Winter Garden/Oakland Homes with Clubhouse Community Features

Winter Garden/Oakland Homes with Clubhouse Community Features

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where the charm of small-town living meets the vibrancy of modern amenities. Nestled in Orange County, this picturesque area is renowned for its lush landscapes, friendly neighborhoods, and rich history, making it a perfect place for families and individuals alike.

Winter Garden is celebrated for its delightful downtown area, brimming with boutique shops, farm-to-table restaurants, and a thriving arts scene. The scenic West Orange Trail winds through the community, offering residents a beautiful path for walking, biking, and enjoying the great outdoors. Meanwhile, Oakland, with its quaint streets and historic architecture, exudes a warm, welcoming atmosphere that captivates all who visit.

One of the standout features of homes in this region is the abundance of clubhouse communities. These neighborhoods foster a strong sense of community, providing residents with access to a variety of amenities designed for leisure and recreation. Imagine enjoying sunny afternoons by the pool, hosting gatherings in beautifully appointed clubhouses, or participating in community events that bring neighbors together. From fitness centers to playgrounds, these communities are designed to enhance your lifestyle, making it easy to connect with others and enjoy everything this vibrant area has to offer.

Whether you’re looking for a cozy single-family home or a spacious townhome, Winter Garden and Oakland provide a diverse range of options to suit your needs. Experience the perfect blend of comfort, community, and convenience in this delightful corner of Florida!

Newest Winter Garden/Oakland Homes with Clubhouse Community Features

$335,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 3 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 3701 at The Grove Resort & Water Park, a fully furnished seventh-floor condo offering 3 bedrooms, 3 bathrooms, and 1,544 square feet of spacious resort-style living just minutes from Walt Disney World. Designed for comfort and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances and quartz countertops, a full-size washer and dryer, and a private screened balcony—perfect for relaxing after a day at the parks. Owners and guests enjoy an impressive collection of resort amenities, including Surfari Water Park with a FlowRider® Double surf simulator, dual water slides, a 695-foot lazy river, and a zero-entry pool. The resort also offers multiple swimming pools, private cabanas, a fitness center, full-service spa, on-site restaurants and bars, the Flip Flop’s Family Fun Center, and recreational activities on scenic Lake Austin. When not enjoying the residence, owners may participate in the professionally managed hotel rental program, subject to applicable terms and restrictions. The Grove is zoned as a condo-hotel, with owner occupancy limited to 179 days calendar year. This turnkey property combines a desirable location, exceptional amenities, and effortless vacation ownership in one of Central Florida’s most popular resort destinations.

14501 Grove Resort Ave, 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
$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 and interior 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
$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
$424,990
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
$2,249,000
5 Beds ⋅ 6 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome to a rare 2020-built lakefront opportunity - the 'Estates Collection' Maranello model by Toll Brothers - in one of Winter Garden's premier communities, Lakeshore Preserve. This stunning two-story Mediterranean estate spans 5 bedrooms, 4 full and 2 half bathrooms, and 4,253 square feet of intentionally designed living space, commanding one of the most coveted settings in the neighborhood - a premium 0.335-acre waterfront homesite with sweeping, unobstructed lake views and no rear neighbors, where a custom travertine-paved patio and freeform pebble-finish pool with a natural stone waterfall spill toward the water's edge for the ultimate Florida indoor-outdoor lifestyle. The privileged positioning continues out front, where you'll enjoy no front neighbors and a serene wooded and golf-course view - Hole 14, nick-named "The Long Man", of Orange County National's Panther Lake course - a rare double-exposure setting that bookends the home with natural beauty and supreme privacy. From the moment you arrive, the home's timeless curb appeal makes a statement: authentic tile roof, warm stucco-and-stone elevation, mature landscaping framed by manicured hedges and boulder accents, and a grand paver motor court leading to the dual garages and double iron-and-glass entry doors. Step inside to a soaring foyer anchored by a sweeping wrought-iron staircase, rich hardwood flooring, elegant crown molding, and designer light fixtures that carry throughout the home. The heart of the home is a gourmet kitchen appointed with an oversized granite island with ample seating, custom raised-panel cabinetry, a full stainless appliance suite with a built-in oven, a tasteful tile backsplash, walk-in pantry, and three statement pendant lights - all opening seamlessly to the family and dining spaces for effortless entertaining. Retreat to the luxurious primary en-suite, a spacious sanctuary featuring a custom walk-in closet system, automated blinds, tranquil lake views, and a spa-inspired bath with dual vanities, quartz counters, an oversized walk-in shower, and refined tile detailing. Generously sized secondary bedrooms, thoughtfully designed living and gathering areas, a second-story loft, and abundant natural light throughout complete the interior. Off of the loft, enjoy stunning lake views, sunrises, sunsets, and Walt Disney World's Magic Kingdom fireworks from the screened balcony. This home has been meticulously enhanced with an impressive list of premium upgrades, including a Tesla level-2 charger, a fully screened lanai with a motorized screen system, an outdoor summer kitchen with stone backsplash and exhaust hood, a whole-house water softener, a utility sink in the garage, UV lights in all 3 HVAC systems, an upgraded outdoor lighting package, stone landscape curbing, decorative boulders, a backyard fence, and premium ceiling fans throughout the interior, lanai, and balcony. Every detail has been curated for comfort, efficiency, and elevated Florida living. Community amenities include a resort-style pool, fitness center, clubhouse, park, and community dock offering unparalleled views of Magic Kingdom fireworks. Ideally situated with easy access to top-rated Horizon West schools, world-class shopping and dining, major roadways, theme parks, and everything Central Florida has to offer, this is the kind of one-of-a-kind lakefront estate that simply doesn't come along often. Contact us to schedule your private tour today!

