Winter Garden Homes with 55+

Winter Garden Homes with 55+

Welcome to Winter Garden, Florida—a charming city nestled in Orange County that beautifully blends small-town warmth with modern amenities. Known for its picturesque landscapes and vibrant community, Winter Garden is a hidden gem just a stone's throw from the bustling attractions of Orlando. With its lush parks, scenic lakes, and a historic downtown area bursting with local shops, cafes, and farmers’ markets, Winter Garden offers a delightful lifestyle for residents of all ages.

For those in the 55+ community, Winter Garden is an ideal destination, boasting a variety of homes designed specifically for active adults. These residences often feature single-story layouts, low-maintenance yards, and access to community amenities such as clubhouses, fitness centers, and swimming pools. Many neighborhoods are thoughtfully planned to foster social connections, offering a range of activities from art classes to fitness programs, ensuring that every day presents an opportunity for engagement and enjoyment.

The city’s proximity to major highways makes it easy to explore Central Florida’s attractions, while its serene environment provides a peaceful retreat. Whether you’re looking to enjoy a leisurely stroll along the West Orange Trail, savor a meal at one of the local eateries, or participate in community events, Winter Garden has something for everyone.

Discover the perfect blend of comfort and community in Winter Garden, where your next chapter awaits in a welcoming 55+ home. Embrace a lifestyle of leisure, connection, and joy in this delightful Florida city!

Newest Winter Garden Homes with 55+

$967,500
3 Beds ⋅ 4 Baths ⋅ O6445249 MLS
Luxury single-level living awaits at 15066 Canopy Cover Drive in Del Webb Oasis, a premier gated Active 55+ community near Orlando's world-class attractions. Built in 2023, this highly upgraded Renown floor plan - the community's largest single-story design - offers 2,955 square feet, 3 bedrooms, 3.5 baths, tons of closet space, office with custom built-ins, an extended gathering room and an extended 3-car garage. Set on a premium conservation lot with approximately 70 feet of frontage, a fenced backyard and no rear neighbor, the home offers exceptional privacy, space and tranquility. Inside, 8-foot doors and Italian porcelain tile flooring create an elegant, open feel. The gourmet kitchen features quartz countertops, ceiling-height upgraded cabinetry, select glass-front display cabinets with accent lighting, two ovens, a cooktop, microwave, refrigerator and wine/beverage refrigerator. Custom built-ins with accent lighting enhance the office/study, while custom closet systems organize both primary-suite closets and the pantry. Upgraded lighting, ceiling fans, window treatments and UV- and glare-reducing window film add comfort and style throughout. Electric Car charging port in garage. Designed for year-round Florida living, oversized screened lanai 14'.5" x 54'/2" features custom Limestone Galala Tumbled Pavers, a screened enclosure, ceiling fans, a mounted outdoor TV and an Aqua Living Spa hot tub. The fenced backyard includes two access gates. Additional features include an EcoWater whole-home water softener, roof gutters, a whole-home surge protector and an ADT alarm system. All appliances convey, including the washer and dryer, as well as the mounted lanai and garage TVs. Enjoy convenient access: minutes to Walt Disney World, Flamingo Crossings Town Center, groceries, shopping, dining and Orlando-area attractions. Orlando International Airport is approximately 30 minutes away, with hospitals and medical facilities nearby. Port Canaveral is approximately one hour away, and Florida's east- and west-coast beaches are within about 90 minutes.

