Osceola Homes with Association Recreation - Owned Community Features

Osceola Homes with Association Recreation - Owned Community Features

Welcome to Osceola County, located in the beautiful state of Florida! Osceola County is a vibrant and diverse community known for its rich history, stunning natural landscapes, and thriving real estate market.

If you're looking for a home in Osceola County with Association Recreation-Owned Community Features, you're in luck! These communities offer a wide range of amenities and activities for residents to enjoy, such as swimming pools, tennis courts, fitness centers, and clubhouse facilities. Living in a community with these features provides a unique opportunity to socialize with neighbors and participate in various recreational activities without ever having to leave the neighborhood.

Whether you're a first-time homebuyer, a growing family, or a retiree looking for the perfect place to settle down, Osceola County has something to offer everyone. From quaint suburban neighborhoods to luxurious gated communities, there is a diverse selection of homes to choose from in this dynamic county.

With its convenient location, excellent schools, and abundance of parks and outdoor recreational areas, Osceola County is an ideal place to call home. Come explore all that this charming county has to offer and find your dream home in a community with fantastic recreation-owned features!

Newest Osceola Homes with Association Recreation - Owned Community Features

$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
$275,000
3 Beds ⋅ 2 Baths ⋅ Emerald Lake SubDv. ⋅ 34758 Zip Code
Welcome to this beautifully maintained townhome in the desirable Emerald Lake community! This 3-bedroom, 2-bathroom home features a bright, open floor plan perfect for modern living. The kitchen is a chef's delight, equipped with sleek stainless steel appliances and plenty of counter space. Enjoy your morning coffee on the enclosed screened patio, which also conveniently houses a private laundry room. Each room is thoughtfully designed with ceiling fans for year-round comfort. Best of all, enjoy a low HOA while still having access to fantastic community amenities like a resort-style pool and playground. Located just minutes from shopping, dining, and major Kissimmee thoroughfares, this one won't last!

2896 Tanzanite Terrace, Kissimmee
$550,000
7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 5a SubDv. ⋅ 34747 Zip Code
Superb opportunity in a sought-after 24-hour guard-gated community! This spacious 7-bedroom, 5.5-bath pool home is approved for short-term rental use and offers outstanding income potential. Features include a newly remodeled kitchen with modern soft-close cabinetry, quartz countertops, SS appliances, spacious living and dining areas, and accommodations for large groups. The private screened heated pool has been recently upgraded with new WiFi controlled pool equipment for worry-free enjoyment. Ideally located just minutes from Walt Disney World, first-class attractions, shopping, dining, golf, and major entertainment venues. Whether you’re seeking a vacation home, investment property, or both, this well-maintained home delivers the perfect combination of location, comfort, and rental appeal. The HOA includes resort-style amenities, community pool, clubhouse sauna, volleyball, tennis, pickleball, mini golf, grass cutting, trees trimming, internet, cable and trash service. A rare opportunity in one of Central Florida’s most desirable vacation rental markets!

8667 La Isla Drive, Kissimmee
$695,000
4 Beds ⋅ 5 Baths ⋅ Weslyn Park SubDv. ⋅ 34771 Zip Code
Virtually Staged. PREMIUM CONSERVATION HOMESITE, exceptional outdoor living and thoughtful upgrades throughout make this Weslyn Park home truly stand out. Completed at the end of 2024 and first occupied in January 2025, this Dream Finders home offers the feel of nearly new construction with an impressive list of enhancements already completed. Backing to conservation with a canal beyond, the homesite offers a private natural backdrop with no homes directly behind you. Step inside to a floor plan as functional as it is beautiful. Double doors open to a flex space at the front of the home, perfect for a private home office, den or study. Also on the main level is a bedroom with its own ensuite bath, ideal for overnight guests, extended family or multigenerational living, along with a conveniently located half bath. The main living space makes an immediate impression with soaring two-story ceilings, abundant natural light and an open design made for gathering. At the center of it all is a beautifully appointed kitchen with an oversized island, abundant cabinetry and counter space, built-in appliances and a walk-in pantry, all flowing effortlessly into the living and dining areas. One of the home’s most desirable features is that every bedroom has its own ensuite bath, offering a level of privacy and convenience rarely found. Every full bath has been beautifully upgraded with tile extending from floor to ceiling in the shower and bath areas, creating a sophisticated, custom feel throughout. Upstairs, the expansive primary suite feels like a true retreat, with plenty of room to create a comfortable sitting area. Its generous walk-in closet connects directly to the laundry room, a brilliantly convenient design feature you’ll appreciate every day. The laundry room itself is finished with built-in cabinetry for added storage and organization. An additional upstairs sitting nook creates a charming bonus space for reading, studying or relaxing. The outdoor living spaces are every bit as impressive. The lanai opens to an expansive extended paver patio overlooking the conservation backdrop, while a second patio with a built-in fire pit creates the perfect setting for evenings outdoors. The fenced backyard combines modern wood and aluminum fencing with three gates, and additional pavers along the side of the home provide even more usable space. Thoughtful upgrades continue throughout with paid-off solar for energy efficiency and low monthly electric bills, Philips Hue smart lighting throughout the home, eight-foot interior doors and a Tesla EV charger. The three-car tandem garage features epoxy flooring, and the already-generous paver driveway has been widened on both sides for additional space. Located within Weslyn Park in Sunbridge, residents enjoy Acorn Park with a neighborhood pool, open-air pavilion, playground and expansive lawns, along with a community garden and miles of trails woven throughout the community. Even more is on the horizon, with a new waterfront amenity center planned for 2027 featuring a zero-entry resort-style pool, fitness center, restaurant and bar, event spaces, trail access and waterfront recreation. Weslyn Park offers a lifestyle centered around nature, recreation and connection, all in a growing St. Cloud location convenient to the Lake Nona area and Orlando.

