Winter Garden/Oakland Homes with Basketball Court Amenities

Winter Garden/Oakland Homes with Basketball Court Amenities

Welcome to Winter Garden and Oakland, a picturesque corner of Central Florida known for its vibrant community spirit, lush landscapes, and an array of recreational opportunities. Nestled within Orange County, this charming region boasts a rich history and a thriving local culture, making it a highly sought-after destination for families and individuals alike.

Winter Garden is renowned for its historic downtown area, where you can stroll along tree-lined streets filled with delightful boutiques, artisanal eateries, and local farmers’ markets. The scenic West Orange Trail offers miles of trails for walking, biking, and enjoying the breathtaking Florida sunshine. Just a stone’s throw away, Oakland complements Winter Garden with its quaint charm and picturesque views, creating an idyllic setting for those who appreciate a slower pace of life.

For those who love to stay active, homes in Winter Garden and Oakland often feature fantastic amenities, including private basketball courts. Whether you’re shooting hoops with friends, hosting family game nights, or simply enjoying a leisurely afternoon, these basketball court amenities provide the perfect backdrop for fun and fitness right in your backyard. Imagine the joy of having a dedicated space to practice your skills or create cherished memories with loved ones.

With a wide range of housing options available, from cozy single-family homes to luxurious estates, Winter Garden and Oakland cater to diverse lifestyles and preferences. Embrace the opportunity to live in a community that celebrates health, wellness, and togetherness. Discover your dream home in this vibrant region today, and experience the perfect blend of suburban tranquility and active living!

Newest Winter Garden/Oakland Homes with Basketball Court Amenities

$489,000
3 Beds ⋅ 2 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
WELCOME HOME TO BLACK LAKE PARK — a gated community where every day feels like a retreat. As you pass through the gates, you're welcomed by the community's stunning 10-acre park, complete with a charming white gazebo and wide-open green space that instantly sets the tone. There's a sense of warmth and connection here that's hard to put into words — you simply feel it. Pulling into the driveway and stepping through the inviting front door, you already know this is more than just a house... it's home.Offering over 1,923 square feet of thoughtfully designed living space, this move-in-ready 3-bedroom, 2-bath home with a 2-car garage has everything you need. Inside, natural light pours through the windows, highlighting the open layout and laminate flooring throughout the main living areas. If you love to cook, gather, and entertain, the remodeled kitchen will absolutely capture your heart, featuring quartz countertops, a glass cooktop, and built-in double ovens. Whether you're hosting a holiday gathering or enjoying a quiet morning coffee, this kitchen truly delivers. Sliders open to the patio — perfect for relaxing evenings or weekend get-togethers.Down the hall, bedrooms 2 and 3 offer comfortable accommodations and share a beautifully appointed guest bath. The primary suite is your private retreat, complete with a spacious walk-in closet, while the en-suite bath features a dual-sink vanity and a walk-in shower — your own personal escape at the end of the day.Living in Black Lake Park means enjoying an array of amenities, including a playground, fitness area, volleyball court, swimming pool, tennis courts, basketball court, pickleball courts, soccer field, private boat ramp and dock, and sidewalks throughout the neighborhood. Imagine ending your day with a walk to the community dock to watch breathtaking sunsets over the water, or enjoying seasonal fireworks lighting up the sky on the 4th of July. The community also hosts memorable events throughout the year, including a Halloween Costume Parade, Christmas caroling and movie night in the park, Easter egg hunts, organized garage sales, and more — creating opportunities to connect and build lasting memories.Location truly completes the package — just minutes from Downtown Winter Garden, Winter Garden Village, and major highways including the 429, the Florida Turnpike, and the 408, and conveniently close to Walt Disney World and other world-class attractions.This is more than a home. It's a lifestyle filled with comfort, connection, and everyday moments that turn into lasting memories.

