Winter Garden Homes with Gated Community - Guard Community Features

Winter Garden Homes with Gated Community - Guard Community Features

Welcome to Winter Garden, Florida—an enchanting city that beautifully blends the charm of small-town living with the vibrancy of modern amenities. Nestled in Orange County, Winter Garden is renowned for its picturesque landscapes, historic downtown, and a welcoming community spirit. With its lush parks, scenic lakes, and a rich tapestry of cultural events, this city offers an ideal backdrop for families, retirees, and everyone in between.

One of the standout features of Winter Garden is its luxurious gated communities, providing a secure and tranquil environment for residents. These guard-gated neighborhoods offer not just peace of mind, but also an array of exclusive amenities designed to enhance your lifestyle. Imagine coming home to beautifully landscaped streets, where your neighbors become friends, and community events foster connections.

Within these gated communities, you’ll find stunning homes that cater to various tastes and preferences. From elegant single-family homes to modern townhouses, each residence is crafted with attention to detail and quality. Many of these homes feature spacious floor plans, gourmet kitchens, and luxurious outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars.

Moreover, living in a guard-gated community means access to fantastic amenities, including clubhouses, swimming pools, fitness centers, and walking trails—all designed to promote an active and engaging lifestyle.

Experience the best of Winter Garden living in a secure, friendly environment that feels like a true sanctuary. Discover your dream home today in one of our exquisite gated communities, and embrace the charm and vibrancy that Winter Garden has to offer!

Newest Winter Garden Homes with Gated Community - Guard Community Features

$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
$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
$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
$219,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii 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!! Beautiful 3-bedroom/2-bathroom Jasmine floorplan available for sale at The Grove Resort and Water Park! This first floor apartment is fully-furnished and has everything you need for a wonderful vacation condo! This spacious unit has 14-foot ceilings in the main living space, giving a light, airy feel, and opens to an enclosed balcony where you can enjoy views of gardens and pond. Full kitchen has everything you need for cooking breakfasts, to family dinners, with a full washer and dryer in a room just off the kitchen. The living room also has a sleeper sofa for extra guests if needed. A short stroll brings you to either the central front desk area where you will find The Marketplace, the well-stocked convenience store, and the gift shop and concierge desk, or to the Springs Pools area where you can choose from three beautiful pools and the hot tub. The Valencia Restaurant, with additional outside seating, is open for breakfast, lunch, and dinner, 7 days a week, and is next to the 24/7 gym. Take a walk down to Lake Austin and try some fishing, or paddle a swan boat! From there you can visit the Surfari water park with its large pool, lazy river, water slides, and splash area! Try out the Flowrider surfing experience, or just watch while enjoying food and drinks from the Longboard Bar and Grill! Flip Flops is the 6000sf games arcade with glow-in-the-dark mini golf, so don't miss that! Free daily shuttles to the Disney parks are available for all owners and guests! This truly is a great place to own a vacation condo while the onsite management company rent out your unit when you are not there! Call for more details!!**

14501 Grove Resort Avenue Unit 2119, Winter Garden
$179,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 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!! Beautiful Palm model 2-bedroom/2-bathroom condo for sale at The Grove Resort and Water Park! This fully-furnished unit has a lovely view over the central fountain and is bright and airy. This floorplan has the desirable two double beds in the second bedroom, providing extra sleeping accommodation for owners and guests. A sleeper sofa in the living room gives extra sleeping space if required. A full kitchen provides all you need for cooking a quick breakfast, or family dinner, and a laundry room is also conveniently situated just off the kitchen. The dining area and living room give plenty of seating for guests, or enjoy a quiet coffee out on the screened balcony. The unit is central to the resort, so all amenities are just a few minutes stroll away. You can enjoy the Surfari water park with its large pool, lazy river, water slides, and splash zone! The Longboard Bar and Grill are also inside the water park, along with the Flowrider surfing experience!! Don't forget to visit Flip Flops, the 6000sf games arcade, with glow-in-the-dark mini golf, or go down to the Springs Pools where you have your choice of three further pools, or relax in the hot tub! You can enjoy a meal at the Valencia Restaurant, or at the outdoor bar, or walk down to Lake Austin and try your hand at fishing, kayaking, or paddling a swan boat! The Front Desk is where you will find the Marketplace convenience store and gift shop, and the concierge for all your theme park tickets or excursions! The Grove Resort also provides FREE daily transportation to the Disney theme parks. Don't miss out on owning a wonderful vacation condo at The Grove, where you can enjoy your vacations, then let the onsite management company rent out your unit for income when you are not using it. Call for more details!!**

14501 Grove Resort Avenue Unit 3406, Winter Garden
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