15066 Canopy Cover Drive, Winter Garden
$459,900
3 Beds ⋅ 2 Baths ⋅ O6443958 MLS
Welcome to Del Webb Oasis in Winter Garden, where everyday living feels like a getaway. Located right next to the clubhouse, allowing residents to easily walk to the community amenities, this 3-bedroom, 2-bath home offers approximately 1,579 square feet of comfortable living space. The spacious kitchen features a gas stove and plenty of cabinet storage, while the primary suite includes a large walk-in closet and a walk-in shower. Two additional bedrooms provide flexibility for guests, a home office, or hobbies, and the second bathroom also features a walk-in shower. The two-car garage includes an electric vehicle charging outlet and a convenient utility sink. With flexible indoor and outdoor spaces, energy-efficient features, and gas heating, the home is designed for comfortable everyday living. Residents can enjoy the Del Webb Oasis clubhouse, fitness center, resort-style pool, pickleball and tennis courts, walking trails, and a variety of social activities, all conveniently located near Winter Garden shopping, dining, and Orlando attractions. Del Webb Oasis is a 55+ community, and occupancy is subject to community requirements.

15193 Aqua Sol Lane, Winter Garden
$409,000
3 Beds ⋅ 2 Baths ⋅ S5157851 MLS
LOCATION, LOCATION, LOCATION, Exceptional value is found with this spacious 3 bedroom, 2 bathroom home. You will appreciate the fully remodeled home with new flooring, kitchen cabinets and countertops, hall and master bathrooms, roof, water heater, pluming, and covered porch. This property is located across the street from Winter Garden High School and 5 minutes away from downtown Winter Garden and convenient access to major highways.

1606 Beulah Road, Winter Garden
$425,000
2 Beds ⋅ 2 Baths ⋅ O6442304 MLS
WOW at this price on a newer construction home. Experience refined Florida living in this beautifully appointed 2024-built residence, ideally situated within the gated community of Del Webb Oasis. Thoughtfully designed with 2 bedrooms plus a versatile bonus room—perfect as a 3rd bedroom, private home office, den, or sitting room—the home offers a desirable split-bedroom floor plan that provides both privacy and comfort. upgrades are showcased throughout, including luxury vinyl flooring, recessed lighting, and contemporary finishes. At the heart of the home, the stylish kitchen features Tier 3 upgraded finishes complemented by Whirlpool appliances, creating an inviting space that seamlessly blends modern design with everyday functionality. Step outside to the screened-in lanai, an ideal setting for peaceful morning coffee, outdoor dining, or relaxing Florida evenings. The 2-car garage is equally well appointed with sleek epoxy flooring and an EV charger for added convenience. Beyond the home, Del Webb Oasis offers a gated, amenity-rich lifestyle designed for recreation, relaxation, and connection. Association fees include cable and internet, while the community provides an exceptional setting to stay active, socialize, and enjoy the best of Florida living. Adding to its appeal, the property is approximately 20 minutes from the Walt Disney World Resort area, depending on traffic—placing world-class dining, shopping, entertainment, and recreation within easy reach. Built in 2024 and beautifully upgraded throughout, this exceptional residence delivers the perfect combination of modern luxury, low-maintenance living, and resort-style convenience.

13418 Princess Street, Winter Garden
$699,430
2 Beds ⋅ 2 Baths ⋅ O6439937 MLS
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
$595,000
3 Beds ⋅ 2 Baths ⋅ S5156584 MLS
Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden
$899,000
3 Beds ⋅ 3 Baths ⋅ O6436813 MLS
Virtually Staged. Welcome home! The neighbors call this one of the best kept secrets in Oasis. One of the few homes in the community that have an amazing view of the Disney fireworks from your screened-in porch. The seller has spared no expense in making this home move-in ready. As soon as you walk in, you'll be greeted by high ceilings, beautiful tile floors and plenty of light. This home features the maximum amount of recessed lighting offered by the builder in every single room. This home has a gourmet kitchen, featuring an oversized kitchen island and plenty of cabinet/countertop space and a KitchenAid refrigerator. The corner pantry features a custom closet by design buildout. This beautiful kitchen will bring out your inner chef. In addition, the kitchen overlooks the dining room and living room, ideal for entertaining. The home features custom smart blinds throughout the first floor. The seller spared no expense in upgrading this property, featuring custom closets by design in the main bedroom, mudroom and laundry room as well as the garage. This home comes with full home water purification system. Fully paid-off solar panels at closing. The upstairs loft and third bedroom have exotic wood throughout. Minutes from Walt Disney World Resort, Hamlin Town Center and downtown Winter Garden. Contact the listing agent today to schedule.

