Kissimmee Homes with Playground Amenities

7 Beds ⋅ 10 Baths ⋅ Reunion West Fairways 17 & 18 SubDv. ⋅ 34747 Zip Code

Exceptional luxury, privacy, and rental appeal await in Reunion Resort’s prestigious Bear’s Den Club. Set on a rare oversized homesite with no rear neighbors and a private park directly behind the property, this fully furnished seven-bedroom residence offers one of the most desirable settings in the community. Professionally designed for unforgettable guest experiences, the home features immersive custom-themed bedrooms, multiple king suites, two creative bunk rooms, a state-of-the-art home theater, a spacious loft with billiards, and a dedicated arcade. The open-concept living area flows seamlessly outdoors to a private pool and spa, covered dining area, and fully equipped summer kitchen—perfect for entertaining and enjoying the Florida sunshine. Located just minutes from Walt Disney World and Orlando’s premier attractions, Bear’s Den offers access to Reunion Resort’s world-class golf courses, dining, tennis, water park, fitness center, and concierge services. An active Reunion Club membership is available, providing immediate access to the resort’s extensive amenities. Whether you’re looking for a luxury vacation retreat or a standout investment property designed to accommodate large groups, this home delivers an exceptional combination of location, entertainment, privacy, and resort living. Be sure to view the video tour!

1063 Jack Nicklaus Court, Kissimmee

$475,000

4 Beds ⋅ 3 Baths ⋅ Preserve At Tapestry Ph 3 & 4 SubDv. ⋅ 34741 Zip Code

Welcome to 2815 Monticello Way—where comfortable living, entertaining space, and a convenient Kissimmee location come together! This 4-bedroom, 2.5-bath two-story home in the Preserve at Tapestry offers 2,328 square feet of living space, a two-car garage, and a large backyard designed for enjoying the outdoors. (*Listing includes some labeled virtually staged photographs.) Inside, the main level is made for gathering. The great room creates an easy flow between the spacious kitchen, large center island, dining area, and living room—giving everyone room to spread out while staying connected. Laminate flooring runs throughout the lower level, creating a clean and practical foundation for everyday living. Upstairs, the private primary suite offers a comfortable retreat with its own ensuite bath, while three additional bedrooms and a guest bath provide flexibility for family, guests, an office, or hobbies. Step outside and the living space continues! The large backyard features a screened porch, patio area, and garden space, creating multiple spots to relax, entertain, enjoy your morning coffee, or simply unwind at the end of the day. The generous yard also provides plenty of room to enjoy the outdoors and make the space your own. Recent updates include: Dishwasher — approximately 6 months old Range — approximately 1.5 years old Washing machine — approximately 1.5 years old Dryer — approximately 3 years old Life in Preserve at Tapestry includes access to community amenities such as a resort-style pool, clubhouse, playground, and trails, all included with the monthly HOA. Scenic ponds, tree-lined streets, and established landscaping contribute to the neighborhood's inviting setting. And then there’s the location! The Loop, shopping and dining along US-192 are just minutes away, while nearby Osceola Parkway provides convenient access toward Walt Disney World, Lake Nona, the Florida Turnpike, and SR 417. Orlando International Airport and Kissimmee Gateway Airport, Disney Springs, the major theme park corridor, Lake Tohopekaliga, and historic Downtown Kissimmee are also within easy reach. Come see 2815 Monticello Way and discover a home that offers space to gather, room to relax, and a Central Florida location that keeps you close to it all!

2815 Monticello Way, Kissimmee

$438,480

4 Beds ⋅ 3 Baths ⋅ Westview 50s Gc SubDv. ⋅ 34758 Zip Code

Under Construction. This new single-story McCartney Next Gen® home features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off the foyer, and a lavish owner’s suite is tucked into a private rear corner, complete with a full bathroom and walk-in closet. Westview is a master-planned community in Poinciana, FL. This amenity-rich, pet-friendly community has something for residents of all ages to enjoy, including a swimming pool, dog park, clubhouse and sports fields. Lake Marion Creek Wildlife Management Area is nearby with hiking trails, as well as Poinciana for shopping, dining and entertainment options. The community is in close proximity to Highway 17 for easy commuting to Greater Orlando.

