Kissimmee Homes with Playground Amenities

Kissimmee Homes with Playground Amenities

Welcome to Kissimmee, Florida, where sunshine and charm meet to create an idyllic community for families and individuals alike! Nestled in the heart of Osceola County, Kissimmee is renowned for its vibrant culture, rich history, and proximity to some of Florida's most famous attractions, including Walt Disney World and Universal Studios. With a warm climate year-round, residents enjoy an outdoor lifestyle filled with recreational activities, parks, and stunning lakes.

Kissimmee is not just about entertainment; it’s a place where families can thrive. One of the standout features of this region is the availability of homes with playground amenities. Imagine stepping outside your door to find a beautifully maintained playground just a stone's throw away. These family-friendly neighborhoods are designed with your children’s happiness and safety in mind, offering secure play areas where they can explore, socialize, and create lasting memories.

Whether you’re seeking a cozy single-family home or a spacious townhouse, Kissimmee boasts a diverse range of properties that cater to every lifestyle and budget. Many of these homes are situated within communities that prioritize family-friendly amenities, making it easy for parents to engage with their children while fostering a sense of community.

Kissimmee is not just a place to live; it’s a place to grow, play, and make lifelong memories. With its perfect blend of suburban tranquility and urban excitement, Kissimmee invites you to discover your dream home where playgrounds and parks are just around the corner. Come explore the endless possibilities that await you in this enchanting Florida gem!

Newest Kissimmee Homes with Playground Amenities

2514 Serenity Garden Drive, Kissimmee
$486,860
5 Beds ⋅ 3 Baths ⋅ Tohoqua SubDv. ⋅ 34744 Zip Code
Under Construction. Tohoqua is the kind of neighborhood you've been looking for, with an exciting amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. The new two-story Trailside home, with 5 bedrooms, 3 bathrooms, a loft, and a 2-car garage is ready for you to move in and start living the life you deserve. Upon entry, you’re welcomed by a beautiful wrap around staircase and a foyer that is flooded with natural light. The foyer leads you toward the heart of the home, where the kitchen, gathering room, and café seamlessly flow together, all overlooking the covered lanai. Your chef-inspired kitchen is a true standout, offering a large center island and stainless-steel Whirlpool appliances, including a refrigerator. White cabinetry with quartz countertops, a single-bowl stainless-steel sink, and upgraded faucet combine to create a stylish and functional space. A guest bedroom and full bathroom are located on the main level, perfect for visitors, a home office, or flexible living space. Upstairs, the Owner’s Suite offers a peaceful retreat with a large walk-in closet and an en suite bath featuring dual sinks, a quartz-topped vanity, a private water closet, and a walk-In shower with a built-in bench. Also located on the second floor, three additional bedrooms, another secondary bathroom, a loft, and a conveniently located laundry room offer both privacy and functionality. Throughout the home, professionally curated design selections and premium finishes elevate the living experience. Wood-look luxury vinyl plank flooring spans the first-floor living spaces; tile graces the bathroom and laundry room floors, while soft, stain-resistant Shaw carpet enhances the bedrooms and second-floor living spaces. Additional touches such as 2” faux wood blinds, Whirlpool washer and dryer, Sherwin Williams Drift of Mist Interior Wall Paint, and brushed nickel hardware and plumbing fixtures add both style and convenience. The open spindle railing at the first-floor staircase completes the home’s elegant feel. This Trailside home is where luxury and practicality meet. Don’t miss your chance to make this exceptional home yours—schedule a tour today!

