Cypresswood Homes for Sale in Winter Haven - 31 homes

Remarks: 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.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Darlene Bice (863-293-1141)

Remarks: Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Melissa Witter (863-206-8744)

Remarks: Virtually Staged. Brand New 2026 Custom Farmhouse Blends Modern Luxury with Exceptional Craftsmanship. Welcome to 4050 Palma Ceia Circle, a stunning new construction one story farmhouse estate located within the gated Cypresswood Golf & Country Club in Winter Haven, Florida. Perfectly positioned on an almost half acre double front golf course lot, this exceptional residence offers the ideal combination of luxury, quality craftsmanship, and modern convenience. Thoughtfully designed for comfortable living and effortless entertaining, this home features 3 bedrooms, 3.5 bathrooms, a dedicated home office, elegant tray ceilings, luxury tile flooring throughout, and an open concept floor plan filled with natural light. The chef's kitchen is the heart of the home, showcasing a large center island, solid wood cabinetry, a generous walk in pantry, a dual fuel stove, and premium finishes that flow seamlessly into the living and dining areas. The primary bedroom offers a peaceful retreat with a large walk in closet and a spa inspired bath featuring a soaking tub and a beautifully tiled walk in shower. Step outside to the paver patio, complete with a fully equipped outdoor kitchen and outdoor shower, creating the perfect setting for relaxing or entertaining year round. Built with exceptional quality and energy efficiency in mind, the home features Huber ZIP System sheathing, James Hardie pre finished siding, Therma Tru exterior doors, an Atlas roofing system, Andersen double pane windows, and two tankless water heaters. The attached three bay garage includes attic storage above and is pre wired for a Level 2 EV charger and generator, offering future ready convenience and peace of mind. Residents enjoy resort style amenities including the 18 hole Ron Garl Championship Golf Course, junior Olympic swimming pool, tennis courts, pickleball courts, fitness center, clubhouse, restaurant, and bar. Conveniently located near Highway 27, I 4, and the Polk Parkway, this exceptional home provides easy access to Orlando, Tampa, Lakeland, and Central Florida attractions. Experience luxury golf course living at its finest. Schedule your private showing today.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Jessica Estrada (863-409-1771)

Remarks: Welcome home to luxury, comfort, and breathtaking golf course living in the prestigious, 24/7 guard-gated Cypresswood Golf & Country Club. Perfectly positioned on the 17th hole, this stunning 3-bedroom, 2-bathroom home offers 2,253 square feet of beautifully updated living space and exceptional curb appeal, highlighted by an extended pavered driveway and lush landscaping. Step inside and feel the warmth and pride of ownership the moment you enter. Soaring ceilings, abundant natural light, and an inviting layout create an instant sense of arrival. The main living areas feature stylish luxury vinyl flooring, while the bedrooms offer plush carpeting for added comfort. This home has been thoughtfully upgraded with peace of mind in mind; including: new roof (2021), top-of-the-line Generac whole-house generator (2021), commercial-grade irrigation system (2024), new hot water heater (2024), new refrigerator (2025), and new dishwasher (2025). Additional updates include exterior painting (2021), interior painting (2023), plantation shutters throughout (2021), and elegant front driveway pavers (2021). The backyard is a private oasis with upgraded landscaping and pavers, Black Diamond crêpe myrtles, and natural hedges that bloom with white flowers in the spring—creating a serene backdrop with direct golf course frontage. Cypresswood residents enjoy resort-style amenities, including an 18-hole championship golf course, junior Olympic-size pool, tennis courts, wellness center, clubhouse dining, and a vibrant social calendar with clubs, classes, and events that foster a true sense of community. This is more than a home—it’s a lifestyle. Schedule your private showing today and experience the best of Cypresswood living.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Tyler Wampler (863-577-1234)

Remarks: 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.

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

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

Remarks: Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of Winter Haven's established gated golf communities. Please note: The professional photos currently showing blue carpet were taken before the recent flooring update. New flooring has now been installed in the living room, dining room, kitchen, hallway, and Florida room. Inside, you'll find an oversized living area filled with natural light, a functional kitchen with ample cabinet space, generously sized bedrooms, and an enclosed Florida room that provides valuable additional living space. The new flooring gives the main living areas a fresh, updated look while maintaining the home's warm and inviting feel. The home has been lovingly cared for over the years and offers a wonderful opportunity for its next owner to move right in or personalize it to their own style over time. The split-bedroom floor plan provides privacy and flexibility, while covered parking and low-maintenance exterior living make everyday life easy and convenient. Residents of Cypresswood enjoy access to golf, tennis, a clubhouse with restaurant, and beautifully maintained grounds, all just minutes from shopping, dining, medical facilities, and major roadways. If you've been searching for space, value, and a relaxed Florida lifestyle in a gated golf community, this home deserves a spot on your must-see list.

