Kissimmee Homes with Gated Amenities

Kissimmee Homes with Gated Amenities

Welcome to Kissimmee, Florida, a vibrant and enchanting city nestled in the heart of Osceola County. Known for its picturesque landscapes and proximity to world-renowned attractions, Kissimmee offers a unique blend of adventure and tranquility. Just a stone’s throw away from the magic of Walt Disney World and Universal Studios, this charming locale is perfect for families, retirees, and anyone seeking a lively community with a touch of Southern hospitality.

Kissimmee boasts a diverse array of neighborhoods, many of which feature stunning homes with gated amenities. These gated communities provide not only security and peace of mind but also a sense of exclusivity and luxury. Imagine returning home to a beautifully landscaped entrance, where you can relax and unwind in a serene environment. Many of these homes come equipped with modern features, spacious floor plans, and private outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars.

Life in Kissimmee is enriched by an abundance of recreational opportunities. Residents can explore the scenic parks, indulge in local dining experiences, or take part in thrilling outdoor activities such as fishing, boating, and hiking. With its warm climate and friendly atmosphere, Kissimmee is not just a place to live—it’s a lifestyle.

Whether you’re looking for a family-friendly neighborhood or a peaceful retreat, Kissimmee’s gated communities offer the perfect blend of comfort, security, and accessibility. Discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Kissimmee Homes with Gated Amenities

3820 Springlake Village Court, Kissimmee
$480,000
4 Beds ⋅ 3 Baths ⋅ Springlake Vlg Ph 1 SubDv. ⋅ 34744 Zip Code
Welcome to the highly sought-after gated community of Springlake Village in Kissimmee! Situated on the largest corner lot in the community, spanning 0.28 acres, this spacious 4-bedroom, 3-bathroom home offers 2,135 square feet of living space with an exceptional combination of privacy, comfort, and outdoor living. Major improvements include a 2020 roof, providing added peace of mind for the next owner. Inside, you'll find a thoughtfully designed floor plan featuring generous living spaces, a formal dining area, and an upgraded kitchen with custom cabinetry and granite countertops. Step outside and enjoy your own private backyard retreat, complete with a swimming pool and spa, an enclosed patio for year-round enjoyment, and a dedicated concrete basketball pad, perfect for shooting hoops and outdoor recreation. The oversized corner homesite provides plenty of additional space to enjoy, entertain, and make the most of the Florida lifestyle. Springlake Village offers residents an outstanding selection of community amenities, including a community pool, clubhouse, playground, and gated access. Conveniently located just minutes from Lake Nona, Medical City, Orlando International Airport, shopping, dining, and major roadways, this home offers the perfect combination of spacious living, unique outdoor features, and convenience. Don't miss your opportunity to own this exceptional home in one of Kissimmee's desirable gated communities!

3820 Springlake Village Court, Kissimmee
1043 La Mirada Court, Kissimmee
$365,000
4 Beds ⋅ 3 Baths ⋅ Lago Buendia Ph 1 SubDv. ⋅ 34744 Zip Code
Beautiful 4-Bedroom Corner-Unit Townhome in a Gated Kissimmee Community! Discover this beautifully maintained, freshly painted, move-in-ready corner-unit townhome featuring 4 bedrooms, a spacious open floor plan, and a generously sized fenced backyard. The modern kitchen offers 42-inch cabinets, quartz countertops, a center island, crown molding, and stainless-steel appliances, seamlessly connecting to the living and dining areas. A convenient first-floor ensuite bedroom provides additional flexibility, while the second-floor features three bedrooms, including a primary suite with dual sinks, quartz countertops, and an oversized walk-in shower. Enjoy a one-car garage plus driveway parking for two additional vehicles. Community amenities include a swimming pool, playground, scenic walking trails, green spaces, a pond, and picnic areas. Conveniently located near shopping, restaurants, major roadways, and essential services, with easy access to Orlando International Airport, Lake Nona Medical City, and Central Florida attractions. Experience comfort, modern living, and an exceptional Kissimmee location. Schedule your private showing today!