502 First Cape Coral Dr, Winter Garden
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Experience refined Florida living in this impeccably maintained single-story 4BD/3BA residence set on an oversized corner lot in the prestigious Waterleigh community. Thoughtfully designed interiors blend elegance with comfort, highlighted by rich finishes, abundant natural light, and a seamless open layout. The gourmet kitchen showcases espresso cabinetry, granite surfaces, a striking center island, modern lighting, stylish backsplash, and a spacious pantry — all appliances included. The primary suite offers a serene retreat with luxury vinyl plank flooring, tray ceiling, quartz dual vanities, a soaking tub, glass-enclosed shower, and an expansive walk-in closet. Step outside to a private oasis featuring a covered screened lanai, brick patio, and a fully fenced yard ideal for quiet relaxation or elevated entertaining. Additional enhancements include a Ring security system, upgraded blinds, garage storage systems, and specialty garage flooring. Just a short stroll from a resident-exclusive clubhouse with a zero-entry pool, fishing pier, lake views, and sand volleyball. Waterleigh’s resort-style amenities elevate daily living with three pools, two fitness centers, tennis and basketball courts, mini golf, splash pad, dog parks, and scenic trails. HOA includes lawn care, irrigation, and tree maintenance. Located near top-rated schools, a nearby fire station, golf, and evening Disney fireworks views, this smoke-free, pet-free home delivers luxury, convenience, and lifestyle in one of Winter Garden’s most coveted communities.

8711 Eden Cove Drive, Winter Garden
$230,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 01 SubDv. ⋅ 34787 Zip Code
Welcome home to this bright, beautifully maintained and thoughtfully updated first-floor condo in the heart of Winter Garden. This 2-bedroom, 2-bath residence offers 918 square feet of comfortable living space with tasteful improvements and smart use of space throughout. Step inside to an inviting, open living and dining area featuring wood-look luxury vinyl flooring throughout, recessed lighting and an abundance of natural light. Recently replaced windows are an especially valuable improvement, enhancing the home’s fresh, updated feel while offering an upgrade buyers will appreciate for years to come. The kitchen has been tastefully refreshed with granite countertops, a stylish tile backsplash, breakfast bar and thoughtful cabinetry updates, creating a functional space that opens naturally to the dining and living areas. A standout feature is the custom reconfigured laundry and pantry area, thoughtfully redesigned to make the most of the available space. The stackable washer and dryer provides convenient laundry access while allowing for additional organized pantry and cabinet storage—an incredibly functional upgrade that you won’t find in every unit. Both bedrooms are comfortably sized, and the continuous wood-look flooring creates a clean, cohesive feel throughout the home. Additional improvements include a tankless water heater, updated lighting and numerous thoughtful touches throughout. Enjoy your own large covered and screened front porch, offering additional space to relax and enjoy the Florida weather. Combined with convenient first-floor living and a well-maintained community setting, this home offers an easy, comfortable lifestyle in a desirable Winter Garden location. Bright, clean, thoughtfully updated and truly move-in ready—this is a condo that stands out from the rest.

27 Windtree Lane Unit 102, Winter Garden
$419,999
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Storey Grove **YES IT HAS A BACKYARD!!*BACKS TO GREENSPACE!!** 2023 built ** Open floorplan * Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, 2 children's playground and green space area. Landscaping and exterior paint included in the HOA. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$758,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this stunning 3-bedroom, 3-full-bathroom residence boasting 2,976 square feet of beautifully designed living space, plus a dedicated office, spacious loft, and versatile bonus room. Perfectly positioned on a premium lakeview homesite, this exceptional property offers tranquil water views and the spectacular bonus of enjoying Disney fireworks from your own backyard. Step outside into your private backyard oasis, where a sparkling pool creates the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. The fully fenced backyard provides both privacy and space, while the premium lot offers a picturesque backdrop that truly sets this home apart. Inside, the home is thoughtfully appointed with upscale details throughout. The gourmet-inspired kitchen features 42-inch cabinetry, complemented by upgraded light fixtures and designer-style ceiling fans throughout the home. The spacious bonus room, enclosed by elegant frosted-glass doors, offers a flexible space ideal for a media room, home office, entertaining, or additional living space. The dedicated office and generous loft provide even more versatility for today’s lifestyle. Additional highlights include a 2024 A/C, 2025 water heater, and an impressive 25-foot extended garage offering exceptional storage and flexibility for vehicles, recreational equipment, or hobbies. Adding to the ease of Florida living, the HOA includes landscaping and hedge trimming, allowing you to spend more time enjoying your home and less time maintaining it. From the premium lakefront setting and private pool oasis to the thoughtful upgrades, expansive floor plan, and unforgettable Disney fireworks views, this is a home that delivers an exceptional blend of luxury, comfort, and lifestyle.

