Kissimmee Homes with Gated Amenities

Kissimmee Homes with Gated Amenities

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the charm of small-town living with the excitement of big-city attractions. Nestled just minutes away from the world-renowned Walt Disney World Resort, Kissimmee boasts an enviable location that offers residents easy access to thrilling theme parks, stunning natural landscapes, and a plethora of recreational activities. With its warm climate, picturesque lakes, and lush greenery, Kissimmee is a haven for outdoor enthusiasts and families alike.

One of the standout features of Kissimmee is its diverse selection of homes, particularly those with gated amenities. These exclusive communities provide a sense of security and privacy that is highly sought after by homeowners. Imagine coming home to a beautifully designed residence, tucked away in a serene, gated enclave where you can unwind after a long day. Many of these homes offer luxurious features such as spacious floor plans, modern kitchens, private pools, and beautifully landscaped gardens, creating an idyllic retreat.

Living in a gated community in Kissimmee not only enhances your lifestyle but also fosters a strong sense of community. Residents can enjoy a range of amenities such as clubhouses, fitness centers, and playgrounds, perfect for social gatherings and family fun. Plus, with 24-hour security, you can have peace of mind knowing that your home is safe and secure.

Whether you’re looking for a primary residence, a vacation home, or an investment property, Kissimmee’s gated communities offer an exceptional quality of life. Discover the charm and convenience that awaits you in this enchanting Florida city!

Newest Kissimmee Homes with Gated Amenities

$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
$540,000
3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code
What's Special: Larger Lot | Flex Room | Pond View | Gourmet Kitchen. New Construction – Ready Now! Welcome to the Ambra at 5676 Nevis Terrace at Esplanade at Westview! The open-concept living area seamlessly connects the great room, spacious kitchen with a large center island, and views of the covered lanai, creating an inviting space for everyday living and entertaining. A formal dining room is conveniently located near the kitchen for special gatherings. At the back of the home, two private primary suites each feature a walk-in closet and en-suite bathroom. A secondary bedroom and full bathroom are situated at the front of the home, while a spacious laundry room just off the garage entry adds everyday convenience. Additional Highlights Include: a bay window in the primary bedroom, a bay window in the second primary bedroom, gourmet kitchen, tray ceiling package, 8' interior doors, and laundry room sink. Photos are for representative purposes only. MLS#O6432452 Experience resort-style living at Esplanade at Westview in Kissimmee! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep Academy of Osceola charter school.

5676 Nevis Terrace, 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
$265,000
4 Beds ⋅ 3 Baths ⋅ Club Cortile SubDv. ⋅ 34746 Zip Code
Welcome to this newly renovated 4-bedroom, 3-bathroom townhome located in the desirable Club Cortile gated community in the heart of Kissimmee. This move-in-ready property features brand-new flooring, fresh interior paint, a new microwave, and a new dishwasher, creating a clean and updated living space. The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, providing plenty of natural light and functional living space. The kitchen features ample cabinetry, generous countertop space, and modern appliances for everyday convenience. The thoughtfully designed layout includes four spacious bedrooms and three full bathrooms, providing flexibility for family living, guests, or a home office. The primary suite includes a private en-suite bathroom and generous closet space. Step outside to the private screened lanai, providing a comfortable outdoor space for relaxing or entertaining. Residents of Club Cortile enjoy access to community amenities including a gated entrance, clubhouse, resort-style swimming pool and spa, fitness center, tennis courts, basketball court, playground, and beautifully maintained common areas. Conveniently located just minutes from Walt Disney World, Universal Orlando, SeaWorld, shopping, dining, golf courses, and major roadways including US-192, Osceola Parkway, SR 417, and Florida's Turnpike, this home provides convenient access to Central Florida's attractions and everyday amenities.

2848 Club Cortile Circle, Kissimmee
$770,000
3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code
What's Special: Covered Extended Lanai | Pond View | Oversized Garage. New Construction - Model Home Available Now! Welcome to the Pallazio at 4364 Curacao Place in Esplanade at Westview! Blending elegant design with everyday comfort, this thoughtfully crafted home offers a spacious open-concept layout centered around a stunning great room, gourmet kitchen, and casual dining area that flow seamlessly to an expansive outdoor living space. The private primary suite serves as a peaceful retreat, while two secondary bedrooms, a versatile flex room, and formal dining space provide flexibility for work, hosting, or relaxation. With abundant natural gathering spaces and inviting details throughout, this home is designed to make every day feel warm, effortless, and beautifully connected. Additional Highlights Include: upgraded appliance package, 4-foot garage extension and paved back yard. Experience resort-style living at Esplanade at Westview in Kissimmee! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep Academy of Osceola charter school. MLS#

4364 Curacao Place, Kissimmee
$309,000
3 Beds ⋅ 3 Baths ⋅ Amber Pointe SubDv. ⋅ 34744 Zip Code
Welcome to 2510 Hassonite Street, a beautifully maintained corner-unit townhome in the desirable gated community of Amber Pointe in Kissimmee. This spacious 3-bedroom, 2.5-bath home offers approximately 1,763 square feet of comfortable living space and features an open, functional floor plan with abundant natural light. The main level features a welcoming living and dining area, a convenient half bath, and a well-appointed kitchen with granite countertops, solid wood cabinetry, and a breakfast/eat-in area. The kitchen opens to the living space, creating an ideal layout for entertaining and everyday living. Tile flooring is featured throughout the first floor, while the second floor offers laminate flooring and generously sized bedrooms. As a corner unit, the home benefits from additional windows, increased natural light, and added privacy. The spacious primary bedroom is located upstairs and features a walk-in closet and private bathroom. Two additional bedrooms and a full bathroom provide plenty of space for family, guests, or a home office. The property also includes an attached one-car garage and convenient interior laundry. Residents of Amber Pointe enjoy access to community amenities including a resort-style swimming pool and playground, all within a gated community. Conveniently located near US-192, Florida's Turnpike, shopping, restaurants, schools, major roadways, and Central Florida's world-famous attractions, this home offers an excellent combination of location, comfort, and convenience. Don't miss the opportunity to make this beautiful Kissimmee townhome your new home! Schedule your private showing today.

