Kissimmee Homes with Playground Community Features

Kissimmee Homes with Playground Community Features

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the magic of Central Florida with the charm of small-town living. Nestled just minutes from the world-renowned attractions of Orlando, Kissimmee offers a unique lifestyle that caters to families, retirees, and everyone in between. With its picturesque landscapes, rich cultural heritage, and a variety of recreational activities, Kissimmee is more than just a destination; it’s a place to call home.

One of the standout features of Kissimmee is its welcoming communities, particularly those with playground amenities that cater to families seeking an active and social lifestyle. Imagine your children playing freely in safe, well-maintained playgrounds, while you enjoy the peace of mind that comes with a family-friendly environment. These communities are designed with families in mind, offering a range of amenities that encourage outdoor play, social interaction, and a sense of belonging.

In addition to playgrounds, many of Kissimmee’s neighborhoods boast community parks, walking trails, and recreational facilities, ensuring that there’s always something fun to do just around the corner. With a strong sense of community spirit, residents often gather for events, barbecues, and seasonal celebrations, fostering lasting friendships and connections.

Living in Kissimmee means enjoying the best of both worlds: a tranquil suburban lifestyle combined with easy access to the excitement of nearby theme parks, shopping, and dining. Whether you’re looking for a cozy single-family home or a spacious townhouse, Kissimmee’s diverse real estate options make it easy to find the perfect fit for your family. Come explore the charm of Kissimmee, where your dream home awaits!

Newest Kissimmee Homes with Playground Community Features

$539,000
4 Beds ⋅ 3 Baths ⋅ Villa Sol Ph 1 Village 5 SubDv. ⋅ 34744 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Welcome to this Spanish-Mediterranean single-family home located in the gated community of Villa Sol in Kissimmee! Offering 4 bedrooms, 3 full bathrooms, a 2-car garage, and 2,351 sq. ft. of heated living space, this single-story residence combines flexible living with pond views. A key feature of the home is the attached in-law suite with its own private exterior back entrance, bedroom, and full bathroom. Inside, an open floor plan is filled with natural light, featuring polished porcelain tile flooring, vaulted ceilings, and architectural archways. The kitchen includes granite countertops, a multi-level breakfast bar, light grey cabinetry, stainless steel appliances, and pendant lighting. The primary bedroom suite offers luxury vinyl plank flooring, vaulted ceilings, a walk-in closet, and sliding glass door access to the pool deck. The en-suite bath features a dual-sink granite vanity, light grey cabinetry, a corner jetted soaking tub, and a separate glass-enclosed shower. Step outside to your private rear screen enclosure featuring an in-ground pool and integrated spa overlooking serene water views on an oversized lot. Villa Sol community amenities include a gated entry, clubhouse, fully equipped fitness center, resort-style community pool, tennis courts, basketball court, and playground, with cable TV and high-speed internet included in the low HOA fee. Perfectly positioned in Kissimmee, this home offers quick access to SR-417, US-192, and Boggy Creek Road, putting Lake Nona, Medical City, and Orlando International Airport (MCO) just a short drive away. Zoned for East Lake Elementary, Neptune Middle, and Tohopekaliga High School, you are also minutes from local shopping centers, dining, Lake Tohopekaliga parks, golf courses, and Central Florida's major theme parks and attractions. Schedule your private tour today!

3133 Riachuelo Lane, Kissimmee
$215,000
2 Beds ⋅ 2 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code
Beautiful and well-maintained 2-bedroom, 2-bathroom first-floor condo offering a comfortable and spacious layout. Designed for everyday living, the functional floor plan provides generous living areas and the convenience of first-floor access, making it an excellent option for first-time buyers, seasonal residents, or investors. Currently tenant occupied. The community allows both short-term and long-term rentals, offering flexibility for future use. Enjoy resort-style amenities, including two swimming pools, a fitness center, tennis courts, a playground, walking paths, picnic and grilling areas, and beautifully maintained grounds. Conveniently located just minutes from The Loop, Publix, Walmart, restaurants, shopping, entertainment, schools, and medical facilities, with easy access to US-192, John Young Parkway, Osceola Parkway, Florida’s Turnpike, and I-4, providing convenient access to Disney, Celebration, and Orlando International Airport. Whether you’re looking for a place to call home or to expand your real estate portfolio, this condo offers the location, flexibility, and lifestyle you’ve been searching for. Schedule your private showing today!

