Kissimmee Homes under $500,000

Kissimmee Homes under $500,000

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, just a stone's throw away from the magical attractions of Orlando. Known for its warm climate and welcoming community, Kissimmee offers a unique blend of suburban charm and urban convenience, making it an ideal place to call home.

As you explore Kissimmee, you’ll discover a diverse array of homes under $500,000, perfect for families, first-time buyers, and anyone looking to invest in a thriving market. From cozy single-family homes adorned with lush landscapes to modern townhouses equipped with the latest amenities, there’s something for everyone in this enchanting city.

Imagine waking up to the sun-kissed skies of Florida, enjoying leisurely strolls along the picturesque Lake Tohopekaliga, or indulging in the vibrant local dining scene. Kissimmee is not just a place to live; it’s a lifestyle filled with adventure. With easy access to world-renowned theme parks, shopping centers, and recreational activities, you’ll find that every day brings a new opportunity for fun and relaxation.

Kissimmee is also known for its excellent schools, making it a perfect choice for families. The community prides itself on its strong sense of belonging, ensuring that residents feel connected and supported.

Whether you're looking to settle down or invest, Kissimmee’s real estate market offers a wealth of possibilities. With homes under $500,000 readily available, now is the perfect time to discover your dream home in this enchanting city. Come experience the magic of Kissimmee – where dreams meet reality!

Newest Kissimmee Homes under $500,000

4913 Pall Mall Street E, Kissimmee
$349,900
5 Beds ⋅ 5 Baths ⋅ Trafalgar Village Ph 3 SubDv. ⋅ 34758 Zip Code
PRICED FOR A REFRESH! Own this 5-bedroom, 4.5-bath pool and spa home in a resort-style, 24-hour guard-monitored gated community in Central Florida! Cosmetic updates will bring this home to its full potential. Make this your dream home, a Sunshine State getaway, or a rental income generator (Airbnb potential!). The HOA covers regular cleaning of the private lap-style pool and spa, plus lawn and shrub trimming, so you can enjoy a true lock-and-leave lifestyle. Entertain on your screened pool deck overlooking mature trees that provide natural PRIVACY! Inside, the flowing floor plan is bright with natural light and features granite kitchen countertops, 18"x18" ceramic tile throughout the living areas, recessed lighting, and cultured marble bathroom vanities. Gather at the clubhouse with its fitness center, movie theater, and game room (billiards, ping-pong, foosball). Resort-style amenities include a community pool and spa, outdoor kitchen, lighted pickleball and tennis courts, sand volleyball, full-court basketball, shuffleboard, BBQ and picnic areas, playground, walking trails, fishing, and more! Located about 14 miles from the feeder highway to world-renowned attractions, golf, and shopping. Bring your paint colors and your style -- update it to your taste and capture the upside before someone else does. Properties with this much space, this many amenities, and this much potential don’t last. Schedule your showing today!

4913 Pall Mall Street E, Kissimmee
1941 Partin Terrace Road, Kissimmee
$499,000
4 Beds ⋅ 4 Baths ⋅ Kindred 100 Rep SubDv. ⋅ 34744 Zip Code
IN-LAW suite with separate entrance; includes its own kitchenette and full bathroom—ideal for multigenerational living or guests. Beautiful move-in-ready home featuring 4 bedrooms, 3.5 baths, and the highly sought-after Camden floor plan with a private in-law suite and its own separate entrance. The main living area offers a bright, open kitchen with granite countertops, custom backsplash, and a water filtration system. Tile and luxury vinyl plank flooring flow throughout the home. A built-in entertainment center with an electric fireplace adds a warm, modern touch. The spacious bonus room is perfect for a home office, hobby room, or additional flex space. Additional upgrades include: • Smart-home technology • Extensive camera system (some cameras convey) • Renovated attic with custom electric lift • Whole-home water softener • Ceiling fans in every room • Custom wine cabinet with extra storage Enjoy access to three clubhouses, three resort-style pools, two fitness centers, miles of scenic nature trails, playgrounds, and a dog park—all with a LOW HOA. Enjoy indoor-outdoor living in the large, enclosed Florida room, leading out to a beautiful paver patio overlooking breathtaking sunset views, rocket launches can even be seen from the backyard. Enjoy the expansive view of the wildlife preserve. The large corner lot features gated rear access, plus a covered shed for added storage.

