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 3618, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
WELCOME TO THE GROVE RESORT & WATERPARK, WINTER GARDENS, ORLANDO FLORIDA. THIS BEAUTIFUL FULLY FURNISHED SABLE DESIGN CONDO IS IN AN EXCELLENT LOCATION WITH GREAT VIEWS OF WATER PARK AND MUCH MORE. THIS BEAUTIFUL SABLE DESIGN CONDO IS ON THE 6TH FLOOR WITH 3 LUXURY BEDROOMS AND 3 GREAT BATHROOMS. AND GREAT VIEWS FROM SCREENED BALCONY. YOU CAN OWN THIS BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO ALL OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING BUT NOT LIMITED TO A GREAT WATER PARK, LAZY RIVER, SWIMMING POOLS , WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTION FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE

14501 Grove Resort Avenue Unit 3618, Winter Garden
14501 Grove Resort Avenue Unit 3239, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and 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 soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like 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 double ovens and 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 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 walk-in shower with a built-in bench and rain shower head, 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, matte black 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!

13055 Sandcastle Drive, Winter Garden
14501 Grove Resort Avenue Unit 1440, Winter Garden
$159,999
2 Beds ⋅ 2 Baths ⋅ The Grove Resort And Spa SubDv. ⋅ 34787 Zip Code
Welcome to Resort-Style Living at Its Finest! Nestled on the 4th floor of Building 1 at the highly acclaimed Grove Resort & Water Park, unit #1440 offers a turnkey 2-bedroom, 2-bathroom condo designed for effortless relaxation and high-value performance. Step inside to discover a bright, open floor plan that flows seamlessly to a private balcony—the perfect spot to enjoy Florida’s warm breezes and tranquil views. Building 1 boasts an enviable location within the resort, placing you just steps from the main lobby, dining options, and world-class amenities, so guests and owners spend less time walking and more time enjoying the retreat. Whether you are looking for a personal vacation sanctuary or a lucrative investment asset, this property delivers an unmatched lifestyle package. The Grove Resort features the exciting Surfari Water Park—complete with a dual-waterslide tower, lazy river, and FlowRider® surf simulator—alongside peaceful heated pools, a full-service spa, fitness center, on-site dining, and watersports on Lake Austin. Positioned just minutes from Walt Disney World®, Universal Studios, premier shopping outlets, and dining destinations, this condo combines luxury living with an irresistible location for vacationers and homebuyers alike.

14501 Grove Resort Avenue Unit 1440, Winter Garden
14501 Grove Resort Avenue Unit 1218, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, where vacation ownership meets the full Orlando resort lifestyle! This beautifully furnished 2-bedroom, 2-bath condo-hotel residence offers a spacious, comfortable retreat just minutes from Walt Disney World and Central Florida’s world-famous attractions. Designed for both relaxation and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances, generous cabinetry and counter space, in-suite washer and dryer, and a private screened balcony—the perfect place to enjoy your morning coffee or unwind after a day at the parks. The spacious primary suite offers a private bath with dual vanities, soaking tub and separate shower, while the second bedroom and full bath provide plenty of room for family and guests. At The Grove, the resort itself is part of the experience. Spend the day at Surfari Water Park featuring a 695-foot lazy river, dual water slides, zero-entry pool, kids’ activity pool and exciting FlowRider® Double surf simulator. Looking for a slower pace? Relax at The Springs Pools with three full-size pools and an oversized hot tub, enjoy the natural beauty of Lake Austin, work out in the 24-hour fitness center, or take advantage of the resort’s restaurants, bars, family activities and recreation. The resort also offers transportation to Walt Disney World, Universal Orlando and SeaWorld, making it easy for guests to experience everything Orlando has to offer. Disney Springs is approximately 11 miles away, with SeaWorld, Universal Orlando, Epic Universe and countless dining, shopping and entertainment destinations all within easy reach. Ownership is made even more convenient by an association fee that includes many of the expenses normally handled separately, including electricity, water, sewer, trash, cable, internet, pest control, security, common-area and building maintenance, and recreational facilities.* Whether you're searching for your own Florida vacation getaway, a second home near the theme parks, or a furnished resort property with vacation-rental potential, Unit 1218 offers the opportunity to own where millions of visitors come to vacation every year. Come for the parks. Stay for the resort. Own a piece of the Orlando vacation lifestyle at The Grove Resort & Water Park.

14501 Grove Resort Avenue Unit 1218, Winter Garden
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 Resort & 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
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