Kissimmee/Celebration Homes under $500,000

Kissimmee/Celebration Homes under $500,000

Welcome to the enchanting region of Kissimmee and Celebration, Florida, where the magic of Central Florida meets the charm of small-town living. Nestled in Osceola County, Kissimmee is a vibrant city known for its proximity to world-renowned attractions like Walt Disney World and Universal Studios. This bustling area offers a unique blend of entertainment, outdoor activities, and a rich cultural tapestry.

Just a stone's throw away lies Celebration, a picturesque community originally developed by the Walt Disney Company. With its tree-lined streets, quaint shops, and delightful parks, Celebration embodies the essence of idyllic suburban life. Residents enjoy a strong sense of community, with events and festivals that celebrate the joys of living in this beautiful locale.

For those seeking affordable housing options, Kissimmee and Celebration have an impressive array of homes available for under $500,000. Whether you're a first-time homebuyer, a growing family, or looking for a vacation retreat, this region offers diverse choices to suit your needs. From charming single-family homes with spacious backyards to modern townhouses with community amenities, you’ll find properties that blend comfort and style without breaking the bank.

Living in Kissimmee and Celebration means you’re never far from adventure. Explore the lush parks, indulge in local dining, or take a quick drive to the stunning beaches of the Atlantic coast. With a welcoming atmosphere and a plethora of activities, this area is more than just a place to live; it's a lifestyle. Discover your dream home in Kissimmee or Celebration today, and embrace the magic that awaits!

Newest Kissimmee/Celebration Homes under $500,000

8834 Geneve Court, Kissimmee
$419,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2b SubDv. ⋅ 34747 Zip Code
Welcome to your own resort-style retreat in Windsor at Westside! This fully furnished 5-bedroom, 4.5-bath end-unit townhome offers 2,265 square feet of thoughtfully designed living space, a private screened pool, and beautiful pond views — all inside a gated community just minutes from Disney. The open-concept main level brings the kitchen, dining, and living areas together, perfect for gathering after a day at the parks. The kitchen is appointed with granite countertops, stainless steel appliances, and a generous center island. A first-floor bedroom with a full bathroom adds flexibility for guests, while the second floor features four more bedrooms — including a spacious primary suite — plus a loft for movies, games, or quiet downtime. Outside, the screened lanai and pool deck overlook the pond with no rear neighbors, an ideal spot for morning coffee, an afternoon swim, or dinner under the Florida sky. Equally suited as a vacation home or a short-term rental investment, this property delivers both lifestyle and income potential. Residents of Windsor at Westside enjoy a 10,000-square-foot clubhouse, a resort pool with waterslide and lazy river, a hot tub, a water playground, a game room, and poolside dining at Tu Casa Bar & Lounge. Come experience the best of Central Florida living — book your private showing today!

8834 Geneve Court, Kissimmee
3238 Wish Avenue, Kissimmee
$315,000
4 Beds ⋅ 3 Baths ⋅ West Lucaya Village SubDv. ⋅ 34747 Zip Code
Enjoy resort-style living in this furnished, 4-bedroom, 3-bathroom end-unit townhome in gated West Lucaya Village. Featuring 1,694 square feet across two stories, this home offers an open living and dining layout, a kitchen with solid-surface countertops and included appliances, and a first-floor primary suite with a walk-in closet, dual sinks, and an en-suite bathroom. Flooring was replaced in October 2026. An electric fireplace and upstairs laundry closet with a washer and dryer add comfort and convenience. Located near the community entrance, just steps from the pedestrian exit along Kissimmee’s popular US-192 corridor, this townhome provides convenient access to dining, shopping, supermarkets, and entertainment, with Walt Disney World and Central Florida’s attractions a short drive away. Community amenities include a resort-style, zero-entry pool, jacuzzi spa, sun deck, and clubhouse with a fitness center, TV lounge, games room, children’s playroom, Wi-Fi, and business center. Enjoy outdoor play areas, BBQ and picnic spaces, and lakeside walking trails. Association fees include cable TV, internet, community pool access, and grounds maintenance. An appealing option for a primary residence, vacation retreat, or rental property, subject to community rules and leasing requirements.