1941 Partin Terrace Road, Kissimmee
3118 Yellow Lantana Lane, Kissimmee
$274,900
3 Beds ⋅ 3 Baths ⋅ Encantada Ph 1 SubDv. ⋅ 34747 Zip Code
Fully Furnished 3 Bedrooms and 2.5 Bath Townhome For Rent Located in the highly sought-after Encantada Resort, a gated community that offers a blend of vacation-style living and residential comfort. It’s an ideal spot for those wanting to be close to the magic of Disney while having a private retreat to call home. Step into a bright, open-concept living space designed for both relaxation and entertaining. This two-story townhome features a seamless flow from the kitchen to the dining and living areas, highlighted by: Private Splash Pool: Enjoy your own screened-in, heated plunge pool—perfect for cooling off after a long day. Modern Flooring: Durable ceramic tile throughout the first floor with stylish laminate upstairs. Fully Equipped Kitchen: Includes all major appliances (refrigerator, range, dishwasher, microwave) and a convenient breakfast bar. Primary Suite: A spacious upstairs retreat featuring an en-suite bathroom and walk-in closet. In-Home Laundry: Washer and dryer included for your convenience. Resort-Style Amenities Living in Encantada means more than just a house; it’s a lifestyle. Residents have access to: Clubhouse: Featuring a fitness center, game room, and business center. Community Pools: Two large resort-style pools and heated spas. On-Site Dining: A restaurant and bar located right within the community. Outdoor Fun: Playground, fishing pier, and beautifully landscaped walking paths. Security: 24-hour gated security for peace of mind. Prime Location You are perfectly positioned to enjoy the best of Central Florida: Disney World: approx. 6 miles away. Shopping & Dining: Minutes from the Margaritaville H2O Water Park, Sunset Walk, and a variety of grocery stores and restaurants along Hwy 192. Easy Commute: Quick access to I-4 and the 429 Toll Road.

3118 Yellow Lantana Lane, Kissimmee
217 Churchill Court, Kissimmee
$265,000
3 Beds ⋅ 2 Baths ⋅ Poinciana Village 2 Nbhd 1 SubDv. ⋅ 34758 Zip Code
Welcome Home to 217 Churchill Court in Kissimmee, Florida! Move right in and enjoy the comfort and convenience of this well-maintained home with many important updates including a renovated kitchen and baths (2019), tile flooring throughout, roof (2022), and water heater (2021). All kitchen and laundry appliances included, two-car garage with an updated garage door and opener, and cable and internet included in the low monthly HOA. All in a convenient location close to major shopping, hospitals, and Central Florida’s world-famous theme parks. Well cared for, thoughtfully updated, and conveniently located—this home is ready for its next owner to move in and make it their own!

217 Churchill Court, Kissimmee
1116 Sunset View Circle Unit 103, Kissimmee
$379,000
3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square Condo Ph 6 SubDv. ⋅ 34747 Zip Code
LUXURY 3-SUITE GROUND-FLOOR GOLF-FRONT CONDO IN REUNION RESORT! Welcome to a turn-key 3BR/3BA condo where each bedroom has its own en-suite bathroom. Truly like new, it has never been rented and has barely been used. It comes fully furnished, and the furniture, housewares and linens are in such immaculate condition that you’ll feel as if everything was delivered yesterday. The ground-floor location gives easy access and opens onto an expansive, sheltered private patio overlooking the par-3 15th hole of the Tom Watson Signature Course, with southwest exposure for beautiful sunsets over the fairway. Inside, the open-concept split floor plan keeps the primary suite apart from the two additional bedrooms, a great layout for a winter getaway or for hosting guests. VALUABLE CLUB MEMBERSHIP INCLUDED WITH SALE! An active Reunion Club membership transfers with the $7,500 deposit waived for the next owner. Short-term rentals are approved in one of Central Florida’s premier resorts. Inside the 2,300-acre gated community you’re close to 3 private signature golf courses, a water park, several neighborhood pools, tennis and pickleball courts, a fitness center, mini-golf, and on-site restaurants and lounges, with a new resort spa planned (opening date TBD). Minutes from Disney and major highways. An excellent investment or vacation getaway!

