Osceola Homes with Association Recreation - Owned Community Features

Osceola Homes with Association Recreation - Owned Community Features

Welcome to Osceola County, Florida—a vibrant and picturesque region that perfectly blends suburban charm with the allure of natural beauty. Nestled in the heart of Central Florida, Osceola County is renowned for its diverse landscapes, from serene lakes to lush parks, making it an ideal place for families, retirees, and outdoor enthusiasts alike.

One of the standout features of living in Osceola County is the abundance of homes situated within Association Recreation-Owned Communities. These neighborhoods offer not only beautiful residences but also a wealth of amenities designed to enhance your lifestyle. Imagine waking up to the gentle sounds of nature, then stepping outside to enjoy a leisurely stroll along tree-lined paths or a refreshing swim in a sparkling community pool.

Residents of these communities benefit from exclusive access to recreational facilities such as tennis courts, fitness centers, and playgrounds, fostering a strong sense of community and togetherness. Whether you’re hosting a barbecue with friends at the clubhouse or enjoying a peaceful afternoon by the lake, these amenities provide endless opportunities for relaxation and recreation.

Osceola County is also strategically located near major attractions like Walt Disney World, Universal Studios, and the stunning landscapes of the Everglades, ensuring that adventure is never far away. With its rich cultural heritage, excellent schools, and thriving local economy, Osceola County is not just a place to live—it's a place to thrive. Come discover your dream home in this enchanting community today!

Newest Osceola Homes with Association Recreation - Owned Community Features

$235,000
4 Beds ⋅ 3 Baths ⋅ Venetian Bay Village Condo Ph 1 SubDv. ⋅ 34741 Zip Code
OWN THIS beautifully updated and fully furnished end-unit townhouse in the 24-hour guard-gated community of Venetian Bay Village. Offering 4 bedrooms, 3 bathrooms, and a flexible two-story layout, this property is ideal as a vacation home, full-time residence, or income-producing investment. Recent 2025 upgrades include new flooring, a new water heater, quartz countertops throughout, and renovated bathrooms, giving the home a fresh and move-in-ready feel. The main level features an open living and dining area, a well-appointed kitchen, and a highly desirable first-floor primary suite with an en-suite bathroom and walk-in closet. Upstairs, a second primary suite provides extra flexibility for guests and family, while two additional bedrooms offer comfortable accommodations for family or visitors. Enjoy the charm of a covered front porch and side porch, along with access to resort-style amenities including community pool, clubhouse, fitness center, playground, tennis courts, and 24-hour security. Located just minutes from Disney, shopping, dining, major roadways, and Central Florida’s top attractions, this turnkey property offers comfort, convenience, and strong rental potential in one of Kissimmee’s established vacation communities. Schedule your showing today!

4006 San Gallo Drive Unit 108, Kissimmee
$275,000
2 Beds ⋅ 2 Baths ⋅ Ventura At Windsor Hills Condo Ph 6 SubDv. ⋅ 34747 Zip Code
Welcome to Windsor Hills, one of Central Florida’s premier resort communities, located approximately two miles from Walt Disney World. This beautifully updated, fully furnished 2-bedroom, 2-bathroom condo offers turnkey convenience for use as a vacation retreat, short-term rental, or combination of both. Situated on the fourth and top floor of an elevator-served building, the condo is just one block from the clubhouse and water park—close enough for an easy walk while offering a peaceful setting. The bright, open-concept interior features a desirable split-bedroom floor plan, providing privacy for owners and guests. The remodeled kitchen includes quartz countertops, stainless steel appliances, generous workspace, and ample cabinetry. The private primary suite features an en-suite bathroom and walk-in closet. The Mickey Mouse-themed second bedroom offers flexible accommodations with a twin-over-queen bunk bed, twin trundle, foosball table, and custom Disney-inspired mural. The living room includes two leather sofas, one with a pullout bed. Both bathrooms have been fully remodeled with quartz countertops, newer soft-close vanities, custom wood backsplashes, and updated mirrors. Extensive improvements completed in 2022 and 2023 include new flooring and interior paint throughout, remodeled kitchen and bathrooms, stainless steel appliances, updated furniture, ceiling fans, lighting, and themed bedroom décor. Additional updates include a water heater replaced in 2022, and a Samsung washer and dryer installed in January 2026. A private balcony provides the perfect setting for morning coffee or relaxing after a day at the parks. Windsor Hills offers an exceptional collection of resort-style amenities, including a water park with three-story slides, an interactive splash zone, lagoon-style zero-entry pool, hot tub, tiki bar, fitness center, playground, 32-seat movie theater, putting green, arcade, convenience store, cybercafé, and tennis, basketball, and volleyball courts. The community also features 24-hour guard-gated security, convenient parking, oversized-vehicle access, and designated RV parking. Zoned for short-term rentals and offered fully furnished, this condo is ready for personal enjoyment or rental use after closing. Windsor Hills provides convenient access to Walt Disney World, Universal Orlando Resort, SeaWorld, area airports, US-192, I-4, and SR-429. Don’t miss this opportunity to own a top-floor condo in one of Central Florida’s most recognized vacation communities. Schedule your private showing today!

