Cypresswood Homes with Gated Community - Guard Community Features

Cypresswood Homes with Gated Community - Guard Community Features

Welcome to Cypresswood, a charming subdivision nestled in the heart of Winter Haven, Polk County, Florida. Known for its picturesque landscapes and serene atmosphere, Cypresswood offers residents a peaceful retreat away from the hustle and bustle of city life.

One of the standout features of Cypresswood is its gated community, providing residents with an added layer of security and privacy. With a guard on duty, you can rest easy knowing that your home and loved ones are well-protected. This sought-after feature is perfect for families, retirees, and anyone who values peace of mind.

Cypresswood boasts a variety of homes, each with its own unique charm and character. From cozy single-family residences to spacious luxury estates, there is something to suit every taste and lifestyle. Whether you prefer a contemporary design or a more traditional style, you'll find the perfect home to call your own in this welcoming community.

Aside from its gated community, Cypresswood offers an array of amenities for residents to enjoy. Take a leisurely stroll along the well-maintained sidewalks, play a round of golf on the championship golf course, or relax by the community pool. There are also tennis courts, a clubhouse, and scenic walking trails, providing endless opportunities for outdoor recreation and socializing with neighbors.

Conveniently located just a short drive away from shopping, dining, and entertainment options, Cypresswood offers the best of both worlds - tranquility and accessibility. Whether you're looking for a place to retire, raise a family, or simply enjoy a peaceful lifestyle, Cypresswood is the perfect place to call home. Come and discover the beauty and charm of this exceptional subdivision today.

Newest Cypresswood Homes with Gated Community - Guard Community Features

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

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

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

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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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