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, nestled in the heart of Orange County, Florida. This vibrant area offers a perfect blend of small-town charm and modern conveniences, making it an ideal place to call home. With its picturesque landscapes, lush parks, and a rich history, Winter Garden is renowned for its inviting atmosphere and strong sense of community.

As you explore the neighborhoods of Winter Garden and Oakland, you’ll discover a variety of homes that cater to diverse lifestyles. Many of these properties are part of exclusive clubhouse communities, where residents can enjoy a wealth of amenities designed to enhance their living experience. Picture yourself unwinding by the sparkling pool, working out in a state-of-the-art fitness center, or hosting gatherings in beautifully appointed event spaces. These clubhouse features not only foster a sense of community but also provide endless opportunities for recreation and socialization.

The area also boasts a vibrant downtown filled with charming boutiques, delightful eateries, and an array of entertainment options. With easy access to major highways and nearby attractions like Disney World and Universal Studios, Winter Garden and Oakland offer the perfect blend of tranquility and excitement.

Whether you’re looking for a family-friendly neighborhood or a serene retreat, the homes in Winter Garden and Oakland—especially those within clubhouse communities—offer the ideal backdrop for creating cherished memories. Embrace the lifestyle you’ve always dreamed of in this captivating corner of Florida!

Newest Winter Garden/Oakland Homes with Clubhouse Community Features

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this beautifully designed new construction bungalow by Toll Brothers in the desirable Winter Garden/Horizon West area, with estimated completion in April 2027. A covered front entry welcomes you into a spacious foyer that opens to a versatile flex space, ideal for a home office or additional living area. The open-concept floor plan features a well-appointed kitchen with a breakfast bar overlooking the dining area and a great expansive room, creating the perfect setting for everyday living and entertaining. Enjoy seamless indoor-outdoor living with access to the private courtyard. The spacious primary suite offers a large walk-in closet and a luxurious bath complete with dual vanities, a separate shower, and a private water closet. Experience thoughtfully designed living in one of Central Florida's most sought-after communities.

13056 Sunset Garden Lane, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to the Crowley townhome by Toll Brothers, located in the desirable Winter Garden/Horizon West area. This thoughtfully designed new construction home features a covered front entry that opens to a spacious, open-concept living area, seamlessly connecting the great room, kitchen, and dining space. Enjoy outdoor living in the private courtyard with convenient access to the detached 2-car garage. Above the garage, a finished loft with a full bathroom adds approximately 550 square feet of flexible living space, perfect for a guest suite, home office, fitness room, media room, or hobby space. The spacious primary suite offers a large walk-in closet and a well-appointed bath featuring dual vanities and a separate shower. Experience low-maintenance living with exceptional design in one of Central Florida's most sought-after communities.

12800 Sunset Walk Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this stunning new construction home by Toll Brothers in the highly sought-after Winter Garden/Horizon West area, with estimated completion in April 2027. Designed with both everyday living and entertainment in mind, this thoughtfully crafted floor plan offers an open-concept great room, kitchen, and dining area that seamlessly flow together. A covered front entry welcomes you inside, while the covered lanai and spacious private courtyard create the perfect outdoor retreat with convenient access to the detached 2-car garage. The luxurious primary suite features a generous walk-in closet and a spa-inspired bath with dual vanities, a separate shower, and a private water closet. Don't miss this opportunity to own a beautifully designed new home in one of Central Florida's most desirable communities.

13038 Sunset Garden Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, this home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. This low maintenance townhome includes a detached two car garage with private fenced courtyard space. The open kitchen boasts plenty of modern upgrades from the AW Collection Coastal such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings. The main living areas feature wood look luxury vinyl plank flooring and the bedrooms include upgraded carpet for comfort, plus find upgraded 8' doors throughout the home. Enjoy the neighborhood amenities including a community pool, clubhouse, shaded playground, and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17398 Sweet Moro Drive, Winter Garden

