Winter Garden/Oakland Homes with Gated Community - Guard Community Features

Winter Garden/Oakland Homes with Gated Community - Guard Community Features

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a hidden gem nestled just a stone's throw from the bustling heart of Orlando. Known for its charming historic downtown, vibrant community spirit, and lush greenery, this area offers a perfect blend of small-town charm and modern conveniences. With its picturesque landscapes, scenic parks, and a variety of outdoor activities, Winter Garden and Oakland are ideal for families, retirees, and everyone in between.

One of the standout features of this region is its exclusive gated communities, which provide an added layer of security and privacy. These guard-gated neighborhoods are designed for those who appreciate peace of mind without sacrificing luxury and comfort. Imagine waking up in a beautifully designed home, surrounded by manicured lawns and stunning architecture, all within a community that prioritizes safety and serenity.

Residents of these gated communities enjoy a wealth of amenities, including resort-style pools, state-of-the-art fitness centers, and beautifully landscaped common areas perfect for leisurely strolls or family gatherings. The sense of community here is palpable, with regular social events and activities that foster connections among neighbors.

With the charm of Winter Garden’s historic district and the natural beauty of Oakland’s lakes and parks, living in a gated community here means you can enjoy the best of both worlds. Whether you’re exploring the local farmers' market, indulging in delightful dining options, or taking a short drive to the theme parks, Winter Garden and Oakland offer a lifestyle that’s simply irresistible. Discover your dream home in this captivating region, where community and comfort come together seamlessly.

Newest Winter Garden/Oakland Homes with Gated Community - Guard Community Features

$249,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing views from this two-bedroom, two-bathroom fully-furnished condo in the beautiful Grove Resort and Water Park Resort! Fourth floor views over the Springs Pools, with Lake Austin beyond that! Enjoy the morning sunrise with a coffee on your screened-in balcony!! These condos are fully managed by the onsite rental company, so when you are not using it, you can earn some income from guest bookings! These are ideal for snowbirds who wish to spend up to 179 nights per year in their unit, and then have the hands free experience of management renting it out when they are not using it! Full kitchen, full size washer and dryer, dining area, sleeper sofa, deep comfortable mattresses, all lend to a home from home for owners and guests! The Valencia Restaurant is located next to the Springs Pools area, which has three separate pools and a hot tub, and the 24/7 gym is also in this area. Take a stroll down the boardwalk to Lake Austin and paddle a swan boat, or try some fishing from the dock! A leisurely stroll takes you to the Surfari water park, with large heated pool, lazy river, water slides, splash area, and the Surfari surfing experience! The Longboard Bar and Grill is excellent for food and refreshing beverages while spending your day there! The Flip Flop games room has over 6000sf of exciting games and mini golf! The Marketplace sells all you need for snacks, food, small necessities, and the gift shop has souvenirs, clothes, sun cream, etc for essentials. The concierge located in the front lobby sells theme park tickets, and will book your seat on the FREE daily shuttle to the Disney Parks! Call NOW for more information!!***

14501 Grove Resort Avenue Unit 1420, Winter Garden
$899,000
3 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home! The neighbors call this one of the best kept secrets in Oasis! One of the few homes in the community that have an amazing view of the Disney fireworks from your screened in porch! The seller has spared no expense in making this home truly move in ready. As soon as you walk in, you'll be greeted by high ceilings, beautiful tile floors and plenty of light! This home features the maximum amount of recessed lighting offered by the builder in every single room. This home truly has a gourmet kitchen, featuring an oversized kitchen island and plenty of cabinet/countertop space and a KitchenAid refrigerator. The corner pantry features a custom closet by design buildout. This beautiful kitchen will truly bring out your inner chef! In addition, the kitchen overlooks the dining room and living room perfect for entertaining! The home features custom smart blinds throughout the first floor. The seller spared no expense in upgrading this property, featuring custom closets by design in the master bedroom, mudroom and laundry room as well as the garage! This home comes with full home water purification system. FULLY paid off solar panels at closing! The upstairs loft and third bedroom have exotic wood throughout. Located minutes from Walt Disney World Resort, Hamlin Town Center & Downtown Winter Garden. Contact the listing agent today to schedule!