5595 Dennery Bay Road, Kissimmee

$509,985

5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1872 Southbury Drive, Kissimmee

$275,000

3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code

Beautiful and spacious 3 bedroom, 3 bathroom townhouse in the GATED COMMUNITY of PARADISE CAY. This LARGER UNIT boasts 1,362 square feet under A/C and features an OPEN FLOOR PLAN with a recently UPGRADED kitchen including GRANITE COUNTERTOPS and FRESHLY PAINTED CABINETS. With 2 BEDROOMS and 2 FULL bathrooms upstairs, and a MASTER BEDROOM WITH FULL BATH ON THE FIRST FLOOR, this home is perfect for families. ALL APPLIANCES ARE NEW OR HAVE BEEN PURCHASED SINCE MARCH 2023 including the dryer, washer, refrigerator, garbage disposal, water heater, and AC/heating unit except for the stove and dishwasher, which were already new when the current owners purchased the home. All bedroom windows have blinds and curtains, while the living room window and patio have blinds. Located within WALKING DISTANCE to US 192, residents will enjoy easy access to restaurants, grocery stores, and other convenient stores. Paradise Cay is a Mediterranean-style community just 4 miles from the Disney main gate, offering a pool, cabana, and playground area for residents to enjoy making this home a great investment opportunity or a comfortable primary residence.

5315 Paradise Cay Circle, Kissimmee

$439,685

4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code

Kindred presents the Cali. This all concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located in the back of the home for privacy, has an en suite bathroom with a double vanity, spacious shower/tub space as well as a spacious walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall you will find a fourth bedroom. This home features a space to fit all your needs. Like all homes in Kindred, the Cali includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1511 Beechmont Drive, Kissimmee

$400,000

3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code

Kindred presents the Allex. This all concrete block constructed, one-story layout optimizes living space with an open concept. As you go down the hallway and enter a spacious kitchen featuring stainless steel appliances with ample counter space and a walk-in pantry for extra storage. The living room is complete with a view to the covered lanai outside. Bedroom one, located at the back of the home for privacy, has an en suite bathroom that features a double vanity sink with a walk-in closet. Two additional guest bedrooms and one bath are tucked away down the hall from the dining room. The laundry room is located at the front of home near the two-car garage. Like all homes in Kindred, the Allex includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1921 Howard Mesa Drive, Kissimmee

$445,690

5 Beds ⋅ 3 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code

MODEL LEASEBACK OPPORTUNITY! A Community Designed for Every Stage of Life. Westview features an intimate collection of 119 single-family homesites, creating a welcoming neighborhood feel with modern, thoughtfully designed floorplans. Whether you’re starting a new chapter or expanding your lifestyle, these homes are built to adapt to your needs. Personalization is at the heart of the experience, you’ll have the freedom to select your ideal homesite, design features, and finishes, allowing you to truly create a home that reflects your style and vision. Amenities That Inspire an Active, Social Lifestyle. At the center of the community is a vibrant social hub designed to bring neighbors together. The Hub clubhouse anchors the experience, offering: A fully equipped fitness center with a free weight room, an exciting rock-climbing wall, a multipurpose gymnasium with basketball court, a movement studio and locker facilities, and a welcoming gathering space with kitchenette and café. Step outside and enjoy an impressive collection of amenities designed for both recreation and relaxation: Pickleball, tennis, basketball, and volleyball courts, a lap pool, a resort-style pool with play features, and a dedicated kids pool, Open fields for baseball and soccer, a tot lot for younger residents, and a separate dog parks for small and large pets. Every detail is designed to support an active, connected, and wellness-focused lifestyle for residents of all ages. The Marina floor plan is the crown jewel of our 30’ collection offering an impressive 2,520 sq. ft. of refined living space. This premium residence features five bedrooms and three baths, including a private first-floor suite perfect for guests or multi-generational living. The heart of the home showcases a chef-inspired kitchen with an expansive island that flows seamlessly into light-filled dining and great room areas. Upstairs, find a luxurious owner’s retreat with dual walk-in closets, three additional bedrooms, and a versatile loft space bathed in natural light from thoughtfully positioned windows. Available in three distinctive elevation options with customizable stone accents. The Marina delivers uncompromising style and functionality for growing families seeking generous space without sacrificing sophistication. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos. Schools: Elem: Koa Elementary School; Middle: Discovery Intermediate School; HS: New Dimensions High School.