2207 Antigua Place Unit 715, Kissimmee
$425,000
4 Beds ⋅ 3 Baths ⋅ Poinciana Village 2 Nbhd 3 SubDv. ⋅ 34758 Zip Code
*Offering interest rate buy down or closing cost credit through preferred lender!* An impressive residence in Poinciana offering the space, flexibility, and distinctive features that are increasingly hard to find. One of the larger homes currently available in the community, this property is situated on a generous corner lot and provides an exceptional amount of living and storage space ideal for a growing household, multi-generational living, entertaining, or simply anyone who wants room to spread out. From the moment you arrive, the home makes a statement with its expansive multi-car paver driveway, providing plenty of parking for residents and guests. The spacious garage adds even more versatility, with ample room for multiple vehicles, storage, recreational equipment, tools, and toys. Step inside and you're immediately greeted by a dramatic living area showcasing soaring approximately 20-foot ceilings that create an incredible sense of openness and scale. One of the home's standout architectural features is the custom staircase with decorative railings, adding character and elegance while overlooking the impressive main living space. The first floor also features a private home office, providing a dedicated space for working remotely, studying, managing a business, or creating a quiet flex room away from the main gathering areas. The spacious floor plan offers multiple areas for everyday living and entertaining, giving everyone room to enjoy the home comfortably. Upstairs, a large loft creates another valuable living space that can easily become a media room, game room, playroom, second family room, fitness area, or additional workspace. The oversized primary suite provides a private retreat with plenty of room for a full bedroom setup and sitting area, complemented by a generously sized primary bathroom designed for comfort and functionality. Outside, the covered lanai extends the living space and provides a shaded setting for outdoor dining, relaxing, grilling, and enjoying Florida's year-round lifestyle. Combined with the oversized corner homesite, there's plenty of opportunity to make the outdoor space your own. With its exceptional size, dramatic ceilings, custom staircase, private office, oversized loft, spacious primary suite, substantial garage and parking, covered lanai, and large corner lot, 331 Ashburton Way delivers the kind of space and versatility that makes a home truly adaptable for years to come. If you've been searching for a large Poinciana home with room for everyone—and everything—this one deserves to be at the top of your list.

331 Ashburton Way, Kissimmee
$324,990
3 Beds ⋅ 2 Baths ⋅ Poinciana Village 2 Nbhd 1 SubDv. ⋅ 34758 Zip Code
Welcome to this beautifully updated POOL HOME featuring an open floor plan, vaulted ceilings, and a spacious layout designed for comfortable everyday living and entertaining. The kitchen offers solid-surface countertops, stainless steel appliances, ample cabinetry, and an open connection to the main living areas. The primary suite features a walk-in closet and a spacious bathroom with dual sinks, a walk-in shower, and a Jacuzzi-style garden tub. The home has been thoughtfully updated throughout, including refreshed bathrooms with attractive tile finishes, and offers a clean, well-maintained interior that is ready for its next owner. Step outside to your own private retreat with a screened-in lanai and swimming pool, offering plenty of space to relax, entertain, or enjoy Florida living year-round. The POOL was resurfaced in 2024, and the pool pump was replaced in 2023. Additional recent improvements include a NEW ROOF and WATER HEATER in 2024, new window blinds in 2026, and fresh interior and exterior paint in 2026. Located in Poinciana Village 2 with no CDD, residents enjoy access to community amenities including internet and cable, a fitness center, community pool, playgrounds, parks, and recreational facilities. Conveniently located near shopping, dining, schools, medical facilities, and major roadways. With numerous recent updates, a private pool, and generous indoor and outdoor living space, this home is ready for its next owner. Schedule your private showing today.

