Winter Haven Homes with Tennis Court(s) Community Features

Winter Haven Homes with Tennis Court(s) Community Features

Welcome to Winter Haven, Florida—a vibrant city nestled in the heart of Polk County, where the sun shines bright and the community spirit thrives! Known for its picturesque lakes and lush landscapes, Winter Haven is a haven for outdoor enthusiasts and families alike. With its charming downtown area filled with unique shops, delightful eateries, and a rich history, there's something for everyone in this welcoming city.

One of the standout features of Winter Haven is its diverse range of residential communities, particularly those that boast homes with tennis courts. Imagine waking up each day in a beautiful home, surrounded by manicured lawns and the sounds of nature, with the convenience of a private tennis court right in your backyard. These properties not only offer a perfect setting for active lifestyles but also foster a sense of community among neighbors who share a passion for the sport.

Living in a home with a tennis court in Winter Haven means you can enjoy year-round access to your favorite game, whether you’re challenging friends, hosting family gatherings, or simply enjoying a peaceful afternoon practice. The community features often include beautifully landscaped common areas, walking trails, and recreational facilities that enhance the quality of life for residents.

With its ideal location, Winter Haven is also just a short drive from the attractions of both Orlando and Tampa, making it a perfect blend of tranquility and accessibility. Whether you’re looking to invest in a family home or a vacation retreat, Winter Haven’s homes with tennis courts offer an exceptional lifestyle in a city that truly feels like home. Come discover your dream home in this enchanting Florida city!

Newest Winter Haven Homes with Tennis Court(s) Community Features

$549,999
3 Beds ⋅ 3 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
*GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the views from the covered and screened lanai are superb! Built in 2019, this home offers TWO PRIMARY SUITES, ONE GUEST BEDROOM and THREE BATHS. The oversized laundry room is a MUST SEE! This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The views from this coveted lot location are spectacular, make sure you bring your binoculars! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, stainless appliances (microwave replaced Sept. 2026) and ample counter top space. The Dinette area is directly off the kitchen and overlooks the golf course and lake. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry was extended at the time of Build and takes up the right wing of the home. It showcases two large walk-in closets, a separate water closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the space. The Primary Bedroom can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home, accessible from the dinette area and the hallway to Bedroom 3. The 2nd Suite with built in closet has an abundance of natural light. The double windows in the bedroom feature views of the golf course and lake. The 2nd Suite Bathroom features a comfort height vanity, walk in shower with glass enclosure and comfort height toilet. A door provides privacy to the 2nd Suite Bedroom in the hallway that leads to Bedroom 3 and Bath 3. Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The oversized Laundry Room is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining guests. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
OVER $19,000 IN RECENT UPGRADES MEANS THE BIG-TICKET WORK HAS ALREADY BEEN DONE! This fully furnished Oakwood Estates home features a new roof (2023), plus new HVAC, electric water heater, rain gutters, and exterior porch tile (2024). Step inside to a bright, welcoming interior filled with natural light from double-pane windows. Luxury vinyl plank flooring flows throughout. The kitchen features stainless steel appliances, white cabinetry, wood-look countertops, and a newer sink. Built-in cabinetry adds charm and storage to the dining area, which opens to a spacious living room. Both bedrooms are generously sized, with a walk-in closet in the primary. A separate laundry room includes the washer and dryer. Enjoy additional living space in the Florida room and enclosed lanai, perfect for relaxing and enjoying the Florida lifestyle. Hurricane shutters, vinyl siding, and an updated electrical panel add even more value. Oakwood Estates is a gated, resident-owned 55+ community with two heated pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a fishing lake and pier, RV and boat storage, library, activities center, and an active social calendar. Major updates done, furnishings included, and ready for you to move in and enjoy!

