Kissimmee Homes with Association Recreation - Owned Community Features

Kissimmee Homes with Association Recreation - Owned Community Features

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the charm of small-town living with the excitement of a bustling tourist destination. Nestled just minutes away from the world-famous attractions of Orlando, Kissimmee offers residents an unparalleled lifestyle, complete with sun-soaked days and a community spirit that welcomes everyone.

Kissimmee is renowned for its stunning natural landscapes, featuring beautiful lakes, lush parks, and scenic walking trails. The city boasts a rich history and a diverse culture, making it an ideal place for families, young professionals, and retirees alike. With a thriving downtown area lined with shops, restaurants, and entertainment options, there’s always something to explore.

For those seeking a home within a community that offers both comfort and recreational opportunities, Kissimmee's Homes with Association Recreation are a perfect choice. These properties not only provide the benefits of a well-maintained neighborhood but also come with exclusive access to community amenities that enhance your lifestyle. Enjoy resort-style features such as swimming pools, fitness centers, clubhouses, and playgrounds, all designed to foster connections among neighbors and encourage an active, social lifestyle.

Living in a community with association recreation means you can enjoy a worry-free lifestyle, as the maintenance of shared spaces is taken care of by the association. This allows you more time to indulge in the beautiful Florida weather, participate in community events, or simply relax in your own backyard oasis.

Discover the charm and convenience of Kissimmee, where your dream home awaits in a community that feels like family. Experience the best of Florida living today!

Newest Kissimmee Homes with Association Recreation - Owned Community Features

$484,900
4 Beds ⋅ 3 Baths ⋅ Villa Sol Village 02 SubDv. ⋅ 34744 Zip Code
Welcome to the former Model Home, the only one like this in the entire community. Discover the perfect blend of comfort & convenience in this spacious 4-bedroom, 3-full-bathroom home. With 2 generous living spaces designed for both everyday living & entertaining. This home offers flexibility for growing families, multi-generational living, or hosting guests. Full kitchen appliances, a fire place, window treatments, plantation shutters, tiled floors, granite countertops, light fixtures and barn doors. The home sits on a premium cul de sac lot with no rear neighbors. Enjoy the view from your expansive 10 x 24 screen in Florida room. Many extras added. Great air b & b, short term rental allowed. This gated community offers all you need, pool, fitness center, tennis & basketball courts. Your HOA includes internet, cable and lawn care. Kissimmee delivers an unbeatable Central Florida lifestyle: you’re just minutes from Walt Disney World & Central Florida’s top attractions, with easy access to shopping, dining, and Lake Tohopekaliga for outdoor recreation. Whether you’re drawn by the theme parks, the warm year-round climate, or the strong sense of community, this location puts it all within reach. 24 hour appointment only please no showings allowed Sunday, Monday or Thursday.

2925 Siesta View Drive, Kissimmee
$309,900
4 Beds ⋅ 3 Baths ⋅ Oaks At Cypress Woods Rep The SubDv. ⋅ 34758 Zip Code
Four bedroom, three full bath single story with 1,854 square feet in The Oaks at Cypress Woods, an established low HOA neighborhood tucked off Cypress Parkway on the Kissimmee side of Poinciana. Homes here sit on real lots with mature trees, and this one has the kind of flexible layout that works for a growing household, remote work, or hosting family from out of town. The property features a 4 bedroom setup with a primary bedroom with a walk-in and a separate built-in closet, and a junior primary bedroom that also has an ensuite full bathroom, an extra sitting room (perfect for gym, sitting room, play room or at home office) and walk-in closet and another built-in closet. The location puts you at the center of everything Poinciana has added in the last few years. Poinciana Lakes Plaza is about a mile down the road with TJ Maxx, Burlington, Petco, and new dining options, and HCA Florida Poinciana Hospital sits right beside it. Valencia College's Poinciana campus is a short drive, and everyday errands stay close with grocery stores and pharmacies along Cypress Parkway and Marigold Avenue. When you need to go farther, the Poinciana Parkway connects you to ChampionsGate and I-4 in about 20 minutes, the theme parks are roughly 35 minutes out, and the Poinciana SunRail station covers the commute into downtown Orlando. Weekends can mean golf close to home or bass fishing on Lake Toho about 15 minutes east. Schools, parks, and community sports fields are all nearby. Schedule your showing today.

