Winter Haven Homes with Tennis Court(s) Amenities

Winter Haven Homes with Tennis Court(s) Amenities

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, renowned for its stunning lakes, vibrant community spirit, and endless recreational opportunities. With its inviting climate, Winter Haven boasts a unique blend of small-town charm and modern amenities, making it an ideal destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

For those who appreciate an active lifestyle, Winter Haven offers a range of homes featuring tennis court amenities, perfect for both casual players and seasoned athletes. Imagine stepping out of your beautifully appointed home and onto your private tennis court, where you can enjoy friendly matches with family and friends, or simply practice your serve while basking in the warm Florida sun. These properties not only provide a space for physical activity but also foster a sense of community, as neighbors come together to share in the joys of the game.

The city’s picturesque lakes, including the famous Chain of Lakes, provide a stunning backdrop for your tennis matches, while nearby parks and nature trails invite you to explore the great outdoors. With excellent schools, shopping, and dining options just a stone's throw away, Winter Haven truly offers a lifestyle that balances leisure and convenience.

Whether you're looking for a family home or a serene retreat, Winter Haven's homes with tennis court amenities promise a lifestyle filled with activity, relaxation, and the joys of community living. Discover your dream home today and experience all that this delightful city has to offer!

Newest Winter Haven Homes with Tennis Court(s) Amenities

$165,000
2 Beds 2 Baths Cypresswood Tennis Villas SubDv. 33884 Zip Code
Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven

$399,900
4 Beds 3 Baths Traditions Ph 02 SubDv. 33884 Zip Code
Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven

$409,000
3 Beds 2 Baths Lake Ashton West Ph I SubDv. 33884 Zip Code
HOME FOR SALE IN LAKE ASHTON! Is 4052 Phoenician Way, Winter Haven, Florida YOUR next address? This 3 Bedroom, 2 Bath home with Golf Cart Entry is located on a large premium lot that abuts to the 13th Fairway of Lake Ashton's West Golf Course. The view from the wrap around covered and screened lanai includes a large pond that borders the 13th Hole with a farm pasture beyond. Home Highlights: CDD Debt Balance Paid in Full; Roof Replaced 2022; Water Heater Replaced 2022; A/C Heat Pump Replaced 2019. This home offers excellent curb appeal with a Widened Drive Way, Poured Curbing, Well Maintained Mature Landscape with Landscape Rock, Quoined Corners, Bay Window on the Front Bedroom, and arched Screened Entry. A paver walkway on the right side of the home connects the access door of the golf cart garage to the rear lanai. The interior of this home is warm and inviting with an Open and Spacious Living area. The Foyer, Dining, LR and Kitchen flow seamlessly together making entertaining a "breeze" in this home. The beautiful Bruce interlocking Engineered natural oak floors and the Plantation Shutters on the Side Lights of the Front Entry Door, Double Sliding Glass Doors in the Living Room, Bedroom 2 and Primary Bedroom accent the interior of this home- adding a touch of class. Crown molding gives definition to the Open Living area. The kitchen upgrades include: Granite counter tops, Maple Cabinets with raised panels, 3 banks of drawers, crown molding and a pantry. The refrigerator, microwave and disposal were replaced in 2026 and the range was replaced in 2023. A breakfast bar/snack bar and Dining areas are perfect for entertaining friends and family. Enter thru the 8' Front entry door with Eyebrow window above. To the left of the foyer are Bedrooms 2 and 3, a Linen Closet in the Hallway and a Guest Bathroom with shower/tub combo, accent window and comfort height vanity. A pocket door provides privacy to the Guest Bedroom area. The EXTENDED Primary Suite is located on the back on the home. It's the perfect place to relax after a long day in the sun. The Primary Suite offers a spacious sitting area and En-Suite with His/Her Walk in Closets, His/Her Separate Vanities, a large corner Soaking tub, a separate water room with a walk in shower with glass doors and linen closet. The laundry room is easily accessible from the garage and kitchen. It has cabinets for storage, a wash tub and the washer/dryer will be included in the sale of the home. The double car garage has hang down storage racks, attic access, storage cabinets, and an access door to the outside. There is a motorized screen on the garage door and a separate entry for the golf cart. The outdoor living space is a destination location in this home. The view is peaceful and the space is cozy with paver floor, ceiling fans and TV hook up. Make an appointment to tour this home today! Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

4052 Phoenician Way, Winter Haven

$159,900
2 Beds 2 Baths Cypresswood Eagle Pond Condominium SubDv. 33884 Zip Code
Don't miss the opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Virtually maintenance-free Florida living doesn't get any better. Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today!

