Cypresswood Homes for Sale

Cypresswood Homes for Sale

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida. Known for its serene landscapes and friendly community atmosphere, Cypresswood offers a unique blend of natural beauty and modern living. With its lush greenery, tranquil lakes, and inviting walking trails, this charming neighborhood is perfect for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Cypresswood is not just a place to live; it's a lifestyle. Residents enjoy access to a variety of amenities, including a beautiful clubhouse, community pool, and tennis courts, making it easy to stay active and engaged. The subdivision is also conveniently located near local shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away.

For those interested in making Cypresswood their home, there are a variety of homes for sale that cater to different tastes and budgets. From cozy single-family residences to spacious modern designs, you'll find a range of options that combine comfort and style. Many of these homes feature open floor plans, updated kitchens, and lush backyards, providing the perfect setting for family gatherings or quiet evenings at home.

Living in Cypresswood means embracing a community that values connection and quality of life. With its stunning surroundings and welcoming atmosphere, it’s no wonder that so many are drawn to this enchanting neighborhood. Come explore the homes for sale in Cypresswood and discover the perfect place to call home in Winter Haven, FL!

Newest Cypresswood Homes for Sale

450 Sandestin Drive, Winter Haven
$185,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
A great opportunity at an improved price! Welcome to The Meadows, a desirable community within Cypresswoods! This well-maintained home offers the perfect combination of comfort, convenience, and beautiful golf course views. Ideally situated along the golf course, you can enjoy your morning coffee while taking in the scenic views of the 13th hole. The home has been thoughtfully maintained and features a 2025 roof and 2023 HVAC system, providing added peace of mind for the next owner. The property also includes an oversized garage with a workbench. Schedule your showing today!

450 Sandestin Drive, Winter Haven
300 Greenfield Road, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
NEW PRICE POINT, SELLER IS MOTIVATED! RECENTLY REMODELED 4 BEDROOM ON THE GOLF COURSE IN THE BEAUTIFUL & GATED COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! Open, spacious floor plan & ready to move in! Enjoy the Cypresswood Country Club lifestyle, including an active clubhouse, junior Olympic size pool, pickle ball courts, tennis, golf and a great restaurant with bar! When you're not enjoying all of the amenities, take a walk or ride your bike on the quiet, tree-lined streets throughout the community! This is a one-of-a-kind, two-story classic home on an extra-large lot, so plenty of room for a swimming pool!!! No rear neighbors, just Florida nature and golf in your backyard! Great place for socializing, family gathering and just lots of relaxing! You can park a dozen cars in your driveway and room to park your fishing boat or up to 6 cars in your garage! The oversized garages come complete with a "golf cart" garage in the rear of the home. Freshly remodeled by Bill Reed Construction, the updates include a freshly painted & neutral color scheme and luxury vinyl flooring throughout. You'll enjoy the golf-course views in the updated kitchen with granite tops and GE appliances. The open & bright kitchen nook area has sliding glass doors, and the family room is adjacent as well as a spacious dining room with lots of windows to enjoy! There is a separate living room with glass sliding doors to the oversized screened lanai and features a brick wood-burning fireplace creating a cozy area with lots of "flex" space. Room for all with 4 bedrooms and the primary suite boasts a walk-in closet, built-ins, dual sinks and a modern barn door. Three of the bedrooms are on the second floor. Mature landscaping and shade trees make perfect areas for enjoying the outdoor beauty and watching golf. Cypresswood is just minutes to Highway 27, great shopping, medical and the new Publix. Right in the heart of Central Florida with a "Chain of Lakes" for boating, fishing and a great "foodie" scene in the charming downtown district. This property has so much for your family to enjoy!!! Call today to schedule your private tour!

300 Greenfield Road, Winter Haven
41 Greenfield Court, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
Premier Location overlooking the pond and the golf course. This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and dining areas, large family room, master suite with dual vanities and dual closets, oversized garage with a shower and a screen enclosed pool. From the pool deck, enjoy watching the varied species of birds that pass by or land for a stroll/swim in the back yard or pond. Cranes, Herons, Ibis, Ducks, etc. Recent updates include a roof, windows, water treatment system, AC including ducts and insulation, kitchen sink, disposal, bathroom faucets and toilet, rebuilt pool pump and filter system, driveaway resurfacing and garage floor embellishment as well as solar panels.

41 Greenfield Court, Winter Haven
1814 Sandhill Lane, 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
683 Broadmoor Circle Unit 683, Winter Haven
$193,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
NEW LOWER PRICE!! This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one, call to view today. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

683 Broadmoor Circle Unit 683, Winter Haven
Start Your Search