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Gated Community Homes for Sale in Winter Garden, FL

Welcome to your dedicated resource for gated community homes for sale in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the gated community properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Gated Community Homes for Sale in Winter Garden, FL

$314,900
2 Beds 2 Baths Grove Residence & Spa Hotel Condo Ii SubDv. 34787 Zip Code
Owner Motivated – Largest 2-Bedroom Floor Plan at The Grove Resort Orlando This exceptional 5th-floor condo offers rare convenience with high ceilings, spacious bedrooms, and immediate access to parking. The primary suite includes a generous sitting area, while the second bedroom features two full beds — an ideal layout for families, groups, or high-occupancy rentals. Positioned on the quieter side of the resort, this unit enjoys a peaceful setting with minimal noise from the amenities, making it a comfortable retreat for owners and guests alike. Fully furnished and turnkey, this condo is ready for immediate personal use or income generation. Just steps away are The Grove's signature amenities: three resort pools, a full waterpark, fitness center, on-site restaurants and bars, game room, glow-in-the-dark mini golf, a boat dock, and water activities on Lake Austin. Located only 15 minutes from Walt Disney World®, owners and guests enjoy the convenience of a daily resort shuttle. Universal's Epic Universe — the most significant theme park expansion in Orlando in decades — opened in 2025, further strengthening the area's appeal and rental revenue potential for years to come. Ownership is completely hands-free. The on-site professional hotel operator manages all marketing, bookings, guest services, repairs, and maintenance. Owners may use their condo anytime and earn income when not in residence. Don't miss this opportunity to own a premium, income-producing resort residence in one of Orlando's most sought-after vacation destinations.

14501 Grove Resort Avenue Unit 2536, Winter Garden

$205,000
2 Beds 2 Baths Grove Resort And Spa Hotel Condominium SubDv. 34787 Zip Code
****Amazing opportunity to purchase a 2-bedroom/2-bathroom vacation condo at the beautiful Grove Resort in Orlando! This fully-furnished condo is very spacious, and has a full kitchen, laundry room, a screened-in balcony, and two bedrooms. There is a sleeper sofa in the living room, so it can sleep six. Buyers must enter into the onsite rental management company, who will do all the bookings, housekeeping, and maintenance for the condo. If owners want to use their condo, simply send an email and block off your desired dates. Owners can use their condo up to 179 nights per year. On site there are plenty amenities, including the Surfari Water Park, with large heated pool, lazy river, water slides, the Flowrider surfing experience, and delicious food and drinks can be purchased from the Longboard Bar and Grill. At the Springs Pools are there are three further pools and a large hot tub! Next to that you can wander down to Lake Austin and do some fishing, or paddle a swan boat! The Valencia Restaurant is a full-service venue where you can eat indoors or outdoors! A spacious 24-hour gym is also located near the Springs Pools. At the Front Desk area you will find the Marketplace, and gift shop, and the concierge who will help you with theme park tickets, restaurant bookings etc. A free daily shuttle to Disney is also available. Call now for more information!!****