4332 Cherrywood Street, Winter Haven
$144,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**LARGE 2 BEDROOM - 2 BATH CONDO - NEW LISTING IN CENTRAL FLORIDA**- AGE 55+, GATED COMMUNITY (however, a slightly younger age may be approved). This up-to-date condo provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Florida. NEW ENERGY-EFFICIENT WINDOWS THROUGHOUT. The monthly fee INCLUDES: water, sewer, trash, fiber optic cable package with Choice HD, digital video recorder & fiber optic internet w/ 1 gig speed, & use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated secured entrances, covered assigned parking space, social events & activities. This well-appointed, move-in-ready condo has a large, bright kitchen w/ lots of cabinets, a tile backsplash, flush-mount LED ceiling lighting, plenty of counter space, all appliances & a pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional FL/bonus area & storage closet. The 16' x 14 ' primary bedroom easily accommodates a king-size bed & has a walk-in closet with a decorative barn door. The beautiful remodeled primary bathroom has an extra-wide door for easy direct access & includes a walk-in shower with a large format designer wall tile, & a comfort-height vanity with a vessel sink. The 2nd bedroom is convenient to the hall bath, which has a tub/shower combination & comfort-height vanity. The WASHER & DRYER are included in the sale. The Flooring throughout is either wood-look luxury vinyl or tile, NO CARPETING. Custom window shades are in place and are included in the sale. An extra assigned storage bin is located on the same floor. Enjoy beautiful views of Spring Lake and the evening sunsets from most rooms. Shopping, medical, hospital, places of worship, groceries, restaurants & bus line are very close by. COVERED ASSIGNED PARKING SPACE. SharePoint electric car charger on site for owners! Measurements are approximate. Information is believed to be accurate but not guaranteed. NON-SMOKING COMPLEX THAT IS WELL MAINTAINED & MANAGED. FURNITURE IS NEGOTIABLE. Make this your full-time or winter home!

1776 6th Street Nw Unit 308, Winter Haven
$200,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 01 SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square home. This one can be a real charmer with your personal touches. Bright, light, and open floor plan. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

2338 Salzburg Loop, Winter Haven
$147,500
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
Welcome to Lakeridge — Easy Florida Living with Beautiful Spring Lake Views! Take a look at this fantastic move-in-ready 2-bedroom, 2-bathroom condo in Lakeridge, a gated 55+ community in Winter Haven with great lake views. With 1,347 square feet of living space, this home offers plenty of room to relax, along with thoughtful updates and beautiful views of Spring Lake. As you step inside, you'll find an updated kitchen with plenty of updates including, soft close cabinets and drawers, granite counter tops, a pantry closet, and stainless-steel appliances. The kitchen opens into the spacious great room, making it easy to cook, visit, and entertain at the same time. The 26' x 14' great room flows into the Florida/bonus room, a comfortable spot to unwind while enjoying the lake view. Furnishings are negotiable! There's also a large storage closet for added convenience in the Florida room. The primary bedroom is approximately 16' x 14', with plenty of space for a king-size bed. It includes a walk-in closet and a private bathroom with a walk-in shower and double vanity. Spring Lake views can be enjoyed from both the primary bedroom and the main living areas. Recent updates include new energy-efficient, double pained windows, carpet and tile. The washer and dryer are included, along with all of the stainless-steel kitchen appliances, so you can move in and settle right away. The entertainment system-65" Smart TV, 5-speaker Surround System w/Subwoofer, Blue Ray, Stereo with AM/FM Radio, Speakers, and Antenna is also included and complements the built-in electric fireplace, creating a cozy space for relaxing or spending time in your space. Lakeridge makes everyday living easy and low maintenance. The monthly condominium fee includes water, sewer, cable, fiber-optic internet, trash removal, reserves, and use of the recreational facilities. Residents can enjoy a heated pool, tennis courts, shuffleboard, a community room, gated entrances, and a covered assigned parking space. An additional assigned storage bin is conveniently located on the same floor. The community also offers social activities for residents who enjoy meeting neighbors and staying involved. When you need to run errands, Lakeridge is close to shopping, grocery stores, restaurants, medical offices, and the hospital. Lakeridge is an age-restricted 55+ community. One small pet may be approved. The property is non-smoking, and an electric vehicle charger is available on-site for owners. If you're looking for a spacious condo with lake views, comfortable living areas, included amenities, and a maintenance-free lifestyle, this home is worth seeing. It could be the comfortable Florida retreat you've been waiting for. Information is believed to be accurate but is not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 504, Winter Haven
$239,900
3 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
3 bedroom, 2 bath ground-floor end-unit condo home with gorgeous views of Lake Winterset and a private 1 car garage—the perfect combination in one of Winter Haven’s most desirable gated communities. Welcome to 701 Magnolia Place, a spacious lakeview residence designed for easy single-level living with approximately 1,180 square feet, durable luxury vinyl plank flooring, and a comfortable, open layout. The living room is anchored by a fireplace and flows naturally into the dining area, creating an inviting space for everyday living and entertaining. The kitchen features white cabinetry, soft close drawers, newer stainless steel appliances, generous counter space, and an adjoining breakfast nook. The primary suite is spacious, measuring approximately 11x16, with lake views, a private bath with walk-in shower, generous closet space and direct access to the back patio. Two additional bedrooms provide flexibility for guests, a home office, hobby room, or den—a combination that makes this 3-bedroom floor plan especially hard to find in Winterset. A second full bath with tub and shower combo completes the interior. Step outside to the private screened porch, where wide-open green space and beautiful Lake Winterset views create the perfect place to enjoy your morning coffee, unwind at the end of the day, and watch sunsets you truly have to see to believe. As an end unit, the home enjoys an added sense of openness and privacy, while the attached one-car garage provides valuable parking and storage. Beyond the residence, the community of Winterset delivers on the Florida lifestyle. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Ground-floor living, an end-unit location, three bedrooms, private garage, screened porch, Chain of Lakes access, resort-style amenities, and gorgeous Lake Winterset views—701 Magnolia Place offers a combination that is difficult to find.

