Kissimmee Homes under $500,000

Kissimmee Homes under $500,000

Welcome to Kissimmee, Florida—a charming city nestled in the heart of Osceola County that perfectly blends small-town warmth with vibrant attractions. Known for its proximity to the world-renowned Walt Disney World Resort, Kissimmee offers a unique lifestyle that caters to families, retirees, and everyone in between. With its sunny climate, beautiful parks, and endless recreational opportunities, it’s no wonder that Kissimmee is a sought-after destination for both residents and visitors alike.

For those seeking a place to call home without breaking the bank, Kissimmee boasts an impressive selection of homes priced under $500,000. Whether you’re a first-time homebuyer, looking to downsize, or searching for a vacation getaway, you’ll find a variety of options to suit your needs. From charming single-family homes in peaceful neighborhoods to modern townhouses with community amenities, Kissimmee’s real estate market offers affordability without sacrificing quality or comfort.

Imagine waking up to the warm Florida sun, enjoying your morning coffee on a spacious patio, or taking a stroll through one of the many nearby parks. With excellent schools, shopping centers, and dining options just minutes away, you’ll have everything you need right at your fingertips. Plus, the easy access to major highways makes commuting a breeze, whether you’re heading to Orlando or exploring the beautiful surrounding areas.

Discover the charm and excitement of Kissimmee today, and find your dream home in this delightful city where affordability meets convenience. Your perfect slice of Florida awaits!

Newest Kissimmee Homes under $500,000

2613 Play Hard Alley, Kissimmee
$340,000
3 Beds ⋅ 3 Baths ⋅ Tohoqua-Ph 1 SubDv. ⋅ 34744 Zip Code
Beautiful home located in the desirable Tohoqua community of Kissimmee (34744)! This stunning property features a modern two story layout with a light filled open concept living and dining area designed for seamless everyday living and entertaining. The well appointed kitchen includes sleek countertops, spacious cabinetry, and a central island. Upstairs bedrooms provide comfort and privacy, including a spacious primary suite with a private full bathroom. Residents enjoy fantastic resort style community amenities including a luxury clubhouse, resort pool, fitness center, tennis courts, playground, and scenic walking trails. Ideally situated with quick access to Florida's Turnpike and US 192, ensuring an easy commute to Lake Nona Medical City, Orlando International Airport, local dining, and shopping. Schedule your private showing today!

2613 Play Hard Alley, Kissimmee
2921 Casabella Drive, Kissimmee
$445,990
4 Beds ⋅ 3 Baths ⋅ Villa Sol Village 2 SubDv. ⋅ 34744 Zip Code
Discover comfort, style, and resort-style living in the beautiful gated community of Villa Sol! This charming home features 4 spacious bedrooms and 3 full bathrooms, offering a wonderful combination of comfort and functionality. The kitchen showcases beautiful granite countertops, adding an elegant touch to the heart of the home. Enjoy the Florida lifestyle year-round in your enclosed porch, the perfect space to relax, entertain guests, or simply unwind after a long day. Residents of Villa Sol enjoy fantastic community amenities, including a resort-style swimming pool, fitness center, and gated access, creating a welcoming environment for everyday living. Conveniently located in Kissimmee, with easy access to shopping, dining, entertainment, and major roadways. Don’t miss the opportunity to make this beautiful property your next home! Schedule your private showing today!

2921 Casabella Drive, Kissimmee
1744 Quail Ridge Loop, Kissimmee
$425,000
3 Beds ⋅ 3 Baths ⋅ Quail Hollow Ph 1 SubDv. ⋅ 34744 Zip Code
NEW PHOTOS COMING SOON! Welcome to 1744 Quail Ridge Loop in Kissimmee's Quail Hollow neighborhood! This two-story, 3-bedroom, 2.5-bath single-family home offers 1,260 sq ft of heated living space, a fireplace, and an attached garage. Unwind on the screened porch and enjoy a low-maintenance lot in flood zone X. Conveniently located near Florida's Turnpike and Florida Parkway for easy access to shopping, dining, schools, and all of Central Florida's attractions. Schedule your private showing today!

