Cypresswood Homes with Gated Amenities

Welcome to Cypresswood, a serene and inviting subdivision nestled in the heart of Winter Haven, Florida. Located in beautiful Polk County, Cypresswood is the perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat.

Cypresswood is renowned for its stunning homes that boast gated amenities, providing residents with an added layer of security and exclusivity. Imagine coming home to a beautifully landscaped community where your privacy is prioritized, and your peace of mind is guaranteed. The subdivision offers a variety of architectural styles, ensuring there’s a perfect home for everyone, from charming single-family residences to spacious estates.

Beyond the gates, residents enjoy a wealth of amenities designed to enhance their lifestyle. Take advantage of the community’s sparkling swimming pool, well-maintained tennis courts, and scenic walking trails that wind through lush greenery. The clubhouse serves as a social hub, hosting events and gatherings that foster a strong sense of community among neighbors.

Cypresswood is also conveniently located near Winter Haven's vibrant downtown area, where you can explore delightful shops, restaurants, and recreational opportunities, including the famous Chain of Lakes. With easy access to major highways, commuting to neighboring cities is a breeze.

Discover the charm of Cypresswood, where a secure and vibrant lifestyle awaits you. Come experience the beauty and warmth of this exceptional community—your dream home is just a visit away!

Newest Cypresswood Homes with Gated 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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