1502 Eagle Pond Drive Unit 15, Winter Haven

$498,500
4 Beds 3 Baths Cypresswood Plantations SubDv. 33884 Zip Code
Located on a quiet cut-de-sac in the desirable Plantations part of the guard gated golfing community of Cypresswood Golf & Country Club, this 4BR/3BA beauty w/ more than 2500 sq ft has upgrades galore & is just what you've been looking for! The home has a fantastic open floor plan w/ split bedrooms, volume ceilings, crown molding, double pane windows, plantation shutters, arched entryways, & super stylish hickory scraped wood looking tile throughout! The lovely formal dining room w/ it's arched entrances flows nicely just off the foyer, while another arch entry leads straight ahead into the spacious great room w/ a tray ceiling & French doors leading to the inviting Florida room. The large eat-in-kitchen features beautiful custom maple cabinets w/ pull-outs, new quartz countertops & tile backsplash, a breakfast bar, soft accent lighting over the cabinets & it comes equipped w/ all of the upgraded appliances including a new stainless steel refrigerator, microwave & gas range, as well as a new kitchen sink & faucet! The quaint breakfast nook has a beautiful picture window that provides lots of natural light while you're enjoying the serene backyard views. The primary suite is huge & features a cozy sitting area w/ French doors leading to the Florida rm & there's an ornate barn door entrance leading into the primary bathroom complete w/ a garden tub, nicely tiled step-in shower, double sink vanity w/ quartz countertop & a walk-in closet. The 2nd & 3rd BR's are situated on the other side of the living areas for added privacy & they have a Jack-n-Jill bath between them that has a double sink vanity w/ quartz countertop as well as a tub & shower combo. The 4th BR is located just down the hall from the Primary bedroom making it a nice option for a nursery/small child's room or an office. It would also be a nice guest room w/ the 3rd bathroom conveniently located right beside it w/ quartz countertop & a step-in shower w/ a nice glass enclosure. The large Florida rm has lots of windows overlooking the landscaped back yard & it even has a wet bar complete w/ mini fridge, a wine fridge & of course ...quartz countertops making it the perfect spot for entertaining. Additional features include an inside laundry room, a double car garage, fairly new C/H/A, a whole house gas generator, a water softner/purificiation system, central vac, & there's even a fire pit in the back yard on this 1/3+ acre property tucked away in Cypresswood Golf & Country Club, with lots of community amenities including a 24 hour manned gated entrance, a community pool for you to enjoy & not have to maintain, plus there's pickleball courts, tennis courts, a large clubhouse w/ fitness center, restaurant, pro shop & surrounded by the lovely golf course! Close to shopping, restaurants, medical, the new Publix, Legoland & more & Conveniently located in the heart of Central Florida between Orlando & Tamps and not far from all of the major attractions. All measurements are approximate and all info should be confirmed by buyers.

3158 Beauchamp Court, Winter Haven

$489,000
3 Beds 2 Baths Village/Spirit Lake Ph 01 SubDv. 33880 Zip Code
Saltwater pool. Boat parking. Private community boat ramp. Welcome to 315 Lanceolate Drive, a beautifully updated 4-bedroom, 2-bath home located in the gated community of The Village at Spirit Lake. Inside, you'll find a completely renovated kitchen and beautifully remodeled bathrooms, creating a fresh, modern feel while maintaining a comfortable and functional layout. Step outside to your own private retreat featuring a sparkling saltwater pool, screened lanai, and a fully fenced backyard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine. The second bathroom provides direct access to the pool area, adding convenience for family and guests. Need extra space? The garage has been converted into two air-conditioned bonus rooms, offering incredible flexibility for a home office, gym, hobby room, playroom, or additional storage to fit your needs. The extended driveway provides the perfect place to park your boat, and residents of The Village at Spirit Lake enjoy exclusive access to a private community boat ramp on Spirit Lake. The neighborhood also features a brand-new playground, pickleball courts, a basketball court, clubhouse, gated entrance, and a very reasonable HOA. Ideally located just minutes from the Polk Parkway, commuting to Lakeland, Tampa, or Orlando is a breeze. The home is also located in unincorporated Polk County, allowing you to enjoy the benefit of county taxes only. Conveniently close to shopping, dining, schools, and Legoland Florida Resort, this move-in-ready home offers the perfect blend of updated finishes, flexible living space, and the Florida lifestyle you've been looking for. Schedule your private showing today and discover everything this exceptional home has to offer.

315 Lanceolate Drive, Winter Haven

$900,000
3 Beds 4 Baths Cypresswood Palma Ceia SubDv. 33884 Zip Code
Virtually Staged. *Special financing incentives may be available through the seller's preferred lender* 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.

