golf, Cypresswood is conveniently located near Winter Haven's vibrant downtown, where you can explore delightful shops, restaurants, and recreational activities. The nearby lakes and parks provide ample opportunities for outdoor adventures, whether it’s fishing, hiking, or simply soaking up the Florida sunshine.

Discover the perfect blend of luxury, community, and leisure at Cypresswood, where your dream home awaits amid the beauty of Winter Haven's golf course lifestyle. Come and experience the charm of this exceptional subdivision today!

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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