Winter Garden Homes with Gated Community - Guard Community Features

Winter Garden Homes with Gated Community - Guard Community Features

Welcome to Winter Garden, Florida – a picturesque city nestled in the heart of Orange County that perfectly blends small-town charm with modern conveniences. Known for its vibrant downtown area, Winter Garden boasts a rich history, beautiful parks, and a thriving arts scene, making it an ideal place to call home. The city is conveniently located just a short drive from Orlando, providing residents with easy access to world-class entertainment, shopping, and dining.

One of the standout features of Winter Garden is its gated communities, offering an exclusive and secure living experience. These guard-gated neighborhoods provide peace of mind for families and individuals alike, ensuring safety and privacy while fostering a sense of community. Residents enjoy beautifully landscaped surroundings, well-maintained amenities, and a variety of recreational options right at their doorstep.

Homes in these gated communities are designed with elegance and comfort in mind, featuring spacious floor plans, modern finishes, and outdoor spaces perfect for entertaining. Whether you’re looking for a cozy single-family home or a luxurious estate, Winter Garden’s gated communities cater to diverse lifestyles and preferences.

With top-rated schools, an array of parks, and a strong sense of community, Winter Garden is more than just a place to live; it’s a place to thrive. Discover the charm of this enchanting city and the exceptional lifestyle offered by its gated communities. Your dream home awaits in Winter Garden!

Newest Winter Garden Homes with Gated Community - Guard Community Features

14501 Grove Resort Avenue Unit 3631, Winter Garden
$164,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3631, Winter Garden
14501 Grove Resort Avenue Unit 2539, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST-PRICED UNIT CURRENTLY AVAILABLE AT THE GROVE RESORT! This 5th-floor Birch residence is located in desirable Tower 2, the newest tower at The Grove and featuring the resort's most updated décor and finishes. Enjoy a peaceful garden view from this fully furnished resort residence just minutes from Walt Disney World. The Grove Resort & Water Park offers an exceptional combination of vacation ownership and resort amenities, including Surfari Water Park, multiple pools, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, market and coffee shop, and on-site resort management. An outstanding opportunity for buyers looking for an entry point into one of Orlando's most established condo-hotel resorts at the best price currently offered. Financial information and ownership details available upon request.

14501 Grove Resort Avenue Unit 2539, Winter Garden
14501 Grove Resort Unit 2304, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Short Sale. Experience the Ultimate Orlando Resort Lifestyle & Investment Opportunity! Welcome to The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations, ideally located just minutes from Walt Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. Enjoy a fully furnished, turnkey 2-bedroom, 2-bath condominium that offers the perfect blend of comfort, style, and investment flexibility. The spacious open-concept floor plan features a beautifully appointed kitchen, bright great room, oversized windows, and a private balcony overlooking the peaceful courtyard. The split-bedroom layout provides privacy, while two spa-inspired bathrooms feature garden tubs, tiled showers, and dual vanities. With a sleeper sofa in the living room, the residence comfortably accommodates up to six guests. Step outside your front door and discover an extraordinary resort experience. The spectacular Surfari Water Park features a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Additional amenities include multiple pools and hot tubs, a 20-acre activity lake with private dock, fishing, fitness center, full-service spa, arcade, game room, and an array of on-site dining options including Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, and Byte. Convenient shuttle transportation to Disney World, Universal Studios, and SeaWorld adds even more appeal for vacation guests. As a short-term rental property, owners may enjoy personal use, while professional on-site management can handle bookings, housekeeping, maintenance, and guest services. Whether you're looking for a personal Orlando getaway, a vacation home, or a hands-off investment opportunity, this property offers an exceptional combination of resort amenities, flexibility, convenience, and income potential. Experience the magic of Orlando while owning your own piece of the vacation lifestyle at The Grove Resort & Water Park!

14501 Grove Resort Unit 2304, Winter Garden
14501 Grove Resort Avenue Unit 2219, Winter Garden
$269,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 2219 at The Grove Resort & Water Park Orlando, where resort-style living meets an exceptional ownership opportunity just minutes from Central Florida’s world-famous attractions. This beautifully appointed 3-bedroom, 2-bath residence comes fully furnished and ready to enjoy. The spacious open-concept layout provides plenty of room for owners and guests, while the private balcony overlooking a peaceful water view creates the perfect setting to relax after a day enjoying everything Orlando has to experience. The primary suite features a spacious bathroom with a separate walk-in shower and soaking tub, offering the comfort and convenience expected from a full-service resort residence. Owners have access to The Grove’s extensive resort-style amenities, including water attractions, multiple swimming pools, dining options, fitness facilities, spa services, recreational areas, and much more. For owners seeking a hands-off approach, The Grove offers an optional professional resort management and rental program, providing the convenience of having the property managed and rented when not being personally enjoyed. Whether you are looking for a Florida vacation home, a furnished resort property, or an investment opportunity with professional management available, Unit 2219 offers a unique combination of comfort, convenience, and resort amenities in the Orlando area.