1025 Derbyshire Drive, Kissimmee
$590,000
7 Beds ⋅ 5 Baths ⋅ Emerald Island Resort SubDv. ⋅ 34747 Zip Code
Welcome to Emerald Island Resort, a gated and guarded vacation community located just minutes from Walt Disney World! This spacious 7-bedroom, 4.5-bathroom home offers the perfect combination of a turnkey short-term rental investment, second home, or full-time Florida residence. Situated on a private conservation lot, the home features a large south-facing heated private pool and spa, extended sundeck, spacious covered lanai, and peaceful conservation views. The open floor plan includes a large kitchen with island, granite countertops and stainless steel appliances, three king-size bedroom suites, themed bedrooms, and a garage converted into a fully air-conditioned game room. The home is being sold fully furnished and is ready for immediate use or continued vacation rental operation. For investors, the property offers the opportunity to assume the existing future bookings, representing upwards of $30,000 in rental revenue, providing an immediate head start for the new owner. Recent improvements include a roof replacement in 2022, a full interior and exterior paint refresh in 2023, resolution of a prior A/C issue in 2026, and a newly replaced pool pump and air blower. Additional features include laminate flooring, updated window treatments, pool/spa heater, and updated upstairs and downstairs A/C systems. Emerald Island Resort offers an exceptional location and resort lifestyle, surrounded by conservation areas and conveniently located near Disney, restaurants, shopping and Central Florida’s major attractions. Owners and guests enjoy access to an impressive array of amenities, including a clubhouse, sauna, fitness center, resort pools and spas, food court and bar, tennis, basketball, volleyball, miniature golf, children’s play areas, walking trails and more. The clubhouse is approximately a 7-minute walk from the home. Whether you’re looking for a proven vacation rental opportunity, a family retreat, or a permanent Florida residence, this beautifully maintained and fully furnished home offers flexibility, privacy, resort amenities and an unbeatable location near the area’s world-famous attractions. Schedule your private showing today!

8452 Secret Key Cove, Kissimmee
$975,000
5 Beds ⋅ 5 Baths ⋅ Bellalago Ph 6h & 6i SubDv. ⋅ 34746 Zip Code
Vacation every day in this luxury lakefront home, extensively renovated in 2024 and designed for both comfort and style. Enjoy the most beautiful view in the community, creating a serene backdrop for everyday living. The home features new luxury vinyl flooring throughout (2024) and custom built-in cabinetry in the kitchen and hearth room, blending functionality with elegance. The spa-inspired primary bathroom has been completely renovated, offering a private retreat. Perfect for entertaining, the home seamlessly connects indoor and outdoor living with custom folding sliding doors that open to a spacious lanai—ideal for gatherings or relaxing evenings by the water. A dedicated media room provides the perfect setting for family movie nights. Dog lovers will appreciate the thoughtfully designed custom dog wash, adding convenience and luxury for every member of the household. Located in a resort-style community, this home offers the ultimate in lakefront living and lifestyle.

3713 Dockside Dr, Kissimmee
$409,900
4 Beds ⋅ 2 Baths ⋅ Eagle Bay Ph 2 SubDv. ⋅ 34743 Zip Code
Welcome to this beautifully maintained, one-owner home conveniently located just 17 minutes from the Lake Nona VA Medical Center and approximately 15 minutes from Orlando International Airport. This 4-bedroom, 2-bath home offers a comfortable and functional layout, a two-car garage, and no carpet throughout. The home has been meticulously cared for and features several recent improvements, including fresh interior and exterior paint completed in July 2026 and a brand-new interior A/C unit, also replaced in July 2026. Additional features include a water softener, high-efficiency water heater, solar panels, a fully fenced yard, and an extended screened-in back porch that provides a comfortable space to relax, entertain, or simply enjoy the Florida weather year-round. With thoughtful upgrades, a well-maintained interior, and a convenient Central Florida location, this home is truly move-in ready and ready for its next owner.

2587 Tanner Terrace, Kissimmee
$274,995
3 Beds ⋅ 3 Baths ⋅ Bellalago Pod G Twnhms SubDv. ⋅ 34746 Zip Code
Settle into a move in ready and well-maintained townhome in the desirable Bella Lago community, where resort-style living offers a private boat lift to Lake Tohopekaliga, sparkling pools, fitness centers, scenic walking and biking trails, restaurants, and 24-hour gated security. The neighborhood boasts lush landscaping and a peaceful, upscale vibe. Conveniently located near attractions, shopping, dining, and major highways, it perfectly blends luxury with convenience. Enjoy tennis and basketball courts, playgrounds, a clubhouse, boat ramp, and fishing pier. This maintenance-free property is even more stunning in person—pictures simply can’t capture its charm!