566 Oak Branch Circle, Kissimmee
$749,000
7 Beds ⋅ 7 Baths ⋅ Solara Residence SubDv. ⋅ 34747 Zip Code
Welcome to an exceptional, fully furnished vacation home in one of Solara Resort’s most desirable and convenient locations. Positioned on a wide homesite directly across from a beautiful park and community pond, this impressive 7-bedroom, 6.5-bathroom residence offers 4,093 square feet of thoughtfully designed living and entertainment space, all just a few steps from Solara’s Grand Clubhouse and resort amenities. The owners have made a substantial investment in renovations, furnishings, décor and entertainment upgrades, creating a polished, turnkey experience that stands apart from typical vacation homes. The expansive open-concept main level provides plenty of room for guests to gather, dine and relax. The spacious kitchen features stone countertops, modern appliances, generous cabinetry and an open connection to the main living and dining areas. The home offers 2 private primary suites, including a first-floor suite with direct access to the pool area and a second primary suite upstairs. A large second-floor gathering area gives guests additional space to spread out and enjoy the home. The entertainment-focused design includes themed bedrooms, arcade games, a movie room, a pool table and multiple spaces created specifically for memorable vacation experiences. Outside, enjoy a private heated pool and spa, pool lighting and a spacious paved deck designed for relaxing in the Florida sunshine. The home’s location near the clubhouse makes it especially convenient for vacationing guests while still providing the privacy and comfort of a single-family residence. Solara Resort is a gated, short-term-rental community offering a zero-entry resort pool, splash pad, FlowRider surf simulator, restaurant, pool bar, coffee bar, fitness center, basketball court, beach volleyball, full-size soccer field, playground and indoor and outdoor gathering areas. Whether used as a vacation rental investment, second home or personal retreat near Walt Disney World, this beautifully upgraded and fully furnished Solara residence delivers the space, location, amenities and guest experience today’s buyers are looking for.

1720 Sawyer Palm Place, Kissimmee
$500,000
5 Beds ⋅ 5 Baths ⋅ Summerville Resort SubDv. ⋅ 34747 Zip Code
Welcome to this stunning 5-bedroom, 5-bathroom fully furnished property, offering the perfect combination of comfort, style, and fun — located in one of Central Florida’s most desirable communities! Step inside and discover a beautifully designed interior featuring spacious living areas, a modern kitchen with stainless steel appliances, and elegant finishes throughout. Each bedroom offers a unique touch, but the highlight is the incredible SpongeBob-themed room — a true showstopper for guests! Enjoy your private screened-in pool and covered lanai, perfect for relaxing afternoons or entertaining after a day at the nearby theme parks, shopping, and dining. Whether you’re looking for a primary residence, a second home, or a short-term rental investment, this property is fully equipped and ready to generate income from day one. Don’t miss this opportunity — schedule your showing today and make this exceptional home yours!

7512 Sunflower Circle, Kissimmee
$196,800
3 Beds ⋅ 2 Baths ⋅ Club Cortile Ph 06 Condo SubDv. ⋅ 34746 Zip Code
This End Unit is on the 2nd floor, the 3 bedroom, 2 bathroom condo with a screened balcony is Fully Furnished, Ready Move In! It is located in the professional managed beautiful "Club Cortiile" Gated community which has many amenities including a large inground pool, spa, tennis court, playground, and much more. The area is close to the entrance of world most well-known theme park: Walt Disney World, which offers both business and entertainments convenience. Sam's Wholesale Club is just around the corner in walking distance from the community, nearby shopping plazas full of named fast food chains, restaurants and specialty stores. Wal-Marts stores are on both east and west sides within 3 miles distance, Target, Marshall Depts. and Publix Supermarket are all around the corners which provide many employment opportunities. This area is in the convenience of all major expressways (417 Greenway, Osceola Parkway) and highways (Hwy 192, 535) which leading to Kissimmee/Orlando business districts and east/west coasts!

2806 Club Cortile Circle Unit B, Kissimmee
$474,000
4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code
Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee
$679,000
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code
This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, Kissimmee
$165,000
2 Beds ⋅ 2 Baths ⋅ Blossom Park Villas Condo SubDv. ⋅ 34747 Zip Code
Welcome to 3038 Blossom Park, Unit 306, a bright 2-bedroom, 2-bathroom condo in a convenient Kissimmee location near Celebration and I-4. The home features new vinyl plank flooring, abundant natural light, dark matte fixtures, updated vanities and mirrors in both bathrooms and an updated kitchen with refreshed cabinetry. A laundry closet with a washer and dryer is conveniently located next to the kitchen. Both bedrooms have walk-in closets, providing generous storage space, while the functional layout offers plenty of potential for additional improvements and personal touches. The community offers a clubhouse, pool, tennis courts and sidewalks. With easy access to major roadways, shopping, dining, entertainment, and Central Florida attractions, this condo is an appealing opportunity for a primary residence, vacation getaway, or long-term investment property.

