Winter Garden/Oakland Homes with Gated Amenities

Winter Garden/Oakland Homes with Gated Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant community is known for its charming downtown, rich history, and picturesque landscapes, making it a perfect place for families, retirees, and everyone in between. With its warm climate and abundant sunshine, residents can enjoy a variety of outdoor activities year-round, from exploring the scenic West Orange Trail to indulging in local farmers' markets brimming with fresh produce and artisanal goods.

One of the standout features of Winter Garden and Oakland is the availability of homes with gated amenities. These exclusive communities offer an added layer of security and privacy, providing peace of mind for residents. Imagine coming home to a beautifully designed property nestled within lush landscaping, where tranquil surroundings and upscale features blend seamlessly. Gated communities in this area often boast luxurious amenities such as sparkling swimming pools, state-of-the-art fitness centers, and beautifully maintained parks, perfect for family gatherings or leisurely strolls with your pets.

Living in Winter Garden and Oakland means embracing a lifestyle filled with convenience and charm. With a plethora of dining, shopping, and entertainment options just a stone's throw away, you’ll find everything you need within easy reach. Plus, the close-knit community spirit fosters connections among neighbors, making it feel like home the moment you arrive. Discover the allure of gated living in this captivating region, where your dream home awaits amidst the beauty of Florida's natural landscape.

Newest Winter Garden/Oakland Homes with Gated Amenities

$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
$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
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$340,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes from Walt Disney World. This spacious 3-bedroom, 3-bath condominium is located on the 3rd floor of Building 2, offering exceptional convenience to the main lobby and resort amenities. Designed for vacation enjoyment and investment potential, the residence features a spacious open floor plan, well-appointed kitchen, comfortable living and dining areas, and three bedrooms and baths providing plenty of room for family and guests. Enjoy your own Orlando vacation retreat and take advantage of rental income . The Grove offers an impressive resort experience with Surfari Water Park, multiple pools, a lazy river, FlowRider surf simulator, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, and complimentary transportation to Walt Disney World. Whether your goal is creating memorable Florida vacations, generating rental income, or enjoying the best of both, this Building 2 location offers convenience, flexibility, and investment potential in one of Orlando’s most popular vacation destinations. Vacation when you want. Earn rental income when you don’t.

14501 Grove Resort Avenue Unit 2342, Winter Garden
$999,270
4 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden
$895,260
5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead White stacked cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring pre-plumbing for an outdoor kitchen to enhance indoor-outdoor living, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed brushed nickel plumbing fixtures and hardware, comfort height toilets, Whirlpool washer and dryer, 2” faux wood blinds, and wood treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, and LED down lights ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

427 Winter Grove Boulevard, Winter Garden
$710,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden
$949,000
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Welcome to this **better-than-new Renown model by Del Webb**, beautifully maintained and only used seasonally. Located on a premium wooded conservation homesite with open green space, this exceptional home offers privacy, breathtaking nature views, and magical nightly Disney fireworks. This spacious home features 3 bedrooms, 3 full baths, a powder room, flex room, and a 3-car garage with abundant storage. The open-concept floor plan is perfect for entertaining, showcasing a gourmet kitchen, white and gray cabinets with Kitchenaid Stainless Steel appliances including NATURAL GAS stove top, DOUBLE Convection ovens, built-in microwave, refrigerator, wine refrigerator, oversized island, 42" soft-close cabinetry, Lyra quartz countertops, mosaic tile backsplash, and walk-in pantry. The gathering room opens through dramatic zero-corner sliding glass doors to an extended covered paver lanai with panoramic screen enclosure and outdoor kitchen plumbing, creating seamless indoor/outdoor living. You'll be spending lots of time enjoying this gorgeous view! The private Owner's Suite features oversized walk-in closets, dual quartz vanities, linen closet, and an upgraded Super Shower. Two additional guest suites each include walk-in closets and private en-suite baths. Luxury upgrades include Plantation shutters, top-down/bottom-up cellular shades, solar shades, designer lighting, upgraded interior doors, luxury vinyl plank flooring, porcelain tile baths, Smart Thermostat, HVAC air quality package, utility sink in the garage, full rain gutters, and LG pedestal washer and gas dryer included, Tankless Natural Gas Water Heater. Enjoy the award-winning Del Webb Oasis 55+ lifestyle with a 12,000+ sq. ft. clubhouse, resort-style pool, fitness center, pickleball and tennis courts, walking trails, coffee bar, wine room, arts & crafts studio, social clubs, and a full-time Lifestyle Director. HOA includes lawn maintenance, landscaping, gated entry, and high-speed fiber internet with streaming TV. Ideally located in Horizon West, just 6-8 miles from Walt Disney World®, 2.4 miles to AdventHealth ER, and minutes to Flamingo Crossings shopping, dining, and entertainment. Move-in ready and truly better than new, experience luxury, comfort, and resort-style living at its finest!

15031 Canopy Cover Drive, Winter Garden
$290,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$219,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code
**Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden
$244,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
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