Cypresswood Villas For Sale in Winter Haven - 11 villas

Remarks: Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.

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

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

Remarks: Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

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 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.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Della Landfear (863-698-8057)

Remarks: JUST REDUCED!!! SPACIOUS THREE BEDROOM ENCLAVE UNIT WITH A TRANQUIL VIEW IN CYPRESSWOOD GOLF & COUNTRY CLUB!!! VILLA WITH OVER 2,000 PLUS SQ. FT. LIVING 3 BEDROOM 3 BATH PLAN AND NEW TILE FLOORING IN THE PRIMARY BATH, NEW ROOF IN 2023. You will enjoy this maintenance-free home, the largest villa floor plan in the Cypresswood Enclave designed with an open floor plan, volume ceilings and tranquil pasture views! Upgrades include beautiful hardwood floors & plantation shutters. The eat-in kitchen boasts real wood cabinets, solid surface counter tops & stainless appliances with a gas stove the "Chef" will appreciate! There is privacy for all with a triple split design featuring 3 bedrooms and 3 full baths with two "En-suite" primary bedrooms that are both spacious with a walk-in shower, dual vanities and separate soaking tub. There is an abundance of walk-in closets & great storage. The skylights allow for extra natural light in this well-cared for home - bright & airy throughout! There are no rear neighbors. You'll love the pasture views & the cattle ranch allows for expansive views for the nature lovers. The 2-car garage with workbench is a perfect hobby spot. Cypresswood is best known for its fabulous Florida lifestyle - golf course, 24 hr. manned security gate, tennis courts, large community pool, biking, walking, and you'll appreciate the clubhouse restaurant with local musical venues! This property is within close proximity to shopping, restaurants, LEGOLAND, and so much more, so call today to set up a private showing!!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture, and the Interior was Freshly Painted. The owners are including the 75 Inch TV with the Entertainment Center in the Living Room. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy your favorite show on TV. The Home is located close to Shopping (New Publix opening soon), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: David Shippey (863-521-4517)

Remarks: Under contract-accepting backup offers. ON THE GOLF COURSE. GORGEOUS VIEWS AND SUNSETS! Well maintained 2 bed / 2 bath golf villa overlooks the 8th fairway and features split bedrooms, large living /dining combo, enclosed lanai with heat and air, partially covered courtyard, rear patio and carport parking space.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

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: Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven. The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened lanai and a 2 car garage with garage door opener. Per the owner, recent upgrades include removal of a wall separating the kitchen from the living area thereby creating a true open-concept living area, upgraded matching stainless kitchen appliances, flooring in the kitchen, living room, foyer, hall and 2 bedrooms, New granite counter-tops, sinks and faucets in the kitchen and both bathrooms, new LED lighting, New front entry door, new window treatments and fresh interior paint. This is truly a move-in-ready villa with quality upgrades that set it ahead of the competition. Come and enjoy the Florida Country Club Lifestyle in this low maintenance villa.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

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)