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

$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

93 Windtree Lane Unit 102, Winter Garden
$500,000
3 Beds ⋅ 2 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden
$815,000
3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code
WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden
$410,000
3 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 1b-3 SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful 3-bedroom, 2.5-bathroom home located in the highly desirable Storey Grove community in Winter Garden. Built in 2020, this modern residence offers approximately 1,717 square feet of thoughtfully designed living space with an open-concept floor plan, abundant natural light, and stylish finishes throughout. The spacious kitchen features stainless steel appliances, quartz countertops, and a large island overlooking the living and dining areas, making it ideal for everyday living and entertaining. The primary suite offers a generous walk-in closet and an elegant en-suite bathroom. Residents enjoy outstanding community amenities, including a resort-style pool, fitness center, clubhouse, playgrounds, walking trails, and parks. Conveniently located near Flamingo Crossings, Horizon West, Walt Disney World, major highways, shopping, dining, and top-rated schools. Don’t miss the opportunity to own this exceptional home in one of Winter Garden’s most sought-after communities!

15066 Book Club Road, Winter Garden
$295,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code
**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden
$574,900
3 Beds ⋅ 2 Baths ⋅ Signature Lks-Pcl 01b SubDv. ⋅ 34787 Zip Code
Discover refined living in this charming 3-bedroom, 2-bathroom home located in the desirable Independence community. This property offers a serene backdrop, backing directly onto a tranquil pond and conservation area. Relax on your screened-in rear porch overlooking the water, or enjoy the classic appeal of the L-shaped front porch—complete with a swing for those quiet afternoons. Inside, you will find an expansive formal dining area seamlessly connected to the living room, ideal for entertaining. The home features a recently replaced A/C system in 2025, premium tile and laminate flooring throughout, providing a clean, low-maintenance, and modern aesthetic in every room. The heart of the home is the open kitchen, featuring 42-inch cabinetry, granite countertops, a functional breakfast bar, and a cozy casual dining nook. The primary suite serves as a true retreat, boasting double-door entry, a spacious walk-in closet, and a bath equipped with a garden tub and dual vanities. Independence living offers unmatched value, with HOA fees covering your Spectrum cable and high-speed internet. Residents enjoy a premium lifestyle with access to two clubhouses, two resort-style pools, fitness centers, tennis and basketball courts, dog parks, and boat access to both Lake Speer and Lake Hancock.

14543 Whittridge Drive, Winter Garden
$429,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Virtually Staged. OBTAINABLE LUXURY IN SUMMERLAKE! This MOVE-IN-READY, Energy Star Certified townhome offers the perfect blend of style, comfort, luxury and convenience with 3 bedrooms, 2.5 baths, a 2-car garage, and 1,738 square feet of thoughtfully designed living space. Recently refreshed with NEW interior PAINT and NEW CARPETING, this home welcomes you from the moment you step onto the covered front porch. Inside, the open-concept floor plan is enhanced by contemporary wood-look tile flooring throughout the first level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen featuring granite countertops, rich 42-inch wood cabinetry, stainless steel appliances, a large center island with sink and breakfast bar, walk-in pantry, and a convenient built-in desk workspace. Whether preparing meals or entertaining guests, the open design keeps everyone connected. Step outside to your private, partially fenced courtyard with brick pavers—an ideal setting for morning coffee, outdoor dining, or relaxing after a busy day. The courtyard leads directly to the detached 2-car garage for added convenience. Upstairs, you'll find all three bedrooms, the laundry area, and new carpeting throughout. The spacious primary suite easily accommodates a king-size bed and features a large walk-in closet and an en-suite bath with dual granite vanities, a garden tub, and separate shower. Two additional bedrooms share a full bath with granite countertops. Located in the highly desirable Summerlake community, residents enjoy outstanding resort-style amenities including a community pool, clubhouse with fitness center and recreation room, pickleball/tennis and basketball courts, playgrounds, zip line, parks, dog park, and scenic walking trails. The home is conveniently located near Summerlake Elementary School and a neighborhood park. Summerlake, Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! As an added entertainment bonus, enjoy spectacular nightly Disney fireworks from designated viewing areas throughout the community. Just minutes from Hamlin Town Center, Cinépolis Luxury Cinemas, Orange County National Golf Center & Lodge, shopping, dining, and major roadways. This luxurious, beautifully updated home offers an exceptional opportunity to enjoy one of Horizon West's most sought-after communities. Experience the perfect combination of modern comfort, recent updates, and an outstanding Florida lifestyle. Lawn maintenance is included. Exterior scheduled to be painted!