1043 La Mirada Court, Kissimmee
1012 Whirlaway Drive, Kissimmee
$419,900
4 Beds ⋅ 4 Baths ⋅ Legacy Park Ph 1 SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome home to this spacious two-story residence nestled in the desirable gated community of Legacy Park in Kissimmee! Featuring 4 bedrooms, an attached garage, and an expansive floor plan, this home offers comfortable living spaces, attractive curb appeal, and the added privacy of no rear neighbors! The inviting covered front porch welcomes you into a versatile layout with plenty of room for everyday living, entertaining guests, or creating your ideal home office. Step outside and enjoy the peaceful backyard setting, perfect for relaxing or spending time outdoors. This property presents a wonderful opportunity to add your personal touches and make it truly your own. Enjoy community amenities, including a swimming pool and playground, along with convenient access to Florida's Turnpike, US-192, shopping, dining, schools, and Central Florida's world-famous attractions. Whether you're looking for a primary residence, vacation getaway, or investment property, this home offers outstanding potential and flexibility! With its convenient location, spacious layout, and desirable community setting, this is an opportunity you won't want to miss. Schedule your private showing today!

1012 Whirlaway Drive, Kissimmee
2711 Summer Retreat Lane, Kissimmee
$349,990
3 Beds ⋅ 2 Baths ⋅ Tohoqua Ph 5a SubDv. ⋅ 34744 Zip Code
Discover the perfect blend of comfort, style, and effortless living in this beautifully upgraded 3-bedroom, 2-bath villa **located in one of Kissimmee’s desirable communities. Featuring 1,579 square feet of thoughtfully designed living space, this move-in-ready home offers a modern open-concept layout with elegant finishes and a relaxed, resort-inspired lifestyle. From the moment you arrive, you’ll appreciate the charming curb appeal, featuring a paver driveway, beautifully maintained landscaping, and a welcoming covered entrance. Step inside to discover a bright and spacious interior filled with natural light, complemented by tile flooring in the entire home, upgraded lighting, and plantation shutters all throughout. The open kitchen seamlessly connects to the dining and living spaces, making it ideal for entertaining guests or enjoying everyday moments with family. The thoughtfully designed split-bedroom floor plan provides added privacy, while the separate room offers flexibility for remote work, a home library, or a personal hobby space. The spacious primary suite features a walk-in closet and a well-appointed en-suite bathroom designed with comfort and convenience in mind. Enjoy Florida living at its best in the covered lanai and fenced in backyard creating the perfect outdoor retreat for relaxing mornings, evening gatherings, or entertaining friends. Additional features include a two-car garage, dedicated indoor laundry room, and easy, low-maintenance living that allows you to spend more time enjoying the things you love. Ideally situated near Lake Nona, Medical City, Orlando International Airport, SR-417, Florida’s Turnpike, and Osceola Parkway, this home offers convenient access to shopping, dining, entertainment, and Orlando’s world-famous attractions.

2711 Summer Retreat Lane, Kissimmee
1029 Wood Cove, Kissimmee
$339,000
3 Beds ⋅ 3 Baths ⋅ Meadow Woods Cove SubDv. ⋅ 34743 Zip Code
Welcome to Meadow Wood Cove, a charming gated community of just 80 homes, offering a peaceful neighborhood atmosphere, privacy, and the convenience of an excellent Kissimmee location! This spacious 3-bedroom, 2.5-bath townhome offers nearly 2,000 square feet of comfortable living space, a beautiful lake view, and the ease of low-maintenance living. From the moment you arrive, you’ll appreciate the inviting covered front porch and welcoming surroundings. Step inside to discover an open floor plan featuring generous living and dining areas, ideal for everyday comfort and entertaining. The eat-in kitchen offers abundant cabinetry for storage, while a large storage area beneath the staircase provides additional space for household essentials. Upstairs, you’ll find three spacious bedrooms, each featuring its own walk-in closet, with an especially generous primary suite offering a comfortable and relaxing retreat. Enjoy the added value of recent improvements, including a NEW A/C SYSTEM installed in 2025, a WATER HEATER replaced in 2024, and a WHOLE-HOUSE WATER FILTRATION SYSTEM that conveys with the property. Additional features include gutters, vinyl fencing, and a spacious TWO-CAR GARAGE. One of the home’s most appealing features is its beautiful LAKE VIEW, which can be enjoyed from the covered back porch, a perfect setting for morning coffee, relaxing evenings, or simply enjoying the peaceful surroundings. What truly sets Meadow Wood Cove apart is its intimate setting of ONLY 80 HOMES, offering the charm of a smaller community without the overwhelming size of larger developments. Residents enjoy gated access, a community swimming pool, sidewalks, and beautifully maintained common areas. The LOW HOA FEE includes exterior maintenance, grounds maintenance, and trash service, providing the convenience of a low-maintenance lifestyle. LOCATION IS ANOTHER GREAT ADVANTAGE! Conveniently situated near major roads and highways, this property offers easy access to Orlando International Airport, Lake Nona, The Loop shopping and dining district, medical facilities, restaurants, shopping, and Central Florida’s popular attractions, including Walt Disney World and Universal Orlando. This location makes everyday living convenient. If you’re looking for generous living space, a beautiful lake view, recent upgrades, and the charm of a quaint gated community, this townhome offers a wonderful combination of comfort, convenience, and value. Schedule your private showing today and discover what makes Meadow Wood Cove such a special place to call home!