4050 Palma Ceia Circle, Winter Haven

$345,000
3 Beds 2 Baths Morningside SubDv. 33884 Zip Code
Every Detail Has Been Thoughtfully Designed. Every Upgrade Has Been Thoughtfully Completed. Welcome to a home where quality craftsmanship, modern style, and everyday comfort come together effortlessly. Nestled on a beautifully landscaped nearly half-acre homesite overlooking peaceful Garden Lake, this impeccably maintained 3-bedroom, 2-bath residence offers the perfect balance of privacy, sophistication, and smart-home convenience. A natural privacy hedge of mature hibiscus surrounds the backyard, creating a tranquil setting that is increasingly difficult to find. From the screened front entry to the spacious screened lanai, every space has been designed to embrace Florida living while showcasing the exceptional care invested throughout the home. Inside, the open-concept floor plan is warm, inviting, and filled with natural light. Smart-home technology allows you to control the lighting, electric fireplace, and garage door opener with ease, while tasteful finishes and thoughtful updates create a contemporary feel that is as functional as it is beautiful. The completely updated kitchen serves as the heart of the home, featuring granite countertops, a farmhouse sink, elegant 42-inch upper cabinetry, redesigned lower cabinetry, recessed lighting, stainless steel appliances, and a generous workspace. The open layout is ideal for entertaining while maintaining a warm, inviting atmosphere for everyday living. The attention to detail continues throughout with beautiful flooring, updated lighting, refreshed bathrooms with granite countertops and modern fixtures, energy-efficient Low-E replacement windows, and countless improvements that reflect exceptional ownership. Outdoor living is equally impressive. Relax year round on the newly screened lanai with its attractive epoxy floor and premium UV-protective screening provides the perfect place to relax while enjoying peaceful views of Garden Lake. This private outdoor retreat is sure to become a favorite gathering place. Significant improvements—including a Bryant HVAC system, water heater, energy-efficient Low-E windows, updated exterior paint, smart garage door opener, and numerous additional upgrades—offer the peace of mind every buyer is looking for. Completing the home is a long-lasting clay tile roof that adds timeless character and enhances the home’s exceptional curb appeal. Located within the highly sought-after gated community of Winterset, residents enjoy exceptional amenities including a heated pool and spa, clubhouse, tennis courts, beautifully maintained grounds, private boat ramp and dock on Lake Winterset, and access to the renowned Winter Haven Chain of Lakes—all with a low HOA. Thoughtfully updated. Beautifully maintained. Perfectly positioned. A home that feels brand new—without the wait.

120 Morning Glory Circle, Winter Haven

$336,000
3 Beds 2 Baths Cypresswood Patio Home SubDv. 33884 Zip Code
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.

728 Canberra Road, Winter Haven

$589,000
3 Beds 2 Baths Lake Ashton West Ph Ii North SubDv. 33884 Zip Code
Modern Elegance! 6209 Pinehurst Loop Winter Haven, Florida 33884. Built in 2021, this custom designed home is located in Lake Ashton, one of Central Florida's Premier 55 Plus community. Perfectly positioned on a quiet street this exceptional home with Northwest exposure offers effortless luxury with modern upgrades. Offering excellent curb appeal with a well manicured lawn and mature landscape this home has an expanded driveway, extended golf cart entry, paver walkway to the back lanai, and a fresh coat of exterior paint (May 2026). Built for both sophistication and peace of mind, this block construction home offers over 2,500 square feet of living area and golf course views. Upon entering the home thru the screened entry, the 6 panel Double Front door opens into a spacious living area with beautiful lighting fixtures, trey ceiling & Engineered hardwood floors that flow seamlessly in the LR, Den, Dining Room, Kitchen & Flex Room. In the Living Room, a custom built wall unit accents the area and is a focal point in the elegant gathering spaces. The formal dining area shares the space, while the chef's kitchen showcases upgraded Cabinetry, Tiled backsplash, Silestone countertops with Eased Edge, Granite composite undermount kitchen sink, RO water system at the kitchen sink, Kitchen Aid Stainless Steel appliances, 36" cooktop with Extended Hood, Built In Wall Oven and Oversized Island with cabinets, great for entertaining. A custom built dry bar with lighting, leathered countertop and back splash accents the hall. The thoughtfully designed split floor plan includes 3 spacious bedrooms, 2 baths, a private study/den with French glass doors, and an oversized flex room with Wash Sink, Washer/Dryer, Wine Refrigerator, Upgraded cabinetry, Quartz counter top and Tiled backsplash. The elegant Primary Suite is a must see! The impressive En-Suite offers a separate water closet, dual sink vanity, a spacious glass enclosed walk in shower with Pietra Art Premier Marble Tile, foot rest and floor to ceiling tile. The boutique style clothing room offers California closet designs with a central dressing island. Plantation Shutters accent the room and allows natural light to filter thru the space. The 8 ft. door ways in this home compliment the high ceilings and the window treatments (Plantation shutters and Power shades) are elegant and designed for comfortable luxury living. Access to the outdoor living area is available thru the dinette area & the living room. You'll transition from the LR to the Lanai thru Triple Glass Sliding Doors that stack and disappear into a pocket providing an unobstructed view of the golf course. The Outdoor living area is equally impressive with a covered and extended screened lanai with epoxy flooring. A pad was added for your grilling pleasure. The double car garage with separate golf cart entry has epoxy flooring and pull down stairs on the attic access door. Make an appointment today to tour this elegant home. Lake Ashton features a Main Clubhouse with Outdoor Pool, Movie Theater, Bowling Lanes, Card, Craft and Billiard rooms, Fitness Center, Bocce Courts, Tennis and More. Residents also enjoy the Health and Fitness Center with large indoor pool, Pickle Ball, Tennis Courts, Fitness Center and MORE! 2-18 Hole Golf Courses are located behind the secure gates of Lake Ashton and Golf Memberships are Available. Boat Slip Rentals and Storage Rentals are available in Lake Ashton.

6209 Pinehurst Loop, Winter Haven

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