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

$459,922
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to The Kendall II, a beautifully designed home in the highly sought-after Northlake at Ovation community of Winter Garden. This spacious two-story floorplan combines modern design with everyday functionality, offering open-concept living spaces filled with natural light. Featuring the AW Collection Coastal, the stylish kitchen features 42” cabinets, quartz countertops, tiled backsplash and stainless steel appliances, perfect for both entertaining and family gatherings. Upstairs, the private primary suite offers a peaceful retreat with a large walk-in closet and spa-inspired bathroom. The detached two car garage offers a private courtyard space for Florida living. Ideally located just 30 minutes from Orlando International Airport, 20 minutes from Walt Disney World® and other theme parks, and 30 minutes from Celebration, this home places you close to the best of Central Florida. Residents will appreciate access to great schools and the charm of downtown Winter Garden, known for its local shops, dining, and historic character. Community amenities include clubhouse, pool, playground and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17392 Sweet Moro Drive, Winter Garden
$487,500
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.*

12086 Shine View Lane, Winter Garden
$899,000
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated on a corner homesite near a cul de sac offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an open flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and zero corner sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where white cabinetry with wood uppers meets luxurious quartz countertops. Thoughtfully designed features like soft-close drawers, easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a frameless glass enclosed shower, garden tub, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, brushed nickel hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

15000 Canopy Cover Drive, Winter Garden
$675,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Seller may consider buyer concessions if made in an offer ~ LIKE-NEW LIVING in one of Winter Garden’s most sought-after communities! Just four years old, this beautiful DAVID WEEKLEY SUMMERTON MODEL is located in McKinnon Square within award-winning Oakland Park – and the GOLF CART IS INCLUDED! High ceilings, abundant natural light and an OPEN CONCEPT design create a bright, welcoming interior made for everyday living and entertaining. At the heart of the home, the GOURMET CHEF’S KITCHEN flows seamlessly into the main living and dining spaces, while the inviting FRONT PORCH adds to the neighborhood feel Oakland Park is known for. All of the bedrooms are upstairs along with a versatile BONUS/LOFT offering endless possibilities as a home office, playroom, media space or second living area. Life here extends well beyond the front door – Oakland Park is a GOLF CART-FRIENDLY COMMUNITY offering a clubhouse, COMMUNITY POOLS, parks, playgrounds, a dog park and recreational amenities, plus easy access to the WEST ORANGE TRAIL and LAKE APOPKA. Cruise by golf cart to HISTORIC DOWNTOWN WINTER GARDEN for award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals and the popular Winter Garden Farmers Market. Everyday convenience is equally impressive, with the elementary school approximately .5 miles away, middle school 1.1 miles, high school 3 miles and Orlando Health Hospital approximately 1.8 miles away. Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike are easily accessible, with shopping, dining, Disney and Central Florida attractions within reach. MOVE-IN READY, nearly new and complete with a golf cart, this Oakland Park home delivers the lifestyle that makes Winter Garden such a desirable place to call HOME!

923 Colie Alley, Winter Garden
$475,000
3 Beds ⋅ 3 Baths ⋅ Hickory Hammock Ph 1c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in this incredible neighborhood, is HERE! Move-in ready and beautifully maintained, this townhome offers 3 bedrooms, 2.5 baths, and a bright, open layout perfect for modern living. A paver driveway and charming stucco exterior with mature landscaping set the tone before you even step inside. The main level features a spacious open-concept living and dining area with tile flooring throughout. Sliding glass doors lead out to a private patio, offering a peaceful spot to unwind while overlooking green common space. The kitchen is a standout, showcasing rich espresso cabinetry, gleaming granite countertops, a designer mosaic tile backsplash, stainless steel appliances, and a large island with pendant lighting — ideal for entertaining or casual family meals. Upstairs, the generously sized primary suite includes plush carpet and an en-suite bath with dual sinks, a walk-in shower, and a linen closet. A second full bath serves the additional bedrooms with a dual-sink vanity and a tub/shower combo, and a convenient half bath is located on the main level for guests. As part of a sought-after community, residents enjoy resort-style amenities including a sparkling community pool, tennis courts, a playground, and scenic lakefront views — all just minutes from Winter Garden's shops, dining, and amazing schools. Don't miss your chance to own this stylish, low-maintenance townhome in one of Winter Garden's most desirable communities!

