Kissimmee/Celebration Homes with 55+

Kissimmee/Celebration Homes with 55+

Welcome to Kissimmee and Celebration, two enchanting communities nestled in the heart of Osceola County, Florida. Renowned for their vibrant atmosphere and close proximity to the magical wonders of Walt Disney World, these areas offer a unique blend of charm, convenience, and community spirit that makes them a sought-after destination for residents of all ages, especially those aged 55 and over.

Kissimmee boasts a rich tapestry of history and culture, with its picturesque downtown area lined with quaint shops, delightful eateries, and beautiful parks. Here, residents can enjoy leisurely strolls along the scenic waterfront, partake in local festivals, or explore the nearby natural wonders of Lake Tohopekaliga. Meanwhile, the adjacent Celebration community embodies a classic small-town feel with its beautifully designed homes, tree-lined streets, and a strong sense of community. Residents can indulge in a variety of activities, from farmers' markets to art shows, all while enjoying the warm Florida sunshine.

For those seeking a vibrant lifestyle in a 55+ community, Kissimmee and Celebration offer a range of attractive housing options tailored to meet the needs of active adults. These homes often feature modern amenities, low-maintenance designs, and access to resort-style facilities such as swimming pools, fitness centers, and social clubs. Whether you’re looking to downsize or simply embrace a new chapter in life, you’ll find a welcoming environment that encourages connection and engagement.

Discover the joys of living in Kissimmee and Celebration, where every day is an opportunity to create lasting memories in a community that feels like home.

Newest Kissimmee/Celebration Homes with 55+

1999 Limestone Trail, Kissimmee
$575,000
3 Beds ⋅ 2 Baths ⋅ O6447154 MLS
Welcome to the Four Seasons of Orlando in Kissimmee a 24 hour guard gated community. This is a ST. THOMAS model home featuring a welcoming foyer with coffered ceilings, dry bar and luxury vinyl flooring throughout the home. The two bathrooms have tile flooring. Enjoy the open concept kitchen, dining room and great room with upgraded cabinets and quarts counters. The owner's suite features luxury vinyl flooring, coffered ceilings and a beautiful primary bath with ceramic tile flooring. There are two additional bedrooms and a guest full bath. Four panel sliders brings you out to the private extended screened in lanai. The lanai is 40 feet wide and faces conservation. The garage houses two cars plus a golf cart space. You will love living at the Four Seasons of Orlando in Kissimmee. We are entwined within the Mystic Dunes Golf Course which offers wonderful views. Our Calypso Clubhouse offers a coffee bar, kitchen, meeting rooms, grand ballroom, ping pong and pool room, card room, excercise room and a state of the art exercise room. Outside enjoy the two pools, hot tub, grilling in the pool courtyard, tennis, pickleball courts and so much more. Our clubhouse has so many activities for you to enjoy from line dancing to yoga classes. You can also walk or use your golf cart to go over to Mystic Dunes Clubhouse and have brunch, lunch or dinner. They give our residents a discount.

1999 Limestone Trail, Kissimmee
1900 Estuary Lane, Kissimmee
$575,000
3 Beds ⋅ 2 Baths ⋅ TB8551414 MLS
Welcome to Four Seasons, a sought-after 55+ gated golf course community where comfort, convenience, and an active lifestyle come together. This beautifully maintained 3-bedroom, 2-bath single-family home offers thoughtfully designed living spaces and numerous upgrades inside and out. Inside, the home features an extended living room and expanded primary bedroom living area, complemented by tray ceilings, crown molding, upgraded lighting, plantation shutters, and ceiling fans throughout. The guest bathroom has been tastefully upgraded, adding to the home's move-in-ready appeal. Enjoy Florida's outdoor lifestyle from the screened front porch or the extended screened lanai, complete with lanai curtains for added comfort and privacy. The spacious rear porch features a 4-inch concrete slab with a stucco finish and is already prepped for an outdoor kitchen with gas, electric, drain, and water connections. Outdoor string lights are connected to a Smart outlet for convenient control. Additional exterior improvements include gutters, fencing, and decorative white marble chips. The garage offers added shelving for storage, while the laundry area is equipped for either gas or electric connections, providing flexibility for your preferred setup. Four Seasons offers an impressive array of amenities, including a clubhouse, exercise facility, swimming pool, recreation room, spa, tennis courts, and golf course. HOA dues are $407 per month and include lawn care, community management, and security. This home offers an exceptional opportunity to enjoy low-maintenance living in a vibrant 55+ community with amenities designed for an active and enjoyable Florida lifestyle.

