Cypresswood Homes with Golf Carts OK Community Features

Cypresswood Homes with Golf Carts OK Community Features

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida. Located in beautiful Polk County, this vibrant community is perfect for those seeking a blend of tranquility and active living. Cypresswood is renowned for its friendly atmosphere, where neighbors become friends, and every day feels like a vacation.

One of the standout features of Cypresswood is its golf cart-friendly environment, making it a unique and convenient choice for residents. Here, you can easily navigate the community with your golf cart, whether you’re heading to the clubhouse, visiting friends, or enjoying a leisurely ride around the scenic streets. This feature not only promotes a relaxed lifestyle but also fosters a strong sense of community among residents.

Cypresswood boasts an array of amenities designed to enhance your living experience. Residents can take advantage of the stunning golf course, perfect for both avid golfers and those looking to enjoy a leisurely day outdoors. The community also features beautifully landscaped parks, walking trails, and recreational facilities, ensuring that there’s always something to do, whether you prefer a quiet stroll or an active day out.

The homes in Cypresswood are thoughtfully designed, offering a variety of styles and sizes to suit every family’s needs. With spacious layouts and modern finishes, each residence is a perfect canvas for creating your dream home.

Experience the charm and warmth of Cypresswood, where a connected community and a golf cart-friendly lifestyle await you. Discover your new home today in this idyllic Winter Haven neighborhood!

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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Brian Scott Smith PA

Before launching his real estate career, Brian Smith spent over a decade in the construction industry, working hands-on with builders throughout Central Florida. That experience gave him an in-depth understanding of the homebuilding process—insight he now brings to his real estate clients, offering a level of expertise that sets him apart from most agents. In 2012, Brian joined his family’s firm, ERA Professional Realty. It was a “sink or swim” environment, and at the time, he wasn’t sure why his parents were so tough on him. Looking back, he’s grateful—they were preparing him for the challenges of a demanding industry, and that foundation shaped the dedicated, knowledgeable agent he is today. Since then, Brian has consistently ranked among the area’s top producers. His success is built on attention to detail, deep market knowledge, and a genuine commitment to client service. He stays current with real estate technology and prides himself on creating a smooth, informed experience for every buyer and seller. Brian has helped countless retirees transition to and from Florida, and he takes particular pride in assisting veterans and seniors through major life changes. In 2015, he was honored as REALTOR® of the Year at ERA Grizzard Real Estate. Today, he continues to list and sell millions of dollars in residential real estate annually and is expanding into commercial properties to serve an even broader range of client needs. A fifth-generation Floridian, Brian was born and raised in Central Florida. His local knowledge runs deep—something clients find to be a true asset when navigating the real estate market. Outside of work, Brian’s greatest pride is being a dad. He enjoys fishing with his son and watching his daughters grow into her own unique spirit. If you’re thinking about making a move, Brian Smith, REALTOR®, is a full-time agent ready to bring hard work, experience, and local expertise to your next real estate transaction.

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