Winter Garden Homes with 55+ Only

Winter Garden Homes with 55+ Only

Welcome to Winter Garden, a charming city located in Orange County, Florida. Known for its picturesque landscapes, historic downtown, and family-friendly atmosphere, Winter Garden is a sought-after destination for those looking to enjoy the best of both worlds - small-town charm with big-city amenities.

For those seeking a vibrant community tailored to residents aged 55 and over, Winter Garden offers an array of homes exclusively designed for this demographic. Whether you're looking for a cozy condo, a spacious single-family home, or a luxurious villa, Winter Garden has a diverse selection of 55+ communities to suit your lifestyle preferences.

Living in a 55+ community in Winter Garden means enjoying resort-style amenities, engaging social activities, and a close-knit neighborhood where like-minded individuals can form lasting friendships. From golf courses and clubhouses to fitness centers and swimming pools, these communities cater to the unique needs and interests of active adults looking to make the most of their golden years.

Discover the perfect blend of relaxation and recreation in Winter Garden's 55+ communities, where every day offers the opportunity to embrace a fulfilling and enriching lifestyle. Experience the beauty and tranquility of this vibrant city while enjoying the comfort and convenience of a home designed with your needs in mind.

Newest Winter Garden Homes with 55+ Only

$419,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code
Short Sale. ***SHORT SALE***Built in 2024, this like new 2 bedroom plus den, 2 bathroom home offers modern finishes, thoughtful upgrades, and a private setting tucked toward the back of the community with no rear neighbors. The flexible den features French doors, making it ideal for a home office, hobby room, or additional living space. The open concept layout is filled with natural light and centers around a beautifully appointed kitchen with white cabinetry, white Ice subway tile backsplash, white quartz countertops, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. The primary suite features an upgraded walk in shower, while ceiling fans in the living room, both bedrooms, and the den provide added comfort throughout the home. Enjoy Florida living from the covered front porch with space for seating or unwind on the screened lanai overlooking the peaceful backyard with exceptional privacy. The 2 car garage includes two overhead storage racks for added organization. Located just minutes from Walt Disney World, Flamingo Crossings, Horizon West shopping and dining, major roadways, and everyday conveniences, this home combines a desirable location with low maintenance, move in ready living.

13640 Splashing Isla Drive, Winter Garden
$870,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code
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. 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
$859,900
4 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Better Than New in Del Webb Oasis at Horizon West! Welcome to 13361 Sunny Retreat Lane, an exceptional, nearly new residence offering the perfect blend of luxury, flexibility, energy efficiency, and low-maintenance living in the highly sought-after Del Webb Oasis community of Winter Garden. Situated on a premium corner homesite with attractive, low-maintenance landscaping, this thoughtfully designed home offers 4 bedrooms, 3 bathrooms, a versatile flex room, and an incredible 1,000+ square-foot bonus room PLUS an additional bedroom and full bath upstairs—creating endless possibilities for multi-generational living, a private guest retreat, home office, media room, fitness space, or hobby area. The open-concept floor plan is designed for both everyday living and entertaining. At the heart of the home, the gourmet kitchen features a center island, built-in microwave, wall oven, cooktop, closet pantry, Florida-inspired backsplash, and sunny breakfast nook overlooking the spacious family room. French doors, plantation shutters throughout, and abundant natural light create a bright and welcoming atmosphere. The primary suite is conveniently located on the first floor, where the ensuite bath offers dual vanities, a spacious walk-in shower, and generous storage. A formal dining room provides additional gathering space, while luxury vinyl plank flooring flows throughout the main living areas, complemented by tile in the bathrooms and carpet in the bedrooms. Designed with both comfort and long-term savings in mind, the home includes a well-appointed laundry room with utility sink, cabinetry, and countertop workspace, a paver driveway, an upgraded 2-car garage with a valuable 4-foot length extension—providing extra space for larger vehicles, storage, or a workshop area—a covered paver lanai, and pre-plumbing for a future outdoor kitchen. Even better, the home is equipped with solar panels that provide significant annual savings on electricity costs—and the seller will pay off the remaining solar panel financing at closing. That means you'll enjoy lower monthly electric bills from day one with no additional financial obligation, putting money back in your pocket month after month and year after year. Located in Del Webb Oasis, residents enjoy resort-style amenities including a clubhouse, fitness center, resort-style pool and spa, pickleball and tennis courts, walking trails, countless social activities, and a full-time lifestyle director. Ideally positioned in Horizon West, you're just minutes from Flamingo Crossings, Walt Disney World, shopping, dining, entertainment, and major roadways. With expansive living spaces, designer upgrades, exceptional energy savings, and an unbeatable location, this better-than-new home offers the lifestyle, flexibility, and value today's buyers have been waiting for.

13361 Sunny Retreat Lane, Winter Garden
$699,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 2 SubDv. ⋅ 34787 Zip Code
Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden
$480,000
2 Beds ⋅ 2 Baths ⋅ Grova Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
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
$495,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
2 bedrooms plus den, 2 bathroom.. Built in 2024, this like-new home is located on a premium cul-de-sac lot within a sought-after community in Winter Garden. Offering exceptional privacy with no rear neighbors, the backyard provides a peaceful setting to relax and enjoy Florida's outdoor lifestyle. The community is designated as 55+; however, buyers of 25 years old are permitted to purchase within the community. This beautifully maintained residence combines modern construction, energy-efficient features, and a desirable open floor plan with access to outstanding community amenities. Conveniently located near shopping, dining, entertainment, and major roadways, this home offers the perfect blend of comfort, privacy, and convenience.

15806 Gem View St, Winter Garden
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