15613 Orange Harvest Loop, Winter Garden
$447,500
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.*

16510 Barbours Creek Way, Winter Garden
$514,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Grvs SubDv. ⋅ 34787 Zip Code
Virtually Staged. ~Seller may consider buyer concessions if made in an offer~Perfectly situated in sought-after Summerlake Groves of Winter Garden, this BEAUTIFULLY MAINTAINED 4-bedroom, 2.5-bath two-story home offers a light and bright OPEN CONCEPT floor plan, over 2,000 SQUARE FEET of living space, a convenient rear-entry garage and the peace of mind that comes with a home built in 2018. MOVE-IN READY and thoughtfully designed for comfortable family living, this home combines everyday functionality with the lifestyle that makes Winter Garden such a desirable place to call HOME. Step inside to find easy-care CERAMIC TILE FLOORS throughout the main living areas and an inviting flow from the spacious Living Room into the Kitchen and Dining area. An abundance of windows fills the Living Room with NATURAL LIGHT, while the open sight lines make gathering with family or entertaining friends effortless. At the heart of the home, the Kitchen overlooks the living space and features GRANITE COUNTERTOPS, stainless steel appliances, a closet pantry and a generous ISLAND with BREAKFAST BAR SEATING and room for counter-height stools. Just beyond, the bright Dining area offers sliding glass door access to the COVERED BRICK-PAVER PATIO, creating an easy transition for morning coffee, weekend cookouts or relaxing outdoors. Upstairs, the PLUSH CARPETED BEDROOMS provide a comfortable retreat away from the main living spaces. The spacious Primary Suite features a decorative TRAY CEILING, DUAL WALK-IN CLOSETS and a private en-suite bath with dual sinks, STEP-IN SHOWER and private WATER CLOSET. Three additional Bedrooms offer plenty of room for family, guests, a home office or hobbies, with some Bedrooms featuring their own WALK-IN CLOSETS. A second Full Bath has been recently retiled, and the conveniently located second-floor Laundry Room comes with a UTILITY TUB and includes the WASHER and DRYER. Outside, the BRICK-PAVER DRIVEWAY and REAR-ENTRY GARAGE add curb appeal while keeping the front of the home welcoming and attractive. Summerlake Groves offers a wonderful FAMILY-FRIENDLY atmosphere with a LOW HOA and amenities designed for enjoying the Florida lifestyle, including a clubhouse, RESORT-STYLE POOL, playground, dog park and TENNIS COURTS. Community events and SEASONAL FESTIVITIES create even more opportunities to get to know your neighbors and enjoy where you live.The Winter Garden location is hard to beat, with DISNEY WORLD just minutes away and HAMLIN TOWN CENTER nearby for shopping, dining and everyday conveniences. Spend the weekend exploring local parks, enjoying the WEST ORANGE TRAIL, grabbing dinner in Hamlin or heading to the nearby attractions. Zoned for EXCELLENT SCHOOLS and surrounded by the shopping, dining, recreation and entertainment that make Winter Garden so popular, this home provides the ideal combination of comfort, community and convenience. Well maintained, MOVE-IN READY, NEWER CONSTRUCTION and perfectly positioned in one of Winter Garden’s most sought-after areas — this is the one you’ve been waiting for! Call today to schedule your private showing and make Summerlake Groves your next HOME.

8016 Sweet Orange Avenue, Winter Garden
$2,600,000
6 Beds ⋅ 6 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 7693 Green Mountain Way in Winter Garden, an impressive two-story lakefront home offering 6 bedrooms, 6 bathrooms, dual primary suites, a spacious loft, balcony, and multiple indoor and outdoor living areas. Designed to accommodate both everyday living and large-scale entertaining, this expansive residence combines flexible living spaces with standout waterfront amenities and scenic lake views. The interior provides an abundance of space across two levels, highlighted by two primary bedrooms that offer added flexibility for multigenerational households, extended guests, or those who simply prefer multiple private retreats. Four additional bedrooms and six full bathrooms provide generous accommodations throughout the home. A large loft adds another dedicated living area that can easily function as a media room, game room, secondary family room, or entertainment space. The balcony extends the living area outdoors and provides another inviting place to unwind while taking in the surrounding views. Multiple gathering areas throughout the home allow plenty of room for entertaining while still providing separation and privacy when desired. The outdoor spaces are designed to make the most of the home's scenic lakefront setting. A welcoming front porch adds curb appeal, while the rear of the home opens to a covered patio, spacious deck, and outdoor kitchen, creating a well-equipped setting for dining, grilling, and entertaining. The centerpiece is the in-ground infinity pool and spa overlooking the lake, where the water's edge blends beautifully with the waterfront backdrop. With dedicated areas for cooking, lounging, swimming, and gathering, the combination of the outdoor kitchen, covered patio, deck, infinity pool, spa, and expansive lake views creates a resort-inspired outdoor retreat ideal for both everyday relaxation and entertaining. Situated in Winter Garden, the property offers access to a vibrant Central Florida community known for its parks, recreational opportunities, shopping, dining, and convenient connections to major roadways and Orlando-area destinations. With six bedrooms, dual primary suites, six bathrooms, a loft, balcony, expansive outdoor living areas, and a lakefront infinity pool and spa, 7693 Green Mountain Way delivers exceptional space, flexibility, and waterfront living in one impressive property

