Osceola Homes with Gated Community - Guard Community Features

Osceola Homes with Gated Community - Guard Community Features

Welcome to Osceola County, Florida, a vibrant and diverse region that beautifully blends natural beauty with modern living. Nestled in the heart of Central Florida, Osceola is renowned for its lush landscapes, family-friendly communities, and a wealth of recreational opportunities. From the enchanting shores of Lake Tohopekaliga to the thrilling attractions of nearby Orlando, residents enjoy a perfect balance of tranquility and excitement.

One of the standout features of Osceola County is its array of gated communities, offering not just homes but a lifestyle defined by security, privacy, and exclusivity. These guard-gated neighborhoods are designed to provide peace of mind, ensuring that residents can enjoy their homes without worry. With 24/7 security personnel and controlled access points, families can feel safe while their children play in the community parks or ride their bikes down tree-lined streets.

Homes within these gated communities boast a variety of architectural styles and sizes, appealing to everyone from first-time buyers to those seeking luxurious estates. Many properties feature modern amenities such as spacious open floor plans, gourmet kitchens, and private backyards, perfect for entertaining or relaxing in the sun. Residents also benefit from community amenities like swimming pools, fitness centers, and clubhouses, fostering a strong sense of community and camaraderie among neighbors.

Living in Osceola County’s gated communities means embracing a lifestyle where comfort, security, and convenience are paramount. Discover your dream home in this enchanting region, where every day feels like a vacation. Come experience the charm of Osceola County today!

Newest Osceola Homes with Gated Community - Guard Community Features

$459,990
4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake 4 SubDv. ⋅ 34746 Zip Code
Welcome to this beautifully furnished 4-bedroom, 3-bathroom townhome located in the highly desirable Storey Lake Resort! This turnkey vacation home offers the perfect combination of personal enjoyment and short-term rental potential, just minutes from Walt Disney World and Central Florida’s world-famous attractions. The open-concept floor plan features a modern kitchen with stainless steel appliances, spacious living and dining areas, and sliding doors leading to your private screened-in pool—perfect for relaxing after a day at the parks. One bedroom and full bathroom are conveniently located on the first floor, with the primary suite and additional bedrooms upstairs. Storey Lake Resort offers exceptional amenities including resort-style pools, a lazy river, water slides, fitness center, mini golf, playgrounds, basketball courts, clubhouse, and more. Conveniently located near Disney, shopping, dining, and major highways. Fully furnished and ready for your next vacation or investment opportunity!

4192 Paragraph Drive, Kissimmee
$560,000
6 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
THE SELLER IS VERY MOTIVATED TO SELL!!!! Exceptional Vacation Home in Solara Resort – Private Pool, Short-Term Rental Approved & Minutes from Walt Disney World®! Welcome to this stunning fully furnished vacation home located in the highly sought-after Solara Resort, one of Central Florida's premier resort communities for short-term rentals. Whether you're looking for a profitable investment property, a vacation retreat, or a second home, this property offers the perfect combination of luxury, comfort, and location. From the moment you arrive, you'll be welcomed by a charming covered front porch and an inviting entryway leading into a bright, open-concept living area. Large sliding glass doors fill the home with natural light and open to a covered lanai overlooking the private screened-in pool, creating the perfect indoor-outdoor living space for relaxing or entertaining. The spacious kitchen is designed for both functionality and style, featuring solid wood cabinetry, a large breakfast bar, generous counter space, and a full set of appliances, making meal preparation effortless. This beautiful home offers 6 spacious bedrooms, 4 full bathrooms, and 1 half bath, plus a versatile upstairs loft ideal as a second family room or game area. The primary suite is conveniently located on the first floor and features a large walk-in closet and an elegant en-suite bathroom with dual vanities and plenty of space. Several bedrooms are professionally decorated with themed designs, creating an unforgettable experience for guests of all ages. The home also includes a 1-car garage. As part of the renowned Solara Resort, owners and guests enjoy access to world-class resort amenities, including a spectacular resort-style pool, FlowRider® surf simulator, clubhouse, fitness center, restaurant and poolside bar, splash pad, water slides, sports simulator, basketball court, beach volleyball court, soccer field, playground, game room, walking areas, and a gated entrance with resort-style security. Ideally located just minutes from Walt Disney World® Resort, Disney's Animal Kingdom, shopping, restaurants, golf courses, major highways, Island H2O Water Park, Sunset Walk, and other world-famous Orlando attractions, this home offers exceptional convenience for both owners and vacation guests. Don't miss this incredible opportunity to own a high-demand vacation home in one of Kissimmee's most desirable resort communities. Schedule your private showing today!