1116 Sunset View Circle Unit 103, Kissimmee
4615 Eaglet Lane, Kissimmee
$400,000
4 Beds ⋅ 2 Baths ⋅ Eagle Pointe SubDv. ⋅ 34746 Zip Code
4615 Eaglet Ln is a one-story Kissimmee home with a split-bedroom layout and a screen-enclosed pool. The kitchen’s peninsula faces the dining and living areas, keeping preparation space connected to the main gathering rooms. A breakfast nook provides a second dining option, while the vaulted living room pairs a fireplace with sliding doors to the covered rear porch. The primary suite includes a walk-in closet and an adjoining bathroom with double sinks, a freestanding tub and a separate shower. Beyond the pool enclosure, lawn and perimeter fencing frame the backyard. An indoor laundry room connects the kitchen to an attached two-car garage, completing a layout centered on indoor-outdoor living. Included 100-Day Home Warranty with buyer activation

4615 Eaglet Lane, Kissimmee
2326 Carriage Run Road, Kissimmee
$469,450
4 Beds ⋅ 3 Baths ⋅ Plantation Rep SubDv. ⋅ 34741 Zip Code
STUNNING FULLY REMODELED WATERFRONT HOME! Welcome to 2326 Carriage Run Road, where modern elegance meets comfort and peaceful waterfront living! Situated in the desirable Shadow Bay/Plantation community of Kissimmee, this beautifully renovated two-story residence offers 4 bedrooms, 2.5 bathrooms, 1,867 square feet of living space, and a spacious two-car garage. From the moment you step inside, you'll be impressed by the soaring vaulted ceilings, abundance of natural light, and spectacular living room featuring a dramatic designer accent wall, contemporary electric fireplace, and stunning modern chandelier. The thoughtfully designed open floor plan creates a seamless connection between the living, dining, and kitchen areas, providing an inviting atmosphere for both everyday living and entertaining. NO EXPENSE HAS BEEN SPARED IN TRANSFORMING THIS BEAUTIFUL HOME! The current owners have completed extensive renovations, including brand-new flooring throughout, fresh interior and exterior paint, beautifully remodeled bathrooms, and elegant new chandeliers and light fixtures throughout the residence. The updated kitchen showcases sleek cabinetry, stainless steel appliances, stylish finishes, and an inviting layout that complements the home's contemporary design. The spacious FIRST-FLOOR PRIMARY SUITE offers convenience and privacy, featuring a walk-in closet and a beautifully remodeled ensuite bathroom complete with a modern double-sink vanity, illuminated mirror, elegant gold fixtures, and a stunning glass-enclosed shower. Upstairs, three additional bedrooms provide plenty of space and flexibility. Beyond the beautiful cosmetic renovations, this home also features several MAJOR UPGRADES, including a NEW ROOF IN 2021, COMPLETE HOME REPIPING WITH PEX PLUMBING IN 2022, AND AN INTERIOR HVAC AIR HANDLER REPLACED IN 2024. Even the attached two-car garage has received special attention, featuring attractive decorative flake-finish flooring. Step outside to your private backyard overlooking a peaceful pond, where beautiful water views create the perfect setting to enjoy your morning coffee, unwind after a long day, or entertain guests against a tranquil waterfront backdrop. Residents enjoy access to community amenities, including a swimming pool and park, along with a convenient location near shopping, dining, schools, major highways, and Central Florida's world-famous attractions. FULLY REMODELED, BEAUTIFULLY UPGRADED, AND WATERFRONT — THIS MOVE-IN-READY HOME TRULY HAS IT ALL! Don't miss this incredible opportunity to own a stunning residence where the major improvements have already been taken care of. Schedule your private showing today!

