Cypresswood Homes with Pool Amenities

Welcome to Cypresswood, a beautiful subdivision nestled in the heart of Winter Haven, Florida, within the scenic Polk County. This charming community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in sunny Florida.

Cypresswood is renowned for its lush landscaping and picturesque surroundings, creating a welcoming atmosphere for residents. The subdivision is characterized by its well-maintained homes, many of which feature stunning pool amenities. Imagine stepping into your own backyard oasis, where you can unwind in your private pool, host summer barbecues, or simply soak up the Florida sun. With pool amenities readily available, your home becomes a sanctuary for relaxation and recreation.

In addition to the inviting homes, Cypresswood boasts a variety of community features that enhance the living experience. Residents enjoy access to walking trails, scenic parks, and community events that foster a sense of belonging. The location is also a stone's throw away from Winter Haven's vibrant downtown, where you can explore delightful shops, restaurants, and entertainment options.

For those who appreciate an active lifestyle, Cypresswood is conveniently located near several golf courses and recreational facilities, ensuring that there's always something to do. Whether you're taking a leisurely stroll through the neighborhood or diving into your pool on a warm afternoon, Cypresswood offers a lifestyle that balances relaxation and activity.

Discover your dream home in Cypresswood, where the charm of Winter Haven meets the comfort of poolside living. Your perfect Florida retreat awaits!

Newest Cypresswood Homes with Pool 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 baseboard trim 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. 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, 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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