3038 Parkway Boulevard Unit 306, Kissimmee
$166,000
Reunion Ph 02 Prcl 01 & 1a SubDv. ⋅ 34747 Zip Code
Amazing opportunity to own a fantastic lot on the 3rd hole of the Palmer signature golf course. Land is hard to come by in Reunion these days so purchase while you can. The homesites do not have a time restriction to begin construction immediately so purchase now or for future generations to own. Build for full time residence or vacation home. Great proximity to all the major theme parks especially WALT DISNEY WORLD being just 2 exits away, makes this vacation community a top choice for visitors of all ages. If you are looking to take a few golf swings while on your vacation you can take the challenge on any of the 3 World Class Championship GOLF COURSES designed by Arnold Palmer, Tom Watson And Jack Nicklaus that are located on-site. Reunion offers many onsite restaurants from hamburgers at The Cove to fine dining at Chophouse and everything in between. There are 14 pools in the community including MULTIMILLION DOLLAR WATER PARK with lazy river & water slide.

7632 Excitement Drive, Reunion
$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 property has a very good rental history, ($81,080.40 in 2025) & ($60,097.00 ytd in 2026). 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
$515,000
2 Beds ⋅ 2 Baths ⋅ Mirasol At Celebration Condo SubDv. ⋅ 34747 Zip Code
The best homes don't just offer a place to live—they offer a lifestyle. Welcome to this beautifully maintained third-floor condominium in the highly sought-after Mirasol at Celebration, where elegant living meets the timeless charm of one of Central Florida's most iconic communities. With 2 bedrooms, 2 bathrooms, and the convenience of elevator access, this residence offers the perfect blend of comfort, sophistication, and low-maintenance living. Step inside to an inviting open-concept floor plan where rich wood flooring flows throughout the main living areas, creating a warm and refined atmosphere. At the heart of the home, the beautifully appointed kitchen features gleaming quartz countertops, stainless steel appliances, a spacious eat-in dining area, and a built-in desk—perfect for working from home, meal planning, or keeping everyday life organized. The thoughtfully designed split-bedroom floor plan provides privacy for owners and guests alike, while plush carpeting adds warmth and comfort to each bedroom. The spacious primary suite serves as a peaceful retreat, complete with an oversized walk-in closet and a spa-inspired ensuite bath featuring a double sink vanity, relaxing garden tub, and separate walk-in shower. Beyond your front door, Mirasol offers an impressive collection of resort-style amenities designed to complement your lifestyle. Residents enjoy a heated swimming pool and spa, a 24-hour fitness center, an on-site day spa and salon, a resident clubroom with billiards, a library, business center with conference room, cyber café, concierge service, and beautifully maintained grounds—all just moments from Celebration's charming downtown. From morning walks along Celebration's scenic trails to evenings spent dining at award-winning restaurants, browsing boutique shops, or attending one of the community's many events, every day feels like a getaway. Conveniently located just minutes from Walt Disney World, Orlando International Airport, and major highways, this exceptional residence offers the perfect balance of tranquility, accessibility, and luxury. Whether you're searching for a full-time residence, a seasonal retreat, or a place to simply enjoy life at a slower pace, this exceptional condominium delivers the Celebration lifestyle you've been waiting for. Welcome home to Mirasol at Celebration—where luxury, convenience, and community come together beautifully.

501 Mirasol Circle Unit 313, Celebration
$254,900
3 Beds ⋅ 2 Baths ⋅ Emerald Lake SubDv. ⋅ 34758 Zip Code
Beautiful 3-bedroom, 2-bath townhome located in the desirable Emerald Lake community! Enjoy the convenience of the community pool and playground just steps from your front door. This well-maintained home features a spacious kitchen with ample cabinet storage and a brand-new refrigerator, stove, and microwave, plus a washer and dryer for your convenience. Stay comfortable year-round with a new A/C system.The open living and dining area flows seamlessly to a screened-in porch with a large storage closet, providing the perfect space to relax. The flexible floor plan offers one bedroom and a full bath on the first floor, while the second floor features two generously sized bedrooms connected by a Jack-and-Jill bathroom, each with large walk-in closets.Conveniently located just off Poinciana Boulevard and Lizzie Brown Road, with easy access to Highway 192, shopping, dining, entertainment, and area attractions.

2868 Tanzanite Ter, Kissimmee
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