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

2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code

LISTED AT APPRAISED VALUE! Welcome to this beautifully updated townhome in the highly desirable gated community of Daniels Landing in Winter Garden. Combining modern upgrades with an ideal location, this move-in-ready residence offers the perfect blend of style, comfort, and convenience. Step inside to discover an inviting open-concept main level featuring a spacious living room, a well-appointed kitchen with granite countertops, ample cabinetry, a dining area, and a convenient half bath for guests. Luxury wood plank flooring flows throughout the living room and both bedrooms, creating a warm and cohesive feel. Upstairs, you'll find two generously sized primary suites, each complete with walk-in closets and private en-suite bathrooms. The bathrooms were fully renovated in 2025 with designer tile flooring, new vanities, LED mirrors, beautifully tiled showers, new toilets, and contemporary fixtures, creating spa-inspired spaces you'll love. A conveniently located upstairs laundry area adds to the home's thoughtful layout. Extensive recent improvements provide exceptional peace of mind, including a complete HVAC system replacement (2022), new garage door and garage door opener (2025), professionally cleaned air ducts with a UV air purification system (2025), new ceiling fans throughout (2025), and a full suite of brand-new LG stainless steel appliances including the refrigerator, dishwasher, microwave, washer, and dryer (2025). Enjoy Florida living in your private courtyard, accessible from the rear-entry garage, offering a quiet outdoor retreat for relaxing or entertaining. Residents of Daniels Landing enjoy an array of community amenities, including a resort-style pool, fitness center, clubhouse, playground, and gated entry. Ideally situated just minutes from the award-winning Downtown Winter Garden, the West Orange Trail, shopping, dining, major highways, and approximately 20 minutes from Walt Disney World, this exceptional home offers the perfect combination of low-maintenance living and an unbeatable location.

241 Deepcove Road, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code

Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Discover elevated living in this thoughtfully designed home at Northlake at Ovation, offering flexible spaces and curated finishes to fit your everyday lifestyle. From the inviting covered lanai to the spacious loft and soaring ceilings, this floor plan provides room to relax, work, and entertain with ease. Inside, you’ll find a balance of bold and neutral finishes from the AW Collection Rosemary. Design upgrades include 8' interior doors, quartz countertops, tiled backsplash, stainless steel appliances and more. Whether you’re hosting gatherings or enjoying quiet evenings at home, the open layout and versatile rooms adapt to your needs. Perfectly located in Winter Garden near some of Central Florida’s most beloved destinations, this home is just 35 minutes from Orlando International Airport, 15 minutes from world-famous Disney theme parks, and 30minutes from charming Celebration. Residents can also enjoy the charm and rich local history of nearby downtown Winter Garden, known for its vibrant shops, and eateries. Paired with great local schools and a peaceful community setting, this home delivers the ideal blend of comfort, convenience, and Central Florida living. Residents also enjoy a clubhouse, community pool, playground areas and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17625 Lake Star Road, Winter Garden

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

Short Sale. ***SHORT SALE***Built in 2024, this like new 2 bedroom plus den, 2 bathroom home offers modern finishes, thoughtful upgrades, and a private setting tucked toward the back of the community with no rear neighbors. The flexible den features French doors, making it ideal for a home office, hobby room, or additional living space. The open concept layout is filled with natural light and centers around a beautifully appointed kitchen with white cabinetry, white Ice subway tile backsplash, white quartz countertops, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. The primary suite features an upgraded walk in shower, while ceiling fans in the living room, both bedrooms, and the den provide added comfort throughout the home. Enjoy Florida living from the covered front porch with space for seating or unwind on the screened lanai overlooking the peaceful backyard with exceptional privacy. The 2 car garage includes two overhead storage racks for added organization. Located just minutes from Walt Disney World, Flamingo Crossings, Horizon West shopping and dining, major roadways, and everyday conveniences, this home combines a desirable location with low maintenance, move in ready living.