7693 Green Mountain Way, 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
$910,000
3 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Built to Impress. Upgraded to Perfection. Welcome to Del Webb Oasis. From the moment you step through the craftsman-style entry onto hardwood floors that run seamlessly through every living space, it becomes clear that every decision in this home was made with intention — and that intention was excellence. Through French glass doors, a private den with tray ceiling offers the quiet focus space today's buyer genuinely needs. Then the kitchen stops you cold. A dramatic galley-style gourmet space with rich wood cabinetry stacked to the ceiling, quartz countertops, gas cooktop with vented hood, built-in wall oven, stainless appliances and a scalloped tile backsplash that earns its own admiration. It connects directly to the side bar — wine refrigerator, diamond-lattice wine rack, quartz countertops and matching backsplash — making the entertaining potential here truly exceptional. The great room beneath soaring double tray ceilings flows naturally through wall-to-wall sliding glass doors to the screened lanai, where a full summer kitchen with granite countertops, built-in grill, stainless hood, refrigerator and sink overlooks a lush conservation backdrop and an oversized fenced yard that is genuinely rare in this community. The primary suite is a proper sanctuary — tray ceiling, dual closets and a spa-caliber ensuite with a dual-sink charcoal vanity, quartz countertops and a floor-to-ceiling tiled walk-in shower with dual shower heads, built-in bench, decorative accent and mosaic tile floor. Two well-proportioned additional bedrooms, a full bath, a polished powder room and a laundry room with cabinetry, utility sink, and full-size washer and dryer complete the picture. Smart home technology, custom water filtration and just off the garage entry, a custom built-in drop zone with beadboard detail, bench, hooks, and shelving creates the perfect transition from the garage into the home — organized, intentional, and exactly where it should be. Now — the address. Del Webb Oasis is not just a community; it's a destination. A boutique, gated 55+ enclave in the heart of Winter Garden, just 2 miles from Disney — close enough that on some evenings, the fireworks are yours to watch from the neighborhood. The 12,000-square-foot clubhouse features a coffee bar, wine lockers, lounge, fitness center, yoga and aerobics studio, arts and crafts room, billiards room, and an indoor-outdoor bar and tavern. Outside: a zero-entry resort pool with lap lanes, spa, cabanas, pickleball and tennis courts, bocce ball, community garden, fire pit, and walking paths. The HOA covers exterior maintenance,and internet — because the only thing on your schedule here is living well. Winter Garden itself offers award-winning Saturday farmers markets, boutique dining on Plant Street, West Orange Trail access, and a charming downtown that genuinely feels like a small town despite being minutes from every major Central Florida corridor.

15084 Canopy Cover Drive, Winter Garden
$493,500
3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 4b SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful end-unit townhome in the desirable Encore at Ovation community. Conveniently located less than 10 minutes from Disney Property, with quick access to US-192, US-27, and SR-429, you’ll be able to enjoy all Central Florida has to offer. The lot features a backloading two-car garage and a private patio area, perfect for a quiet morning coffee or a cookout with friends. The home is also set between a quaint tree-lined sidewalk to the front and open green space to the back, adding to the feeling of privacy. Inside, enjoy a thoughtfully designed layout that includes an open concept kitchen/living/dining area, ample counter and cabinet space, a dedicated pantry, a large laundry room with plenty of storage, and a separate den for multiple gathering spots. Upstairs, relax in your large primary suite with a walk-in closet and updated ensuite bathroom. You can even catch the Magic Kingdom fireworks from your window! This home is not only immaculately maintained but also upgraded for your convenience. A whole-house water filtration/softener system, kitchen sink reverse osmosis (RO) system, HVAC air ionizer and UV light system have all been recently installed. Additionally, the roof, exterior painting, driveway upkeep, yard maintenance, landscaping, and pest control are all taken care of by the HOA, making this property perfect for those using it as a secondary home, or simply looking for a low-maintenance lifestyle. Reach out to book your private showing today!

15877 Tollington Alley, Winter Garden
$398,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
** PRICED TO SELL!! Excellent opportunity for homeowners or investors in the highly desirable Winter Garden area! This nearly new bright corner-unit townhome in Osprey Ranch offers 3 bedrooms, 2.5 bathrooms, a 1-car garage, and 1,536 sq ft of comfortable living space, with added privacy and abundant natural light. The open-concept main floor features tile flooring, a spacious living and dining area, and a kitchen with granite countertops, clear cabinetry, stainless steel appliances and a large island. Decorative details include a custom TV accent wall and a stone-look accent panel on the kitchen island. Upstairs, all three bedrooms provide privacy, along with a versatile landing area that can be used as a home office or study space. Residents enjoy Osprey Ranch amenities including a resort-style community pool, splash pad, playground and dog park, with a low HOA fee of only $202 month. Ideally located near Hamlin, SR-429, shopping, dining and Walt Disney World. The property is currently zoned for the newly opened Ovation Elementary School, according to OCPS Find My School. Buyers should independently verify current school zoning with OCPS. An exceptionally well-priced opportunity for homeowners or investors looking to own in one of Winter Garden’s growing communities.

15056 Windflower Alley, Winter Garden
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