2326 Carriage Run Road, Kissimmee
2007 Forage Drive, Kissimmee
$360,000
3 Beds ⋅ 2 Baths ⋅ Storey Creek SubDv. ⋅ 34746 Zip Code
Short Sale. Welcome home to this beautiful Aspire floorplan in Storey Creek! Built in 2025, this 3-bedroom, 2-bath home features a 3-car garage, an open-concept layout, and neutral finishes throughout. The kitchen offers a spacious island with breakfast bar, white Shaker-style cabinetry, and quartz countertops, all overlooking the dining and living areas. The private owner’s suite is tucked away at the back of the home and features an en-suite bathroom with dual sinks, a walk-in shower, and a generous walk-in closet. Two additional bedrooms are located near the front of the home and share a full bathroom with a shower/tub combination. A spacious laundry room just off the garage offers added convenience and wire shelving for storage. Enjoy the outdoor patio and spacious backyard, with plenty of room to add a fence. Storey Creek residents enjoy an array of amenities, including a resort-style pool, fitness center, clubhouse, tennis and basketball courts, volleyball court, playground, and walking trails. The low monthly HOA of $181 includes lawn maintenance. Conveniently located near SR 535, I-4, and US 192, with easy access to shopping, dining, and Central Florida attractions.

2007 Forage Drive, Kissimmee
11 York Court, Kissimmee
$300,000
3 Beds ⋅ 2 Baths ⋅ Poinciana Nbhd 3 Vlg 2 SubDv. ⋅ 34758 Zip Code
This house comes with a REDUCED RATE through the seller’s preferred lender. This is a lender-paid rate buydown that reduces the buyer’s interest rate and monthly payment. Welcome to this move-in ready, fully furnished 3-bedroom, 2-bathroom single-family home in Poinciana Village, offering 1,888 square feet of comfortable living space! Furniture is included in the asking price, with the option to have it removed if preferred From the moment you step inside, vaulted ceilings, arched doorways, and abundant natural light create a bright, open feel. The thoughtfully designed layout features a formal dining room, spacious living room, and separate family room with access to the backyard, providing plenty of room for everyday living and entertaining. The kitchen offers stainless steel appliances, generous cabinet space, and a sunny breakfast nook. The private primary suite features dual vanities, a jetted garden tub, and a separate walk-in shower. Two additional bedrooms, an indoor laundry room, and a 2-car garage with a wide driveway add convenience and functionality Enjoy Florida living year-round in the expansive screened-in Florida room, perfect for relaxing or entertaining. The fully fenced backyard also features a patio and paver walkway, offering additional outdoor space for gatherings, pets, and play. Major home features include a 2016 roof, 2017 HVAC system, storm windows, and a paid-off water softener system. Conveniently located in Poinciana Village near shopping, dining, schools, Walmart Supercenter, and Sprouts Farmers Market, with access to Central Florida attractions including Walt Disney World, Universal Orlando Resort, and SeaWorld Orlando. Whether you’re searching for a primary residence, second home, or investment property, this Poinciana home offers space, comfort, and convenience, along with an opportunity to take advantage of a reduced interest rate through the seller’s preferred lender. Schedule your private showing today!

11 York Court, Kissimmee
3077 Caribbean Soul Drive, Kissimmee
$370,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 7 SubDv. ⋅ 34747 Zip Code
Welcome to this stunning, like-new 3-bedroom, 3-bathroom single-family home, offering the perfect combination of luxury, comfort, and resort-style living in one of Central Florida's most desirable vacation communities. Beautifully appointed with stylish finishes and numerous upgrades, this exceptional property is ideal as a primary residence, vacation getaway, or investment opportunity. Nestled within an exclusive guard-gated community, the home is just a 3-minute stroll from Margaritaville's spectacular resort pools, fitness center, Salty Rim Bar & Grill, and hotel. Only an 8-minute walk away, Sunset Walk offers an incredible selection of restaurants, shopping, a movie theater, live entertainment, and nightlife. Ideally located just minutes from Walt Disney World, Celebration Hospital, and world-class attractions, with convenient access to US-192 and SR-429. CURRENTLY TENANT-OCCUPIED WITH A LEASE IN PLACE THROUGH OCTOBER 2027, OFFERING INVESTORS THE OPPORTUNITY TO ACQUIRE AN INCOME-PRODUCING PROPERTY WITH AN EXISTING TENANT!