3238 Wish Avenue, Kissimmee
2711 Oakwater Drive Unit 2711, Kissimmee
$299,900
3 Beds ⋅ 2 Baths ⋅ Oakwater Condo Ph 15-19 SubDv. ⋅ 34747 Zip Code
THREE BEDROOMS, A PRIVATE GARAGE, AND DISNEY JUST 2 MILES AWAY—ALL FOR UNDER $300,000! Fully furnished and turnkey, this ground-floor condo in gated Oakwater Resort pairs a convenient location with a $495 monthly HOA that includes high-speed internet, cable TV, roof and exterior building maintenance, and resort amenities. Whether you’re looking for everyday Florida living, a vacation getaway, or a short-term rental opportunity, this home deserves a closer look. With approximately 1,255 square feet, the open floor plan features travertine flooring throughout, designer furnishings, a fully equipped kitchen, and a spacious primary suite with an en-suite bath. Enjoy morning coffee on your private screened lanai and the convenience of an attached one-car garage for parking and additional storage. Ground-floor living means no interior stairs to navigate when bringing home groceries or unpacking for your stay. Oakwater’s amenities make it easy to enjoy time close to home, with a resort-style swimming pool, clubhouse, fitness center, tennis, pickleball, basketball courts, and playground. Head to Walt Disney World without using I-4, or explore nearby Sunset Walk, shopping, and restaurants. Universal Orlando Resort, SeaWorld Orlando, championship golf courses, and Orlando International Airport are also within convenient driving distance. Furnished, ground floor, private garage, and just 2 miles to Disney—put this Oakwater condo at the top of your showing list!

2711 Oakwater Drive Unit 2711, Kissimmee
980 Abby Ridge Court, Kissimmee
$254,900
3 Beds ⋅ 2 Baths ⋅ Indian Ridge Unit 1 SubDv. ⋅ 34747 Zip Code
This 3-bedroom, 2-bathroom single-story home offers seamless main-level living paired with an attached 2-car garage. The thoughtfully planned interior features an open living room and dining room combo, providing a flexible layout for entertaining and everyday relaxation. The updated kitchen is a highlight, equipped with elegant granite countertops, sleek stainless steel appliances, and a dedicated eating space for casual meals. Combining single-story convenience, modern kitchen upgrades, and versatile dining areas, this home is built for comfortable, functional living.

980 Abby Ridge Court, Kissimmee
7593 Gathering Drive Unit 708, Kissimmee
$220,000
1 Beds ⋅ 1 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code
**Property has an active Reunion Resort Membership Available** Welcome to the Reunion Grande, located in the renowned golf community of Reunion Resort! Comprised of 82 individually owned condos, 4 restaurants on site, and all of the amenities of a 4 diamond resort hotel, the Reunion Grande is a the epitome of luxury living. This condo is 1 of only 6 one bedroom condos in the Grande, making it a rarity. As you enter. this tastefully appointed condo you will immediately notice the penthouse ambience, featuring an open concept kitchen, dining, living room space that flows together perfectly, with diamond pattern laid travertine tile flooring covering the main living area, dining room and kitchen. Positioned on the 7th floor, this condo has amazing views out every window, stepping out on your oversized covered balcony you will enjoy unobstructed views of the Watson and Palmer golf courses, beautiful sunrises, and a panoramic view of the beautiful community of Reunion Resort. Pride in ownership can be seen throughout this condo, as it has been meticulously maintained. Being sold fully furnished, this condo will come to you turnkey. Reunion Resort is a luxury resort, that also allows short term rental, if you're looking for a home away from home, while also being able to generate short term rental revenue, this condo is for you! Reunion Resort is positioned with quick access to all the major theme parks, especially Disney World, being Just 2 Exits Away, making Reunion Resort top choice for visitors of all ages. If you are looking to take a few golf swings while on your vacation you can take the challenge on any of the 3 world class championship golf courses, Designed By Arnold Palmer, Tom Watson, And Jack Nicklaus, that Are Located within the gates of Reunion. There Are 12 Pools In The Community, Including a multimillion dollar water park, Complete with a lazy river, splash park for the little ones, tiki bar, & Water Slide. This condo is turnkey, With so much to desire, it is now your turn to call Reunion Resort your new home, or home away from home, welcome home!

7593 Gathering Drive Unit 708, Kissimmee
7601 Recife Drive, Kissimmee
$420,000
4 Beds ⋅ 5 Baths ⋅ Magic Village SubDv. ⋅ 34747 Zip Code
Discover resort-style living at Magic Village Resort! Located in a gated community just minutes from Orlando's famous theme parks, shopping, and dining, this beautifully furnished and tastefully decorated 4-bedroom, 4.5-bath townhome offers a blend of resort amenities and the comfort of a private retreat. Enjoy soaring living room ceilings, two spacious primary suites, one downstairs and another upstairs with a balcony, and a covered lanai with an outdoor grill, perfect for relaxing after a day at the parks. Resort conveniences include concierge services, a 24/7 clubhouse, fitness center, kids' playroom, housekeeping services, and an on-site restaurant. Make unforgettable memories with family and friends while enjoying the opportunity to generate rental income when you're not using the home.

