Remarks: Under contract-accepting backup offers. Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner Villa with wooded view. The charming kitchen has upgraded wood cabinets, solid surface counter tops, breakfast bar, and two pantry storage closets. The spacious great room has recently updated Luxury Vinyl Plank floors for easy care. Other recent updates include AC system in 2022, and Roof 3/2026.This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Marti Sutton (863-206-0563)

Remarks: Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: 1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all new flooring, paint, and granite counter tops. Make your appointment TODAY!!

Listing is courtesy of: JOHN WEBB INC (863-422-2999)

Listing Agent: Robert Webb (863-557-6229)

Remarks: Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space. With a mostly furnished interior and quick occupancy available, you can step right in and start enjoying it from day one. Located inside the gated CypressWood golf community, this home delivers true resort-style living. Spend your days enjoying the sparkling pool, tennis courts, and scenic golf course surroundings, all while the HOA takes care of lawn maintenance and exterior upkeep so you don’t have to. The location ties it all together. Just minutes from LEGOLAND Florida Resort, shopping, and dining, with quick access to Highway 27 and I-4, you’re perfectly positioned between Orlando and Tampa for work, travel, or a day out. Whether you’re looking for a full-time home or a seasonal escape, this is low-maintenance Florida living done right.

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

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

Remarks: Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open layout flows seamlessly to a peaceful sitting lanai overlooking the heated community pool—the perfect spot to enjoy your morning coffee or unwind in the evenings. Major updates add peace of mind, including a resurfaced roof with a 15-year warranty, a tankless hot water heater, and an updated electrical system. The low HOA fee of just $270/month covers water, high-speed internet, cable, gas, and all grounds maintenance—you only pay for electric! The property includes 2 assigned parking spaces, with one under a carport, and the community has ample visitor parking. Enjoy easy access to shopping, dining, and downtown Winter Haven events, all while embracing a relaxed, low-maintenance lifestyle close to the lake. Whether you’re downsizing, snowbirding, or looking for carefree Florida living, this villa checks all the boxes. Property is eligible for FHA Financing! Move in, relax, and enjoy the best of Winter Haven living!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Michele Elchin (863-514-6880)

Remarks: Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Larry King (404-441-5050)

Remarks: Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive living and dining areas with laminate flooring, a bright kitchen with updates and ceramic tile flooring. An open-concept layout that includes a wet bar with cabinet storage—perfect for entertaining. A bonus Florida room with air conditioning overlooks an open field and pond, providing a peaceful view right from your home.The primary bedroom boasts a sliding glass door leading to the enclosed lanai, filling the space with natural light and offering relaxing backyard views. Recent updates include a NEW metal roof for peace of mind. Plus, the HOA covers exterior paint, roof maintenance, lawn care, and pest control, making this home truly move-in-ready.The Cypresswood community offers incredible amenities:An 18-hole championship golf course designed by Ron Garl, Junior Olympic-sized pool, Lighted tennis courts, Fitness center & clubhouse with pro-shop, On-site restaurant and event space.Whether walking, biking, or taking the golf cart, all amenities are conveniently close by. You’ll also love the location—just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, and plenty of shopping and dining options.Don’t miss your chance to enjoy the Florida country club lifestyle in this affordable, stylish villa. Schedule your private showing today!

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: Under contract-accepting backup offers. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.

Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)

Listing Agent: Bill Sprys (407-574-9724)

Remarks: **PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Cheryl Brewer (863-224-0045)

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: 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)