14501 Grove Resort Avenue Unit 2219, Winter Garden
14501 Grove Resort Avenue Unit 3703, Winter Garden
$178,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to Your Premier Vacation Gateway at The Grove Resort & Water Park! Located just minutes from Walt Disney World and Orlando’s world-class attractions, this fully furnished 2-bedroom, 2-bathroom condo-hotel unit (#3703) offers the perfect blend of vacation luxury and income-generating potential! ***PRIME CENTRAL VIEW: Positioned directly facing the lush central garden and courtyard, providing a peaceful, scenic backdrop and elevated tropical views right from your private space. ***UNRIVALED RESORT AMENITIES: Guests and owners enjoy full access to the renowned Surfari Water Park, dual water slides, lazy river, FlowRider® surf simulator, zero-entry pools, spa, game room, and multiple on-site dining options. ***TURNKEY & HASSLE-FREE: Professionally managed with on-site rental program options, making personal vacation stays and short-term rentals seamless.*** Whether you're seeking a vacation home, a smart investment property, or a hybrid of both, Unit #3703 delivers unbeatable lifestyle and convenience in the heart of Central Florida's tourism corridor. Schedule your showing today!!

14501 Grove Resort Avenue Unit 3703, Winter Garden
14501 Grove Resort Avenue Unit 3201, Winter Garden
$245,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
FULLY FURNISHED/TURNKEY LUXURIOUS 3/3 Corner Unit at The Grove Resort & Spa, Orlando Welcome to your dream oasis at The Grove Resort & Spa Orlando! This magnificent corner unit boasts the LARGEST floor plan available, featuring 3 spacious bedrooms and 3 elegant bathrooms. Experience the ultimate blend of comfort and luxury in this stunning condo-hotel located just six miles from Walt Disney World® Theme Parks, The Grove Resort & Spa offers unparalleled access to Orlando’s world-famous attractions. Enjoy daily transportation to Walt Disney World®, Universal Orlando, and SeaWorld, making it effortless to explore all that Orlando has to provide. Indulge in a variety of resort amenities designed for both relaxation and adventure. The Surfari Water Park features thrilling water slides, a lazy river, and the exhilarating FlowRider® Double surf simulator. Unwind at The Springs Pools, with three full-sized pools, an oversized hot tub, and poolside bar service. At Lake Austin, engage in catch-and-release fishing, paddle boating, or simply savor the serene views of the surrounding nature preserve. Stay active with a fully-equipped fitness center and scenic jogging paths. Families will love Flip Flop’s Family Fun Center, offering the latest arcade games and a glow-in-the-dark mini golf course. This corner unit is designed with a modern touch, offering a spacious open-plan living area, a gourmet kitchen, and stylish furnishings throughout. Each bedroom is a private retreat, complete with luxurious bedding and ample storage. Owning a unit at The Grove Resort & Spa offers not only a luxurious vacation spot but also a fantastic stress-free investment opportunity. Don’t miss the opportunity to own a piece of paradise at The Grove Resort & Spa, where every day feels like a vacation. Contact us today to schedule a private viewing and experience the exceptional lifestyle that awaits you.

14501 Grove Resort Avenue Unit 3201, Winter Garden
1118 Maidenmoor Road, Winter Garden
$460,000
4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden
14501 Grove Resort Avenue Unit 2608, Winter Garden
$255,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden
14501 Grove Resort Avenue Unit 3403, Winter Garden
$170,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program and a prime location near Central Florida’s top attractions, this turnkey condo offers an easy, hands-off ownership opportunity while giving you your own place to enjoy when visiting Orlando.

14501 Grove Resort Avenue Unit 3403, Winter Garden
13056 Sandcastle Drive, Winter Garden
$699,430
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decorative tile backsplash. The Whirlpool stainless steel appliances—including a built-in natural gas cooktop and a refrigerator—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 extended covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a rain shower head and a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. The additional spare bedroom and bathroom, along with the enclosed flex room, provide ample space for everyone. The upgraded laundry room with built-in cabinetry, quartz countertop, utility sink, and a Whirlpool washer and dryer make daily tasks a breeze. Designer-curated finishes elevate every corner of this home, including wood-look tile flooring throughout, pendant light pre-wire and under cabinet lighting in the kitchen, 2” faux wood blinds, and brushed nickel hardware and plumbing fixtures. The 2-car garage offers extra tandem storage space with an epoxy finish on the floor, ensuring that every part of your home is both beautiful and practical. With its stunning design and thoughtful touches, the Mystique home provides the perfect blend of luxury and functionality for today’s lifestyle.

13056 Sandcastle Drive, Winter Garden
14501 Grove Resort Avenue Unit 3534, Winter Garden
$199,000
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
2420 Balforn Tower Way, Winter Garden
$599,900
3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Most evenings, unforgettable sunsets stretch across the pool and lake, casting a breathtaking glow over this premier cul-de-sac homesite. Set on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted vantage points—serene water views paired with sweeping Back 9 sceneries, 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. From the moment you step inside, you’ll 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 throughout the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Step outside to your private oasis: 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 includes fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly positioned 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
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