7601 Recife Drive, Kissimmee
2910 Castaway Lane, Kissimmee
$299,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 7 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully appointed 3-bedroom, 3-bathroom villa in the highly desirable Margaritaville Resort Orlando, just minutes from Walt Disney World! Offering a sought-after floor plan, peaceful views of lush green space, and a prime location just a short stroll from the neighborhood pool, this charming villa perfectly combines comfort, style, and the relaxed Florida lifestyle. Step inside to discover a bright and airy interior featuring soaring ceilings, abundant natural light, and an inviting open-concept design ideal for both everyday living and entertaining. Expansive sliding glass doors seamlessly connect the spacious living and dining areas to a private outdoor patio, creating the perfect setting to unwind and enjoy Florida's beautiful weather. Thoughtfully selected finishes include elegant wood-look tile flooring, quartz countertops, beautiful wood staircases, and a stylish kitchen that opens effortlessly to the main living space. A private owner's closet offers additional convenience and secure storage. Whether you're searching for a full-time residence, a personal vacation getaway, or an income-producing investment, this versatile villa offers exceptional possibilities. The property is currently not enrolled in a rental program, yet short-term vacation rentals are permitted, giving future owners the flexibility to enjoy the property personally or take advantage of its vacation rental potential. Beyond the villa, discover the vibrant tropical atmosphere and exceptional amenities of Margaritaville Resort Orlando, one of Central Florida's most popular resort destinations. Inspired by the laid-back charm of island living, this gated community offers beautifully landscaped grounds, multiple resort-style swimming pools, restaurants, bars, a fitness center, a full-service spa, and scenic walking trails. Residents and guests can also enjoy nearby Sunset Walk, a lively entertainment district featuring an impressive selection of dining, shopping, live music, and year-round events. Island H2O Water Park adds another exciting recreational option just moments away. With beautifully maintained common areas, exterior and lawn maintenance services, and 24-hour gated security, ownership offers the convenience of a low-maintenance resort lifestyle. Ideally located near Walt Disney World, Universal Orlando, championship golf courses, premier shopping, and countless dining and entertainment destinations, this property presents a wonderful opportunity to own a piece of paradise in the heart of Central Florida.

2910 Castaway Lane, Kissimmee
8105 Coconut Palm Way Unit 303, Kissimmee
$215,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 6 SubDv. ⋅ 34747 Zip Code
Virtually Staged. Welcome to 8105 Coconut Palm Way, Unit 303, an outstanding opportunity to own a fully furnished 3 bedroom condo in the highly sought after Windsor Palms Resort community at an incredibly affordable price. Located on the third floor with beautiful views, this well maintained condo offers exceptional flexibility as a vacation home, Airbnb, long term rental, or full time residence. One of the biggest advantages of this property is that it is being sold fully furnished, allowing the next owner to enjoy a nearly turnkey vacation home or rental property without the added expense of purchasing furniture. Whether you're looking for your own Florida getaway, an income producing investment, or an affordable primary residence, this condo offers tremendous value. Inside, you'll find a spacious split bedroom floor plan that provides additional privacy for owners and guests while offering flexibility for different rental arrangements. The property has been well maintained and features a newer HVAC system along with a brand new washer and dryer, helping reduce some of the immediate expenses associated with purchasing a property. What truly sets Windsor Palms apart is the incredible collection of amenities and services included through the HOA. Residents and guests enjoy 24 hour staffed gated security, cable, internet, pest control, a beautiful resort style swimming pool with massive water slides, a fantastic fitness center, a huge video arcade, movie theater, concierge services, bar and grill, and an onsite convenience store. Outdoor recreation is equally impressive, with tennis courts, a sand volleyball court, basketball courts, parks, and playgrounds. The location is another major advantage. Windsor Palms is conveniently situated near Walt Disney World and Central Florida's world famous attractions, with countless restaurants, shopping destinations, entertainment options, and major highways just a short drive away. This makes the property especially appealing to vacationers while also providing everyday convenience for full time residents. Unlike communities that restrict how owners can use their properties, Windsor Palms offers the flexibility of short term vacation rentals, long term rentals, or owner occupancy, allowing you to choose the option that best fits your lifestyle and investment goals, subject to applicable community requirements. With its attractive price, fully furnished interior, desirable third floor location, split bedroom layout, newer HVAC system, brand new laundry appliances, and access to an impressive lineup of resort amenities, 8105 Coconut Palm Way, Unit 303 offers an exceptional opportunity to own in one of the area's most established vacation resort communities. If you've been searching for an affordable, move in ready property near Disney with outstanding amenities and multiple ownership possibilities, this condo deserves your attention.