6236 Trailblaze Bend, St Cloud
$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
$849,999
3 Beds ⋅ 3 Baths ⋅ Celebration South Village Unit 5 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully appointed David Weekley “Arabella” Craftsman, ideally situated on a quiet, tree-lined cul-de-sac and nestled against a peaceful conservation setting. A charming covered front porch and distinctive ribbon driveway create an inviting first impression, while a decorative mosaic medallion in the entryway adds an elegant custom touch. Inside, the bright and airy floor plan is filled with abundant natural light and thoughtfully designed for both everyday living and entertaining. Luxury vinyl plank flooring flows throughout the main living areas, while an electric fireplace creates a warm and inviting focal point in the spacious great room. The adjoining sunroom offers a wonderful additional living space, perfect for morning coffee, reading, or enjoying the tranquil surroundings. The updated kitchen features granite countertops, a convenient bar-height countertop for casual dining and entertaining, and all-new appliances. The formal dining room, kitchen, and bathrooms feature new light fixtures, adding fresh finishing touch throughout the home. A versatile office/flex room provides additional space for a home office, study, or hobby room. Upstairs, all three bedrooms provide privacy and comfort, along with a charming open balcony overlooking the great room below, creating a dramatic sense of space and architectural character. The primary suite features newly installed ceramic tile and a spacious walk-in closet, while the third bedroom also includes a walk-in closet. New carpeting throughout the second floor completes the fresh, updated feel. Outside, the large conservation lot offers a peaceful backdrop and generous backyard space. The covered front porch provides the perfect spot to relax and enjoy the quiet surroundings. Recent improvements provide added peace of mind, including fresh paint completed in December, a roof replaced in 2022 with gutters, and a 2017 water heater and A/C. An oversized 2½-car garage provides exceptional flexibility for vehicles, storage, hobbies, or additional workspace. With its classic Craftsman architecture, elegant custom details, extensive updates, inviting sunroom, open upstairs balcony, generous storage, oversized garage, and serene conservation setting, this exceptional Arabella offers a blend of timeless charm, contemporary comfort, and everyday Florida living.

1103 Banks Rose Court, 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
$227,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 6 SubDv. ⋅ 34747 Zip Code
Short Sale. SHORT-SALE OPPORTUNITY IN WINDSOR PALMS! This fully furnished 3-bedroom, 2-bath condo offers approximately 1,268 square feet in a gated resort community just minutes from Walt Disney World. Suitable for personal occupancy, a vacation home, or short- or long-term rental use, subject to applicable association rules, licensing, and governmental requirements. Documented 2023 updates include the A/C system, luxury vinyl flooring, interior paint, granite countertops, bathroom vanities and sinks, kitchen sink, dishwasher, and washer/dryer. Televisions were updated in 2025. Community amenities include gated entry, resort-style pool, clubhouse, sports courts, movie theater, arcade, and bar. Conveniently located near Disney-area attractions, shopping, dining, entertainment, major roadways, and Orlando-area airports. Sale price, terms, and closing timeline require the seller’s lender approval. Buyer must verify measurements, property condition, included furnishings, HOA fees and assessments, rental requirements, licensing, insurance, financing, and association information.

8107 Coconut Palm Way Unit 201, Kissimmee
$770,000
8 Beds ⋅ 5 Baths ⋅ Storey Lake 2 50 Resort SubDv. ⋅ 34746 Zip Code
Turnkey and fully furnished, this impressive 8-bedroom, 5-bathroom vacation home is located in the highly desirable Storey Lake Resort—just minutes from Walt Disney World, Disney Springs, shopping, dining, and Orlando's top attractions. With over 4,300 square feet of thoughtfully designed living space, the home features an open-concept floor plan, two spacious primary suites, a large loft, and a private screened pool and spa, making it ideal for large groups and vacation guests. Whether you're expanding your portfolio or searching for a second home that generates income, this property offers outstanding short-term rental potential in one of Central Florida's premier resort communities. Owners and guests enjoy world-class amenities, including a lazy river, water slides, resort-style pools, fitness center, mini golf, sports courts, playgrounds, and a tiki bar. Don't miss this opportunity to own a high-demand vacation home in one of Orlando's most sought-after resort destinations.

4536 Target Boulevard, Kissimmee
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