Cypresswood Homes for Sale

Cypresswood Homes for Sale

Cypresswood is a charming subdivision located in Winter Haven, Polk County, Florida. This sought-after community offers a mix of single-family homes and townhouses, making it an ideal place for families, retirees, and young professionals alike. With well-maintained streets, lush landscaping, and a tranquil atmosphere, Cypresswood provides residents with a peaceful retreat while still being conveniently located near shopping, dining, and entertainment options.

Homes for sale in Cypresswood are known for their spacious layouts, modern amenities, and beautiful architectural designs. Whether you're looking for a cozy two-bedroom home or a larger property with multiple bedrooms and a backyard, Cypresswood has something to offer for every taste and budget. From cozy townhouses perfect for first-time buyers to luxurious estate homes with golf course views, there is a diverse range of options available in this desirable neighborhood.

If you're considering making Cypresswood your new home, now is a great time to explore the available properties and find your perfect match in this lovely community.

Newest Cypresswood Homes for Sale

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 the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and dishwasher. As you enter, you will find the open and bright kitchen with all Stainless Steel appliances on the immediate right hand side of entryway. The dining room is open to the living room and it will handle a large dinning room set for company dinning. The living room opens to a slight step down into a less formal family room area which overlooks the lush setting of the tropical, backyard landscaping, a beauty to enjoy from your rear windows. The community clubhouse, restaurant and swimming pool are just a few steps away. The tennis courts and pickle ball courts are currently being resurfaced.

1052 Medinah Drive, 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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Kristi Grady- Broker/ Owner

Meet Kristi Grady When it comes to buying or selling a home, having the right real estate professional by your side can make all the difference. At HomeTrust Real Estate & Property Management, we believe every client deserves honest advice, expert guidance, and exceptional service throughout the entire process. Kristi Grady, Broker and Co-Owner of HomeTrust, brings more than 12 years of experience helping buyers, sellers, investors, and families successfully navigate the real estate market throughout Lakeland, Polk County, and Central Florida. Whether you're purchasing your first home, upgrading to your dream home, selling a property, or building an investment portfolio, Kristi is committed to making the process as smooth and stress-free as possible. For buyers, Kristi provides personalized guidance, local market expertise, and skilled negotiation to help clients find the right property at the best possible price. For sellers, she utilizes professional marketing strategies, high-quality photography and video, social media advertising, and proven pricing techniques designed to maximize exposure and achieve top dollar. As a local market expert, Kristi understands the neighborhoods, schools, market trends, and property values that impact buying and selling decisions. Her knowledge and experience help clients make informed decisions with confidence. Kristi also has extensive experience working with real estate investors, assisting with the acquisition, management, and sale of income-producing properties and investment portfolios. She understands the unique goals of investors and provides strategic guidance to help maximize returns and long-term success. In addition, Kristi has a special passion for helping seniors and their families navigate major life transitions. Whether downsizing, relocating closer to family, or moving into assisted or supportive living environments, she provides compassionate guidance and personalized support during what can often be an emotional and challenging process. Known for her communication, professionalism, and dedication to her clients, Kristi takes pride in building lasting relationships and delivering results. Her goal is simple: to help every client achieve their real estate goals while providing a level of service that exceeds expectations. When you're ready to buy, sell, invest, or plan your next move, Kristi is ready to put her experience and expertise to work for you.

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Ryan Grady- REALTOR®/Owner

Meet Ryan Grady Real estate is more than buying and selling homes—it's helping people make some of the biggest financial decisions of their lives with confidence. Ryan Grady, Co-Owner of HomeTrust Real Estate & Property Management, has spent more than 12 years helping buyers, sellers, investors, and landowners navigate the real estate market throughout Lakeland, Polk County, and Central Florida. His passion for helping people, combined with extensive market knowledge and strong negotiation skills, has earned him a reputation for delivering exceptional results while providing a level of service that keeps clients coming back and referring their friends and family. Whether you're a first-time homebuyer, relocating to Florida, searching for investment opportunities, selling a family home, or purchasing commercial land, Ryan understands that every client and every transaction is unique. He takes the time to listen, understand your goals, and develop a strategy designed to help you succeed. One of the qualities clients appreciate most about Ryan is his commitment to communication. Real estate transactions can be stressful, but Ryan believes clients should never be left wondering what comes next. From the initial consultation through closing day, he keeps clients informed, answers questions promptly, and guides them through every step of the process. As a lifelong resident of Polk County, Ryan brings invaluable local knowledge to every transaction. He understands neighborhood trends, school districts, growth patterns, investment opportunities, and the factors that impact property values. This local expertise allows him to help clients make informed decisions whether they are buying, selling, or investing. Ryan and his wife, Kristi, founded HomeTrust Real Estate & Property Management with a simple mission: provide honest advice, exceptional service, and a client-first approach that puts relationships above transactions. Together, they have helped hundreds of families and individuals successfully navigate the real estate process while building a business rooted in trust, integrity, and results. Today, HomeTrust proudly serves buyers, sellers, investors, landlords, and tenants throughout Central Florida. Through professional marketing, expert negotiation, cutting-edge technology, and a commitment to personalized service, Ryan works tirelessly to help clients achieve their real estate goals. When you're ready to make your next move, Ryan is ready to put his experience, knowledge, and dedication to work for you. Your goals become our mission, and your success becomes our success.

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