Winter Garden Homes with Pickleball Court(s) Amenities

Winter Garden Homes with Pickleball Court(s) Amenities

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County that combines small-town charm with modern conveniences. Known for its picturesque downtown area, Winter Garden boasts a vibrant community atmosphere, rich history, and an abundance of outdoor recreational opportunities. With its lush parks, scenic trails, and beautiful lakes, residents enjoy a lifestyle filled with nature and adventure.

One of the unique features of homes in Winter Garden is the growing popularity of properties equipped with pickleball courts. This exciting sport has taken the nation by storm, and Winter Garden is no exception. Imagine stepping out of your beautiful home and onto your very own pickleball court, where you can enjoy friendly matches with neighbors or practice your serves in the comfort of your backyard. These homes not only offer the convenience of having a court at your disposal but also foster a sense of community and active living.

In addition to pickleball, Winter Garden is home to a variety of amenities, including top-rated schools, shopping centers, and dining options that cater to every palate. The city’s commitment to preserving its historical roots while embracing modern developments makes it an ideal place for families, retirees, and everyone in between.

Whether you’re looking to invest in a new home or simply want to explore the vibrant lifestyle that Winter Garden has to offer, you’ll find that this city is a true gem in Florida. Discover your dream home with a pickleball court today and embrace a life of fun, fitness, and community in Winter Garden!

Newest Winter Garden Homes with Pickleball Court(s) Amenities

3 Beds ⋅ 3 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail. Link to interactive floor plan: https://www.zillow.com/view-imx/6a573be4-fd0d-4649-9df8-88349b2426f6?initialViewType=pano

263 Deer Isle Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decorative tile backsplash. The Whirlpool stainless steel appliances—including a built-in natural gas cooktop and a refrigerator—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the extended covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a rain shower head and a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. The additional spare bedroom and bathroom, along with the enclosed flex room, provide ample space for everyone. The upgraded laundry room with built-in cabinetry, quartz countertop, utility sink, and a Whirlpool washer and dryer make daily tasks a breeze. Designer-curated finishes elevate every corner of this home, including wood-look tile flooring throughout, pendant light pre-wire and under cabinet lighting in the kitchen, 2” faux wood blinds, and brushed nickel hardware and plumbing fixtures. The 2-car garage offers extra tandem storage space with an epoxy finish on the floor, ensuring that every part of your home is both beautiful and practical. With its stunning design and thoughtful touches, the Mystique home provides the perfect blend of luxury and functionality for today’s lifestyle.

13056 Sandcastle Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Most evenings, unforgettable sunsets spill across the pool and water, casting a breathtaking glow over this premier cul-de-sac homesite. Positioned on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted viewpoints—serene water vistas paired with sweeping Back 9 scenery, including uninterrupted sightlines to the 13th green and 14th tee. Welcome home to an immaculate 3-bedroom, 2-bath split-plan retreat that is truly move-in ready. Step inside and immediately feel the care, quality, and comfort woven throughout. Thoughtful upgrades include brand-new plantation shutters, a custom built-in kitchen nook with outlet, updated light fixtures and fans, and a new refrigerator. Major systems add peace of mind with a roof, HVAC, hot water heater, and interior paint all less than 3 years old. The open living area impresses with a striking white stone accent wall and durable wood-like tile flooring that flows seamlessly through the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Outside, your private oasis awaits: a covered lanai overlooking a stunning saltwater pool with sun shelf and water features, all less than 5 years old. The backdrop is pure magic—tranquil water, golf course views, and sunsets that feel like a nightly masterpiece. The fully fenced yard offers fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly situated on a quiet cul-de-sac next to the residents’ gate, this home blends privacy with convenience. Community amenities are exceptional: golf course, playgrounds, pickleball, tennis, basketball, hockey court, resort-style pool, gym, and the Stoneybrook restaurant. Zoned for highly rated schools and just minutes from Winter Garden Village with easy access to the 429, the location is unbeatable. Additional highlights include built-in garage storage and shelving, a fenced yard, and standout curb appeal. This home delivers comfort, style, and a lifestyle that’s hard to match. Call today for a private showing!

2420 Balforn Tower Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code

Affordable luxury in Winter garden! Welcome to one of Central Florida's premier 55+ communities. This beautifully appointed Ellenwood villa offers 2 bedrooms, 2 baths each with walk-in showers, a versatile flex room and a bright, open layout designed for easy Florida living. It has a pretty view with no homes behind it. Gorgeous luxury vinyl plank flooring flows throughout the home with no carpet, creating a clean, modern look and low-maintenance lifestyle. Ceiling fans have been added in both bedrooms and the living room for added comfort. The stylish kitchen features a gas range, while the home also includes an electric washer and gas dryer. The extended lanai is already plumbed for water and gas; perfect for an outdoor kitchen. Epoxy garage floors and sealed pavers ensure years of maintenance-free driveway. Del Webb Oasis delivers an exceptional resort-style lifestyle with an impressive pool, inviting fire pits, sun cabanas, a well-equipped fitness center, dedicated yoga and movement studio, plus both pickleball and tennis courts. Whether your ideal day includes staying active, relaxing poolside, or spending time with neighbors, the amenities offer something for nearly every lifestyle. The location is equally impressive. Enjoy convenient access to Walt Disney World and Hamlin Town Center, both less than 15 minutes away, along with nearby shopping, dining, entertainment, and everything Winter Garden has to offer. Beautiful finishes, thoughtful upgrades, outstanding amenities, and an unbeatable Central Florida location make this Del Webb Oasis villa an exceptional place to call home.

