Winter Garden Homes with Clubhouse Community Features

Winter Garden Homes with Clubhouse Community Features

Welcome to Winter Garden, Florida—a charming city nestled in Orange County that perfectly blends small-town nostalgia with modern conveniences. Known for its picturesque downtown, Winter Garden boasts a vibrant arts scene, delightful dining options, and an array of outdoor activities. With its lush parks and scenic West Orange Trail, residents enjoy an active lifestyle surrounded by natural beauty.

One of the standout features of Winter Garden is its welcoming community atmosphere. The city hosts a variety of events throughout the year, including farmers' markets, seasonal festivals, and outdoor concerts, making it easy for neighbors to connect and create lasting friendships.

For those seeking a home in this enchanting area, the Clubhouse Community features are a true highlight. Imagine living in a neighborhood where social interaction and recreational activities are woven into the fabric of daily life. Homes within these communities often come equipped with stunning amenities, including a beautifully designed clubhouse that serves as a hub for gatherings, events, and leisure activities. Residents can enjoy swimming pools, fitness centers, and even tennis courts—all right at their doorstep.

Whether you’re a young family, a retiree, or looking for a vibrant community to call home, Winter Garden offers a variety of housing options that cater to diverse lifestyles. With its warm climate, friendly neighbors, and a strong sense of community, Winter Garden is not just a place to live—it’s a place to thrive. Come discover your dream home in this delightful city!

Newest Winter Garden Homes with Clubhouse Community Features

$910,000
3 Beds 3 Baths Del Webb Oasis SubDv. 34787 Zip Code
Built to Impress. Upgraded to Perfection. Welcome to Del Webb Oasis. From the moment you step through the craftsman-style entry onto hardwood floors that run seamlessly through every living space, it becomes clear that every decision in this home was made with intention — and that intention was excellence. Through French glass doors, a private den with tray ceiling offers the quiet focus space today's buyer genuinely needs. Then the kitchen stops you cold. A dramatic galley-style gourmet space with rich wood cabinetry stacked to the ceiling, quartz countertops, gas cooktop with vented hood, built-in wall oven, stainless appliances and a scalloped tile backsplash that earns its own admiration. It connects directly to the side bar — wine refrigerator, diamond-lattice wine rack, quartz countertops and matching backsplash — making the entertaining potential here truly exceptional. The great room beneath soaring double tray ceilings flows naturally through wall-to-wall sliding glass doors to the screened lanai, where a full summer kitchen with granite countertops, built-in grill, stainless hood, refrigerator and sink overlooks a lush conservation backdrop and an oversized fenced yard that is genuinely rare in this community. The primary suite is a proper sanctuary — tray ceiling, dual closets and a spa-caliber ensuite with a dual-sink charcoal vanity, quartz countertops and a floor-to-ceiling tiled walk-in shower with dual shower heads, built-in bench, decorative accent and mosaic tile floor. Two well-proportioned additional bedrooms, a full bath, a polished powder room and a laundry room with cabinetry, utility sink, and full-size washer and dryer complete the picture. Smart home technology, custom water filtration and just off the garage entry, a custom built-in drop zone with beadboard detail, bench, hooks, and shelving creates the perfect transition from the garage into the home — organized, intentional, and exactly where it should be. Now — the address. Del Webb Oasis is not just a community; it's a destination. A boutique, gated 55+ enclave in the heart of Winter Garden, just 2 miles from Disney — close enough that on some evenings, the fireworks are yours to watch from the neighborhood. The 12,000-square-foot clubhouse features a coffee bar, wine lockers, lounge, fitness center, yoga and aerobics studio, arts and crafts room, billiards room, and an indoor-outdoor bar and tavern. Outside: a zero-entry resort pool with lap lanes, spa, cabanas, pickleball and tennis courts, bocce ball, community garden, fire pit, and walking paths. The HOA covers exterior maintenance, internet, and pest control — because the only thing on your schedule here is living well. Winter Garden itself offers award-winning Saturday farmers markets, boutique dining on Plant Street, West Orange Trail access, and a charming downtown that genuinely feels like a small town despite being minutes from every major Central Florida corridor.

15084 Canopy Cover Drive, Winter Garden

$493,500
3 Beds 3 Baths Encore/Ovation Ph 4b SubDv. 34787 Zip Code
Welcome to this beautiful end-unit townhome in the desirable Encore at Ovation community. Conveniently located less than 10 minutes from Disney Property, with quick access to US-192, US-27, and SR-429, you’ll be able to enjoy all Central Florida has to offer. The lot features a backloading two-car garage and a private patio area, perfect for a quiet morning coffee or a cookout with friends. The home is also set between a quaint tree-lined sidewalk to the front and open green space to the back, adding to the feeling of privacy. Inside, enjoy a thoughtfully designed layout that includes an open concept kitchen/living/dining area, ample counter and cabinet space, a dedicated pantry, a large laundry room with plenty of storage, and a separate den for multiple gathering spots. Upstairs, relax in your large primary suite with a walk-in closet and updated ensuite bathroom. You can even catch the Magic Kingdom fireworks from your window! This home is not only immaculately maintained but also upgraded for your convenience. A whole-house water filtration/softener system, kitchen sink reverse osmosis (RO) system, HVAC air ionizer and UV light system have all been recently installed. Additionally, the roof, exterior painting, driveway upkeep, yard maintenance, landscaping, and pest control are all taken care of by the HOA, making this property perfect for those using it as a secondary home, or simply looking for a low-maintenance lifestyle. Reach out to book your private showing today!