1744 Quail Ridge Loop, Kissimmee
2155 Jeremiah Way Unit 2155, Kissimmee
$280,000
3 Beds ⋅ 3 Baths ⋅ Cypress Lakes Twnhms Ph 2 Unit 1 SubDv. ⋅ 34743 Zip Code
Modern Comfort Meets Ultimate Energy Efficiency! Nestled on an attractive tree-lined brick-paver drive, this move-in-ready 3-bedroom, 2-bath home provides approximately 1,300 sq. ft. of smartly designed living. From the moment you arrive, quality and convenience stand out, headlined by PAID-OFF solar panels that deliver huge everyday energy savings with zero panel lease or loan to assume! Inside, you’ll love the fresh, contemporary feel of brand-new luxury vinyl plank (LVP) flooring extending across the living and sleeping areas. The open-concept living and dining area is perfect for gathering, while the primary suite offers an en-suite bath featuring double sinks, a soaking tub/shower, and ample closet space. Out in the garage, electric vehicle owners will appreciate the built-in EV charging setup. When you're ready to unwind, step outside and enjoy the community's premier amenities, including a sparkling swimming pool, relaxing cabana, and playground area just around the corner. Centrally located near top Kissimmee dining, shopping, major commuter corridors, and theme parks. Don’t miss this rare opportunity to own a tech-forward, money-saving home!

2155 Jeremiah Way Unit 2155, Kissimmee
111 Cattail Court, Kissimmee
$405,000
4 Beds ⋅ 3 Baths ⋅ Coralwood SubDv. ⋅ 34743 Zip Code
$5,000 TOWARD BUYER’S CLOSING COSTS, A PRIVATE POOL, AND EXTRA SPACE THAT MAKES THE DIFFERENCE! Located on a cul-de-sac in Coralwood, this 4-bedroom, 2.5-bath pool home offers approximately 1,938 square feet and an additional upstairs living area with potential for conversion into a fifth bedroom. The first-floor primary bedroom offers added convenience, and all four bedrooms have closets. An attached two-car garage provides additional practicality. This versatile upstairs space could also serve as a home office, media room, or second gathering area. A double-height entry creates a welcoming first impression. The kitchen, remodeled in 2024, along with the updated primary bathroom and half bath, adds appeal and comfort. Outside, enjoy your private screened-in pool, remodeled in 2022—an inviting place to relax and entertain. Additional improvements include a water heater installed in 2024 and roof repairs completed in 2025. Located approximately 3 minutes by car from Florida’s Turnpike access at Osceola Parkway, with connections to SR 417 and access to Disney Springs and shopping and dining at The Loop. Plus, the seller offers $5,000 toward the buyer’s closing costs. Schedule your showing and explore the possibilities!

111 Cattail Court, Kissimmee
2430 Marcasite Loop, Kissimmee
$449,999
4 Beds ⋅ 3 Baths ⋅ Emerald Pointe Ph 3 SubDv. ⋅ 34743 Zip Code
Spacious 4BR/2.5BA home featuring 2,419 sq. ft. of living space on an oversized 0.33-acre lot. This two-story residence offers generous living areas, spacious bedrooms, an attached garage, and plenty of outdoor space for entertaining or future improvements. Conveniently located near shopping, dining, major highways, Orlando attractions, and Orlando International Airport. A rare opportunity to own a spacious home with a large lot in an established Kissimmee community. Room measurements are approximate and must be verify by the buyer and or buyer's agent.

2430 Marcasite Loop, Kissimmee
1903 Binnacle Street, Kissimmee
$398,500
3 Beds ⋅ 2 Baths ⋅ Neptune Pointe SubDv. ⋅ 34744 Zip Code
Beautiful single-story 3-bedroom, 2-bath home located in a gated Kissimmee community with low HOA and no CDD. This home features a desirable split-bedroom floor plan, a dedicated den area ideal for a home office or flex space, and an open-concept living area. The gourmet kitchen is enhanced with new cabinetry and quartz countertops, while new flooring flows throughout the home. Enjoy a covered front porch, covered rear porch, and a private fenced backyard with plenty of room to relax, play, or entertain. Conveniently located in the greater Kissimmee area—schedule your showing today!

