Winter Garden Homes with Security Community Extras

Winter Garden Homes with Security Community Extras

Welcome to Winter Garden, Florida, a vibrant city nestled in the heart of Orange County. Known for its charming historic downtown, Winter Garden offers a delightful blend of small-town warmth and modern conveniences. With its picturesque streets lined with brick-paved sidewalks, eclectic shops, and inviting eateries, residents enjoy a unique sense of community that is hard to find elsewhere. The city is surrounded by lush landscapes and scenic lakes, making it a haven for outdoor enthusiasts and families alike.

Winter Garden boasts a range of beautiful homes, many of which are situated within secure communities that enhance the peace of mind for residents. These homes come equipped with top-notch security features, providing a safe and serene living environment. Whether you’re looking for a cozy single-family home or a spacious townhome, Winter Garden’s real estate market has something to suit every taste and budget.

In addition to security, many of these communities offer a variety of amenities designed to enhance your lifestyle. Enjoy access to community pools, fitness centers, and beautifully landscaped parks, perfect for family gatherings or leisurely strolls with your furry friends.

With its excellent schools, proximity to major highways, and a wealth of recreational opportunities, Winter Garden is not just a place to live—it’s a place to thrive. Discover your dream home in this enchanting city and experience the best of Florida living. Embrace the charm of Winter Garden, where community spirit and modern living come together in perfect harmony!

Newest Winter Garden Homes with Security Community Extras

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. 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 5 bedrooms, 4 full bathrooms, a loft, 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, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a 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. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth 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.

285 Crystal Wood Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Welcome to resort-style living in the highly desirable Waterleigh community! This beautifully maintained home combines comfort, thoughtful upgrades, and an incredible Horizon West location just minutes from Walt Disney World. Upon entering, you’ll find a private first-floor bedroom complete with a walk-in closet and its own full bathroom, creating an ideal space for guests, extended family, or a private home office. Continue into the open-concept living and dining areas, where the spacious layout provides the perfect setting for everyday living and entertaining. The interior was professionally painted and enhanced with upgraded Hunter ceiling fans throughout, updated vanity and lighting fixtures, a new entry pendant light, and a beautiful dining room chandelier! Upstairs, the spacious primary suite features a large walk-in closet and private en-suite bathroom. Two additional generously sized bedrooms provide plenty of space for family, guests, or a home office. The upstairs loft adds valuable flexible living space and is just steps from your private screened-in balcony, complete with an exterior ceiling fan, creating the perfect place to relax and enjoy the Florida evenings! Step outside to the screened-in lanai featuring FLORIDA GLASS for additional privacy and comfort, overlooking a FULLY FENCED backyard. Additional improvements include RAIN GUTTERS, a newer washing machine, a transferable Massey Total Coverage Termite Protection Plan with the most recent renewal completed in August 2026, and an HVAC Platinum Plus Maintenance Plan with preventative maintenance most recently completed in May 2026! One of the best benefits of living in Waterleigh is the low-maintenance lifestyle, with HOA-INCLUDED LAWN MAINTENANCE allowing you to spend more time enjoying the incredible RESORT-STYLE AMENITIES, beautiful community spaces, golf cart-friendly streets, and year-round community events. Enjoy being just minutes from Disney and even catching views of the Disney fireworks from within the community. The location is hard to beat, with convenient access to shopping, dining, Publix, and everything Horizon West has to enjoy. Even more is coming to the area, including the NEW HORIZON WEST LIBRARY and HORIZON WEST REGIONAL PARK, along with a new county park featuring basketball and pickleball courts COMING SOON to the community! Families will also appreciate being zoned for highly rated local schools, including ATWATER BAY ELEMENTARY. This is more than a home, it’s the Waterleigh lifestyle. Enjoy resort-style amenities, HOA-included lawn maintenance, highly rated schools, nearby shopping and recreation, and the magic of Disney just minutes away. Schedule your private showing today and discover everything 16644 Point Rock Drive has waiting for you!