14501 Grove Resort Avenue Unit 3304, Winter Garden

$1,574,000
4 Beds 4 Baths Lakeview Reserve 46/149 SubDv. 34787 Zip Code
COMPLETELY REMODELED WATERFRONT HOUSE WITH COVERED PRIVATE DOCK AND BOAT LIFT ON THE LARGEST LAKE IN CENTRAL FLORIDA!!! A highly energy-efficient house with owned solar panels ($30 monthly grid surcharge vs. $500-600 electric bill before). The cost of solar panels is included in the purchase price. The price can be reduced by $37K if the buyer assumes a solar panel loan at 3.49%. Experience the ultimate LAKEFRONT living with this stunning, COMPLETELY REMODELED HOUSE ($400K investment) on Lake Apopka in Winter Garden, in the heart of a highly desirable GOLF CART DISTRICT. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm. Every inch of this home has been meticulously upgraded, creating a move-in-ready oasis with high ceilings, open-concept living, designer lighting and upgraded finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, PANORAMIC WINDOWS. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, a wine fridge and a modern backsplash. Entertain effortlessly in the expansive high-ceiling dining room and living room, framing incredible LAKE APOPKA VIEWS, GORGEOUS SUNRISES AND BREATHTAKING SUNSETS! The spacious master suite on the ground floor is a serene retreat with a high ceiling, two walk-in closets, an oversized bathroom with two sinks, Jacuzzi and a massage shower and a private screened patio. Two additional bedrooms on the ground floor boast lake views, California closets and high ceilings. A second-floor oversized loft offers a full bathroom, a walk-in closet, separate HVAC and noise-reducing flooring and window treatment —perfect for another master bedroom or entertainment room. Two Florida rooms on both floors provide stunning panoramic lake views. A dedicated office/den on the ground floor is ideal for work or study. All bathrooms have windows and exhaust. Enjoy 90 feet of open-view waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized COVERED BOAT DOCK has electric BOAT LIFT, lighting, WATER, and a Margaritaville-themed bar. The backyard features a RECENTLY RESURFACED SALTWATER POOL with a NEW PUMP, NEW POOL FILTER, a REFENCED PRIVATE YARD, fruit trees & mature, landscaped greenery. Additional highlights include NEW WINDOWS, HVAC, SOLAR PANELS, SMART THERMOSTAT, upgraded irrigation and landscaping, a TWO-CAR GARAGE with a lot of built-in storage and an OVERSIZED DRIVEWAY to park multiple boats or vehicles. Located in a quiet, family-friendly GATED COMMUNITY with golf-cart-friendly streets and DIRECT ACCESS to the scenic WEST ORANGE TRAIL and high-rated elementary and middle SCHOOLS NEARBY. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the farmer's market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways. There are 6 highly rated Golf Clubs within a 5-mile radius. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun!

261 Zachary Wade Street, Winter Garden

$460,000
3 Beds 3 Baths Grove Resort And Spa Hotel Condo 1 SubDv. 34787 Zip Code
Experience resort-style living and exceptional investment potential with this luxurious first floor condo located in The Grove Resort & Water Park, Orlando’s premier vacation destination. Ideally situated just 5 minutes from Walt Disney World, this fully furnished, turnkey residence offers a perfect combination of elegance, comfort, and convenience. Notice the Soaring Ceilings in this beautiful condo in every room. The sitting area in the primary bedroom sets the perfect ambiance. The spacious open-concept floor plan is filled with natural light and features modern décor, high-end finishes, and stylish furnishings throughout. The gourmet kitchen is equipped with stainless steel appliances, quartz countertops, and ample cabinetry, making it perfect for entertaining or extended stays. A full-sized washer and dryer provide added convenience. Residents and guests enjoy access to world-class amenities, including the Surfari Water Park with a FlowRider Surf Simulator, Lazy River, Water Slides, and Zero-entry Pools. Relax in multiple swimming pools and oversized hot tubs, or reserve a private cabana for the ultimate day of leisure. Additional amenities include a full-service spa, 24-hour fitness center, on-site dining at Valencia Restaurant, Longboard Bar & Grill, and Elements Bar & Lounge, plus the Flip Flop’s Family Fun Center. Outdoor enthusiasts can enjoy kayaking, fishing, and paddle boating on the 22-acre Lake Austin. A daily resort shuttle provides effortless access to Walt Disney World, Universal Studios, and SeaWorld, while nearby golf courses, shopping, dining, and major highways make The Grove Resort perfectly positioned for both relaxation and adventure. When not in use, owners can take advantage of the professionally managed hotel rental program, generating income while enjoying hassle-free ownership. With its prime location, full-service amenities, and strong rental potential, this condo at The Grove Resort & Water Park is an ideal vacation retreat and investment opportunity—all just minutes from Orlando’s most iconic attractions. The Grove Resort and Spa is zoned as a Condo/Hotel. Owners are allotted 179 days in a calendar year to stay on property.

14501 Grove Resort Avenue Unit 2101, Winter Garden

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