2514 Serenity Garden Drive, Kissimmee
4375 Silver Creek Street, Kissimmee
$599,900
5 Beds ⋅ 3 Baths ⋅ Creekside At Boggy Creek Ph 1 SubDv. ⋅ 34744 Zip Code
Welcome to 4375 Silver Creek Street, where elegance meets modern comfort in the heart of Kissimmee! This beautifully designed two-story residence offers the perfect blend of sophistication, space, and functionality. Step inside to discover an inviting floor plan featuring elegant tile flooring, a stunning wood staircase with decorative iron railings, and spacious living areas ideal for both everyday comfort and entertaining. The beautifully appointed kitchen flows seamlessly into the expansive family room, while separate formal living and dining areas add a touch of elegance. The first floor also features a versatile bonus room that can easily serve as a fifth bedroom, private home office, or guest retreat. Upstairs, you'll find four generously sized bedrooms, including a spacious owner's suite with two closets and a private bathroom, along with a large loft perfect for entertainment or relaxation. Enjoy Florida living at its finest with an extended covered lanai, ideal for outdoor gatherings, and a convenient two-car garage. A remarkable home offering elegance, versatility, and exceptional living space. Schedule your private showing today!

4375 Silver Creek Street, Kissimmee
1895 Cassidy Knoll Drive, Kissimmee
$375,000
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
MOVE-IN READY in KINDRED with HOA UNDER $11/MONTH! This 2019 single-story home offers 3 bedrooms, 2 baths and 1,676 sq ft in one of Kissimmee’s most sought-after communities. A bright, open-concept layout connects the living and dining areas to a kitchen with a large center island and breakfast bar, plenty of cabinet space and pendant lighting, ideal for everyday living and entertaining. The split-bedroom floor plan adds privacy, and the primary suite includes a spacious bath with dual sinks and a walk-in shower. Step out to the screened lanai overlooking a generous, fully fenced backyard with plenty of room to play, garden or relax. Other highlights include an interior laundry room, tile in the main traffic areas and a two-car garage. Kindred offers resort-style amenities: community pools, fitness centers, clubhouses, tennis courts, playgrounds, dog parks and walking trails, plus on-site elementary and middle schools. Minutes to Florida’s Turnpike, NeoCity, Lake Nona Medical City, shopping, dining and Central Florida’s world-famous attractions. Space, comfort, amenities and outstanding value. Schedule your private showing today!

1895 Cassidy Knoll Drive, Kissimmee
221 Westmoreland Circle, Kissimmee
$425,000
4 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr F SubDv. ⋅ 34744 Zip Code
OVER $50,000 IN UPGRADES! FULLY RENOVATED! GOLF COURSE VIEW! MOVE-IN READY! WHY PAY MORE FOR NEW CONSTRUCTION? Welcome to 221 Westmoreland Circle, Kissimmee, FL 34744, a beautifully remodeled 4-BEDROOM, 2-BATHROOM, 1,767 SQFT single-family home located in the desirable REMINGTON GOLF COMMUNITY! Featuring beautiful GOLF COURSE VIEWS, modern finishes, and over $50,000 IN RECENT UPGRADES, this meticulously updated home offers exceptional value without the higher price tag often associated with new construction! The sellers have invested extensively in improvements, including a BRAND-NEW KITCHEN, BEAUTIFULLY UPDATED BATHROOMS, UPDATED FLOORING, NEW WATER HEATER, FRESH INTERIOR AND EXTERIOR PAINT, and a beautifully finished EPOXY-COATED GARAGE FLOOR! Additional features include RAIN GUTTERS and a spacious 2-CAR GARAGE. Step inside and experience a bright, inviting floor plan with soaring ceilings, beautifully updated living spaces, and contemporary finishes throughout. The completely renovated kitchen serves as the heart of the home, while the updated bathrooms and flooring create a fresh, modern atmosphere. Enjoy the added benefit of SCENIC GOLF COURSE VIEWS, providing a beautiful backdrop for everyday living, relaxing evenings, and entertaining guests. Used primarily as a SEASONAL WINTER RESIDENCE by its owners, this home has been enjoyed during their winter visits to Florida and thoughtfully maintained. Located in the established REMINGTON GOLF COMMUNITY, this property offers convenient access to FLORIDA'S TURNPIKE, US-192, SHOPPING, RESTAURANTS, PUBLIX, WALMART, AND EVERYDAY ESSENTIALS. Enjoy approximately 5–10 MINUTES TO SHOPPING AND GROCERY STORES, 8–10 MINUTES TO FLORIDA'S TURNPIKE, 20–25 MINUTES TO ORLANDO INTERNATIONAL AIRPORT (MCO), 25–30 MINUTES TO LAKE NONA, 35–40 MINUTES TO DOWNTOWN ORLANDO AND WALT DISNEY WORLD, AND 40–45 MINUTES TO UNIVERSAL ORLANDO, depending on traffic and route. Whether you're searching for a PRIMARY RESIDENCE, SECOND HOME, VACATION RETREAT, OR MOVE-IN READY HOME NEAR ORLANDO, this property offers the perfect combination of location, comfort, and modern upgrades! WHY WAIT FOR NEW CONSTRUCTION AND PAY EXTRA FOR UPGRADES WHEN YOU CAN OWN A METICULOUSLY REMODELED HOME WITH GOLF COURSE VIEWS IN AN ESTABLISHED COMMUNITY? With over $50,000 invested in improvements, scenic surroundings, and an excellent Central Florida location, this property is truly a must-see! SCHEDULE YOUR PRIVATE SHOWING TODAY! PLEASE NOTE: Select listing photos have been virtually enhanced with wall art and decorative accents. The furniture shown in the photographs is physically staged inside the property.