701 Magnolia Place, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
This home can be purchased with NO MONEY DOWN or NO INCOME VERIFICATION! Welcome to Lakefront Living at Its Finest! Experience serene waterside tranquility with breathtaking views of Lake Winterset in this inviting 2-bedroom, 2-bath unit, all at an affordable price. As you step inside, you'll be greeted by soaring ceilings that enhance the open and airy atmosphere. The thoughtfully designed open floor plan seamlessly connects living and dining areas, perfect for both entertaining and relaxation. Both bedrooms offers ample space for comfortable living. The master bedroom also offers a spacious walk-in closet, and sliding glass doors leading to your rear screened porch. Enjoy your morning coffee or unwind in the evenings on the screened porch, where nature's beauty serves as your stunning backdrop. This desirable gated community not only offers a Clubhouse, pool, and spa but also features tennis and pickleball courts, as well as a convenient boat ramp for easy access to the lake. Ideally located near Legoland and in the heart of the Florida Peninsula, with lots of lakes, or just over an hour drive to the Gulf or Atlantic beaches, Tampa & Orlando for airports, shopping, entertainment and more. This home perfectly blends comfort and convenience. Don't miss your chance to embrace the Florida lakefront lifestyle you've always dreamed of!

410 Laurel Cove Way, Winter Haven
$114,995
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The guest bedroom is attached to the guest bathroom offering privacy and convenience to your guests. The Lanai which is also air conditioned (vent behind the couch) offers a wonderful area to sit and enjoy your morning coffee where you can watch the world go by. Oakwood Estates offers many activities and amenities including two pools, two clubhouses, tennis courts, shuffle board, miniature golf and much more. You can stay as busy as you like or just sit back and enjoy the peaceful community. The golf cart is included in the sale of the home. The Sellers have a home warranty in place and with a reasonable offer will pay for three month to continue the plan. Make your appointment today to see this beautiful home.

