Cypresswood Homes with Tennis Court(s) Amenities

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida, within the scenic Polk County. This charming community is characterized by its lush landscapes, friendly atmosphere, and an array of amenities that cater to both relaxation and recreation.

One of the standout features of Cypresswood is its commitment to an active lifestyle, highlighted by the presence of tennis courts that invite residents to engage in friendly matches and enjoy the sunshine. Whether you're a seasoned player or just looking to pick up a racket for the first time, these courts provide the perfect setting for fun and fitness. The well-maintained facilities ensure that you can enjoy a game at your leisure, fostering a sense of community among neighbors and friends.

The homes in Cypresswood are designed with comfort and style in mind, offering a variety of floor plans to suit different tastes and lifestyles. Many properties feature spacious yards, perfect for outdoor gatherings or simply soaking up the Florida sun. The community's peaceful ambiance, combined with the vibrant social opportunities provided by the tennis courts, makes it an ideal place to call home.

Beyond the gates of Cypresswood, you'll find the charm of Winter Haven, known for its beautiful lakes, parks, and a welcoming community spirit. With easy access to shopping, dining, and entertainment, residents enjoy the perfect balance of tranquility and convenience.

Discover the allure of Cypresswood, where your dream home awaits, complete with the amenities and lifestyle you've always desired. Come and experience the warmth of this delightful community today!

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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