8150 Red Stopper Lane, Winter Garden
$945,000
4 Beds ⋅ 5 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Currently occupied by tenant. Tenant will move out Jan 2027. Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled with elegant touches throughout. As you step inside, you’re greeted by a custom full-length glass wall in the hallway, adding depth and openness to the floorplan. The first room on the left is a fully equipped office. Adjacent is a sophisticated formal dining room with stylish wallpaper. The soaring ceilings and oversized family room are designed for both entertaining and everyday comfort, featuring stunning window treatments, a high-resolution projector, and a built-in surround sound system—perfect for cinematic nights at home. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a large quartz countertop, a summer kitchen layout, and designer pendant lights, all of which can remain with the home. The first-floor master suite is a true retreat with blackout window treatments, a spa-like bath with a soaking tub, and a generous walk-in closet. Upstairs, you’ll find three additional bedrooms, a spacious loft, a study/den, and a one-of-a-kind themed game room with a hand-painted moon mural, cloud accents, twinkling ceiling lights, and a second surround sound system. Step outside to a covered patio with a heat-block screen and ambient ceiling lighting—ideal for evening gatherings. Located just a short walk from the luxury clubhouse and nearby commercial plaza, you’ll enjoy resort-style amenities including pool, a fitness center, fire pit, waterslides, tennis and basketball courts—all with a low HOA. This home offers the perfect combination of luxury, convenience, and community living. There are four lights have been removed compared to the original listing photos: • The fixture in the front study room • The one in the formal dining room • The light above the staircase• The one in the morning/breakfast area Please call for showing.

9567 Meadow Hunt Way, Winter Garden
$217,500
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautiful 1BR/1BA condo with a bright open floor plan, spacious solarium/flex space, granite countertops, walk-in closet, and interior laundry. Located in the gated Southern Pines community featuring a resort-style pool, fitness center, indoor basketball and racquetball courts, tennis courts, playground, and clubhouse. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and entertainment. Northeast-facing unit with abundant natural light and excellent community amenities.

Winter Garden
$689,999
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Located in the sought-after community of Waterleigh, Welcome Home to this freshly upgraded four-bedroom, three bath residence. Step through the front door and you will find its turn key. Built in 2023, this like-new residence offers over 2,000 square feet of thoughtfully designed living space with an open-concept floor plan perfect for both everyday living and entertaining. Inside you will discover a bright and open floor plan, the spacious living area flows seamlessly into the dining space and kitchen, creating a warm and inviting atmosphere. The kitchen features upgraded cabinetry and modern stainless steel appliances. The private primary suite offers a generous walk-in closet and a beautifully appointed en-suite bathroom designed for comfort and functionality. Three additional bedrooms provide flexibility for guests, a home office, or growing family needs, while the additional baths are thoughtfully designed for convenience. Enjoy Florida’s sunshine year-round in the backyard that is deal for barbecues, gardening, or simply unwinding after a long day. With a two-car garage and plenty of storage throughout, this home checks all the boxes. Located in the amenity-rich Waterleigh community offering resort-style pools, walking trails, playgrounds, fitness centers, and scenic green spaces, all just minutes from shopping, dining, top-rated schools, and convenient access to major highways, theme parks, and everything Orlando has to offer. This is an incredible opportunity to own a home in one of Central Florida’s most promising communities. Schedule your tour today, and welcome to your New Home!

11043 Jackson Cove, Winter Garden
$775,000
5 Beds ⋅ 4 Baths ⋅ Summerlake Pd Ph 1b-A Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. ... Summerlake Community ... This 5 bedroom 3.5 bath 2 car garage is seeing the water view from the front entrance. It has a large kitchen integrated with dining room and living room. Lots of windows and the view.... Newly painted inside and outside... The upstairs offers a lot of spaces for playroom and study room. The house is zoomed for Summerlake Elementary School, Hamlin Middle School, and Horizon High School. Don't forget, it is just minutes away from Hwy 429 and the shopping area in Hamlin. The community offers heated zero entry pool, Yes, heated pool. Tennis courts, Zip liner, gym, dog parks, and more.

14741 Snowy Egret Street, Winter Garden
$950,000
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to Silverleaf in Horizon West, where luxury, space, and convenience come together just minutes from world-class attractions and approximately 25 minutes from Disney. Hamlin Town Center is also just a few minutes down the road, offering all of the staples in addition to dining, shopping, and nightlife. This stunning 5-bedroom, 4.5-bath residence offers nearly 4,000 square feet of thoughtfully designed living space with exceptional upgrades throughout. The heart of the home is the beautifully appointed gourmet kitchen featuring ceiling-height cabinetry, quartz countertops, an extended designer backsplash, and abundant storage, all opening seamlessly to the spacious great room—perfect for entertaining and everyday living. A private guest area with a full bath off the rear hallway provides comfort and flexibility for visitors or multigenerational living. Step outside to an expansive backyard with no rear or side neighbors, creating a private setting for relaxation and recreation. The covered lanai is pre-plumbed for an outdoor kitchen and ready for your vision of the ultimate backyard oasis. A striking open staircase with modern wire railing leads to the second floor, where a massive loft serves as a central gathering space surrounded by three secondary bedrooms and the luxurious primary suite. The spacious primary retreat includes a versatile bonus room ideal for a home office, fitness area, nursery, or private sitting room. The spa-inspired primary bath features a large soaking tub, frameless glass shower, a tasteful tile package, and a walk-in closet with a custom organization system. Additional highlights include a second-floor laundry room with upgraded cabinetry and utility sink, extra recessed lighting throughout, a newly installed EV charger,, and an epoxy-coated garage floor, and a covered front porch with room for chairs to sit and watch the world go by. You are also just steps from Hamlin Elementary and Hamlin Middle school making it easy to avoid that dreaded drop off/pick up loop by walking or biking your kiddos to school. Located in the highly desirable Horizon West area near shopping, dining, top-rated schools, and major roadways, this exceptional home offers the perfect blend of elegance, functionality, and Florida living.

16043 Silver Brook Way, Winter Garden
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