221 Westmoreland Circle, Kissimmee
2628 Clear Night Avenue, Kissimmee
$373,400
3 Beds ⋅ 3 Baths ⋅ Tohoqua SubDv. ⋅ 34744 Zip Code
Under Construction. Tohoqua is the kind of neighborhood you've been looking for, with an exciting amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. Introducing the Camden bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. Sarsaparilla cabinetry and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor living spaces, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

2628 Clear Night Avenue, Kissimmee
255 Strathmore Circle, Kissimmee
$469,900
4 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr B SubDv. ⋅ 34744 Zip Code
Immaculate golf course home overlooking the 18th hole, featuring a sparkling pool, spa, and gorgeous tile deck perfect for outdoor entertaining! This well-appointed home offers a NEW ROOF, vinyl plank flooring, shutters throughout, crown molding in the main living areas, decorative chair rail, and premium ceiling fans. The kitchen features granite countertops, a center island, decorative backsplash, and stainless-steel appliances. Vinyl plank flooring extends throughout most of the home and the spacious 3-car garage features epoxy-coated floors and an 18,000 BTU A/C wall unit. Must see home!

255 Strathmore Circle, Kissimmee
1805 Lee Janzen Drive, Kissimmee
$550,000
3 Beds ⋅ 3 Baths ⋅ Kissimmee Bay SubDv. ⋅ 34744 Zip Code
Virtually Staged. GOLF COURSE VIEWS, WATERFRONT SERENITY & YOUR OWN PRIVATE POOL! Experience resort-style Florida living in the desirable gated community of Kissimmee Bay Country Club! This stunning 3-bedroom, 3-bath POOL home offers 2,155 sq. ft. of living space and a 2-car garage. Featuring a desirable split-bedroom floor plan, formal living and dining rooms, and an inviting family room with fireplace. The kitchen boasts granite countertops, stainless steel appliances, custom cabinetry, and a charming breakfast area. The spacious primary suite features dual closets, a luxurious bath with dual vanities, soaking tub, separate shower, and direct pool access. STEP OUTSIDE TO YOUR OWN PRIVATE PARADISE! Enjoy breathtaking pond and golf course views from the expansive screened pool enclosure, complete with a brick-paver deck and covered lanai—perfect for entertaining or relaxing year-round! Kissimmee Bay offers an exceptional lifestyle with an 18-hole golf course, clubhouse restaurant, tennis courts, community dock, boat and RV storage, and playground. HOA benefits include basic cable, internet, nighttime security, and irrigation water. Certain amenities may require additional fees or memberships. Don't miss this incredible opportunity to own your own slice of Florida paradise! Schedule your private showing today!

