Kissimmee Homes under $500,000

Kissimmee Homes under $500,000

Welcome to Kissimmee, Florida—a vibrant city nestled in the heart of Osceola County that offers a delightful blend of charm, culture, and convenience. Known for its close proximity to world-renowned attractions like Walt Disney World and Universal Studios, Kissimmee is not just a tourist haven; it’s also an inviting community for families and individuals looking to settle in a dynamic environment.

Kissimmee boasts a rich history and a diverse population, offering a warm and welcoming atmosphere for residents. With a plethora of parks, recreational facilities, and outdoor activities, families can enjoy quality time together while soaking up the beautiful Florida sunshine. The city also hosts various cultural events and festivals throughout the year, making it easy to immerse yourself in the local community.

For those searching for a home in this enchanting locale, Kissimmee offers a fantastic selection of properties under $500,000. Whether you’re looking for a cozy single-family home, a modern townhouse, or a spacious condo, the options are plentiful. Many of these homes feature contemporary designs, vibrant neighborhoods, and easy access to local amenities, schools, and shopping centers.

With its affordable housing market and an array of entertainment options, Kissimmee is an ideal place to call home. Experience the magic of Florida living and discover your perfect property in this charming city today! Let us guide you in finding a home that suits your lifestyle and budget in beautiful Kissimmee.

Newest Kissimmee Homes under $500,000

1881 Red Canyon Drive, Kissimmee

1881 Red Canyon Drive, Kissimmee

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

4743 Ormond Beach Way, Kissimmee

4743 Ormond Beach Way, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Terra Verde Villas Ph 1 SubDv. ⋅ 34746 Zip Code

Welcome to this FULLY FURNISHED, MOVE-IN READY 3-bedroom, 2.5-bathroom, two-story townhome located in the highly desirable, guard-gated Terra Verde Resort community! Whether you're searching for a vacation getaway, investment opportunity, or primary residence, this property offers the perfect combination of comfort, convenience, and resort-style living. Step outside to your private screened-in courtyard featuring a relaxing hot tub, ideal for unwinding after a day at the theme parks or entertaining family and friends. Located just steps from the community pool and amenities, Terra Verde Resort offers an impressive selection of recreational facilities, including a zero-entry swimming pool, spa, fitness center, Tiki bar, tennis courts, movie theater, miniature golf, beach volleyball, basketball court, and scenic fishing lake. ZONED FOR SHORT-TERM RENTALS, this fully furnished property offers excellent flexibility for personal use or vacation rental opportunities. Conveniently situated approximately 7.2 miles from Walt Disney World Resort, with easy access to shopping, restaurants, outlet malls, major attractions, and Orlando International Airport. Enjoy the convenience of owning a furnished property in one of Kissimmee's established resort communities. Schedule your private showing today and discover everything this Terra Verde townhome.

4743 Ormond Beach Way, Kissimmee

5469 Gingham Drive, Kissimmee

5469 Gingham Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code

Pre-Construction. To be built. A Community Designed for Every Stage of Life. Westview features an intimate collection of 119 single-family homesites, creating a welcoming neighborhood feel with modern, thoughtfully designed floorplans. Whether you’re starting a new chapter or expanding your lifestyle, these homes are built to adapt to your needs. Personalization is at the heart of the experience, you’ll have the freedom to select your ideal homesite, design features, and finishes, allowing you to truly create a home that reflects your style and vision. Amenities That Inspire an Active, Social Lifestyle. At the center of the community is a vibrant social hub designed to bring neighbors together. The Hub clubhouse anchors the experience, offering: A fully equipped fitness center with a free weight room, an exciting rock-climbing wall, a multipurpose gymnasium with basketball court, a movement studio and locker facilities, and a welcoming gathering space with kitchenette and café. Step outside and enjoy an impressive collection of amenities designed for both recreation and relaxation: Pickleball, tennis, basketball, and volleyball courts, a lap pool, a resort-style pool with play features, and a dedicated kids pool, Open fields for baseball and soccer, a tot lot for younger residents, and a separate dog parks for small and large pets. Every detail is designed to support an active, connected, and wellness-focused lifestyle for residents of all ages. Welcome to the Heritage Bay! The Heritage Bay is a new two-story home design replacing the Hadley Bay, offering enhanced features for modern families. It features an open-concept first floor with high ceilings and ample natural light, a versatile first-floor bedroom, and a flex room. The second floor includes a loft and luxurious owner's suite. The home emphasizes indoor-outdoor living with a large patio, a gourmet kitchen, smart storage solutions, and family-friendly design elements. Two charming elevation options are available, with customizable exterior features. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. Actual home may differ from photos. Schools: Elem: Koa Elementary School; Middle: Discovery Intermediate School; HS: New Dimensions High School.