16644 Point Rock Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code

***Beautiful bright and airy 3-bedroom, 2-bathroom condo in the Grove Resort and Water Park Resort!!! Ideal for snowbirds who want to stay a few months in the winter, and have the onsite rental management company rent out the unit to vacationers when not in use! Buyers have the best of both worlds when owning at The Grove! Stay up to 179 nights per year in your unit, and the management do the rest of the work and enable you to earn when you are not there! This unit has a lovely south-facing balcony on the fifth floor, plus it has all the comforts of home - spacious living room, TV's in main room and all bedrooms, full kitchen, full washer and dryer, and screened-in balcony to enjoy quiet time! The resort has amazing amenities - the Springs Pools area has three heated pools plus a hot tub! Located nearby is the Valencia Restaurant, the 24/7 gym, and the boardwalk takes you to Lake Austin where you can fish off the dock, or paddle a swan boat! A short stroll takes you to the Surfari Water Park with a large heated pool, lazy river, water slides, and splash area! Try your skill on the Flowrider surfing experiences where instructors will help you ride the waves! Enjoy delicious food and drinks at the Longboard Bar and Grill, while listening to the relaxing music played on the hidden speakers! All ages can enjoy the Flip Flops games arcade, which also has a 9-hole mini golf course! At the Front Desk area you will find the Marketplace, selling convenience items, food, drinks, Starbucks coffees, and gifts. The concierge will help you with theme park tickets, and if you need transportation to the Disney theme parks, there is a FREE daily shuttle! For more information please give me a call!!!***

14501 Grove Resort Avenue Unit 3534, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Most evenings, unforgettable sunsets spill across the pool and water, casting a breathtaking glow over this premier cul-de-sac homesite. Positioned on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted viewpoints—serene water vistas paired with sweeping Back 9 scenery, including uninterrupted sightlines to the 13th green and 14th tee. Welcome home to an immaculate 3-bedroom, 2-bath split-plan retreat that is truly move-in ready. Step inside and immediately feel the care, quality, and comfort woven throughout. Thoughtful upgrades include brand-new plantation shutters, a custom built-in kitchen nook with outlet, updated light fixtures and fans, and a new refrigerator. Major systems add peace of mind with a roof, HVAC, hot water heater, and interior paint all less than 3 years old. The open living area impresses with a striking white stone accent wall and durable wood-like tile flooring that flows seamlessly through the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Outside, your private oasis awaits: a covered lanai overlooking a stunning saltwater pool with sun shelf and water features, all less than 5 years old. The backdrop is pure magic—tranquil water, golf course views, and sunsets that feel like a nightly masterpiece. The fully fenced yard offers fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly situated on a quiet cul-de-sac next to the residents’ gate, this home blends privacy with convenience. Community amenities are exceptional: golf course, playgrounds, pickleball, tennis, basketball, hockey court, resort-style pool, gym, and the Stoneybrook restaurant. Zoned for highly rated schools and just minutes from Winter Garden Village with easy access to the 429, the location is unbeatable. Additional highlights include built-in garage storage and shelving, a fenced yard, and standout curb appeal. This home delivers comfort, style, and a lifestyle that’s hard to match. Call today for a private showing!

2420 Balforn Tower Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 22019039615 SubDv. ⋅ 34787 Zip Code

The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! This 5th-floor corner unit is the largest "Sable" model in the community, offering 1,544 sq ft with an open living/dining/kitchen area, a separate in-unit utility/laundry room, and a screened balcony. The kitchen features stainless steel appliances and granite counters. The primary suite includes an extra sitting area/solarium with direct balcony access, a bath with double sinks, a separate shower and soaking tub, and a large walk-in closet with a safe. Each bedroom includes a flat-screen TV. This condo-hotel offers an in-house hotel rental program that generates income to offset the cost of ownership — an ideal opportunity to own an Orlando/Disney-area vacation home just 6 miles from Walt Disney World. Resort amenities are exceptional. Surfari Water Park features the FlowRider Double Surf Simulator (one of only a few double units in the U.S.), dual water slides, a 695-foot lazy river, a zero-entry pool, and a kids' activities pool. The Springs Pools offer three full-sized pools, an oversized hot tub, a splash area, and private cabanas. Lake Austin provides catch-and-release fishing, watersports, and a lakeside pier overlooking the nature preserve. Additional amenities include a 24-hour fitness center, Flip Flop's Fun Center with a glow-in-the-dark indoor mini golf course and arcade, and a Kids' Activity Center. Dining options abound: The Springs Bar & Grill for relaxed poolside dining, Longboard Bar & Grill overlooking the FlowRider, Alfresco Market for outdoor cafe seating, and DYVE at The Terraces above the upscale pool area. The resort also offers daily transportation to Walt Disney World, Universal Orlando, and SeaWorld, plus complimentary resort-wide Wi-Fi. A rare chance to own a turnkey resort residence in one of the Orlando area's premier destinations.

14501 Grove Resort Avenue Unit 2542, Winter Garden

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

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

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

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

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

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

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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