13355 Sunny Retreat Lane, Winter Garden
$849,990
3 Beds ⋅ 4 Baths ⋅ O6435981 MLS
Step into the Renown, a new construction, single-story home situated on a corner homesite near a cul de sac offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an open flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and zero corner 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 white cabinetry with wood uppers meets luxurious quartz countertops. Thoughtfully designed features like soft-close drawers, 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 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 zero-corner 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 frameless glass enclosed shower, garden tub, 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, brushed nickel 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!

15000 Canopy Cover Drive, Winter Garden
$840,000
4 Beds ⋅ 4 Baths ⋅ O6424765 MLS
JUST REDUCED $20,000 Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home with office/den, offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus room with a full bath, there is room for everyone to live, work, gather, and unwind. At the heart of the home, the centrally located kitchen brings everything together, opening naturally to the main living areas and creating an ideal setting for both entertaining and daily life. Appointed with granite countertops, a center island, double ovens, and a pantry, it is as functional as it is inviting. Beautiful crown molding, decorative wall details, and tile flooring throughout the main living spaces add warmth and character, while the bedroom spaces provide comfort and privacy. The primary suite is a peaceful retreat, privately positioned and complete with two walk-in closets, dual vanities, a soaking tub, and a separate shower. Secondary bedrooms are thoughtfully arranged, including a Jack-and-Jill bath, while the bonus room provides flexible space for guests, a media room, a playroom, or multi-generational living. Step outside and enjoy your own private Florida oasis. The screened saltwater pool, convenient pool bath, and expansive paver deck with both covered and open-air areas create the perfect backdrop for quiet mornings, weekend gatherings, and year-round outdoor living. Backing to a green area, the setting feels peaceful and private, offering a rare sense of escape while still being close to everything. Virtually staged images included Located near Winter Garden Village, Highway 429, top-rated schools, shopping, and dining, this exceptional home offers not just a place to live, but a lifestyle to love. Make sure to check out the 3D tour and Virtual tours.

2139 Tillman Avenue, Winter Garden
$755,000
3 Beds ⋅ 2 Baths ⋅ O6420975 MLS
Experience effortless luxury just 2 miles from Walt Disney World in this impeccably maintained, like-new 2024 residence located within the highly sought-after Del Webb Oasis community. Perfectly positioned directly across from the spectacular amenity campus, you'll enjoy the rare convenience of simply strolling across the street to indulge in world-class resort-style living every day. From the impressive 12,000-square-foot clubhouse featuring a coffee bar, resident lounge, and wine lockers to the zero-entry resort pool, hot tub, state-of-the-art fitness center, tennis and pickleball courts, every luxury is just moments from your front door. Designed with both elegance and functionality in mind, this stunning home welcomes you with an expansive open-concept floor plan that seamlessly connects the chef's kitchen, dining area, and spacious living room, creating the perfect setting for entertaining or relaxed everyday living. The gourmet kitchen is beautifully appointed with upgraded quartz countertops, a large eat-in breakfast bar island, 42-inch cabinetry, premium stainless steel appliances including a gas range, and an extra-deep double-basin sink. Beautiful upgraded flooring flows throughout the home, offering both timeless style and easy maintenance. Step outside to your own private outdoor retreat, where a screened-in pool and covered lanai create an inviting space to enjoy Florida's year-round sunshine. Whether sipping morning coffee on the charming front patio or unwinding with a glass of wine beside your sparkling pool in the evening, you'll appreciate the peaceful surroundings and exceptional privacy. The thoughtfully designed split-bedroom floor plan offers an ideal balance of comfort and privacy. Tucked away at the rear of the home, the luxurious primary suite is filled with natural light and features a spacious walk-in closet and an elegant spa-inspired bath complete with dual quartz vanities and an oversized walk-in shower. A generously sized secondary bedroom and beautifully finished guest bath are situated at the front of the home, providing a welcoming retreat for family and visitors alike. Additional highlights include a large laundry room, convenient drop zone, and an energy-efficient tankless water heater for endless hot water. Beyond the gates, you'll find yourself just minutes from Disney, championship golf, premier shopping, exceptional dining, and Central Florida's most desirable attractions. Combining an unbeatable location, refined finishes, and unparalleled walkability to Del Webb Oasis' extraordinary amenities, this exceptional home offers a truly elevated lifestyle where every day feels like a luxury vacation.

