Cypresswood Homes with Pool Amenities

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida. Known for its serene landscapes and vibrant community spirit, Cypresswood offers a perfect blend of comfort and convenience, making it an ideal choice for families and retirees alike.

As you stroll through the tree-lined streets, you'll immediately notice the charming homes that define this neighborhood. Many of these residences feature stunning pool amenities, providing a refreshing oasis right in your backyard. Imagine spending sun-soaked afternoons lounging by your sparkling pool, hosting barbecues with friends, or enjoying peaceful evenings under the stars. In Cypresswood, your dream of a private retreat is not just a fantasy—it's a reality.

The subdivision boasts a variety of home styles, ensuring there’s something for everyone. Whether you’re looking for a cozy single-family home or a spacious residence perfect for entertaining, you’ll find it here. With well-maintained properties and lush landscaping, Cypresswood radiates a welcoming atmosphere that invites you to settle in and make lasting memories.

Beyond the homes, Cypresswood is conveniently located near a wealth of amenities. Residents enjoy easy access to shopping, dining, and recreational activities, including the nearby lakes and parks that Winter Haven is famous for. Plus, with its close-knit community vibe, you'll quickly feel at home among friendly neighbors.

Discover the charm of Cypresswood—where your ideal home with pool amenities awaits in beautiful Winter Haven, Florida. Embrace the lifestyle you’ve always dreamed of and make Cypresswood your new sanctuary today!

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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