1900 Estuary Lane, Kissimmee
1646 Key Bay Trail, Kissimmee
$345,000
2 Beds ⋅ 2 Baths ⋅ O6441509 MLS
This is a two bedroom plus office Sandpiper Villa. Featuring extended lanai enclosure, luxury vinyl plank flooring. Four Seasons is a gated community with a 24 hour gate guard. Enjoy the two heated pools with lap lanes, hot tub, tennis and pickle ball courts, shuffleboard and the beautiful clubhouse featuring kitchen, game rooms, ping pong and pool table enjoyment. State of the art gym, lockers, showers, card room and the grand ballroom which holds all the community activities. Four Seasons at Orlando is a guard gated 55+ community with private gate access to the Mystic Dunes which offers a discount for our residents.

1646 Key Bay Trail, Kissimmee
7969 Hanson Bay Place, Kissimmee
$749,000
3 Beds ⋅ 3 Baths ⋅ O6439998 MLS
Experience the best of 55-plus living with this hard-to-find opportunity in an exceptional setting at Four Seasons at Orlando. Beautifully decorated and tastefully fully furnished, this residence has the feel of a model home. A recently added private pool and spa open to an unobstructed view of the 10th green of Mystic Dunes Golf Club, while a panoramic screen enclosure enhances the connection to the surrounding landscape. Twenty-three fully owned solar panels add another significant advantage. Built in 2019, the three-bedroom, two-and-one-half-bath residence offers 2,194 square feet of single-level living designed for comfort and entertaining. The extended floor plan features 10-foot ceilings, crown molding, a tray ceiling and abundant natural light. A 12-foot sliding glass door connects the main living area to the lanai. The kitchen centers around an oversized island with granite countertops, 42-inch cabinetry, a gas cooktop, stainless steel appliances and pantry. Cookware, dishes, glassware, small appliances and kitchen essentials are included, making it easy to settle in from day one. Go outside to your private Florida retreat. Completed in March 2024, the large private pool and integrated spa provide generous space to swim, relax and entertain while enjoying the golf course setting. The 725-square-foot extended lanai expands the outdoor living experience with a built-in outdoor kitchen and comfortable furnishings. Beyond the backyard, the property's cul-de-sac location is surrounded by the golf course and mature trees, adding to the open feel of the setting. Immediately enjoy the efficiency of the solar system, with recent electricity costs of approximately $500 annually based on historical expense records. Monitor solar production and performance directly from your smartphone. A protective barrier over the panels helps protect them from golf-ball impact. Take advantage of a thoughtfully connected smart home, especially convenient for year-round or seasonal living. Manage lighting and access remotely from your smartphone. Intrusion and fire protection, along with water sensors throughout the residence, provide additional peace of mind while you are home or away. An 85-inch television paired with an excellent indoor-outdoor sound system creates an impressive entertainment experience. A Pure Touch water filtration and softening system, plus a Rinnai tankless gas water heater, add everyday comfort and convenience. The two-car garage offers an epoxy floor, storage, electrical surge protection, an installed electric-vehicle charging adapter, and included garden and do-it-yourself tools, with space for vehicles or a golf cart. Simply arrive and start enjoying your Florida home. High-end, nearly new furnishings, coordinated decor and outdoor furnishings are included, allowing for an easy transition into a primary or secondary residence. Four Seasons at Orlando extends the experience beyond the home with extensive recreational and social amenities, with activities coordinated by a dedicated lifestyle director. Association-maintained landscaping and irrigation leave more time to enjoy Florida lifestyle. The community is approximately 10 minutes from the Walt Disney World entrance and 30 minutes from Orlando International Airport.

7969 Hanson Bay Place, Kissimmee
2016 Flora Pass Place, Kissimmee
$675,000
3 Beds ⋅ 2 Baths ⋅ O6438603 MLS
Golf-course views and a screened pool lanai shape the experience of this single-story home, creating an easy connection between the main living spaces and the outdoors. The kitchen, dining area and living room flow together beneath detailed ceilings and across luxury laminate wood-plank flooring, with a wide bank of sliding glass doors opening directly to the lanai. Granite counters, 42-inch cabinetry, a generous island with seating and pantry storage make the kitchen functional for everyday meals while keeping it connected to the gathering spaces. The three-bedroom, two-bath split layout places the primary suite at the rear of the home, where the same plank flooring continues into the bedroom and the en suite bath offers dual sinks and an oversized walk-in shower with a built-in bench. Two secondary bedrooms and a full guest bath provide additional flexibility, while built-in cabinetry near the garage entry creates a practical drop zone. Outdoors, the screened travertine-tiled lanai expands the living area around a private pool, dedicated firepit seating area and covered grilling station. The two-car garage also provides additional golf-cart parking. Positioned along the 16th fairway of Mystic Dunes Golf Course, the home is located within Four Seasons at Orlando, a 55+ community with a clubhouse, community pools, fitness center, tennis, pickleball and bocce courts, plus spaces for crafts, yoga and community activities. Walt Disney World, Celebration, shopping, dining and major roadways are also nearby, bringing together golf-course views, poolside living and an adaptable single-story layout in a well-established amenity-rich community.