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

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

Remarks: PRICE REDUCED $15,000! 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 and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. 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 the view from your Screened Porch. The Home is located close to Shopping (New Publix), 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: 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.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

Listing is courtesy of: BOARDWALK REALTY ASSOCIATES, LLC (800-567-0535)

Listing Agent: Ralph Eugene (813-263-8432)

Remarks: WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!

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

Listing Agent: Erin Floyd (863-412-2286)

Remarks: Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cypresswood Golf & Country Club, one of Winter Haven's premier gated golf communities. Built in 2023 and situated on 1.17 acres, this exceptional 4-bedroom, 3-bathroom residence offers luxury, privacy, and modern living with expansive views of the 2nd green and 9th tee of the Ron Garl-designed championship golf course. A long private driveway lined with Florida-friendly landscaping leads to an expansive paver parking courtyard and oversized three-car garage featuring a professionally finished epoxy floor. Ebony-finished tongue-and-groove ceilings on both the front entry and rear screened lanai create an impressive first impression, while the Therma-Tru insulated front door with decorative glass insert welcomes you inside. The thoughtfully designed OPEN-CONCEPT FLOOR PLAN features luxury vinyl plank flooring throughout, soaring ceilings with decorative beam details, custom millwork, recessed lighting, and large windows that fill the home with natural light. The spacious great room is anchored by a custom shiplap feature wall with an electric fireplace and opens seamlessly to the covered lanai through oversized sliding glass doors. A premium Denon surround sound system serves both the great room and lanai, making entertaining effortless. The gourmet kitchen combines style and functionality with quartz countertops, a large center island, solid wood cabinetry, under-cabinet lighting, a walk-in pantry with custom shelving, Frigidaire Professional Series stainless steel appliances, and a natural gas cooktop. The spacious primary suite offers a tray ceiling with decorative beams, an oversized walk-in closet, and a luxurious ensuite bath featuring dual vanities, a garden tub, walk-in shower, and private water closet. The split-bedroom floor plan provides privacy for family and guests, and every bedroom includes a walk-in closet. Step outside and enjoy the freedom of owning more than an acre with panoramic golf course views and plenty of room to create your dream outdoor living space. Residents of Cypresswood Golf & Country Club enjoy an 18-hole championship golf course, clubhouse, restaurant, junior Olympic-sized pool, tennis and pickleball courts, and scenic roads perfect for walking, running, and biking. Conveniently located near US-27, I-4, the Polk Parkway, downtown Winter Haven, and LEGOLAND Florida Resort, this home offers an exceptional combination of luxury, space, and location.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Jessica Estrada (863-409-1771)

Remarks: Opportunity Knocks! Build sweat equity in this 3 bedroom 2 bathroom villa that is ready for some cosmetic updates. Make this home your own with fresh paint, new flooring and anything else you might desire. The unit is currently in habitable condition so you can live there and work at your own pace. Priced well below market value to allow room for cosmetic upgrades. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

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

Remarks: This meticulously maintained and professionally updated 2 bedroom 2 bath villa is 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. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

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

Remarks: New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

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

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: Under contract-accepting backup offers. BRAND NEW ROOF INSTALLED NOVEMBER, 2025. New flooring May 2026. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates.

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

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

Remarks: Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new microwave. MOVE IN CONDITION. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

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

Remarks: Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a formal living room and an open-concept family room, dining area, and kitchen, creating a bright and inviting atmosphere ideal for both everyday living and hosting. Also features granite countertops, resurfaced garage, private office, freshly painted interior, paver driveway, and so much more. Enjoy the comfort, privacy, security, and lifestyle that come with living in one of Winter Haven’s premier golf communities.

Listing is courtesy of: LBJ REALTY AND ASSOCIATES LLC (863-206-1552)

Listing Agent: Lovett Johnson (863-206-1552)

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: 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.

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

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