13640 Splashing Isla Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code

Welcome to 10439 Austrina Oak Loop, a beautifully upgraded 3-bedroom, 2.5-bath home with over 2,080 square feet of thoughtfully designed living space in the highly sought-after Watermark community. From the moment you step inside, you'll appreciate the luxury vinyl flooring throughout the first floor, upgraded 8-foot interior doors, designer hardware, and abundant natural light that enhances the home's bright, open-concept layout. The spacious main room flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for everyday living and entertaining. The kitchen features stainless steel appliances, upgraded cabinetry lighting above and below the cabinets, modern stairs with wire handrails, and stylish finishes that blend beauty with functionality. Upstairs, a versatile loft provides the ideal space for a home office, media room, fitness area, or playroom. All three bedrooms are conveniently located on the second floor, offering privacy and comfort. The spacious primary suite features an elegant tray ceiling, oversized walk-in closets, and a luxurious ensuite bath with dual vanities, a large walk-in shower, and plenty of natural light. The secondary bathroom also offers dual sinks, providing added convenience for family and guests. The upstairs laundry room is both practical and well-appointed with upgraded cabinetry and a large utility sink. For those who work remotely, the dedicated office area includes hard-wired internet for reliable high-speed connectivity. The oversized two-car garage is equipped with a 240-volt outlet, making it ready for electric vehicle charging. Enjoy the added benefit of a professional installed whole-water treatment system with dual treatment tanks and pre-filter, helping provide cleaner, conditioned water throughout the home while protecting plumbing and appliances. Enjoy relaxing on the inviting covered front porch, and each evening step outside to catch views of the spectacular Magic Kingdom fireworks. Residents of Watermark enjoy exceptional resort-style amenities, including a clubhouse, resort pool, splash pad, fitness center, tennis courts, playgrounds, scenic walking trails, and beautifully maintained green spaces. The home is just minutes from The Mark at Watermark, featuring Starbucks, Walgreens, New York Beer Project, restaurants, and everyday conveniences. You'll also enjoy close proximity to Orange County National Golf Center, Winter Garden Village, Walt Disney World Resort, highly rated local schools, and convenient access to State Road 429. Offering an exceptional combination of premium upgrades, an unbeatable location, and outstanding community amenities, this move-in-ready home presents an incredible opportunity to enjoy the very best of Central Florida living.

10439 Austrina Oak Loop, Winter Garden

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

Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Waterleigh community in Winter Garden. Built in 2021, this move-in ready home features an open-concept floor plan with a spacious living area, a modern kitchen with stainless steel appliances, granite countertops, and a large island perfect for entertaining. Upstairs, the primary suite offers a walk-in closet and a private en-suite bathroom, while two additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy a private patio, attached one-car garage, and low-maintenance living. Waterleigh offers resort-style amenities including multiple pools, fitness center, clubhouse, playgrounds, walking trails, tennis courts, beach volleyball, mini golf, and scenic lakes. Conveniently located near Hamlin Town Center, shopping, dining, top-rated schools, major highways, and Walt Disney World. Don't miss this incredible opportunity to own a home in one of Winter Garden's most desirable communities!

10108 Salt Point Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code

RARE FIND! Experience resort-style living in this exceptional home on a rare OVERSIZED 0.15-acre homesite, ideally located JUST MINUTES from the vibrant HAMLIN Town Center in one of Winter Garden's most desirable areas. Featuring a stunning nearly NEW HEATED SALTWATER PRIVATE POOL, premium summer kitchen, expansive covered lanai, elegant travertine patio, and a fully fenced backyard, this property offers the Florida lifestyle today's buyers are looking for. Offering 2,990 square feet, 4 spacious bedrooms, and 2.5 bathrooms, this home perfectly blends luxury, comfort, energy efficiency, and everyday functionality. Designed with flexibility in mind, it also features a versatile flex room with the potential to serve as a future fifth bedroom, home office, or study, as well as a spacious upstairs bonus room ideal for a media room, playroom, or additional family living space. The primary suite is complemented by an oversized walk-in closet. The fully fenced backyard is a true private retreat designed for entertaining and relaxing year-round. The nearly new heated saltwater pool was built with all required permits, offering the confidence and peace of mind that come with a recently constructed, modern pool system. Outdoor living is completed by the covered lanai and travertine deck, a premium summer kitchen, and low-maintenance artificial turf. A convenient first-floor half bathroom with direct access to the backyard makes entertaining even more enjoyable. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. The FULLY PAID-OFF SOLAR PANEL SYSTEM, valued at over $30,000, means no lease or loan to assume and helps keep the average monthly electric bill at approximately $80, even during Florida's summer months. That's hundreds of dollars in energy savings every month, providing exceptional long-term value and sustainability for the next homeowner. Additional upgrades include a beautifully remodeled upstairs bathroom with a frameless glass shower enclosure, custom closet systems, two independent HVAC systems for enhanced comfort and efficiency, professionally installed gutters, an epoxy-coated garage floor, and overhead garage storage racks. The location adds even more value: just minutes from Hamlin Town Center, with convenient access to top-rated schools, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you'll enjoy standout amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully upgraded throughout, this home offers a rare combination of outdoor living, energy efficiency, and prime Winter Garden location. Schedule your private showing today! All information, including room dimensions, square footage, HOA fees, community amenities, and restrictions, is deemed reliable but not guaranteed and should be independently verified by the buyer and buyer’s agent.

7594 Lake Hancock Boulevard, Winter Garden

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