1414 Anchor Bend Way, Kissimmee
$399,000
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome Home to Kindred living at its finest! Built in 2022, this move-in-ready, single-story home offers 4 spacious bedrooms, 2 full bathrooms, and 1,846 sq. ft. of open-concept living space. Step inside to discover a bright, airy floor plan featuring seamless flow between the living, dining, and kitchen areas—perfect for everyday living and effortless entertaining. The kitchen comes equipped with ample cabinetry, counter space, and a center island, overlooking the expansive living room filled with natural light. The primary suite serves as your private retreat, complete with a generous walk-in closet and an en-suite bathroom featuring dual sinks and a walk-in shower. Three additional bedrooms provide flexibility for family, guests, or a dedicated home office. Unbeatable Neighborhood Location: Situated on Park Side Ave, this home is conveniently located close to both the community Kindred K-8 school and Kindred’s main clubhouse complex, making daily routines and weekend relaxation effortless! Beyond the front door, experience the ultimate Florida lifestyle with Kindred’s resort-style amenities, including multiple community pools, splash pads, fully equipped fitness centers, sports courts (tennis and volleyball), miles of walking trails, tot lots, and a dedicated dog park. Prime Connectivity: Minutes from Neptune Road, US-192, and the Florida Turnpike for easy commuting. Conveniently located near NeoCity (Central Florida’s premier high-tech hub), Lake Tohopekaliga, Lake Nona, and Orlando International Airport (MCO). Schedule your private showing today and make this gorgeous Kindred home yours!

1735 Park Side Avenue, Kissimmee
$499,000
4 Beds ⋅ 3 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code
Welcome Home to Kindred living at its finest! Built in 2021, this impressive single-story home features 4 spacious bedrooms, 3 full bathrooms, over 2,100 sq. ft. of beautifully designed open-concept living space, and no rear neighbors! Step inside to an expansive floor plan boasting high ceilings and seamless flow between the living, dining, and chef’s kitchen areas. The open kitchen features modern finishes, a large center island, and plenty of cabinet storage—making it perfect for hosting guests or enjoying family meals. With a 3-full-bathroom layout, this floor plan offers exceptional convenience, ideal for multi-generational living, guests, or a private home office setup with its own dedicated bath. The primary suite serves as a tranquil retreat with a walk-in closet and a spa-like en-suite bathroom. Step outside to your own private backyard retreat with no rear neighbors, featuring a variety of bearing fruit trees including oranges, grapefruit, star fruit, ice cream bananas, and concord grapes. Unbeatable Neighborhood Location: Located directly on Park Side Ave, this home is within easy walking distance to the community Kindred K-8 Elementary school as well as Kindred’s main clubhouse, resort pool, and amenity complex—giving you effortless daily access right out your front door! Beyond the home, enjoy Kindred’s resort-style community amenities, including multiple pools, splash pads, fully equipped fitness centers, sports courts (tennis and sand volleyball), Soccer field, miles of walking trails, tot lots, and a dedicated dog park. Prime Connectivity: Minutes from Neptune Road, US-192, and the Florida Turnpike for smooth daily commutes. Conveniently located near NeoCity (Central Florida’s premier high-tech hub), Lake Tohopekaliga, Lake Nona, and Orlando International Airport (MCO). Schedule your private showing today to experience everything about this home and community!

1621 Park Side Avenue, Kissimmee
$215,000
3 Beds ⋅ 2 Baths ⋅ Villas At Somerset The SubDv. ⋅ 34746 Zip Code
Virtually Staged. Move-In Ready First-Floor Condo – Resort-Style Living & Investment Opportunity! Welcome home to this move-in ready first-floor condo, offering the perfect opportunity for both investors and primary homeowners. Enjoy a resort-style lifestyle with exceptional community amenities, including tennis courts, basketball courts, a fitness center, community pool, clubhouse, and more. This well-maintained condo provides convenient first-floor living with easy access and a comfortable layout designed for everyday enjoyment. Whether you are looking for a full-time residence, vacation home, or investment opportunity, this property offers flexibility to meet your needs. The seller is open to long-term rental opportunities, making this an attractive option for investors seeking rental potential. Don’t miss the opportunity to own a condo in a desirable community with great amenities and a convenient location. Schedule your showing today!

2723 N Poinciana Boulevard Unit 153, Kissimmee
$423,000
4 Beds ⋅ 3 Baths ⋅ Hammock Trails SubDv. ⋅ 34758 Zip Code
Great spacious corner lot property. Amazing space, check out this 4 bedroom 2.5 bath with large loft, formal dining, 2 living rooms, breakfast area and private office. The gourmet kitchen with ample cabinet/surface space and large walk in pantry. The master room is large enough for a king size bed and separate sitting area. The master bath is equipped with a garden tub, raised vanity with double sinks and stand up shower. New roof. New AC unit.

4664 Caverns Drive, Kissimmee
Start Your Search