2817 Almaton Loop Unit 402, Kissimmee
$564,900
4 Beds ⋅ 4 Baths ⋅ Bellalago Ph B-2 SubDv. ⋅ 34746 Zip Code
NEWER ONE OWNER HOME, WELL LOCATED IN THE FANTASIC SUBDIVISION OF BELLALOGO, TO MANY FEATURES TO LIST, LAKE FRONT COMMUNITY, PARKS, PLAYGROUNDS, DOG PARK, COMMUNITY POOL, ETC. HOME FEATURES AN OPEN LAYOUT FOR FAMILY AND GREAT GET TOGETHERS, BIG REAR YARD TO ALLOW EXTENDED LIVING OUTSIDE WITH FRIENDS FAMILY AND NEIGHBORS. 4 LARGE BEDROOM AND 3.5 BATHS, GAME ROOM, ETC . CHIEF STYLE KITCHEN WITH ALL THE FEATURES YOU WOULD EXPECT. WELL APPOINTED FEATURES THROUHTOUT THE HOME. ALSO INCLUDES THE EXTRA LARGE AND VERY MUCH DESIRED 3 CAR GARAGE, PROVIDING BOTH CONVENYENCE AND MULITPLE STORAGE OPTIONS. THIS HOME HAS IT ALL AND IS PRICED TO MOVE.

2931 Agostino Terrace, Kissimmee
$274,900
3 Beds ⋅ 2 Baths ⋅ Lucaya Village Ph 1 SubDv. ⋅ 34746 Zip Code
Welcome to Lucaya Village! This charming 3-bedroom, 2-bathroom home offers approximately 1,300 sq. ft. of living space in a gated community ideally located in the heart of Kissimmee. The functional two-story floor plan features a bedroom and full bathroom on the first floor, providing added convenience and flexibility, while two additional bedrooms and a second bathroom are located upstairs. Enjoy the comfort of central air conditioning and a well-equipped kitchen featuring a refrigerator, range, microwave, and dishwasher. The community offers a swimming pool and additional amenities, while the HOA includes services such as cable TV, internet, exterior maintenance, pest control, and 24-hour guard service. Conveniently located near US-192 with easy access to shopping, dining, entertainment, and Central Florida's world-famous attractions. Whether you're looking for a primary residence or an investment property, this home offers an excellent opportunity in one of Kissimmee's most convenient locations. Schedule your private showing today!

2952 Lucayan Harbour Circle Unit 103, Kissimmee
$325,000
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Great investment opportunity in the highly sought-after Regal Oaks Resort, a gated community ideally located near Central Florida’s world-famous attractions. This fully furnished 3-bedroom, 2.5-bath luxury townhome offers an open-concept floor plan designed for both comfort and vacation living.The main level features a spacious living and dining area, a well-appointed kitchen with granite countertops, and a convenient powder room. Sliding glass doors lead to a private screened-in lanai featuring a heated spa and sun loungers, creating the perfect space to relax and enjoy the Florida lifestyle.Regal Oaks offers an impressive selection of resort-style amenities, including a state-of-the-art clubhouse, resort pools with dueling water slides, poolside bar and snack bar, cabanas, restaurant and lounge, fitness center, tennis court, and convenience store. HOA services include cable TV, internet, exterior and grounds maintenance, pest control, guard-gated entrance, and valet trash.The community allows short-term rentals and may also be enjoyed as a second home or primary residence, offering excellent flexibility for owners. With its desirable location and strong appeal among vacation guests, this property presents an excellent opportunity to own a fully furnished home in one of the area’s most popular resort communities.

2774 Corvette Lane, 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
$340,000
3 Beds ⋅ 3 Baths ⋅ Mandalay At Bella Trae SubDv. ⋅ 33896 Zip Code
Virtually Staged. Come tour this spacious end-unit townhome in Bella Trae, a gated community in ChampionsGate! Featuring vaulted ceilings, a neutral color palette, and an open-concept living and dining area, this home offers comfort, privacy, and low-maintenance living. The kitchen features granite countertops and stainless steel appliances, while the first-floor primary suite includes dual sinks, a walk-in shower, and relaxing soaking tub. Also downstairs are a laundry room, powder room, and attached two-car garage. Upstairs, a versatile loft is ideal for a home office or flex space, alongside two guest bedrooms and a full bathroom with dual sinks. Enjoy the enclosed back lanai with no side or rear neighbors for added privacy. Bella Trae HOA dues include lawn care, basic cable, and internet, plus access to resort-style amenities including a zero-entry pool, hot tub, clubhouse, fitness center, tennis courts, putting green, billiards room, and community grills. Ideally located near ChampionsGate shopping and dining, championship golf courses, Orlando attractions, and world-famous theme parks, this Bella Trae townhome combines location, lifestyle, and convenience.

1406 Milledge Lane, Davenport
$229,999
2 Beds ⋅ 2 Baths ⋅ Promenades At Bellatrae Condo Ph 25 Bldg 48 SubDv. ⋅ 33896 Zip Code
Virtually Staged. This beautifully maintained Spoonbill floor plan offers 1,797 square feet of thoughtfully designed living space and is ideally situated at the end of a quiet cul-de-sac with a west-facing rear exposure overlooking peaceful conservation views. Featuring 2 bedrooms, 2 bathrooms, a versatile den, and an attached 1-car garage, this lightly lived-in second home is move-in ready. The open-concept great room boasts soaring vaulted ceilings, creating a bright and spacious atmosphere that's perfect for entertaining or everyday living. The kitchen is beautifully appointed with granite countertops, stainless steel appliances, upgraded cherry cabinetry, and ample workspace for the home chef. Unwind on the screened lanai as you enjoy tranquil conservation views and watch colorful hot air balloons drift across the evening sky. Bella Trae offers an exceptional, maintenance-free lifestyle with lush landscaping, elegant architecture, and a luxurious amenity center. Residents enjoy access to a resort-style pool, state-of-the-art fitness center, pickleball and tennis courts, and a vibrant calendar of community activities. Conveniently located in Champions Gate, you'll have easy access to premier shopping, dining, golf courses, grocery stores, and major highways including US-27 and I-4, making travel throughout Central Florida effortless.

1218 Bella Cara Court, Davenport
$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
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