15877 Tollington Alley, Winter Garden

$675,000
4 Beds 2 Baths Covington Chase Ph 2b SubDv. 34787 Zip Code
Virtually Staged. This is not your typical "fully upgraded" listing - this home has been thoughtfully and extensively renovated throughout. Featuring 4 bedrooms, 2 bathrooms, a dedicated office and an additional flex/formal space, it offers exceptional versatility for modern living. The completely remodeled kitchen showcases custom oversized upper cabinetry, upgraded finishes, as a wine/beverage fridge and a rare oversized walk-in pantry not found in the original Ryan Homes floor plan. Both bathrooms have been fully transformed into spa-inspired retreats with luxury bidet features and a full-body shower system, delivering a true at-home spa experience. Even the light switches have been updated, reflecting the level of detail throughout the home. The main living area includes a custom built-in entertainment center, creating a refined focal point ideal for entertaining or everyday relaxation. Step outside to an oversized, fully fenced back yard offering endless potential for a future pool, outdoor kitchen, firepit, garden or custom outdoor living space. Ideally located just minutes from historic Downtown Winter Garden and Plant Street, residents enjoy easy access to dining, shopping, breweries, farmers markets and community events. The West Orange Trail funs through the neighborhood providing direct access to walking, biking, and outdoor recreation. Convenient proximity to major highways ensures quick access to Orlando and surrounding Central Florida destinations. A truly move-in-ready Winter Garden home combining extensive upgrades, flexible living spaces and an unbeatable location, this is a home designed to be lived in, not just listed.

527 Copperdale Avenue, Winter Garden

$689,000
4 Beds 3 Baths Stoneybrook West D SubDv. 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden

$350,000
2 Beds 3 Baths Signature Lks-Pcl 01a SubDv. 34787 Zip Code
Welcome to this charming and spacious 2-bedroom, 2.5-bath town-home located in the highly sought-after Signature Lakes / Independence Community. This beautifully designed town-home features an open-concept floor plan that seamlessly connects the kitchen and family room, creating a bright and inviting living space. Upstairs, both bedrooms feature en-suite bathrooms for maximum privacy, with the oversized owner’s suite boasting a luxurious bath and a walk-in closet. The exterior of the home features a fenced paver patio in the backyard, providing a private outdoor retreat that connects to the detached two-car garage. Residents of Signature Lakes enjoy access to exceptional amenities, including two clubhouses with resort-style pools, fitness centers, tennis courts, basketball courts, and playgrounds. The community also offers boat ramps, scenic parks, nature trails, a business center, a community room, and well-maintained green spaces, creating the perfect setting for an active and vibrant lifestyle. Beyond its impressive amenities, Independence is known for its dynamic community atmosphere, enhanced by dedicated community event organizers who plan a variety of immersive events throughout the year. Residents enjoy seasonal festivals, fireworks displays, and food truck gatherings, fostering a true sense of connection and entertainment. Located just minutes from Walt Disney World, Universal Studios, and other major attractions, this town-home offers a unique blend of comfort, convenience, and resort-style living. Schedule your showing today!

14448 Pleach Street, Winter Garden

$229,900
2 Beds 1 Baths Southern Pines Condo SubDv. 34787 Zip Code
Beautifully refreshed and ready to move in today, this charming 2-bedroom, 1-bath corner condo offers an inviting combination of modern updates, natural light, and exceptional community amenities. The bright, crisp interior is filled with loads of natural light and features fresh paint throughout, brand-new carpet, new door handles, and stylish modern finishes. All appliances are included, making this home truly move-in ready. The attached garage has also been washed and painted, creating a clean and functional space for parking and storage. And when it comes to value, this one is hard to beat. This is currently the most aggressively priced 2-bedroom condo with an attached garage on the market, making it a rare opportunity for a buyer looking for the combination of price, updates, and convenience. The A/C system was newly installed in June 2026, adding another significant update and valuable peace of mind. The community offers an impressive lineup of amenities designed to enhance everyday living, including a resort-style pool and relaxing hot tub, fully equipped fitness center, indoor basketball and racquetball courts, tennis court, and a convenient car wash area. Conveniently located near 429 and the Florida Turnpike, this home provides easy access to shopping, dining, major roadways, and a short drive to Orlando's theme parks and either coastline. With its desirable corner-unit location, attached garage, extensive updates, incredible amenities, and unmatched price point, this is a rare find that won't be easy to duplicate. If you're looking for a move-in-ready 2-bedroom with an attached garage at the best value currently available, this one deserves a look!

233 Southern Pecan Circle Unit 101, Winter Garden

$464,990
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16534 Barbours Creek Way, Winter Garden

$414,990
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16546 Barbours Creek Way, Winter Garden

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