8105 Coconut Palm Way Unit 303, Kissimmee
8504 Crystal Cove Loop, Kissimmee
$258,000
3 Beds ⋅ 3 Baths ⋅ Emerald Island Resort Ph 2 SubDv. ⋅ 34747 Zip Code
3 beds, 2.5 baths in Emerald Island Resort. Here is your chance to own in one of Florida's sought after location to enjoy Disney and all the other theme parks! Turn key and ready to be rented. Gain equity while having others pay for it and use it whenever you wish. With reasonable fees this one should not be missed. Clean and ready to go. Ask about financing options with our preferred lender and invest in your future!

8504 Crystal Cove Loop, Kissimmee
2923 Banana Palm Drive, Kissimmee
$349,000
4 Beds ⋅ 3 Baths ⋅ Paradise Palms Resort Ph 4 SubDv. ⋅ 34747 Zip Code
Completely Renovated, Professionally Decorated & Beautifully Furnished Home in Paradise Palms! Discover this stunning, recently renovated home in the sought-after Paradise Palms Resort community, featuring luxury vinyl flooring throughout the entire home, professional interior decorating, and stylish modern furnishings. Just minutes from Walt Disney World and Orlando’s major attractions, this beautifully updated property offers 4 spacious bedrooms, 3 full bathrooms, and a private pool, making it an excellent opportunity for a vacation home, primary residence, or investment property. The thoughtfully designed open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for entertaining family and friends. The modern kitchen features beautiful wooden cabinetry, an elegant marble island, a full suite of appliances, and a large window that fills the space with natural light. The spacious bedrooms feature walk-in closets and charming decor, combining comfort, functionality, and style. Step outside to enjoy your private pool, perfect for relaxing and embracing the Florida lifestyle. Paradise Palms residents also enjoy an impressive selection of resort-style amenities, including a community pool with water slides, tennis courts, a barbecue area, a movie theater, a game room, and additional recreational facilities. Conveniently located near shopping centers, restaurants, supermarkets, and Orlando’s world-famous attractions, this property combines a desirable location with comfort and versatility. Whether you are looking for a beautifully furnished vacation home or an investment property with potential for short-term or long-term rental income, this exceptional Paradise Palms residence is an opportunity worth exploring. This property is used for short-term rentals. Please contact the listing agent to verify availability and schedule a showing.

2923 Banana Palm Drive, Kissimmee
7912 Spectrum Drive, Kissimmee
$349,000
3 Beds ⋅ 3 Baths ⋅ Spectrum At Reunion Ph 2 SubDv. ⋅ 34747 Zip Code
Branad new townhome in Reunion. Fully Furnished membership INCLUDED full access golf pickaball tennis, 7 pools.

7912 Spectrum Drive, Kissimmee
2906 Pembridge Street, Kissimmee
$399,000
4 Beds ⋅ 3 Baths ⋅ Lindfields Unit 3 SubDv. ⋅ 34747 Zip Code
Virtually Staged. Some homes just make everyday life feel easy, and this single-story home does exactly that, with defined spaces for every occasion and a backyard made for slowing down. A formal living room and separate formal dining room give you gracious spaces for gathering, while the kitchen and family room combination keeps everyone connected day to day. The kitchen offers generous solid wood cabinetry, tile counters, a breakfast bar and an eat-in space for casual mornings, and a propane fireplace adds warmth for cozy nights in. The split-bedroom layout gives everyone their privacy, and the primary suite is a true retreat with a garden tub, a separate shower and a large walk-in closet. Step out to the covered rear porch and take in the fenced, nearly quarter-acre backyard, complete with a play area, garden space and a storage shed, perfect for weekend projects or simply unwinding outdoors. An attached two-car garage, central heating and air and no HOA round out the practical perks, and the convenient location puts area attractions, shopping, dining and major highways within easy reach. Schedule your private showing today.

2906 Pembridge Street, Kissimmee
Start Your Search

How much is your home worth?

Get instant property value now!