Winter Haven Homes with Clubhouse Community Features

Winter Haven Homes with Clubhouse Community Features

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County that beautifully blends a vibrant community spirit with a serene, picturesque landscape. Known for its stunning chain of lakes, Winter Haven is a paradise for water enthusiasts and nature lovers alike. With its inviting climate, abundant recreational opportunities, and rich history, this city offers a perfect backdrop for families, retirees, and everyone in between.

One of the standout features of Winter Haven is its diverse range of homes, particularly those within clubhouse communities. These residences not only provide comfortable living spaces but also foster a sense of community and togetherness. Imagine waking up to the gentle sounds of nature and stepping outside to enjoy a wealth of amenities right at your doorstep.

Homes in clubhouse communities often feature luxurious pools, state-of-the-art fitness centers, and beautifully landscaped common areas, perfect for social gatherings and recreational activities. Whether you're looking to relax poolside, engage in a spirited game of tennis, or participate in community events, these neighborhoods are designed to enhance your lifestyle and create lasting memories with friends and neighbors.

Additionally, Winter Haven's strategic location allows for easy access to major highways, making it convenient for commuting to nearby cities like Orlando and Tampa. With its unique blend of small-town charm and modern conveniences, Winter Haven is not just a place to live; it’s a place to thrive. Discover your dream home in this vibrant community and embrace the Florida lifestyle!

Newest Winter Haven Homes with Clubhouse Community Features

2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code

Completely renovated, ground-floor condo with expansive lake views on the Winter Haven Chain of Lakes! Welcome to Winterset, where this beautifully reimagined 2-bedroom, 2-bath residence 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 the home feels 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 redesigned kitchen has been expanded for greater functionality and features granite countertops, soft-close cabinetry with crown molding, black appliances, a gas range, dishwasher, 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 oversized primary suite is one of the home's standout features, offering beautiful lake views and direct access to the private screened porch—a peaceful spot for morning coffee, an afternoon book, or simply enjoying the breeze and ever-changing colors of sunsets over the water. An exceptionally large walk-in closet provides impressive storage, while the completely renovated en-suite bath features a double vanity with undermount sinks and granite countertop, updated 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. 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

3 Beds ⋅ 2 Baths ⋅ Morningside SubDv. ⋅ 33884 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Every day feels like a vacation in this beautiful home located in Traditions, a sought-after 55+ gated lakefront community offering the best of Florida living. This move-in ready residence showcases pride of ownership from the moment you arrive, featuring a brick paver driveway and a meticulously cared-for interior. Inside, you’ll find updated stainless steel appliances, a water softener, and thoughtful upgrades throughout. The enclosed and cooled Florida room creates the perfect year-round retreat for relaxing or entertaining. Additional highlights include gutters, a painted garage floor, and a golf cart included for your convenience. Traditions offers an unmatched lifestyle with resort-style amenities, including community boat slips, a dock, and fishing pier with water access—perfect for lake lovers. Residents also enjoy a clubhouse, fitness center, heated resort-style pool, sauna, tennis and pickleball courts, dog park, and golf cart-friendly streets. Plus, you’re a minute from the new Publix, making everyday living effortless. If you’re ready to enjoy an active, low-maintenance lifestyle in a vibrant lake community, this home is a must-see.

4134 Bedford Avenue, Winter Haven

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

2 Beds ⋅ 2 Baths ⋅ Village Park SubDv. ⋅ 33880 Zip Code

Welcome to easy, affordable Florida living! This well-maintained 2-bedroom, 2-bath manufactured home is nestled in Village Park, a desirable 55+ community in Winter Haven and offers the perfect blend of comfort, convenience, and an active lifestyle. With a low HOA and NO LOT FEES, you'll enjoy affordable, low-maintenance living. Inside, you'll find a bright and inviting floor plan featuring a spacious living room, a designated dining area, and a functional kitchen complete with a breakfast bar—perfect for casual meals or entertaining guests. The primary suite serves as a private retreat with a walk-in closet and an en suite bathroom. One of the home's standout features is the generously sized screened-in porch overlooking the peaceful community pond, providing the perfect place to enjoy your morning coffee or unwind while taking in the tranquil water views. Situated at the end of a quiet street with no through traffic, this home offers added privacy and a serene setting. A covered carport provides convenient parking. Residents of this welcoming 55+ community have access to fantastic amenities, including a sparkling community pool, clubhouse, shuffleboard courts, and a full calendar of social activities designed to keep you active and connected with your neighbors. Conveniently located just minutes from shopping, restaurants, medical facilities, parks, and everyday conveniences, this move-in-ready home is vacant and easy to show. Whether you're looking for a full-time residence or the perfect Florida getaway, this charming home offers the relaxed lifestyle you've been searching for.

489 Village Circle Sw, Winter Haven

3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code

Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

New Carpet throughout most of the home. Plus many of the windows have been updated to thermal pane insulated windows. If that is not enough the TPO roof was installed in December 2023. The home has a nice layout with a huge primary bedroom with huge walk in closet. Location is convenient in Oakwood Estates, a 55+ community, right across from the office and close proximity to one of the pools. Enjoy the many amenities at Oakwood including two pool, two clubhouses, miniature golf, fishing pier, shuffleboard and much, much more. Join in on the many activities including weekly Koffee Klatch, potluck meals, and dances. The two heated pools offer many hours of relaxation. Or just sit out on the screened front porch and watch the world go by. This home is priced to sell. Check it out today!!

4027 Rolling Oaks Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven

2 Beds ⋅ 1 Baths ⋅ Parkland Village SubDv. ⋅ 33880 Zip Code

Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as vertical blinds, mirrored closet doors, and storm doors and shutters. The home also includes a private courtyard, perfect for relaxing or entertaining, along with a 1-car carport and a storage closet with a washer and dryer. Residents enjoy access to a recreation building and shuffleboard courts, while the low monthly HOA fee of just $110 includes grounds maintenance, making for easy, low-maintenance living. Conveniently located near shopping, banks, and restaurants, this home offers the perfect combination of comfort, convenience, and affordability. Don't miss this opportunity—schedule your private showing today!

790 Avenue Q Se, Winter Haven

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

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! This Jupiter plan is Traditional elevation. The inviting front porch opens to a gracious foyer with the Primary suite on the first floor; it boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The spacious family room is open to the dining area and adjacent kitchen. The 2nd level offers a spacious loft and 3 secondary bedrooms each with walk-in closets and a full bathroom.

349 Meredith Boulevard, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and 4 Bedrooms! This Naples is in Coastal Elevation. The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft, 3 secondary bedrooms, each with walk-in closets, a full bathroom and a convenient laundry room.

816 Andrew Street, Winter Haven

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