1903 Binnacle Street, Kissimmee
3209 Turret Drive, Kissimmee
$399,900
3 Beds ⋅ 3 Baths ⋅ Saratoga Park Ph 4b SubDv. ⋅ 34743 Zip Code
PRICED TO SELL! MOTIVATED SELLER! FAST CLOSING PREFERRED! Don't miss this opportunity to own a spacious two-story home in the desirable Saratoga Park community of Kissimmee! Offering 2,307 square feet of living space, this home features 3 bedrooms, 2.5 bathrooms, and a versatile loft with the potential to be converted into a 4th bedroom! The flexible loft provides additional living space, perfect for a family room, home office, entertainment area, or future bedroom conversion to suit your needs. The inviting open-concept layout seamlessly connects the main living area and kitchen, creating an ideal setting for everyday living and entertaining. Upstairs, you'll find generously sized bedrooms, including a spacious primary suite featuring dual sinks, a soaking tub, and a separate shower. Step outside to enjoy the screened-in rear porch overlooking the backyard, perfect for relaxing or entertaining. Additional highlights include an attached two-car garage and a functional floor plan offering flexibility and room to grow. SELLER IS MOTIVATED AND SEEKING A TIMELY SALE! Whether you're looking for extra living space, flexibility, or the opportunity to customize a home to fit your lifestyle, this property offers excellent potential. Schedule your private showing today!

3209 Turret Drive, Kissimmee
1842 Katz Crossing Drive, Kissimmee
$299,000
3 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Discover comfortable living in this inviting 3-bedroom, 2.5-bath townhome located in the sought-after Kindred community. The open-concept floor plan offers a spacious feel, with a bright, well-appointed kitchen overlooking the living area and providing easy access to the private back patio—perfect for relaxing or entertaining. Enjoy an exceptional lifestyle with an impressive selection of resort-style amenities, including a lap pool, a 3,000-square-foot clubhouse, a state-of-the-art fitness center, tennis and pickleball courts, sand volleyball, playgrounds, a dog park, a soccer field, and scenic nature trails. Conveniently located near E. Bronson Memorial Highway and the Florida Turnpike, this community offers easy access to nearby shopping, dining, and everyday essentials. Residents also benefit from access to highly rated schools. For added convenience, the washer and dryer are included. Don't miss this opportunity to own a beautiful townhome in a vibrant community that combines comfort, convenience, and an active lifestyle!

1842 Katz Crossing Drive, Kissimmee
1881 Red Canyon Drive, Kissimmee
$310,000
3 Beds ⋅ 3 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Welcome to this beautiful 3 bedroom, 2.5 bathroom townhouse in the desirable Kindred community of Kissimmee, offering comfortable living and resort-style amenities! Step inside to a spacious kitchen and family room combination, creating an inviting space for everyday living and entertaining. All three bedrooms are conveniently located upstairs, providing separation from the main living areas. Additional highlights include a rear-entry one-car garage and an alkaline water system included with the home. Living in Kindred means enjoying more than just a beautiful home! Residents have access to an impressive selection of amenities, including three swimming pools, three fitness centers, tennis and volleyball courts, a soccer field, a dog park, and approximately five miles of trails for walking, jogging, and biking. Whether you enjoy staying active, spending time outdoors, or relaxing by the pool, there's something for everyone to enjoy. Location is another major advantage! Conveniently situated near the Florida Turnpike, SR 417, and SR 528, with shopping and dining just a short drive away. Orlando International Airport is approximately 25 minutes away, and Central Florida's world-famous theme parks and attractions are also within easy reach. With its spacious layout, one-car garage, included alkaline water system, and incredible community amenities, this townhouse offers the Florida lifestyle you've been looking for. Schedule your private showing today!

1881 Red Canyon Drive, 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!From Florida’s Turnpike, take Exit 244 to US-192 E. Turn onto Amber Pointe Blvd, enter the gated community, then turn onto Hassonite St. Property is located at 2501 Hassonite St.

2501 Hassonite Street, Kissimmee
121 Lochness Lane, Kissimmee
$399,000
3 Beds ⋅ 2 Baths ⋅ Cypress Lakes Ph 3 SubDv. ⋅ 34743 Zip Code
Beautifully remodeled pool home with NO HOA! This 3-bedroom, 2-bath property also features a versatile bonus room, ideal for a home office, guest room, playroom, or additional flex space. Thoughtfully updated just two years ago, the home offers a modern open-concept kitchen, beautifully renovated bathrooms, and fresh interior and exterior paint. Major improvements include a NEW A/C installed in 2024 and a 2021 roof, offering added peace of mind for the next owner. The spacious living area flows effortlessly toward the fully fenced backyard, where your private pool creates the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle year-round. A bright breakfast nook filled with natural light adds to the home's warm and inviting feel. Conveniently located near shopping, dining, entertainment, and everyday essentials, this move-in-ready home combines comfort, flexibility, and valuable updates all with no HOA. Schedule your private showing today!

121 Lochness Lane, Kissimmee
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