3077 Caribbean Soul Drive, Kissimmee
2514 Serenity Garden Drive, Kissimmee
$486,860
5 Beds ⋅ 3 Baths ⋅ Tohoqua SubDv. ⋅ 34744 Zip Code
Under Construction. Tohoqua is the kind of neighborhood you've been looking for, with an exciting amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. The new two-story Trailside home, with 5 bedrooms, 3 bathrooms, a loft, and a 2-car garage is ready for you to move in and start living the life you deserve. Upon entry, you’re welcomed by a beautiful wrap around staircase and a foyer that is flooded with natural light. The foyer leads you toward the heart of the home, where the kitchen, gathering room, and café seamlessly flow together, all overlooking the covered lanai. Your chef-inspired kitchen is a true standout, offering a large center island and stainless-steel Whirlpool appliances, including a refrigerator. White cabinetry with quartz countertops, a single-bowl stainless-steel sink, and upgraded faucet combine to create a stylish and functional space. A guest bedroom and full bathroom are located on the main level, perfect for visitors, a home office, or flexible living space. Upstairs, the Owner’s Suite offers a peaceful retreat with a large walk-in closet and an en suite bath featuring dual sinks, a quartz-topped vanity, a private water closet, and a walk-In shower with a built-in bench. Also located on the second floor, three additional bedrooms, another secondary bathroom, a loft, and a conveniently located laundry room offer both privacy and functionality. Throughout the home, professionally curated design selections and premium finishes elevate the living experience. Wood-look luxury vinyl plank flooring spans the first-floor living spaces; tile graces the bathroom and laundry room floors, while soft, stain-resistant Shaw carpet enhances the bedrooms and second-floor living spaces. Additional touches such as 2” faux wood blinds, Whirlpool washer and dryer, Sherwin Williams Drift of Mist Interior Wall Paint, and brushed nickel hardware and plumbing fixtures add both style and convenience. The open spindle railing at the first-floor staircase completes the home’s elegant feel. This Trailside home is where luxury and practicality meet. Don’t miss your chance to make this exceptional home yours—schedule a tour today!

2514 Serenity Garden Drive, Kissimmee
1739 Good Neighbor Loop, Kissimmee
$436,000
3 Beds ⋅ 2 Baths ⋅ Tohoqua Ph 2 SubDv. ⋅ 34744 Zip Code
Move into comfort and ease in the sought-after community of Tohoqua. Built in 2022 and meticulously maintained, this 3-bedroom, 2-bathroom, single-story home offers over 2,000 square feet of bright, open-concept living. With no stairs and a thoughtfully designed layout, this home offers the comfort and convenience you deserve. Step inside to a welcoming foyer that flows into a spacious great room, perfect for gatherings, movie nights, or simply unwinding at the end of the day. The kitchen features sleek quartz countertops, stainless steel appliances, and a large pantry, making everyday cooking and entertaining a breeze. The owner's suite offers a relaxing retreat with dual quartz vanities, a soaking tub, and a separate walk-in shower. Outside, the private screened lanai is the perfect spot for morning coffee or evening relaxation, overlooking a fully fenced backyard with plenty of space for pets, play, and outdoor enjoyment. A covered front porch adds curb appeal and provides a welcoming place to enjoy the Florida breeze. Additional highlights include a smart home setup with a Ring video doorbell and Wi-Fi thermostat, an attached 2-car garage, and a versatile flex room that can serve as a home office, nursery, or playroom. Tohoqua offers resort-style amenities, including a community pool, while the home's Flood Zone X designation may provide insurance advantages, depending on the property's coverage and insurer. Conveniently located near schools, shopping, dining, and major highways, this home combines comfortable living with everyday convenience. Don't miss this opportunity to own a move-in-ready home in one of Kissimmee's desirable communities. Schedule your private tour today!

1739 Good Neighbor Loop, Kissimmee
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