15475 Shorebird Lane, Winter Garden
$849,000
5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully upgraded five-bedroom, five-bath home in the gated community of Lakeview Preserve. Built in 2022 and offering 4,495 square feet, this impressive corner-lot home features a three-car garage, spacious living areas, thoughtful upgrades, and an incredible backyard designed for entertaining and enjoying the Florida lifestyle. The main level features an open and functional floor plan with luxury vinyl plank flooring throughout, a spacious living room, separate dining area and a beautifully appointed kitchen with quartz countertops, oversized island, soft-close cabinetry, under-cabinet lighting and a custom-designed pantry. The living room and kitchen open through multi-slide pocket doors to the covered lanai, creating an ideal indoor-outdoor living space. The backyard is a standout feature, with a stunning saltwater pool complete with five waterfalls, lighting, a sun shelf, Badu swim jets and an attached spa (not heated). The covered lanai includes two fans, surround sound, a full bath and is prepped for an outdoor kitchen. It is the ideal setting for relaxing, entertaining and enjoying beautiful Florida weather. The spacious primary suite is on the first floor and features a custom-designed walk-in closet, tray ceiling, and beautifully upgraded bath with dual shower heads and soft-close cabinetry. Two additional bedrooms are downstairs, including one with a private en-suite bath, along with a versatile flex room featuring a custom built-in wall unit that can easily serve as an office or additional living space. Upstairs offers even more room to spread out with a large loft, two additional bedrooms, a full bath and an impressive private theater featuring a 120-inch screen, projector, surround sound and motorized blackout shades. The home also offers an extensive list of upgrades and conveniences, including whole-home water filtration, hybrid water heater, recessed lighting, built-in TV wiring, Wi-Fi boosters, two air-conditioning units, security cameras, alarm system, and smart-home controls for many of the home's lights, air conditioner, garage doors and locks. The three-car garage features a durable polyaspartic floor. Lakeview Preserve offers residents an array of amenities, including a fitness center, resort-style pool, cabana, splash pad, playground, and direct access to Johns Lake with a kayak launch and dock. The community is conveniently near shopping, dining, golf, the West Orange Trail, Disney, Universal, Winter Garden, and major roadways including SR 50 and the 429. This is a home that offers the space, upgrades and outdoor living that make Florida living so enjoyable.

3362 Hanging Tide Street, Winter Garden
$870,000
5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
A truly special luxury residence in the highly desirable Harvest at Ovation community of Winter Garden. Professionally designed and curated by a team of high-end architects and interior designers, this magazine-worthy home features soaring ceilings, premium finishes, designer furnishings, elegant décor, and exceptional attention to detail throughout. A standout feature is the fully finished private studio above the garage, complete with full bathroom, walk-in closet, and independent access—perfect as a guest suite, additional apartment, executive office, or private workspace. The gourmet kitchen features premium finishes and a state-of-the-art smart double-door refrigerator with internet connectivity. Enjoy Florida living in the screened outdoor area with mosquito protection, electric retractable awning, outdoor grill, and fenced yard. Additional upgrades include fully paid solar panels, whole-home water filtration, premium kitchen water purification, epoxy garage flooring, LED ceiling lighting, EV charger, and paver waterproofing. Ideally located near excellent schools, shopping, dining, major highways, and Central Florida attractions. **Designer furnishings and décor are negotiable.** A rare opportunity to own a beautifully designed luxury home where every detail has been thoughtfully perfected. This is one you truly need to see in person.

16192 Honey Harvest Street, Winter Garden
$399,999
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation Phase 1 SubDv. ⋅ 34787 Zip Code
BACK ON THE MARKET AND PRICED TO SELL!! Why wait for new construction when this move-in-ready Ashton Woods home in Northlake at Ovation is ready for you now? Tucked away among the beautiful conservation areas of Horizon West, this hidden Winter Garden gem offers modern style, fantastic amenities, and an unbeatable location. The award-winning Kendall II floor plan features 3 bedrooms, 2.5 baths, 1,584 sq. ft., a private brick-paver courtyard, and a full-size 2-car garage. The open-concept first floor showcases wood-look ceramic tile and a stylish kitchen with quartz countertops, stainless steel appliances, designer lighting, and modern finishes, flowing seamlessly into the dining and living areas. Upstairs, the spacious Owner’s Suite offers a walk-in closet and private bath with dual vanities and an oversized shower. Two additional bedrooms, a full bath, and a versatile loft/landing provide plenty of room for guests, a home office, or additional living space. Enjoy the Northlake lifestyle with a community clubhouse, resort-style pool, playground, and dog run. Publix, restaurants, shopping, schools, and bike paths are just minutes away, along with convenient access to Disney, SR-429, and I-4. Newer construction without the wait—and priced to MOVE! Schedule your showing today before this Winter Garden opportunity is gone!

17723 Japonica Bloom Drive, Winter Garden
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$774,990
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
Start Your Search