Kissimmee Homes with Gated Amenities

Kissimmee Homes with Gated Amenities

Welcome to Kissimmee, Florida—a vibrant city that perfectly blends the magic of theme parks with the tranquility of suburban living. Nestled just south of Orlando, Kissimmee is renowned for its rich history, picturesque landscapes, and a plethora of recreational activities. With its close proximity to world-famous attractions like Walt Disney World and Universal Studios, Kissimmee offers an unparalleled lifestyle for families and adventure seekers alike.

One of the standout features of Kissimmee is its diverse array of homes, particularly those nestled within gated communities. These homes provide not just a residence but a lifestyle marked by security, exclusivity, and community. Imagine waking up each day in a beautifully designed home surrounded by lush greenery and well-maintained landscapes, all within a safe, gated environment.

Gated amenities in Kissimmee often include resort-style pools, fitness centers, playgrounds, and walking trails, making it easy to enjoy an active, engaging lifestyle. Whether you’re hosting a summer barbecue by the pool or enjoying a peaceful evening stroll through your neighborhood, these communities foster a sense of belonging and camaraderie among residents.

The charm of Kissimmee extends beyond its homes. The city boasts a rich cultural scene, with local festivals, farmers' markets, and an array of dining options that cater to every palate. With its warm climate, friendly community, and endless entertainment options, Kissimmee is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting city today!

Newest Kissimmee Homes with Gated Amenities

$275,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code
Fully Furnished First Floor Condo Near Disney! This beautifully maintained 3 bedroom, 2 bathroom FIRST FLOOR condo in the gated Wyndham Palms Resort Community offers exactly that lifestyle, with the added benefit of being FULLY FURNISHED and APPROVED for SHORT TERM RENTALS and AIRBNB. Whether you are searching for a vacation home, an income producing investment, or a primary residence close to the parks, this property is ready to deliver from day one. The open concept layout centers around a kitchen with STAINLESS STEEL APPLIANCES (2025), flowing easily into the living and dining spaces. NEW LUXURY VINYL PLANK FLOORING, FRESH PAINT, and REPLACED WINDOWS throughout give the home a clean, updated feel, while BRAND NEW LIVING ROOM FURNITURE means it is truly move in ready. The split bedroom design offers privacy for owners and guests alike, and a dedicated office space adds flexibility for remote work or managing your rental. Both bathrooms feature new shower doors for a fresh, modern touch. Imagine mornings on your private patio with coffee in hand, evenings by the resort pool, and easy access to Walt Disney World whenever the mood strikes. Step outside and you are directly across from the clubhouse, where residents enjoy 24 hour guard gated security, a resort style pool, splash pad, jacuzzi, sand volleyball, tennis and basketball courts, a movie theater, game room, and more. Location is everything here. You are minutes from Walt Disney World, Margaritaville Resort Orlando, Island H2O Water Park, Sunset Walk, Celebration, Old Town, championship golf, and Orlando International Airport, with quick access to US 192, SR 429, I 4, and Osceola Parkway. This is more than a condo. It is a chance to own a piece of the Central Florida lifestyle, fully turnkey and ready for you to enjoy

2307 Butterfly Palm Way Unit 104, 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
$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
$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
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