1805 Lee Janzen Drive, Kissimmee
2802 Quiet Water Trail, Kissimmee
$760,000
5 Beds ⋅ 5 Baths ⋅ North Shore Village SubDv. ⋅ 34744 Zip Code
Virtually Staged. YOUR PRIVATE FLORIDA RETREAT AWAITS! OVER 4,300 SQ. FT. OF RENOVATED MEDITERRANEAN ELEGANCE, SPECTACULAR SUNSETS, WATER VIEWS & RESORT-STYLE LIVING—JUST MINUTES FROM LAKE NONA! Discover one of Central Florida’s best-kept secrets in The Landings at North Shore, a beautiful gated community near the shores of East Lake Tohopekaliga. This impressive 5-bedroom, 5-bathroom executive residence, built by Centerline Homes, offers an extraordinary combination of space, elegance, modern upgrades, and location. Recently transformed with extensive improvements, this home welcomes you with soaring ceilings, a majestic staircase, and an inviting floor plan designed for both everyday comfort and unforgettable entertaining. Freshly painted inside and out, the residence features new water-resistant flooring and baseboards throughout the second floor and portions of the first floor, FIVE beautifully renovated bathrooms with modern cabinetry, quartz countertops, illuminated mirrors, and new toilets. The refreshed gourmet kitchen showcases updated cabinetry, stunning quartz countertops, and BRAND-NEW appliances. Both A/C systems have received significant component upgrades, and the pool features newly replaced valves and professional weekly maintenance. The thoughtfully designed first floor offers a private office with French doors opening to the front patio, elegant formal living and dining rooms, and a spacious family room filled with natural light. French doors invite you outside to the covered lanai, screened pool, and spa, where your very own Florida paradise begins. IMAGINE ENDING EVERY DAY WITH A SUNSET! Perfectly positioned on the WEST SIDE of the residence, the poolside retreat enjoys beautiful afternoon sunshine and breathtaking sunset skies overlooking the peaceful pond. Whether sipping your morning coffee, hosting weekend gatherings, or unwinding beneath the colors of a Florida sunset, this outdoor oasis makes every day feel like a vacation. The spacious primary suite offers tranquil water views, a generous walk-in closet, and an inviting bathroom with a jetted soaking tub, separate glass-enclosed shower, and dual vanities. Upstairs, an expansive bonus room with kitchenette, adjoining bedroom, and private bathroom creates an exceptional opportunity for multigenerational living, visiting guests, or a private entertainment retreat. Additional generously sized bedrooms, bathrooms, and a pond-view sitting area provide flexibility for today’s evolving lifestyles. LOCATION, LIFESTYLE & CONVENIENCE! Enjoy the benefits of living near Lake Nona’s thriving Medical City without sacrificing space or the charm of an established gated community. Conveniently located near the Orlando VA Medical Center, UCF’s medical campus, USTA National Campus, Orlando International Airport, and Austin-Tindall Sports Complex, with easy access to SR 417 and SR 528 connecting you to downtown Orlando, theme parks, shopping, dining, and Florida’s beaches. Offering approximately 4,323 square feet of living space, a THREE-CAR GARAGE, five bedrooms, five bathrooms, extensive recent upgrades, and a private pool and spa with picturesque water views, this residence is more than a home—IT’S THE FLORIDA LIFESTYLE YOU’VE BEEN DREAMING OF! Discover the space, experience the transformation, and fall in love with the sunsets. Schedule your private showing today!