5469 Gingham Drive, Kissimmee

2218 Grand Cayman Court Unit 1335, Kissimmee

2218 Grand Cayman Court Unit 1335, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code

LOCATION, FLEXIBILITY AND RESORT-STYLE LIVING IN THE HEART OF KISSIMMEE! Discover this spacious 2-bedroom, 2-bath condominium offering 1,026 square feet in the desirable Villas del Sol community. The residence features a comfortable and functional layout with a spacious living and dining area, an updated kitchen, two well-sized bedrooms and two full bathrooms. The property is currently tenant-occupied with a lease through December 31, providing rental income in place while offering flexibility for future plans. Villas del Sol offers resort-style amenities including two swimming pools, fitness center, tennis courts, playground, clubhouse and inviting common areas. The location adds even more value. Conveniently situated near The Loop for shopping, dining and entertainment, with easy access to US-192, Osceola Parkway, Florida’s Turnpike and I-4, connecting you to Orlando, area attractions and destinations throughout Central Florida. Whether considering a property for your real estate portfolio or planning for future personal use, this condo brings together space, flexibility, community amenities and a convenient Kissimmee location. Schedule your private showing and discover the possibilities this property has!

2218 Grand Cayman Court Unit 1335, Kissimmee

2307 Butterfly Palm Way Unit 302, Kissimmee

2307 Butterfly Palm Way Unit 302, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code

Location, convenience, and resort-style living come together in this beautifully updated, fully furnished 2-bedroom, 2-bath top-floor condo in the highly desirable Windsor Palms community. Ideally positioned just steps from the clubhouse, pool, and community amenities, this turnkey condo also features a north-facing private balcony with distant views of Disney fireworks in the evenings. Located approximately 3 miles from Walt Disney World attractions, Windsor Palms offers the perfect combination of proximity to Central Florida's world-famous entertainment and the privacy of a gated resort community. Residents and guests enter through a 24-hour manned gatehouse and enjoy beautifully maintained grounds along with an impressive collection of amenities, including a resort-style swimming pool, splash area, large whirlpool spa, tiki bar, convenience store, fitness center, game room, private movie theater, tennis courts, basketball courts, and volleyball. Inside, the condo offers an inviting and functional layout designed for easy Florida living. Previous improvements include tile flooring throughout, interior paint, updated furnishings, replacement beds and bedding, and additional updates completed by the owners over the years. A high-efficiency A/C system was installed in August 2021. The property is being offered fully furnished, including furniture, appliances, flat-screen TVs, décor, kitchenware, plates, silverware, and more, providing a convenient turnkey opportunity for a primary residence, vacation home, or investment property subject to applicable community rules and regulations. A secured owner's closet provides additional convenience for owners who wish to store personal belongings while away. The HOA provides additional value by including water, sewer, basic cable, Wi-Fi, and valet trash pickup. Best of all, Windsor Palms has NO CDD. Whether you're looking for your own Florida getaway, a low-maintenance residence near the attractions, or a property with vacation-rental potential, this condo offers an outstanding combination of location, amenities, convenience, and value. Bring your suitcase and start enjoying the Florida lifestyle!

2307 Butterfly Palm Way Unit 302, Kissimmee

8516 Crystal Cove Loop, Kissimmee

8516 Crystal Cove Loop, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Emerald Island Resort Ph 2 SubDv. ⋅ 34747 Zip Code

Enjoy resort-style living in this furnished 3-bedroom, 2.5-bath townhome in gated Emerald Island Resort! Offering 1,291 square feet of living space, the home features an open-concept living and dining area, a balcony, and an included washer and dryer. Short-term rentals are permitted, offering flexibility for a vacation retreat or investment property, subject to community rules and existing reservations. Community amenities include a resort-style pool, tiki bar, fitness center, tennis and basketball courts, playground, sauna, game room, and nature trail. Conveniently located near Walt Disney World, Island H2O Water Park, shopping, and dining. Schedule your private showing to explore this Central Florida getaway!