1029 Wood Cove, Kissimmee
4375 Silver Creek Street, Kissimmee
$599,900
5 Beds ⋅ 3 Baths ⋅ Creekside At Boggy Creek Ph 1 SubDv. ⋅ 34744 Zip Code
Welcome to 4375 Silver Creek Street, where elegance meets modern comfort in the heart of Kissimmee! This beautifully designed two-story residence offers the perfect blend of sophistication, space, and functionality. Step inside to discover an inviting floor plan featuring elegant tile flooring, a stunning wood staircase with decorative iron railings, and spacious living areas ideal for both everyday comfort and entertaining. The beautifully appointed kitchen flows seamlessly into the expansive family room, while separate formal living and dining areas add a touch of elegance. The first floor also features a versatile bonus room that can easily serve as a fifth bedroom, private home office, or guest retreat. Upstairs, you'll find four generously sized bedrooms, including a spacious owner's suite with two closets and a private bathroom, along with a large loft perfect for entertainment or relaxation. Enjoy Florida living at its finest with an extended covered lanai, ideal for outdoor gatherings, and a convenient two-car garage. A remarkable home offering elegance, versatility, and exceptional living space. Schedule your private showing today!

4375 Silver Creek Street, Kissimmee
1805 Lee Janzen Drive, Kissimmee
$535,000
3 Beds ⋅ 3 Baths ⋅ Kissimmee Bay SubDv. ⋅ 34744 Zip Code
Virtually Staged. GOLF COURSE VIEWS, WATERFRONT SERENITY & YOUR OWN PRIVATE POOL! Experience resort-style Florida living in the desirable gated community of Kissimmee Bay Country Club! This stunning 3-bedroom, 3-bath POOL home offers 2,155 sq. ft. of living space and a 2-car garage. Featuring a desirable split-bedroom floor plan, formal living and dining rooms, and an inviting family room with fireplace. The kitchen boasts granite countertops, stainless steel appliances, custom cabinetry, and a charming breakfast area. The spacious primary suite features dual closets, a luxurious bath with dual vanities, soaking tub, separate shower, and direct pool access. STEP OUTSIDE TO YOUR OWN PRIVATE PARADISE! Enjoy breathtaking pond and golf course views from the expansive screened pool enclosure, complete with a brick-paver deck and covered lanai—perfect for entertaining or relaxing year-round! Kissimmee Bay offers an exceptional lifestyle with an 18-hole golf course, clubhouse restaurant, tennis courts, community dock, boat and RV storage, and playground. HOA benefits include basic cable, internet, nighttime security, and irrigation water. Certain amenities may require additional fees or memberships. Don't miss this incredible opportunity to own your own slice of Florida paradise! Schedule your private showing today!