9012 Egret Mills Terrace, Kissimmee
$648,000
7 Beds ⋅ 7 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Step into your next high-performing investment at 1633 Nassau Point Trail! This breathtaking, fully furnished 7-bedroom, 6.5-bathroom retreat in the premier gated Solara Resort is a proven revenue generator built for ultimate guest satisfaction. Perfectly positioned just steps from the clubhouse and adjacent to convenient extra guest parking, this turnkey powerhouse delivers high-yield performance alongside effortless vacation living. Guests can cool off in the private screened-in pool and spa, catch the big game on multiple outdoor TV setups, or unwind in the air-conditioned, tiki-themed garage lounge—a massive hit for both adults and teens. Inside, custom hand-painted murals and immersive themed bedrooms elevate the guest experience, driving stellar reviews and consistent bookings. The numbers speak for themselves: this top-performing property boasts an impressive 70% overall occupancy rate over the last 12 months, surging to an incredible 82% occupancy so far in 2026. For savvy investors or vacation home buyers, Solara Resort offers unmatched marketing power, attracting global travelers directly and through travel agency networks, as well as major booking platforms. The resort itself is a major draw, featuring world-class amenities, including the famous FlowRider® surf simulator, a zero-entry pool, a splash pad, a fitness center, a bar and grill, and sports courts. Located just minutes from Orlando’s world-renowned theme parks, premier dining, and top shopping destinations, this income-generating asset is completely plug-and-play and ready to start delivering returns from day one.

1633 Nassau Point Trail, Kissimmee
$270,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Fully furnished 2-bedroom, 2.5-bath townhome in Regal Oaks Resort, conveniently located next to Old Town and minutes from Central Florida’s top attractions, shopping, dining, and entertainment. The home features a private rear setting with mature trees providing a natural privacy buffer from neighboring properties. The main level includes an open living and dining area, a well-appointed kitchen with stainless steel appliances and granite countertops, and convenient access to the outdoor living space. Upstairs, both bedrooms feature private en-suite bathrooms, making the layout ideal for both owners and guests. Regal Oaks offers resort-style amenities, including a pool complex, renovated ZAC’s Sports Bar & Grill, clubhouse, and more. Whether you’re looking for a vacation property, investment opportunity, or your own Central Florida getaway, this furnished townhome offers a convenient location within one of the area’s established resort communities.

2711 Coupe Street, Kissimmee
$338,000
4 Beds ⋅ 3 Baths ⋅ Bellavida Ph 1 SubDv. ⋅ 34746 Zip Code
Welcome to Bella Vida Resort! This beautifully maintained home offers a fantastic opportunity to own a property in one of Kissimmee’s popular resort-style communities. Featuring a spacious and comfortable layout, this home is ideally located near world-class theme parks, dining, shopping, and major highways. Bella Vida residents enjoy an array of resort-style amenities, including a clubhouse, community pool, fitness center, and recreational areas. Whether you are looking for a vacation home, investment property, or primary residence, this home offers an excellent combination of location, comfort, and convenience. Don’t miss the opportunity to make this Bella Vida property your own!

1050 Las Fuentes Drive, Kissimmee
$419,900
5 Beds ⋅ 4 Baths ⋅ Stoneybrook South North Prcl Ph 1 SubDv. ⋅ 33896 Zip Code
**MOTIVATED SELLER!** Seller is offering **$1,000 toward Buyer’s closing costs with a full-price offer!** Let’s get to the point—this one checks the boxes! Beautiful, **MODERN, BRIGHT, AND FULLY FURNISHED**, THIS RARE **5-BEDROOM, 4-BATHROOM END-UNIT** OFFERS THE PERFECT COMBINATION OF SPACE, PRIVACY, AND RESORT-STYLE LIVING. Being an END UNIT MEANS MORE PRIVACY, EXTRA NATURAL LIGHT, AND PEACEFUL VIEWS OF THE NATURE BEHIND THE PROPERTY a wonderful bonus when you want to enjoy the resort lifestyle without feeling surrounded. The smart 5-bedroom/4-bathroom layout is especially attractive for larger families, groups, or guests who appreciate having their own space and independence. great condition, stylish modern interiors, and a full range of resort entertainment and amenities, and you have a property that is truly ready to enjoy from day one. The community offers a true resort-style lifestyle, with amenities like golf, tennis courts, a lazy river, water slides, a beach-style pool, spa, fitness center, and more—many of them included in the HOA. The home is currently part of a short-term rental program. There’s plenty more to say… but this home is much better seen in person! Call or text to schedule your private showing.