4234 Rolling Oaks Drive, Winter Haven
$229,900
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
Virtually Staged. Completely renovated ground-floor condo with beautiful lake views of Lake Winterset on the world-famous Winter Haven Chain of Lakes! Welcome to Winterset, where this stunning remodeled 2 bedroom, 2 bath condo combines a spacious interior, private screened porch, exceptional water views, and the amenities of one of Winter Haven's most desirable gated communities. From top to bottom this unit is fresh, bright, and remarkably spacious. New flooring flows throughout, complemented by updated lighting, contemporary ceiling fans, modern fixtures, and a crisp neutral palette. The open living and dining areas provide plenty of room to relax and entertain, while large windows frame the expansive lawn and sparkling waters of Lake Winterset beyond. The expanded kitchen delivers the wow factor with elegant granite countertops, soft-close cabinetry with crown molding, black appliances including a gas range and dishwasher, a generous breakfast bar, and abundant cabinet and counter space. Open to the dining and living areas, it creates an easy flow throughout the main living space. The primary suite offers beautiful lake views, a huge walk-in closet and a luxurious master bath with double vanity undermount sinks, granite countertop, sleek chrome fixtures and a frameless glass walk-in shower surrounded by custom tile. Positioned separately from the primary suite, the spacious second bedroom offers two closets and convenient access to the beautifully renovated guest bath, complete with granite-topped vanity and custom-tiled tub and shower. The thoughtful layout also includes an interior laundry area and additional storage. Stepping outside to the private screened porch you'll find the perfect spot to unwind while watching the water and the most amazing sunsets you have to see to believe. Beyond the residence, Winterset delivers the Florida lifestyle buyers come here to enjoy. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Beautifully renovated, ground-floor living, an unusually spacious primary suite, private screened porch, resort-style amenities, Chain of Lakes access, and a gorgeous water view right outside your windows—this is the kind of Winter Haven condo that's easy to fall in love with.

503 Sweet Bay Circle, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Morningside SubDv. ⋅ 33884 Zip Code
PRICE DROP OF $5,000! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly desirable Morningside at Winterset, a 24/7 gated community offering comfort, security, and resort-style living. This spacious property features an inviting foyer that opens into a bright great room and dining area, enhanced by elegant plant shelves and sliding glass doors leading to a large all-weather screened porch with vinyl panels—perfect for relaxing year-round. The well-appointed kitchen offers abundant cabinetry, a breakfast bar, and a full appliance package including a smooth-top range, built-in microwave, dishwasher, and side-by-side refrigerator. The generous primary suite includes private porch access, a walk-in closet, and a luxurious bathroom with a jacuzzi tub. Additional highlights include a separate laundry room with washer, dryer, utility sink, and extra storage, plus a 2-car garage. The home features 16” ceramic tile throughout the main areas and neutral carpet in the bedrooms, creating a warm and comfortable feel. Residents of Winterset enjoy access to community amenities, including a clubhouse, pool, tennis courts, and beautifully maintained grounds. This home offers a wonderful blend of space, convenience, and community living in SE Winter Haven

140 Morning Glory Circle, Winter Haven
$355,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
1124 Sawgrass Drive Winter Haven, Fl. 33884 is located in Lake Ashton, an Exclusive Florida Retirement Community offering tailored activities and amenities to those seeking an Active 55 Plus lifestyle. Built in 2022 with 1,917 sq. ft. living area, this ST. MARKS floor plan home is MOVE IN READY and is located on the 10th Fairway of the West Golf Course in Lake Ashton. When you enter this home you have a direct view of the golf course thru the Triple Sliders that separate the LR from the Lanai. This Split Floor Plan offers: Formal and Casual Dining areas, a Living Room, Laundry Room, Primary Suite, 2 Bedrooms and a Flex Room with Built In Shelves. The living room is at the center of the this home with the Kitchen, Formal Dining, Primary Suite and Dinette areas flowing into the LR area. The Kitchen is spacious and offers a Breakfast Bar, SS Appliances, Recessed Lighting, Pull Out Drawers, Ample 42" Cabinetry and Granite Countertops. The Dinette area is easily accessible to the kitchen and Flex Room and Double Sliders provide direct access to the Covered and Screened Lanai. The Open and Spacious Floor Plan makes entertaining a BREEZE! The comfortable and spacious Primary Suite offers His/Her Walk in Closets, an attractive Primary Bath area with His/Her separate vanities, large soaking tub, walk in shower, separate water closet and linen closet. Glass Block accents the Primary Bath and provides an abundance of natural light into the room. Bedroom 2 and Bedroom 3 are separated by the Guest Bathroom with shower/tub combo and comfort height vanity. Each Bedroom has a built in Closet. The laundry room (washer/dryer included in the sale of the home) is sizable and is the passage from the garage to the kitchen. The garage has a separate golf cart entry and the golf cart is included with the sale of the home. Grab a great book and a cup of coffee and relax on the screened and covered lanai. 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!

1124 Sawgrass Drive, Winter Haven
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