4760 Goodmans Bay Drive, Kissimmee

$345,000

4 Beds ⋅ 3 Baths ⋅ Paradise Palms Resort Ph 2 SubDv. ⋅ 34747 Zip Code

Your ideal vacation retreat is right here in this fully furnished, tastefully designed 4-bedroom, 3-bath residence located inside the desired gated community of Paradise Palms. Paradise Palms provides a secure living environment with a 24-hour manned security gate for peace of mind. Perfectly positioned with a backyard view of the community pond and currently one of the closest units to the clubhouse with its impressive selection of resort-style amenities. The thoughtful floor plan includes an open-concept living area on the main level, along with a convenient first-floor bedroom suite. The remaining bedrooms and bathrooms are located upstairs for added privacy. The living room, dining room, and kitchen are freshly painted. The kitchen showcases granite countertops, a generous breakfast bar, and stainless steel appliances. The spacious living area is the perfect place to unwind after a day of fun, and the dining area offers access to the private pool deck. The upstairs master suite includes its own ensuite bathroom, and every bathroom features granite vanities. Outside, your covered private screened in lanai and heated pool are perfect for lounging and dining whether you prefer shade or sunshine. And when you want to enjoy the community, you’ll love the exceptional Clubhouse is just a short walk away, which features a resort-style pool and spa complete with sloped beach-entry, waterfall features, a splash area, a waterslide, cabanas, and an outdoor café. Additional amenities include tennis courts, basketball, beach volleyball, a fitness center, sauna, playground, and even a convenience store. Whether you’re searching for a personal getaway or a high-performing income-producing rental the location is unbeatable, just 2 miles from a grocery plaza and approximately 7 miles from the Disney parks. Discover why this home and the Paradise Palms community stand out as one of the best opportunities in the area! This property is active in a short-term rental program—contact the listing agent to confirm showing times.

3027 Beach Palm Avenue Unit 3027, Kissimmee

$825,000

3 Beds ⋅ 3 Baths ⋅ Celebration Charleston Place SubDv. ⋅ 34747 Zip Code

Welcome to 323 Celebration Boulevard, a beautifully renovated "ISSA BUILT" 3-story townhome offering 3 bedrooms, 2.5 baths, and an exceptionally flexible floor plan. (Room on 2nd floor that can be an additional bedroom). Extensive improvements were completed in 2018, including the removal of walls and reconfiguration of the staircase to create an open-concept first floor. Wood-look tile flooring flows throughout the main level, complemented by recessed lighting and a beautifully redesigned fireplace with custom built-ins. The custom kitchen features a deep farmhouse sink, upgraded appliances, abundant cabinetry, and plenty of deep drawers for additional storage. The second floor offers the spacious primary suite, an additional bedroom, and a versatile den that could serve as a guest room, nursery, or home office. The primary bathroom was completely redesigned with an enlarged, fully tiled shower featuring a frameless glass enclosure, a freestanding soaking tub, and new vanities. The guest bathroom was also updated with new vanities and tile. The finished third floor features a closet, updated flooring and railing, and its own variable-speed air-conditioning system with dedicated ductwork. Currently used as an office, this spacious bonus area could also serve as a bedroom, workout room, media room, or creative studio. Additional upgrades include recessed lighting throughout, an upgraded main electrical service to provide increased power to the home, and a dedicated electrical panel for the third floor. Step through the rear door to a beautiful patio with a custom-built deck, creating an inviting space for relaxing or entertaining, with convenient access to the detached two-car garage. With extensive renovations, flexible living spaces, and a desirable Celebration location, this thoughtfully updated townhome is ready to welcome its next owner!

323 Celebration Boulevard, Celebration

$460,000

5 Beds ⋅ 3 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code

Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a nice sized living/foyer space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1929 Howard Mesa Drive, Kissimmee

$471,990

5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a nice sized living/foyer space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1945 Howard Mesa Drive, Kissimmee

Kissimmee Homes with Playground Amenities

Newest Kissimmee Homes with Playground Amenities