Cypresswood Homes with Golf Carts OK Community Features

Cypresswood Homes with Golf Carts OK Community Features

Welcome to Cypresswood, a charming subdivision nestled in the heart of Winter Haven, Florida, within the scenic Polk County. This vibrant community is perfect for those who appreciate the beauty of nature and the joys of a close-knit neighborhood. Cypresswood offers a unique blend of tranquility and convenience, making it an ideal place to call home.

One of the standout features of Cypresswood is its welcoming atmosphere, where golf carts are not just permitted, but embraced! Residents enjoy the freedom of cruising through the neighborhood and accessing nearby amenities in style. Picture yourself gliding along tree-lined streets, greeting friendly neighbors, and soaking in the sunshine—all from the comfort of your golf cart.

Cypresswood boasts a variety of beautifully designed homes, each reflecting a commitment to quality and comfort. Whether you’re seeking a cozy single-family residence or a spacious family home, you’ll find options that cater to your lifestyle. The community is thoughtfully designed with lush landscaping, serene walking paths, and recreational areas that encourage outdoor activities and social interactions.

In addition to its picturesque surroundings, Cypresswood offers convenient access to local shopping, dining, and entertainment options. Enjoy the nearby lakes and parks, perfect for weekend picnics or leisurely strolls. With its golf cart-friendly environment and community-focused spirit, Cypresswood is more than just a place to live—it's a lifestyle waiting to be embraced. Come discover the charm of Cypresswood and make it your new home in Winter Haven!

Newest Cypresswood Homes with Golf Carts OK Community Features

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

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

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has been thoughtfully updated with stainless steel appliances, quartz countertops, and all new cabinetry, along with a convenient passthrough window to the large glass-enclosed sunroom with A/C, making entertaining effortless while enjoying the view. The interior also features crown molding, new luxury vinyl plank flooring throughout the living areas, and new carpet in the bedrooms. Both bathrooms have been fully updated and include dual sink his-and-her vanities. Additional highlights include a new roof, a formal dining space, a side-entry two-car garage, fresh front landscaping, and a welcoming covered front porch, all combining to create a move-in-ready home in a desirable golf community setting. Cypresswood Golf & Country Club is a gated community with a 24 hour guard that hosts social and recreational events and features an 18-hole championship golf course designed by award-winning designer Ron Garl. In addition to golf, the facilities include a pro shop, wellness center, lounge, dining rooms, swimming pool, tennis courts, and trails. They also offer excellent practice facilities, including a putting green, chipping green and driving range. Golf carts are allowed throughout the community.

241 Greenfield Road, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.

1012 Medinah Dr Se, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

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

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Corey Lott

As a Native Floridian, and with 23 years of experience in Real Estate sales, 13 Years as a Broker, I pride myself in consistently providing exemplary services that I provide my clients. I guide you through the process of selling or buying your NextHome, and make that experience a positive outcome that helps you reach your goals! When you hire me, I am your confidant, your trusted partner, leading you through the sale or purchase of your NextHome with diligence, care, and persistence, as your advocate throughout the transaction and for years to come! I am a Florida Native, a career educator, a Master’s Degree in Leadership, and a Seasoned Real Estate Broker for over 20 years. Coverage Area includes all of Central Florida, Palm Beach, Broward, St. Lucie, Martin, as well as Miami-Dade. My brokerage is a member of Orlando Regional Realtor Associations covering 19 counties, Lake-Sumter, and Beaches MLS.

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Eric Stalnaker - Realtor

Eric-Stalnaker

I’m here to make your real estate journey not just smooth, but truly rewarding. Whether you’re buying your first home, upgrading, or investing, you deserve an agent who leads with honesty, patience, and care—and that’s exactly what I bring to the table. As a retired elementary school teacher, I know the value of trust, courtesy, and commitment. Just as I once guided my students with dedication, I now guide my clients with that same steady hand—always taking the time to listen, explain, and go the extra mile. With me, you’ll never feel rushed or pressured. Instead, you’ll have a trustworthy partner who ensures you’re informed and confident every step of the way. From navigating the market to negotiating the best deals, I’ll always put your needs first—and our relationship will never end at the closing table. Let’s build more than a transaction. Let’s build a partnership rooted in trust and care. I’d be honored to help you find your place to call home—reach out today, and let’s begin this exciting journey together.

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Shannon Bass

Looking for an agent who is both committed to your needs and capable of delivering results? Your search ends here - I am a full-time agent who provides top-notch service. With a strong work ethic and a focus on my clients' best interests, I work alongside a team of skilled professionals who know how to get the job done. As a NextHome agent, I prioritize #humansoverhouses and am excited to demonstrate my abilities to you.I am passionate about real estate for a variety of reasons! The excitement of buying or selling a property, the challenge of negotiating deals, the opportunity to help people find their dream homes or investments, and the satisfaction of seeing a project through from start to finish in a constantly changing and dynamic industry are just a few!I serve the Central Florida area specializing in Lake, Sumter, Marion, and Citrus counties. I live in Grand Island, Florida and enjoy helping my friends and neighbors find their next home, first home, or sell their current home! Not ready to buy? I can also help you find a rental!

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