2016 Flora Pass Place, Kissimmee
1983 Limestone Trail, Kissimmee
$549,000
3 Beds ⋅ 2 Baths ⋅ O6430654 MLS
WHY WAIT TO BUILD WHEN THIS EXCEPTIONAL, LIKE-NEW HOME OFFERS APPROXIMATELY $65,000 IN BUILDER UPGRADES, A $45,000 PREMIUM LOT, AND PAID-OFF SOLAR PANELS? Ideally positioned on a quiet CUL-DE-SAC with NO REAR NEIGHBORS, this fully fenced homesite offers a rare level of privacy within the desirable guard-gated 55+ community of Four Seasons at Orlando. Electronic keyless entry welcomes you inside, where LUXURY VINYL PLANK FLOORING FLOWS THROUGHOUT—THERE IS NO CARPET ANYWHERE IN THE HOME. The open, thoughtfully designed floor plan feels bright, spacious, and beautifully finished, making it equally suited for relaxed everyday living and effortless entertaining. At the heart of the home, the GOURMET KITCHEN impresses with gleaming QUARTZ COUNTERTOPS, abundant cabinetry accented by crown molding, generous preparation space, and an open connection to the main living and dining areas. Continue through the home to the stunning glass doors, which FULLY OPEN to create a seamless transition between the interior living space and the EXTENDED LANAI. Whether hosting friends, enjoying morning coffee, or unwinding at the end of the day, this inviting indoor-outdoor setting overlooks the private, fully fenced backyard with no homes directly behind it. The spacious primary suite provides a peaceful retreat with room to relax and an IMPRESSIVE OVERSIZED WALK-IN CLOSET. Quartz countertops continue into the bathrooms, creating a cohesive and elevated finish throughout the home. The newer washer and dryer will also remain for the convenience of the next owner. One of the home’s most valuable features is the PAID-OFF SOLAR PANEL SYSTEM, which transfers to the new owner and offers the potential for SIGNIFICANT MONTHLY ENERGY SAVINGS without an additional solar loan payment. The garage is already equipped with a 240-VOLT OUTLET FOR EV CHARGING, adding even more efficiency and future-ready convenience. Four Seasons at Orlando delivers the active, resort-inspired lifestyle today’s 55+ buyers are looking for. Residents enjoy a 12,000-square-foot clubhouse, resort-style pool and spa, fitness center and movement studio, pickleball, tennis and bocce courts, arts and crafts space, card and billiards rooms, social events, clubs, and a full-time activities director. The community is situated alongside Mystic Dunes Golf Club and is conveniently located near Walt Disney World, shopping, restaurants, everyday services, major roadways, and the endless recreation and entertainment of Central Florida. PRIVATE PREMIUM LOT. EXCEPTIONAL BUILDER UPGRADES. PAID-OFF SOLAR. MOVE-IN-READY LUXURY. This is the Four Seasons home buyers have been waiting to find.