302 Ocean Course Avenue, Davenport
$249,000
2 Beds ⋅ 2 Baths ⋅ Stoneybrook South North Prcl Ph 2 SubDv. ⋅ 33896 Zip Code
FULL GOLF AND TENNIS MEMBERSHIP INCLUDED!!! Beautifully maintained and thoughtfully designed, this open-concept 2-bedroom, 2-bathroom villa is the perfect blend of luxury and comfort. IMMACULATE! LIGHT AND BRIGHT! Conveniently located just a short stroll from the neighborhood pool. The kitchen showcases elegant quartz countertops, slate-finish appliances, and a spacious breakfast bar, ideal for casual dining and entertaining. The primary suite offers a large, custom walk-in closet, dual sinks, and a walk-in shower. A generously sized secondary bedroom is ideal as an office or den. Additionally, a versatile flex room provides the option a separate Dining Room. This villa features high-end flooring, screened lanai, epoxy garage floor, and separate laundry room. Enjoy the ease of golf cart access throughout the entire community! This gated, resort-style community offers an unparalleled lifestyle centered around three exclusive clubhouses. The Oasis Club features a 14,000 sq ft clubhouse with a full-service restaurant, movie theater, fitness center, game room, tiki bar, lazy river, cabanas, and more. The private, resident-only Plaza clubhouse offers a second restaurant and bar, fitness center, game room, two pools, and pickleball courts—perfect for an active and social lifestyle. Now open, The Retreat Club features an exciting waterpark that brings even more fun for residents and guests. The HOA includes full access to all three clubhouses and their amenities, a complete golf and tennis membership, food and beverage credit, gated entry, full lawn maintenance, security monitoring, cable, phone, and internet. CDD and trash services are included in the property taxes. ChampionsGate Country Club offers the ultimate Florida lifestyle—whether you’re enjoying a round of golf, relaxing poolside, or dining with friends at one of the three clubhouses. All of this, just minutes from world-renowned theme parks, championship golf, premier shopping, and endless dining options in the Orlando area!

1064 Blackwolf Run Road, 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
$648,800
5 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Welcome to this exceptional home in Solara Resort. This is a rare opportunity! Although located in one of Orlando’s most sought-after short-term rental communities, this home has never been used as a vacation rental. It has had only one owner and has been enjoyed exclusively by the same family since it was built. The home has been very well cared for and remains in outstanding condition. The first floor features a large suite, perfect for the owners or guests. Upstairs, there is a loft that can be used as a media room, game room, or family lounge, plus another spacious suite and three additional bedrooms. Two of the bedrooms share a convenient Jack and Jill bathroom. Offered fully furnished and move-in ready, this home is located just minutes from Walt Disney World, Universal Orlando, shopping, dining, and entertainment. Solara Resort offers great amenities including a clubhouse, resort-style pool, splash park, FlowRider® surf simulator, fitness center, sports courts, playgrounds, restaurant, café, and 24-hour gated security. Perfect as a primary residence, vacation home, or investment property with excellent short-term rental potential.