15873 Gem View Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Welcome to Stoneybrook West, a gated golf and recreation community in Winter Garden! This beautiful 3-bedroom, 2-bath home features luxury vinyl flooring, stainless steel appliances, and a washer and dryer. Enjoy resort-style amenities including an 18-hole golf course, swimming pool, fitness center, tennis and pickleball courts, playground, sports fields, boat ramp, fishing/viewing pier, and 24-hour guarded gate access. HOA also includes Spectrum TV and high-speed internet up to 400 Mbps. Conveniently located near shopping, dining, entertainment and major highways.

2628 Balforn Tower Way, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Step into the Renown, a new construction, single-story home situated on a corner homesite near a cul de sac offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an open flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and zero corner sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where white cabinetry with wood uppers meets luxurious quartz countertops. Thoughtfully designed features like soft-close drawers, easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a frameless glass enclosed shower, garden tub, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, brushed nickel hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

15000 Canopy Cover Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

WHY WAIT TO BUILD? BETTER THAN NEW + NO CDD! Seller offering a 1-Year Home Warranty + Closing Cost Assistance to Help Buy Down Your Rate! Even more incentives may be available when using our preferred lender. Welcome to this beautifully upgraded, move-in-ready home in Silverleaf Reserve. Less than two years old and situated on a fully fenced corner lot, this home offers the benefits of new construction without the wait—or the CDD fee. A fresh exterior repaint completed in 2026 adds to its like-new appeal. The open-concept Ellison floor plan features a gourmet kitchen with 42-inch cabinetry, quartz countertops, stainless steel appliances, upgraded backsplash, and a dedicated coffee station. Upstairs, you’ll find four bedrooms, a versatile loft with a built-in office, laundry room, and a spacious owner’s suite featuring a custom walk-in closet and frameless glass shower. More than $47,000 in builder upgrades are complemented by additional enhancements, including custom closet systems, an extended paver driveway, and epoxy-finished garage floors with LED Hex lighting. Meritage Homes’ energy-efficient construction and smart-home features provide added comfort and efficiency. Enjoy Silverleaf’s resort-style amenities, including a community pool, pickleball, tennis and basketball courts, playgrounds, sports fields, and walking trails. A-rated elementary and middle schools are within walking distance, while Hamlin Town Center is less than two miles away. With convenient access to SR 429, Disney, Downtown Winter Garden, shopping, dining, and entertainment, this home delivers location, upgrades, and value. Like new. No CDD. A-rated schools within walking distance. Home warranty and closing costs available. Why wait to build?

4981 Coral Bean Alley, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

Virtually Staged. 2023 CONSTRUCTION • PRIVATE CUL-DE-SAC • FIRST-FLOOR BEDROOM & FULL BATH • FLEX ROOM • NO CARPET • SCHOOLS APPROXIMATELY 0.2 MILES AWAY • MINUTES FROM DISNEY Tucked away on a quiet cul-de-sac with no through traffic, this upgraded 4-bedroom, 3-bath Kenton home offers 2,931 square feet of thoughtfully designed living space in the resort-style Waterleigh community. A pond and conservation area at the end of the street add to the peaceful setting, with Water Spring Elementary and Middle School conveniently located nearby. Inside, the open-concept layout features a flexible first-floor room ideal for a home office, playroom, or potential fifth bedroom, plus a separate first-floor bedroom and full bath, perfect for guests or multigenerational living. The upgraded gourmet kitchen showcases quartz countertops, 42-inch shaker cabinetry, a 7-foot island, wall oven and microwave, five-burner cooktop, walk-in pantry, and built-in coffee bar. The spacious living area opens to a covered lanai and backyard for effortless indoor-outdoor living. Upstairs, you’ll find a generous primary suite, large loft, two additional bedrooms, and a conveniently located laundry room with a utility sink. Additional upgrades include whole-house water filtration, reverse osmosis, upgraded lighting and ceiling fans, and a video doorbell. Waterleigh residents enjoy resort-style pools, clubhouses, fitness centers, tennis courts, parks, and included lawn care, all just minutes from Walt Disney World and Central Florida’s best shopping, dining, and entertainment.

11031 Jackson Cove, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2d SubDv. ⋅ 34787 Zip Code

*Some photos are virtually staged. Video Tour Available.* SELLER IS OFFERING A $5,000 CLOSING COST CREDIT WITH A FULL PRICE OFFER! NEW AC (2026 with a 10-year warranty)! NEW DISHWASHER (2026)! Waterleigh offers the best of Orange County just outside your front door. The community itself offers TENNIS and PICKLEBALL courts, community POOLS, a FITNESS CENTER, a DOG PARK, CLUBHOUSE, a 6-HOLE MINI GOLF COURSE and PLAYGROUNDS. LAWN MAINTENANCE IS INCLUDED IN THE HOA DUES. Plus, Waterleigh is just minutes from theme parks, restaurants, shopping, the 429, I4, and the Turnpike. The curb appeal is charming and the WATER VIEW is beautiful. Inside you’ll find an OPEN FLOORPLAN that is perfect for relaxing and entertaining. The kitchen has GRANITE countertops and STAINLESS STEEL appliances. The dedicated dining space is open to the spacious living room that spills open to the PATIO. There’s a half bath downstairs and the laundry closet upstairs for convenience. The primary suite offers a GRANITE countertop, double sinks, tub and shower plus a large walk-in closet. The hall bath has a granite countertop with a tub and shower. Additional upgrades include CEILING FANS in all of the bedrooms, a built-in bench near the garage entrance, fantastic storage and gutters. Don’t miss your chance to make this great townhome yours!

9991 Schroeder Alley, Winter Garden

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