Cypresswood Homes with Tennis Court(s) Amenities

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida, within beautiful Polk County. This charming community is not just a place to live; it’s a lifestyle choice that offers a perfect blend of tranquility and recreation. Cypresswood is renowned for its lush landscapes, friendly neighbors, and a strong sense of community, making it an ideal setting for families, retirees, and everyone in between.

One of the standout features of Cypresswood is its exceptional amenities, particularly for those who enjoy an active lifestyle. The community boasts several homes equipped with private tennis courts, providing residents with the opportunity to indulge in their favorite sport right in their own backyard. Whether you're a seasoned player or just starting out, these courts offer the perfect venue for friendly matches, family fun, or even a bit of competitive spirit. Imagine enjoying a sunny afternoon rallying with friends or hosting a neighborhood tournament just steps from your door!

In addition to tennis, Cypresswood offers a variety of recreational amenities, including walking trails, swimming pools, and beautifully maintained common areas that encourage outdoor gatherings and social events. With its prime location in Winter Haven, residents also have easy access to shopping, dining, and the stunning lakes that make this area so desirable.

If you’re looking for a place that combines the charm of a close-knit community with the luxury of recreational amenities, Cypresswood is the perfect destination to call home. Explore the possibilities and discover your dream home today in this wonderful Winter Haven community!

Newest Cypresswood Homes with Tennis Court(s) 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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