9083 Sunshine Ridge Loop, Kissimmee
$3,199,999
11 Beds ⋅ 13 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Welcome to an exceptional luxury estate located within the prestigious Reunion Resort, where sophisticated design, expansive living spaces, and resort-style entertainment come together to create an extraordinary Central Florida retreat. Spanning three thoughtfully designed levels, this impressive 11-bedroom, 11-bath residence has been curated for both luxurious everyday living and the highly desirable vacation rental market. The main level welcomes you with beautifully appointed living and dining spaces anchored by a spacious gourmet kitchen designed for entertaining. An impressive game room offers skeeball, basketball, air hockey, arcade games and shuffleboard, while multiple gathering areas throughout the home provide plenty of space for guests to relax and entertain. Step outside to your private resort-style pool and spillover spa surrounded by generous patio space, outdoor seating and a built-in barbecue—creating the perfect setting for enjoying Florida's year-round sunshine. Entertainment continues throughout the upper levels with a dedicated movie theater featuring reclining theater seating, fitness area, playroom, billiards room, dual gaming stations and multiple screened balconies. The home's extensive bedroom configuration includes multiple king suites along with imaginative themed bunk rooms, offering exceptional flexibility for large families and vacationing groups. Located within Reunion Resort's sought-after Legends Corner neighborhood, the property combines privacy with convenient access to the world-class attractions, dining, golf and entertainment that make the Orlando area one of the world's premier vacation destinations. Whether envisioned as an impressive personal retreat, second home or luxury vacation-rental investment, this remarkable Reunion estate delivers the space, amenities and entertainment today's resort buyer is looking for—all in one unforgettable property.

550 Muirfield Loop, Kissimmee
$915,000
8 Beds ⋅ 5 Baths ⋅ Cove/Storey Lake Iii SubDv. ⋅ 34746 Zip Code
Enjoy the Perfect Blend of Vacation and Investment! Experience the best of Central Florida with this stunning, fully furnished 8-bedroom, 5-bathroom home with a private pool and spa in the highly desirable Storey Lake Resort, one of Orlando's premier vacation communities. Ideally located in the heart of Kissimmee, this exceptional property is just 7 minutes from Walt Disney World and minutes from Universal Orlando Resort, SeaWorld, shopping, restaurants, hospitals, major highways, and toll roads. Designed to comfortably accommodate up to 26 guests, this spacious luxury vacation home offers exceptional income potential while providing the perfect retreat for family vacations. Whether you're looking for a primary residence, a second home, or a turnkey short-term rental investment, this property is an excellent opportunity. Enjoy the convenience of being just steps away from the exclusive resort-style clubhouse, where residents and guests can take advantage of incredible amenities including a water park, resort-style swimming pools, fitness center, sports courts, playgrounds, and much more. With two amenity-filled clubhouses, Storey Lake Resort offers endless entertainment and relaxation for all ages without ever needing to leave the community.

2746 Oxymoron Way, Kissimmee
$345,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Pb 3b & 4a SubDv. ⋅ 34747 Zip Code
Experience resort-style Florida living in this beautifully upgraded 2-bedroom, 2-bath home located in the highly desirable Four Seasons 55+ guard-gated community in Kissimmee. Move-in ready and thoughtfully enhanced throughout, this home combines stylish upgrades, excellent storage, comfortable living spaces, and an exceptional amenity-filled lifestyle. Inside, you'll find upgraded flooring extending through the living areas, bedroom and closets, along with beautiful French doors, window blinds and draperies, upgraded ceiling fans and lighting throughout, and an elegant upgraded dining room light fixture. The kitchen features a stylish backsplash, additional cabinetry and cupboards, an added bank of drawers for convenient storage, decorative cabinet and drawer pulls, and an exhaust fan over the stove. These thoughtful additions provide both functionality and an attractive finished look. The laundry room offers additional cabinetry and storage, decorative hardware, a coordinating backsplash and plumbing already in place for a laundry sink. Both bathrooms feature attractive finishes, including a guest shower and an upgraded beveled-edge finish in the primary shower. Enjoy Florida's beautiful weather from the screened-in lanai, creating an inviting additional space for morning coffee, relaxing, entertaining family and friends, or simply enjoying the Florida lifestyle. Additional improvements include gutters and upgraded garage shelving, providing even more convenient storage and organization. And the lifestyle doesn't stop at your front door. Four Seasons offers an outstanding resort-style 55+ lifestyle within a guard-gated community, complete with an impressive clubhouse offering a wide variety of activities and social opportunities, oversized swimming pools, fitness center, pickleball courts, tennis courts, golf, and much more. Whether you enjoy staying active, playing golf, relaxing poolside, participating in community activities, or spending time with friends at the clubhouse, Four Seasons offers something for virtually every lifestyle. With extensive upgrades already completed, generous living and storage space, outstanding community amenities, and a desirable Kissimmee location, this home offers the opportunity to simply move in and start enjoying everything Central Florida has to enjoy. This is more than a home—it's the Florida lifestyle you've been looking for. Schedule your private showing today and experience Four Seasons for yourself!

1667 Key Bay Trail, Kissimmee
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