13175 Sunny Retreat Lane, Winter Garden
$859,900
4 Beds ⋅ 3 Baths ⋅ O6419110 MLS
Better Than New in Del Webb Oasis at Horizon West! Located within this sought after gated, age qualified 55 plus community, this exceptional, nearly new residence offers an ideal combination of luxury, flexibility, energy efficiency, and low maintenance living. Community occupancy requirements apply and should be independently verified by the buyer. Some listing images have been virtually staged or generated using AI for illustrative purposes. Furnishings and decor shown in those images are not physically present. Situated on a premium corner homesite with attractive landscaping, this spacious home features 4 bedrooms, 3 bathrooms, a versatile flex room, and an impressive second floor bonus area spanning more than 1,000 square feet. The upstairs space includes a bedroom and full bathroom, creating excellent possibilities for a private guest retreat, media or game room, fitness area, home office, hobby space, or additional flexible living space. The open concept main level is designed for comfortable everyday living and entertaining. Eight foot doors throughout the first floor add to the home’s bright and spacious feel. The gourmet kitchen features a large center island, built in microwave, wall oven, cooktop, closet pantry, Florida inspired backsplash, and a sunny breakfast nook overlooking the spacious family room. French doors, plantation shutters, and abundant natural light create a warm and inviting atmosphere. The primary suite is conveniently located on the first floor and features dual vanities, a spacious walk in shower, and generous storage. A formal dining room provides additional gathering space. Luxury vinyl plank flooring flows throughout the main living areas, complemented by tile in the bathrooms and carpet in the bedrooms. Additional features include a well appointed laundry room with a utility sink, cabinetry, and countertop workspace, a paver driveway, a three car tandem garage with an additional four foot extension, a covered paver lanai, and preplumbing for a future outdoor kitchen. Solar panels are currently installed and may provide energy savings based on individual usage and utility rates. The panels may be negotiated to remain with the home or be removed before closing, depending on the buyer’s preference and the terms agreed upon by the parties. Residents of Del Webb Oasis enjoy resort style amenities including a clubhouse, fitness center, resort style pool and spa, pickleball and tennis courts, walking trails, year round social activities, and a full time lifestyle director. Ideally positioned in Horizon West, the home is just minutes from Flamingo Crossings, Walt Disney World, shopping, dining, entertainment, and major roadways. With expansive living spaces, thoughtful upgrades, flexible use options, and an outstanding location, this home offers the lifestyle and value today’s buyers are looking for. Room sizes are to be verified by buyer and buyer’s agent.

13361 Sunny Retreat Lane, Winter Garden
$480,000
2 Beds ⋅ 2 Baths ⋅ O6414956 MLS
Welcome to The Grove Resort & Water Park, a luxury vacation condo-hotel community offers owner privacy and convenience. Located 5 minutes from Walt Disney World, ownership of the largest 2-bedroom provides a family friendly place to vacation and relax. Let's discuss more about this 2B When you step through the door, you enter directly into the living space. The unit features in-unit laundry, with full-size washer and dryer. The kitchen is well-equipped with all major appliances, so you can certainly cook here if desired. The living space is spacious, and also includes a dining area. You can be making $ on the day of closing! Financial statements are available! Please note that this is a condo-hotel, so you could not live here full time due to zoning restrictions

14501 Grove Resort Avenue Unit 3425, Winter Garden
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