Cypresswood Homes with Gated Amenities

Welcome to Cypresswood, a serene and picturesque subdivision nestled in the heart of Winter Haven, Florida. Known for its stunning landscapes and vibrant community, Cypresswood offers residents a perfect blend of tranquility and modern living. This charming neighborhood is situated in Polk County, where the sun shines bright and outdoor activities abound.

Cypresswood is not just a place to live; it’s a lifestyle. The subdivision features an array of beautiful homes, each thoughtfully designed to cater to diverse tastes and preferences. With a variety of architectural styles, from cozy single-family residences to spacious estates, there’s something for everyone in this inviting community. Each home is surrounded by lush greenery and meticulously maintained yards, creating a warm and welcoming atmosphere.

One of the standout features of Cypresswood is its gated amenities, ensuring a secure and peaceful environment for all residents. The gated entrance provides an added layer of privacy, allowing you to enjoy your surroundings without worries. Residents can take advantage of the community’s recreational facilities, including a sparkling swimming pool, tennis courts, and walking trails that wind through the scenic landscape.

Living in Cypresswood means you are just minutes away from the vibrant culture and attractions of Winter Haven, including beautiful lakes, shopping centers, and local dining hotspots. Whether you’re looking for a family-friendly neighborhood or a peaceful retreat, Cypresswood is the perfect place to call home. Come and experience the charm of this exceptional community where comfort and convenience meet.

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 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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