1983 Limestone Trail, Kissimmee
7748 Four Seasons Boulevard, Kissimmee
$695,000
3 Beds ⋅ 3 Baths ⋅ V4950940 MLS
Welcome home to this gorgeous golf course front pool home in the Four Seasons at Orlando 55+ Resort Style Gated Golf Community!! With over 2,700 square feet of living space, this 2022 built "Saint Lucia Bonus" model offers 3 bedrooms, 3 full baths, an office/den (or potential 4th bedroom), and upstairs 12'x20' living area. With 10' high ceilings and 8' interior doors, natural light flows throughout the home. The chef's kitchen is the center of attention overlooking the dining area, living room with tray accent ceilings, and beautiful screened in swimming pool on the golf course- hole #3. Wood plank tile can be found in most of the main living areas with carpeted bedrooms for a cozy feel. Kitchen features include 42" solid wood cabinetry with crown molding, quartz countertops, classic subway tile backsplash, stainless appliances gas cook top, large pantry and so much more! There's even space just outside the kitchen for overflow to create a butler's pantry, wine bar, etc. The main floor primary en-suite features it's own access to the pool and patio and oversized bathroom with both shower and soaking tub. Every bedroom is spacious and there is plenty of storage throughout the home. The community showcases two gorgeous palm tree lined heated pools and clubhouse offers year-round activities from pickle ball to bocce ball, fitness center and ballroom dancing to billiards and of course the Mystic Dunes 18-hole golf course. Designed by former PGA Tour player and TV analyst Gary Koch, the Par-72, 7,012-yard course features two distinct styles- a British Isles links-style front nine and a Carolina "low country" style back nine. You don't need to leave your neighborhood for things to do, but just beyond the gates is everything Orlando has to offer from theme parks, world class dining experiences, shopping, and easy drive to some beautiful beaches. Let the true Florida lifestyle surround you inside and out!

7748 Four Seasons Boulevard, Kissimmee
2042 Key Bay Trail, Kissimmee
$355,000
2 Beds ⋅ 2 Baths ⋅ O6438140 MLS
Enjoy this upscale, fun filled resort lifestyle at K. Hovnanian's FOUR SEASONS at ORLANDO'S 55+ private gated community located only 7-8 miles from the Disney Theme Parks. You will experience endless sunshine one beautiful day after day in this outdoor paradise. You will also love this "SANDPIPER" Villa (1583 sq. ft). Open concept kitchen (with beautiful cabinets and quarts counter tops), dining and great room. The primary bedroom and the second bedroom are on separate ends of the Villa which allows for complete privacy. The office with french doors can also be used as a 3rd bedroom. All rooms have wood like tile flooring and French Doors out to the backyard. There are so many activities for you to enjoy here at the Four Seasons, two beautiful pools, one with a lap lane and hot tub. If you like pickle ball you will love joing the teams and competitions. The clubhouse offers, coffee station, lounge, pool and ping pong room, kitchen, ballroom, card room,nice size gym and yoga room. Many owners enjoy riding around the community in their golf carts visiting neighbors and enjoying the community. New gutters installed, driveway sealed and power washed. Screened in Lanai just installed.

2042 Key Bay Trail, Kissimmee
2160 Antilles Club Drive, Kissimmee
$419,999
2 Beds ⋅ 2 Baths ⋅ O6437814 MLS
Step into this stunning, fully upgraded home that blends elegance, comfort, and privacy. The spacious kitchen is a showstopper, featuring quartz countertops, an oversized island, soft-close cabinetry, and stainless steel appliances — perfect for both everyday living and entertaining. Gorgeous wood-plank tile floors flow throughout, complemented by crown molding for a refined touch. Relax on the covered, screened-in lanai, where you’ll enjoy peaceful views and complete privacy with no rear neighbors. The home’s location within the community is ideal — quiet, convenient, and just a short drive to Disney and area attractions. Located in a premier 55+ community, residents enjoy resort-style amenities including a golf course, sparkling pools, tennis, pickleball, and bocce courts, a state-of-the-art fitness center, and a beautiful clubhouse offering a full calendar of social activities and events. This home is truly move-in ready and waiting for you to start your next chapter in style!

2160 Antilles Club Drive, Kissimmee
7789 Four Seasons Boulevard, Kissimmee
$549,000
3 Beds ⋅ 3 Baths ⋅ O6432349 MLS
Welcome to refined Florida living in the sought-after Four Seasons at Orlando 55+ community. Set on a **premium conservation-view homesite within walking distance of the clubhouse and amenities**, this beautifully upgraded Dominica model offers 2,360 square feet of thoughtfully designed living space and exceptional indoor-outdoor living. The home features **2 bedrooms, 2.5 bathrooms, and a dedicated office with a closet that can function as a third bedroom**. The private guest suite includes its own full bath, while the expanded primary suite offers **2 walk-in closets with custom built-ins** and an upgraded bath with dual vanities, granite countertops, and an oversized walk-in shower. The kitchen features **GE Profile appliances, enhanced lighting, additional outlets, and a redesigned pantry with custom shelving**. The laundry room includes added cabinetry and storage, while the office is enhanced with **wall-to-wall book shelves and a large custom desk**. Additional garage shelving and a separate storage area provide even more functionality. A true highlight is the private outdoor living space. **Seamless corner glass sliders** open to an expansive covered lanai overlooking the peaceful conservation setting. The custom summer kitchen includes a **gas grill, 2 burners, refrigerator, sink, and ample storage**, representing an estimated $17,000 investment. The beautifully landscaped yard features approximately **40 to 50 recently added plants**, professionally maintained pavers, and significant **drainage and erosion improvements already completed**. The home has been exceptionally well maintained and shows beautifully. **Furniture is negotiable, and TVs may remain.** Jimmy Buffett and Disney-themed memorabilia and media do not convey. Residents of **Four Seasons at Orlando** enjoy 24-hour guarded entry, a 13,000-square-foot clubhouse, 2 resort-style pools, spa, fitness center, tennis, pickleball, and bocce courts. HOA fees include exterior landscaping for truly low-maintenance living. Just minutes from **Walt Disney World®**, dining, shopping, and entertainment, this home combines a premium location, conservation views, meaningful upgrades, and resort-style living in one exceptional residence. **Schedule your private showing today and experience Four Seasons living for yourself.**