14735 Snowy Egret Street, Winter Garden
$710,000
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
$859,500
5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to your dream home in the highly desirable community of Wincey Groves! This stunning 5-bedroom, 3.5-bath single-family residence, built in 2021, boasts contemporary design and upscale finishes throughout. Enjoy soaring 10-foot ceilings with elegant fascia, and a chef-inspired modern kitchen featuring luxurious quartz countertops and top-of-the-line stainless steel appliances. Experience custom-built cabinetry and exquisite upgraded millwork that add character and style to every room. The spacious primary suite offers generous walk-in closets, a versatile bonus fifth bedroom, perfect for guests or a home office. Step outside to an upgraded back patio and balcony, where you'll find a fully equipped outdoor kitchen with a wine fridge, refrigerator, built-in grill, and a cozy fire pit—ideal for entertaining or relaxing under the stars. Ideally situated just one mile from Hamlin Town Center, you'll have easy access to premier shopping, dining, and entertainment options.

5128 Breezy Acres Street, Winter Garden
$290,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$2,600,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful custom home on Hancock Lake was built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat w/lift and 2 jet ski lifts. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and whimsical Disney characters embedded in the rock facade. Relax to lake views, or pull down the projector screen for a movie. After your show, stay tuned for the nightly fireworks over the lake from the Disney park. The home has a freshly painted exterior and interior with crown trim throughout. Spectacular front entrance with impressive light fixtures and an abundance of natural light where you'll catch the first glimpse of the lake. The Kitchen is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating merging with the open Family Room where sliders open to the patio and lake. A cabana bath and Den/Office/possible bedroom are down a separate wing behind the Kitchen providing additional patio access. The first level’s primary suite has private patio access and a lovely bay window styled seating area. Previous Owners used this room as a media room complete with surround sound that remains intact. The loft has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. Upstairs are two additional ensuites, 3 more bedrooms (two with balconies) and a laundry room. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$244,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$434,900
4 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in the highly desirable Storey Grove community of Winter Garden. Thoughtfully designed with the primary suite on the first floor, this home offers the perfect blend of comfort and functionality. Inside, you'll find an open living and dining room combination, a convenient first-floor half bath, and a spacious kitchen featuring white cabinetry, a large 42-inch island, stylish pendant lighting, a pantry, and plenty of workspace for cooking and entertaining. The first-floor primary suite includes a walk-in closet and an en-suite bath with dual sinks, and a walk-in shower. Upstairs, a versatile loft with built-in cabinetry provides the perfect space for a media room, home office, or play area. All three secondary bedrooms are generously sized, with two featuring walk-in closets, while the fourth bedroom, currently used as a den, includes a standard closet and can easily serve as a bedroom. The upstairs bathroom offers a tub/shower combination, single vanity, and linen closet. Step outside to enjoy the pavered patio overlooking the fully fenced backyard and walkway to garage—ideal for relaxing or entertaining. Additional features include garage storage racks that convey with the home and an A/C system equipped with a UV light for enhanced indoor air quality. Located in the sought-after Storey Grove community, residents enjoy resort-style amenities including a clubhouse, fitness center, resort-style swimming pool, splash pad, playgrounds, walking trails, and tennis courts, all with convenient access to Hamlin Town Center, Horizon West shopping and dining, major roadways, and top-rated Orange County schools. This move-in ready home offers the perfect opportunity to enjoy the sought-after Winter Garden lifestyle.

10607 Words Drive, Winter Garden
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