1805 Lee Janzen Drive, Kissimmee
2802 Quiet Water Trail, Kissimmee
$760,000
5 Beds ⋅ 5 Baths ⋅ North Shore Village SubDv. ⋅ 34744 Zip Code
Virtually Staged. YOUR PRIVATE FLORIDA RETREAT AWAITS! OVER 4,300 SQ. FT. OF RENOVATED MEDITERRANEAN ELEGANCE, SPECTACULAR SUNSETS, WATER VIEWS & RESORT-STYLE LIVING—JUST MINUTES FROM LAKE NONA! Discover one of Central Florida’s best-kept secrets in The Landings at North Shore, a beautiful gated community near the shores of East Lake Tohopekaliga. This impressive 5-bedroom, 5-bathroom executive residence, built by Centerline Homes, offers an extraordinary combination of space, elegance, modern upgrades, and location. Recently transformed with extensive improvements, this home welcomes you with soaring ceilings, a majestic staircase, and an inviting floor plan designed for both everyday comfort and unforgettable entertaining. Freshly painted inside and out, the residence features new water-resistant flooring and baseboards throughout the second floor and portions of the first floor, FIVE beautifully renovated bathrooms with modern cabinetry, quartz countertops, illuminated mirrors, and new toilets. The refreshed gourmet kitchen showcases updated cabinetry, stunning quartz countertops, and BRAND-NEW appliances. Both A/C systems have received significant component upgrades, and the pool features newly replaced valves and professional weekly maintenance. The thoughtfully designed first floor offers a private office with French doors opening to the front patio, elegant formal living and dining rooms, and a spacious family room filled with natural light. French doors invite you outside to the covered lanai, screened pool, and spa, where your very own Florida paradise begins. IMAGINE ENDING EVERY DAY WITH A SUNSET! Perfectly positioned on the WEST SIDE of the residence, the poolside retreat enjoys beautiful afternoon sunshine and breathtaking sunset skies overlooking the peaceful pond. Whether sipping your morning coffee, hosting weekend gatherings, or unwinding beneath the colors of a Florida sunset, this outdoor oasis makes every day feel like a vacation. The spacious primary suite offers tranquil water views, a generous walk-in closet, and an inviting bathroom with a jetted soaking tub, separate glass-enclosed shower, and dual vanities. Upstairs, an expansive bonus room with kitchenette, adjoining bedroom, and private bathroom creates an exceptional opportunity for multigenerational living, visiting guests, or a private entertainment retreat. Additional generously sized bedrooms, bathrooms, and a pond-view sitting area provide flexibility for today’s evolving lifestyles. LOCATION, LIFESTYLE & CONVENIENCE! Enjoy the benefits of living near Lake Nona’s thriving Medical City without sacrificing space or the charm of an established gated community. Conveniently located near the Orlando VA Medical Center, UCF’s medical campus, USTA National Campus, Orlando International Airport, and Austin-Tindall Sports Complex, with easy access to SR 417 and SR 528 connecting you to downtown Orlando, theme parks, shopping, dining, and Florida’s beaches. Offering approximately 4,323 square feet of living space, a THREE-CAR GARAGE, five bedrooms, five bathrooms, extensive recent upgrades, and a private pool and spa with picturesque water views, this residence is more than a home—IT’S THE FLORIDA LIFESTYLE YOU’VE BEEN DREAMING OF! Discover the space, experience the transformation, and fall in love with the sunsets. Schedule your private showing today!

2802 Quiet Water Trail, Kissimmee
2501 Hassonite Street, Kissimmee
$290,000
3 Beds ⋅ 3 Baths ⋅ Amber Pointe SubDv. ⋅ 34744 Zip Code
Spacious 3-bedroom, 2.5-bath townhouse for rent in the heart of Kissimmee. This well-maintained home offers a bright, comfortable interior with a functional layout that separates the living and private areas, giving everyone room to relax and gather. Unbeatable location: supermarkets and pharmacies are directly across the street, and major highways are minutes away for easy commutes to Orlando, the theme parks, shopping, dining, and employment centers. A move-in-ready rental with comfort and convenience in a central Kissimmee location. Schedule your showing today! (the roof was replaced in 2019-2020.)

2501 Hassonite Street, Kissimmee
91 Club Villas Lane, Kissimmee
$289,000
2 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr A SubDv. ⋅ 34744 Zip Code
Looking for a maintenance free home where peaceful golf course living meets everyday convenience? You've found it right here in the gated Club Villas community within Remington! Perfectly positioned on a cul-de-sac overlooking the Remington Golf Course, this charming 2-bedroom, 2-bathroom villa offers 1,306 heated square feet of comfortable living space and picturesque views extending across the fairway to a serene pond beyond. Step through the covered, enclosed front porch into a spacious open-concept living area, where the living room features soft carpet flooring and sliding glass doors leading to a second covered and enclosed porch—the perfect place to unwind while taking in the beautiful surroundings. The kitchen offers a bright, crisp aesthetic with white cabinetry, white and grey granite countertops, tile flooring, and an adjoining dining area. A cozy dinette framed by a bay window overlooks the golf course, creating an ideal spot for morning coffee, casual meals, or simply enjoying the view. Both bedrooms are generously sized, while the primary suite features a private en-suite bathroom and dual closets. Beyond the villa, residents enjoy the added privacy of a gated community tucked inside Remington, an active community centered around the Remington Golf Course. The location places you approximately one mile from the Florida Turnpike entrance and within close proximity to shopping, dining, medical facilities, and schools. The Saint Cloud Lakefront is also nearby, offering four miles of walking paths, a splash pad and playground, marina and fishing pier, along with waterfront dining at Crabby Bill’s. With golf course and water views, two enclosed porches, a cul-de-sac location, and convenient access to so many of the area’s amenities, this villa offers a lifestyle and location ready to welcome its new owners.