13355 Sunny Retreat Lane, Winter Garden
$419,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Affordable luxury in Winter garden! Welcome to one of Central Florida's premier 55+ communities. This beautifully appointed Ellenwood villa offers 2 bedrooms, 2 baths each with walk-in showers, a versatile flex room and a bright, open layout designed for easy Florida living. It has a pretty view with no homes behind it. Gorgeous luxury vinyl plank flooring flows throughout the home with no carpet, creating a clean, modern look and low-maintenance lifestyle. Ceiling fans have been added in both bedrooms and the living room for added comfort. The stylish kitchen features a gas range, while the home also includes an electric washer and gas dryer. The extended lanai is already plumbed for water and gas; perfect for an outdoor kitchen. Epoxy garage floors and sealed pavers ensure years of maintenance-free driveway. Del Webb Oasis delivers an exceptional resort-style lifestyle with an impressive pool, inviting fire pits, sun cabanas, a well-equipped fitness center, dedicated yoga and movement studio, plus both pickleball and tennis courts. Whether your ideal day includes staying active, relaxing poolside, or spending time with neighbors, the amenities offer something for nearly every lifestyle. The location is equally impressive. Enjoy convenient access to Walt Disney World and Hamlin Town Center, both less than 15 minutes away, along with nearby shopping, dining, entertainment, and everything Winter Garden has to offer. Beautiful finishes, thoughtful upgrades, outstanding amenities, and an unbeatable Central Florida location make this Del Webb Oasis villa an exceptional place to call home.

15873 Gem View Street, 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
$400,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Minutes from Walt Disney World | Resort-Style 55+ Living | Low-Maintenance Villa | Located in guard-gated Del Webb Oasis, this beautifully upgraded Ellenwood villa has been used only as a personal vacation residence and offers an exceptional combination of location, condition, and carefree living. Exterior maintenance is handled through the community, leaving more time to enjoy the extensive resort-style amenities or nearby Walt Disney World. Inside, 10-foot ceilings, 8-foot doors, abundant windows, luxury vinyl plank flooring, porcelain tile baths, upgraded lighting and fixtures, and extensive recessed LED lighting create a bright, polished interior. The white kitchen features 42-inch soft-close shaker style cabinetry, quartz countertops, subway tile backsplash, and a gas range. The primary bath offers a glass-enclosed step-in shower. A covered paver lanai includes gas and water connections for a future summer kitchen. Additional features include a Nest thermostat, tankless water heater, gutters, paver driveway, and two-car garage. Del Webb Oasis is a guard-gated 55+ community with a clubhouse, resort-style pool, fitness and recreation amenities, and an active lifestyle just minutes from Disney, shopping, dining, and entertainment. No CDD Fees.

15819 Gem View Street, Winter Garden
$194,900
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Il SubDv. ⋅ 34787 Zip Code
Welcome to a turnkey resort ownership opportunity at The Grove Resort & Water Park, one of Central Florida’s most amenity-rich vacation destinations. Designed exclusively for short-term resort use, this fully furnished condo offers a spacious, comfortable layout with an open living and dining area, full kitchen with stainless steel appliances, generous cabinetry and ample counter space. The primary suite features a beautifully appointed bath with dual sinks, soaking tub and separate glass-enclosed shower, while modern finishes, updated flooring and neutral tones create a clean, inviting atmosphere throughout. Beyond the unit, The Grove delivers the kind of resort experience Orlando visitors are looking for. Amenities include Surfari Water Park with a lazy river, water slides, zero-entry pool and FlowRider surf simulator, additional resort pools, Lake Austin recreation, fitness facilities, family activities and multiple on-site dining options. Guests can spend the day enjoying the resort or take advantage of convenient access to Central Florida’s world-famous attractions. With the unit offered fully furnished and positioned within an established vacation resort, this property offers an easy way to own a piece of the Orlando vacation market without the responsibilities of a traditional second home.

14501 Grove Resort Avenue Unit 3438, 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
$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
$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
$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
$199,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
Located on the second floor of Building 3, closest to the Safari Water Park, this fully furnished, two-bedroom, two-bathroom condo offers fantastic pond views and excellent proximity to resort amenities. This property is perfect for vacation home buyers seeking a true resort experience. Owners will enjoy resort-style living with access to multiple pools, a water park, a full-service spa, on-site restaurants, a state-of-the-art fitness center, and a large game room. For investors, this unit presents a compelling opportunity in Central Florida's booming tourism market. Located just minutes from Walt Disney World, Universal Studios, SeaWorld, upscale shopping, and diverse dining, this property promises strong rental potential and the flexibility to generate income while serving as a personal escape.

14501 Grove Resort Avenue Unit 3215, 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
Start Your Search