7789 Four Seasons Boulevard, Kissimmee
1667 Key Bay Trail, Kissimmee
$339,500
2 Beds ⋅ 2 Baths ⋅ O6431972 MLS
Experience resort-style Florida living in this beautifully upgraded 2-bedroom, 2-bath home located in the highly desirable Four Seasons 55+ guard-gated community in Kissimmee. Move-in ready and thoughtfully enhanced throughout, this home combines stylish upgrades, excellent storage, comfortable living spaces, and an exceptional amenity-filled lifestyle. Inside, you'll find upgraded flooring extending through the living areas, bedroom and closets, along with beautiful French doors, window blinds and draperies, upgraded ceiling fans and lighting throughout, and an elegant upgraded dining room light fixture. The kitchen features a stylish backsplash, additional cabinetry and cupboards, an added bank of drawers for convenient storage, decorative cabinet and drawer pulls, and an exhaust fan over the stove. These thoughtful additions provide both functionality and an attractive finished look. The laundry room offers additional cabinetry and storage, decorative hardware, a coordinating backsplash and plumbing already in place for a laundry sink. Both bathrooms feature attractive finishes, including a guest shower and an upgraded beveled-edge finish in the primary shower. Enjoy Florida's beautiful weather from the screened-in lanai, creating an inviting additional space for morning coffee, relaxing, entertaining family and friends, or simply enjoying the Florida lifestyle. Additional improvements include gutters and upgraded garage shelving, providing even more convenient storage and organization. And the lifestyle doesn't stop at your front door. Four Seasons offers an outstanding resort-style 55+ lifestyle within a guard-gated community, complete with an impressive clubhouse offering a wide variety of activities and social opportunities, oversized swimming pools, fitness center, pickleball courts, tennis courts, golf, and much more. Whether you enjoy staying active, playing golf, relaxing poolside, participating in community activities, or spending time with friends at the clubhouse, Four Seasons offers something for virtually every lifestyle. With extensive upgrades already completed, generous living and storage space, outstanding community amenities, and a desirable Kissimmee location, this home offers the opportunity to simply move in and start enjoying everything Central Florida has to enjoy. This is more than a home—it's the Florida lifestyle you've been looking for. Schedule your private showing today and experience Four Seasons for yourself!

1667 Key Bay Trail, Kissimmee
7964 Hanson Bay Place, Kissimmee
$485,000
4 Beds ⋅ 3 Baths ⋅ O6426137 MLS
Welcome to the Four Seasons of Orlando's 55+ Private Gated Community. This home is a "STELLA" model home featuring four true bedrooms and three full baths (one guest bedroom with its own private en suite). Inviting entry foyer with tile flooring throughout the main living area. All bedrooms have carpeting. The primary bedroom features a coffered ceiling and a triple window looking out on to the lanai. Open concept living with a beautiful kitchen, dining room and living room opens up to the extended paved lanai and patio. Special feature is the electric 12 foot awning and the extended paved patio. Watch the sunsets right from your own lanai. Four Seasons is adjacent to the Mystic Dunes Country Gold Club which we have gate access to and they give our residents a discount on food, bar and golf. There are so many activities that go on at the Four Seasons. From line dancing, pool table, ping pong, game room, card room, exercise room and a large gym. You will love living here and we are only a few miles away from all the Disney Theme Parks. Life is good at the Four Seasons of Orlando in Kissimmee. Come be our neighbor. Rooms with furniture in them are staged.

7964 Hanson Bay Place, Kissimmee
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