Winter Haven Villas For Sale - 27 villas

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: Turn-key elegance in one of Winter Haven’s 55+ community! Welcome home to Oakview, an immaculate, highly sought-after hidden jewel. This smokefree, move-in ready 2BR/2BA residence delivers the perfect balance of relaxation and functionality. You will love the attached neighbors. The heart of the home features a bright, open-concept living/dining area flowing into a kitchen with abundant cabinetry and appliances. Guests appreciate the split-bedroom layout, while the owner enjoys a serene suite with a large walk-in shower. Bonus space includes a flexible rear den—ideal for a library/hobby room. Truly low-maintenance living: the low $165/mo. HOA covers your roof replacement, exterior painting, and lawn care! Spend your days exploring local dining, shopping, and Legoland, or travel easily via nearby Orlando and Tampa airports. Schedule a showing today! Move right in and enjoy! Room sizes are approximate. Buyer's agent to check HOA requirements. Attached to MLS. 5 unit building.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Rich Gant (813-502-9360)

Remarks: NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath with 2 car garage. The beautifully finished kitchen comes complete with a full stainless steel appliance package, granite tops, and modern gray cabinets. These lovely cabinets, and countertops also complement both the primary bath, and the guest bathroom. Neutral colors offer a nice finish to this well designed floor plan. Enjoy the privacy from your screened patio with no back door neighbors. Easy living awaits without the big worries. Exterior paint, roof replacement, irrigation water, yard maintenance, and Spectrum Internet/TV package is included in the reasonable monthly fees. Enjoy the social activities with the neighbors, splash in the community pool, or make a hit on the tennis/pickleball courts. The convenient location, and reasonable monthly fees makes this 55+ community an easy choice. 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: Welcome to 2825 Attwater Drive, a beautifully maintained villa in the sought after gated 55+ community of Traditions at Lake Ruby, where low maintenance living meets an active Florida lifestyle. This thoughtfully designed home offers comfortable living spaces, a desirable open layout, and the perfect setting for year round enjoyment. From the porch, enjoy a peaceful glimpse of the neighboring golf course, adding an extra touch of scenic beauty without leaving your own backyard. Life in Traditions is about more than just the home, it’s about the lifestyle. Residents enjoy a stunning lakefront clubhouse, resort style heated pools and spa, fitness center, pickleball and tennis courts, walking trails, social clubs, planned activities, and private access to beautiful Lake Ruby for fishing and boating. The location is equally impressive. Situated in the heart of Winter Haven, you’re just minutes from LEGOLAND Florida Resort, the Chain of Lakes, medical facilities, golf, restaurants, and everyday conveniences. A brand new Publix shopping center is located just across the street, with additional shopping and dining options including Panera Bread, ALDI, pharmacies, and major retailers only minutes away. Easy access to US 27 makes commuting throughout Central Florida simple, while new commercial growth, including a planned Target nearby, continues to add value and convenience to the area. Whether you’re looking for a full time residence or the perfect place to enjoy Florida’s active adult lifestyle, this home offers the ideal combination of comfort, convenience, and community. Schedule your private showing today and experience everything Traditions has to offer.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Jason Prieto (877-366-2213)

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 Vienna Square in Winter Haven, Florida! This 55+ Community is beautiful and offers their homeowners many activities and amenities to enjoy. Amenities include a Community Pool and Spa, Tennis and Pickleball Court, Fitness Center, Billiards Room, Library, Card Room, and a Large Clubhouse for events. Be sure to visit the Clubhouse for a list of activities offered each month. Let’s talk about this Featured Home now available. This Home is For Sale and Move in Ready! It is an end Villa which is larger than the interior Villas. As you pull into the driveway, you will notice the Paver Driveway and Sidewalk to the front door. The entrance is landscaped with beautiful Palm Trees. This Villa features 2 Bedrooms, 2 Baths, 2 Car Garage, and a Screened Lanai. A Big Plus for this Villa is the 2 Car Garage. Many villas do not have a Garage or Carport. The entire home has Ceramic Tile Flooring. The Kitchen features Granite Countertops, Stainless Steel Appliances, Pantry, Breakfast Bar, Wood Cabinets with Pot Drawers, Recessed Lighting, and Pendant Lights. The Pendant Lights and Chandelier were updated in 2025. The Guest Bath was updated with a Mildew Resistant Shower ($20,000 value) in 2026. The Living Room features a triple sliding door into your Screened Lanai. The Screened Lanai provides views of a pond with ducks and birds. No neighbors directly behind you. This Villa was built in 2019, so the Air Conditioner, Water Heater, and Roof are only 7 years old. All sizes are approximate. The Home is located close to Shopping (New Publix), Restaurants, and Downtown. Call for your Showing Today!

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

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

Remarks: Virtually Staged. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.