91 Club Villas Lane, Kissimmee
2502 Crown Ridge Circle, Kissimmee
$349,900
4 Beds ⋅ 2 Baths ⋅ Remington Prcl H Ph 1 SubDv. ⋅ 34744 Zip Code
CHECK OUT THE HUGE PRICE ADJUSTMENT TO THIS PROPERTY. THIS 4 BED 2 BATH HOME IN THE GATED GOLF COMMUNITY OF REMINGTON IS LOOKING FOR A NEW OWNER. SITUATED IN A QUIET CIRCLE OF THE MAIN REMINGTOM BLVD THE HOUSE COMES WITH NO REAR NEIGHBOURS. THIS IS AN OPEN SPLIT FLOORPLAN WITH A LANAI AND FLORIDA ROOM TO THE REAR. THE HOUSE COMES WITH CERMAMIC TILE THROUGHOUT THE HOUSE TO HELP COOL AND FOR EASY CLEANING. THE CURRENT OWNER REPLACED THE HOTWATER TANK WITH A TANKLESS SYSTEM GIVING HOT WATER ON DEMAND THUS REDUCING YOUR ELECTRIC BILL. THE A/C HAS BEEN REPLACED WITH AN UPGRADED SYSTEM BOTH INSIDE AND OUT. THE DRIVE WAY IS ONE OF THE FEW ON THE ROAD WITH BRICK PAVERS WHICH ADDS TO THE CURB APPEAL. WITH A LITTLE TLC THIS HOUSE COULD BE A PALACE IN THE MAKING. SCHEDULE A VIEWING AND LET YOUR IMAGINATION RUN RIOT.

2502 Crown Ridge Circle, Kissimmee
2512 Brookstone Drive, Kissimmee
$452,000
4 Beds ⋅ 3 Baths ⋅ Remington Prcl I SubDv. ⋅ 34744 Zip Code
Virtually Staged. MUST SEE! Discover an exceptional combination of space, flexibility, and indoor-outdoor living in this impressive 2,469-square-foot home located in the gated Remington Golf Resort community. Featuring 4 bedrooms, a flexible lower level bonus room that can be used as a fifth bedroom, 3 full bathrooms, and a 3-car garage, this home offers the generous living space and versatility today’s buyers are searching for. Even better—a NEW ROOF will be installed before closing with a full price offer! Step inside to a bright, expansive floor plan with updated flooring (2023), refreshed lighting (2023), updated bathroom spaces, abundant natural light, and generously sized rooms throughout. The flexible bonus room provides valuable additional living space and can be used as a fifth bedroom, home office, media room, playroom, or guest retreat. HVAC installed 2021, Water heater 2023, appliances - stove, microwave, dishwasher and washer/dryer 2023. The spacious primary suite opens through French doors to a private deck—an ideal setting for morning coffee, evening relaxation, or your own outdoor retreat. A separate screened patio creates even more space to relax, entertain, and enjoy Florida living throughout the year. The freshly painted exterior makes a striking first impression with Web Gray, Extra White accents, and a Loyal Blue front door. Additional highlights include Ring cameras positioned at the front, side, and rear of the home; dusk-to-dawn front exterior lighting; storage; multiple flexible living areas; a 3-car garage; a low HOA; and the added value of a new roof before closing. Conveniently located near shopping, dining, major roadways, Central Florida attractions, and area recreation, this move-in-ready home delivers the space, updates, and lifestyle features that are increasingly difficult to find. Schedule your private showing—this is a must-see opportunity! Seller is Listing Agent.

2512 Brookstone Drive, Kissimmee
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