2802 Quiet Water Trail, Kissimmee
1894 Cassidy Knoll Drive, Kissimmee
$540,000
5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to 1894 Cassidy Knoll, an exceptional home in the highly sought-after Kindred community featuring one of the largest and most desirable floor plans ever offered in the neighborhood. No longer available from the builder, this expansive design is known for its generously sized rooms, outstanding functionality, and flexible living spaces. The enormous first-floor primary suite offers exceptional privacy and convenience, complete with a massive walk-in closet and a unique, code-compliant doorway providing direct access to the garage. This thoughtful upgrade allows homeowners to come and go without disturbing the rest of the household. The home also features another spacious bedroom with a private en-suite bathroom, ideal for guests or multigenerational living, along with a versatile flex room that could serve as a formal dining room, home office, or potential sixth bedroom. What truly separates this home from others in Kindred is the extensive investment in aftermarket upgrades. The backyard features a massive 44-by-15-foot professionally installed paver lanai, offering approximately 660 square feet of outdoor entertaining space. A newly fenced backyard and a 7-by-7-foot shed/workshop, which conveys with the property, provide even more functionality. Inside, all carpeted areas have been replaced with premium luxury vinyl plank flooring. Exterior improvements include a widened driveway designed to accommodate larger vehicles and a paver walkway connecting to the driveway. The garage is equally impressive, featuring epoxy flooring, multiple 220-volt outlets suitable for electric vehicle charging equipment, a granite-topped utility sink, and additional washer and dryer hookups. While the main laundry room is upstairs, the garage provides the flexibility for a second laundry area. Two separate garage access points and a newer whole-home water softener and filtration system add even more convenience. Kindred offers an outstanding location just minutes from Florida's Turnpike, allowing residents to bypass much of the congestion along US 192. Shopping, dining, and everyday conveniences are nearby, while Walt Disney World is approximately 25 to 30 minutes away. The community also features its own K-8 school and resort-style amenities, including a swimming pool, clubhouse, fitness center, tennis courts, and basketball courts. A future commercial section is also planned within the community. With its rarely available floor plan, oversized bedrooms, first-floor primary suite, incredible outdoor entertaining space, and extensive upgrades, 1894 Cassidy Knoll offers a combination of size, comfort, and functionality that is increasingly difficult to find in today's new construction.

1894 Cassidy Knoll Drive, Kissimmee
1884 Southbury Drive, Kissimmee
$513,985
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.*

1884 Southbury Drive, Kissimmee
1888 Southbury Drive, Kissimmee
$491,790
4 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Inside this beautiful 4-bedroom, 3-bathroom home welcomes the Multi-Gen where you will find 2,077 square feet of comfortable living. The first Bedroom on the left has it’s own bathroom and sitting area with a kitchenette and a private entry to come and go as you please. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances. You'll never be too far from the action with the living and dining area right there. Find RevWood Select Flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. The primary bedroom has its own attached bathroom that features a walk-in closet and 2 sink vanity. *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.*

1888 Southbury Drive, Kissimmee
91 Club Villas Lane, Kissimmee
$289,000
2 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr A SubDv. ⋅ 34744 Zip Code
Looking for a maintenance free home where peaceful golf course living meets everyday convenience? You've found it right here in the gated Club Villas community within Remington! Perfectly positioned on a cul-de-sac overlooking the Remington Golf Course, this charming 2-bedroom, 2-bathroom villa offers 1,306 heated square feet of comfortable living space and picturesque views extending across the fairway to a serene pond beyond. Step through the covered, enclosed front porch into a spacious open-concept living area, where the living room features soft carpet flooring and sliding glass doors leading to a second covered and enclosed porch—the perfect place to unwind while taking in the beautiful surroundings. The kitchen offers a bright, crisp aesthetic with white cabinetry, white and grey granite countertops, tile flooring, and an adjoining dining area. A cozy dinette framed by a bay window overlooks the golf course, creating an ideal spot for morning coffee, casual meals, or simply enjoying the view. Both bedrooms are generously sized, while the primary suite features a private en-suite bathroom and dual closets. Beyond the villa, residents enjoy the added privacy of a gated community tucked inside Remington, an active community centered around the Remington Golf Course. The location places you approximately one mile from the Florida Turnpike entrance and within close proximity to shopping, dining, medical facilities, and schools. The Saint Cloud Lakefront is also nearby, offering four miles of walking paths, a splash pad and playground, marina and fishing pier, along with waterfront dining at Crabby Bill’s. With golf course and water views, two enclosed porches, a cul-de-sac location, and convenient access to so many of the area’s amenities, this villa offers a lifestyle and location ready to welcome its new owners.

91 Club Villas Lane, Kissimmee
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