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

Listing Agent: Holly Patterson (717-668-9598)

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: Under contract-accepting backup offers. Welcome to Vienna Square — a vibrant, beautifully maintained 55+ gated community where resort-style living meets true low-maintenance comfort. This charming 2-bedroom, 2-bath villa offers 1,231 sq ft of thoughtfully designed living space, highlighted by an open-concept layout and an inviting Florida Room with its own portable A/C, giving you year-round flexibility for relaxing, crafting, reading, or entertaining. Inside, you’ll find a bright living and dining area, a well-appointed kitchen, and a desirable split bedroom floor plan that provides privacy for you and your guests. The Florida Room adds valuable extra square footage and seamlessly extends your living space. Life at Vienna Square is all about ease and enjoyment. Residents have access to an impressive lineup of amenities, including a clubhouse, tennis courts, heated community pool, hot tub, movie room, billiards room, fitness center, and a full calendar of weekly social activities that make it easy to stay active and connected. The HOA takes care of the details so you don’t have to — yard maintenance is included, along with exterior paint every 10 years and roof replacement every 15 years. Perfectly located just minutes from the brand-new Publix, dining, medical facilities, and all that Winter Haven has to offer, this home delivers the ideal blend of comfort, convenience, and an engaging active-adult lifestyle. Move-in ready, beautifully maintained, and set within one of Winter Haven’s most desirable 55+ communities — this villa is a standout opportunity.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Tina Bircher (321-228-4267)

Remarks: Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Beena Kokeram (813-458-6634)

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: 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: NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

Listing is courtesy of: DGCF REALTY ADVISORS LLC (877-791-9907)

Listing Agent: Austin Schreiber (863-287-8877)

Remarks: YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT, THIS GREAT GATED COMMUNITY HAS CLUBHOUSE, FITNESS CENTER, POOL, TENNIS COURTS AND OFFERS SO MUCH TO YOUR OVER 55 LIFESTYLE. CONVENIENT TO SHOPPING, RESTAURANTS AND ONLY MINUTES TO DOWNTOWN WITH SOMETHING FOR EVERYONE. THIS VILLA HAS AN OPEN FLOOR PLAN WITH HIGH CEILINGS, CEILING FANS, CERAMIC TILE IN THE LIVING AREA AND CARPETING IN THE BEDROOMS. RELAX ON YOUR ENCLOSED LANAI OVERLOOKING THE SERENE ATMOSPHERE OF THE PEACEFUL WOODED AREA BEHIND YOUR UNIT WITH NO REAR NEIGHBORS. THE MONTHLY HOA FEE INCLUDES EXTERIOR PAINT, ROOF, IRRIGATION WATER, LAWN MAINTENANCE AND RECENT ADDITION OF SPECTRUM TV/WIFI SERVICE. THIS VILLA HAS BEEN CLEANED AND READY FOR YOUR MOVE.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: Under contract-accepting backup offers. Situated in the desirable, maintenance-free gated community of Traditions, this gorgeous 2-bedroom, 2-bath villa with a flex room offers the perfect opportunity to enjoy a truly leisurely lifestyle. Designed for comfort, efficiency, and style, this home delivers the feel of single-family living with the convenience of condominium maintenance. Upon arrival, you’re welcomed by a charming screened-in front porch with pavers, setting the tone for the inviting interior. The well-equipped kitchen is a chef’s dream, featuring timeless 42" espresso-stained cabinetry with crown molding, brushed nickel hardware, and a classic subway tile backsplash. The breakfast bar—embellished with quartz countertops and pendant lighting—serves as a stunning focal point. Additional functional highlights include two closet pantries, recessed lighting, a USB receptacle outlet, and a stainless steel appliance package. The spacious great room is adorned with 17 inch porcelain tile flooring and oversized sliding glass doors that enhance natural light and create an open, airy feel. The open-concept layout also includes a charming dining area accented with custom pendant lighting—ideal for both everyday living and entertaining. The primary bedroom suite features luxury vinyl plank flooring and a large walk-in closet. The primary bathroom is beautifully appointed with a comfort-height vanity featuring pull-out shelves, quartz countertops, dual sinks, and a tiled walk-in shower with a glass enclosure. This eco-friendly home offers impressive energy-efficient features, including foam-filled block wall insulation, a programmable thermostat, Energy Star–rated appliance package, Low-E double-pane windows, and an irrigation system. Additional Features, Laundry room with cabinetry and high-efficiency washer & dryer, Hallway linen closet, Alarm system, Water Softener Salt System, Gutters, Paved walkway and driveway, One-car garage with garage door opener and overhead storage rack. As part of the active 55+ community of Traditions, you'll have access to a lakefront clubhouse, a boat ramp and dock, a heated pool and spa, a fitness center, a dog park, tennis courts, bocce ball, pickleball, a billiard room, shuffleboard, and much more. Experience the feel of single-family home living with the convenience of a condominium lifestyle. Monthly fees cover exterior maintenance—including roofs and exterior painting—plus cable (three cable boxes included), internet, lawn service, irrigation water, and exterior building insurance, ensuring a truly worry-free lifestyle. Conveniently located near shopping, restaurants, Legoland, Bok Tower Gardens, and major routes, this exceptional villa offers the perfect blend of comfort, convenience, and carefree living. This home is being sold partially furnished.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

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: 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)