2510 Hassonite Street, 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
$325,000
2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code
**LIMITED-TIME LAUNCH PRICING — secure this Reunion Grande residence at its introductory price before it returns to market-value pricing after Week 3!** Welcome to Unit #307, a fully furnished 2-bedroom, 2-bath residence offering one of the most compelling features in Reunion: direct, unobstructed views toward Walt Disney World from your own private balcony, where you can take in spectacular Florida sunsets and nightly Disney fireworks. Offering approximately 1,430 square feet, the residence features an open and inviting floor plan with upgraded finishes, crown molding, granite countertops, and a kitchen that flows seamlessly into the living and dining areas. The split-bedroom configuration creates two private bedroom suites with well-appointed bathrooms, making the layout equally suited for personal use, vacationing, or hosting guests. Offered fully furnished and turnkey, #307 is positioned for immediate enjoyment and offers the flexibility of primary, second-home, or vacation-rental use. An active Reunion Resort membership is included and transferable to the new owner, providing access to Reunion's renowned resort lifestyle, including three signature golf courses designed by Arnold Palmer, Tom Watson, and Jack Nicklaus, the multimillion-dollar water park, resort pools, tennis and pickleball, fitness facilities, and additional amenities. Within the Reunion Grande itself, enjoy front desk concierge service, valet parking for members, 7593 Chophouse, a lobby-level sushi bar, Starbucks coffee and gift shop, plus the rooftop restaurant and pool overlooking the surrounding resort and Central Florida skyline. Located just minutes from Walt Disney World and convenient to Orlando's other world-famous attractions, #307 combines location, flexibility, resort amenities, and a view that is difficult to replicate. **With launch pricing available for only the first three weeks, this is the opportunity to act before the property returns to market value.**

7593 Gathering Drive Unit 307, Kissimmee
$325,000
2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code
**LIMITED-TIME LAUNCH PRICING — take advantage of this introductory price before the property returns to market-value pricing after Week 3!** Welcome to Unit #706 at the Reunion Grande, an exceptional opportunity to own a fully furnished, turnkey 2-bedroom, 2-bath residence in the heart of Reunion Resort. Positioned on the 7th floor with desirable east-facing exposure, this spacious 1,430-square-foot condo offers beautiful morning light, elevated resort views, and comfortable shaded afternoons from your private balcony. Inside, an open-concept layout connects the kitchen, dining, and living spaces, while the split-bedroom design provides privacy for owners and guests alike. Offered fully furnished and ready for immediate enjoyment, this residence offers tremendous flexibility as a primary residence, second home, vacation retreat, or short-term rental opportunity. Located inside the iconic Reunion Grande, owners and guests are surrounded by resort-style conveniences including valet parking, front desk concierge service, on-site dining, Starbucks coffee and gift shop, the acclaimed 7593 Chophouse, sushi bar, and an 11th-floor rooftop restaurant and pool offering panoramic views across Central Florida. Beyond the Grande, Reunion Resort encompasses approximately 2,300 acres and is home to three signature championship golf courses, resort pools, dining, fitness and recreation opportunities, and its multimillion-dollar water park. Best of all, you're approximately 6 miles from Walt Disney World with convenient access to Orlando's world-famous attractions and major highways. Whether you're looking for your own Central Florida getaway or a furnished property with vacation-rental flexibility, #706 delivers the location, lifestyle, and versatility Reunion is known for. **The launch price is available for a limited three-week window — don't wait for the price to return to market value.**

7593 Gathering Drive Unit 706, Kissimmee
$350,000
Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
Build your dream home in the prestigious Reunion Resort! This homesite offers a fantastic location within the community, surrounded by beautiful luxury homes and just steps from Reunion’s renowned golf courses. Enjoy the opportunity to design a custom residence or vacation retreat in one of Central Florida’s premier resort communities, conveniently located near Walt Disney World, dining, shopping, and Orlando’s world-class attractions.

1006 Coyote Creek Way, Kissimmee
$695,000
6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
TURNKEY VACATION RENTAL INVESTMENT MINUTES FROM DISNEY WORLD! This beautifully decorated and totally renovated 6-bedroom, 3.5-bath single-family home is located in the highly desirable Windsor Hills Resort—one of the closest vacation home communities to Walt Disney World. Designed to stand out in the competitive vacation rental market, this home is being offered turnkey and is ready for its next owner and guests. The updated interior features stylish décor, granite countertops in the kitchen and bathrooms, and fun Star Wars-themed bedrooms that are sure to be a hit with younger guests. Outside, enjoy a south-facing private pool with no rear neighbors, providing excellent sun exposure and added privacy. One of the home's standout features is the poolside theater, allowing guests to watch movies, sports and TV while relaxing in or around the pool. The converted garage has been transformed into a fun, air-conditioned game room, adding another guest-favorite amenity and entertainment space. Location within the resort is another major advantage. The home is just a short 3-block walk to the Windsor Hills clubhouse, resort pool and water park. With its combination of location, renovations, privacy, themed bedrooms and guest-focused amenities, this property offers an outstanding opportunity for buyers seeking a turnkey Disney-area vacation home and short-term rental investment.

2630 Dinville Street, Kissimmee
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