Winter Haven Villas For Sale - 23 villas

Remarks: Welcome to this well-kept home in the highly sought-after Cypresswood Golf and Country Club, a gated community known for its beautiful grounds and exceptional amenities. Inside, you’ll find bright, open living spaces that flow seamlessly from the living room to the dining area and kitchen, creating a warm and functional layout for everyday comfort. The kitchen offers ample cabinetry and a practical design, while the bedrooms provide generous space and a relaxing atmosphere. The bathrooms are clean, comfortable, and thoughtfully maintained. At the front of the home, a charming courtyard gives you a private spot to unwind or personalize with your own touches. Residents of Cypresswood enjoy access to golf, tennis, and an on-site clubhouse restaurant, all within a peaceful, well-established community. With convenient access to Winter Haven’s shops, dining, lakes, and major roadways, this home offers a perfect blend of comfort, lifestyle, and location.

Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)

Listing Agent: Darin Dobson (407-947-6773)

Remarks: Best-Priced 2BR Villa with Garage in Vienna Square – and it’s a corner! Built 2022 Welcome to one of the best values in Vienna Square—this corner unit is a light-filled 2-bedroom, 2-bath villa with a 2+ car private garage. You’ll have low-maintenance living in one of Winter Haven’s most sought-after 55+ communities. Built in 2022, this home features a bright, open-concept layout with a seamless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The kitchen offers modern finishes, tons of cabinets, and great sightlines into the main living space. New stainless refrigerator and microwave in December 2025! In-unit laundry closet for convenience! The spacious primary suite includes a private bathroom and 2 generous walk-in closets. The second large bedroom and full bath provide flexibility for guests or a home office. Enjoy your morning coffee or unwind in the evening on the screened lanai, offering a quiet and comfortable outdoor retreat. Refreshed inside and out with most main furniture included. Vienna Square is known for its active, pet-friendly lifestyle and amenities, including a clubhouse, resort-style pool, fitness center, and social activities—all with a convenient location close to shopping, dining, and medical facilities. Association fees include: • Exterior paint • Roof maintenance • Irrigation water • Lawn mowing • Shrub trimming • Spectrum Internet and TV Priced to sell—schedule your showing today. Easy to show for buyer’s agents using ShowingTime.

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Discover comfortable, low-maintenance living in this inviting 2 bedroom, 2 bath villa located in a small 55+ community in Winter Haven. This well-designed home features vaulted ceilings, great natural light, and a spacious split bedroom layout, giving you and your guests plenty of privacy. Both bedrooms offer generous proportions and walk-in closets, and the primary suite includes a convenient step-in shower.The living room opens to a 12x12 covered patio through sliding glass doors, creating an easy indoor-outdoor flow for relaxing or enjoying fresh air. The one-car garage includes an electric roll-down screen, perfect for ventilation while keeping the space shaded and tidy. Additional highlights include a whole-house water treatment and softener, plus a new roof in 2024 for added peace of mind.The low HOA covers exterior paint, building and roof maintenance, irrigation system repairs, the community wall, and road upkeep, making day-to-day living simple and stress free.This community offers a convenient location near the bus line, medical offices, hospitals, shopping, and dining. You are also close to Winter Haven’s vibrant downtown filled with boutiques, restaurants, and year-round events, along with the city’s beautiful Chain of Lakes known for boating, fishing, and waterfront dining. Ideal for full-time residents or seasonal buyers looking for comfort, convenience, and a welcoming 55+ setting.

Listing is courtesy of: KEYSTONE RESIDENTIAL GROUP LLC (407-556-3249)

Listing Agent: Lisa Bertossa (407-709-1447)