8516 Crystal Cove Loop, Kissimmee

8831 Grand Palms Cir, Apt B, Kissimmee

8831 Grand Palms Cir, Apt B, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Grand Palms Condo SubDv. ⋅ 34747 Zip Code

Your Florida getaway awaits just minutes from Disney! Welcome to this inviting 3-bedroom, 2-bathroom second-floor condo in the desirable Grand Palms community, offering the perfect combination of location, comfort, and investment potential. Freshly painted throughout, this condo features a bright, open floor plan with spacious living and dining areas, three comfortable bedrooms, and plenty of room for family and guests. Whether you're looking for a vacation retreat, primary residence, or short-term rental investment, this property offers wonderful flexibility, subject to applicable rental restrictions. Enjoy resort-style community amenities including a sparkling swimming pool, fitness center, and tennis court, all within a beautifully maintained setting. Conveniently located just minutes from Walt Disney World, with easy access to Universal Orlando, shopping, restaurants, golf, entertainment, and major highways. With three bedrooms, fresh interior paint, desirable amenities, and an outstanding location near Central Florida's world-famous attractions, this Grand Palms condo is an opportunity you won't want to miss. Schedule your private showing today!

8831 Grand Palms Cir, Apt B, Kissimmee

1640 Talon Court, Kissimmee

1640 Talon Court, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Eagles Nest At The Oaks SubDv. ⋅ 34746 Zip Code

Don’t miss the opportunity to make this beautiful home in a desirable Kissimmee community your own. This well-maintained 3-bedroom, 2-bath home offers a comfortable and functional floor plan with spacious living areas and plenty of natural light. The freshly painted interior and brand-new carpet give the home a clean, move-in-ready feel. The kitchen features abundant cabinetry, ample counter space, a breakfast bar, and a convenient open connection to the dining and living areas-perfect for everyday living and entertaining. The spacious primary suite offers a private retreat, while the additional bedrooms provide flexibility for family, and guests. Step outside to the screened-in porch, where you can relax and enjoy peaceful views of the lush backyard and mature trees. The home also features a NEWER A/C system installed in 2025, providing added peace of mind. Location is another major highlight! Close to John Young Parkway, with shopping, restaurants, banking, and grocery stores conveniently nearby. Plus, Disney and the major attractions are less than 30 minutes away, making this an excellent location for enjoying everything Central Florida has to offer.

1640 Talon Court, Kissimmee

7959 Delwin Lane, Kissimmee

7959 Delwin Lane, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Reunion Village SubDv. ⋅ 34747 Zip Code

Nothing compares to this exceptional home in Kissimmee! Located in the highly sought-after Reunion Village, this beautifully maintained 3-bedroom, 2.5-bath residence, built in 2021, offers the perfect blend of modern comfort, quality construction, and resort-style living. Step inside to bright, open living spaces, elegant finishes, and a welcoming layout designed for both everyday living and entertaining. Enjoy the feeling of being on vacation every day while being just minutes from Walt Disney World, Orlando’s world-class attractions, shopping, dining, and entertainment. Whether you’re looking for a primary residence, second home, or investment opportunity, this property offers an outstanding combination of location, lifestyle, and convenience. Opportunities like this in one of Central Florida’s most sought-after communities don’t come along every day. Come see for yourself why 7959 Delwin Ln stands apart—schedule your private showing today and make this exceptional Kissimmee property your next home or investment! Opportunities like this in one of Central Florida’s most sought-after communities don’t come along every day. Come see for yourself why 7959 Delwin Ln stands apart! Schedule your private showing today and make this exceptional Kissimmee property your next home or investment!

7959 Delwin Lane, Kissimmee

4030 Santa Barbara Road, Kissimmee

4030 Santa Barbara Road, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Oak Pointe SubDv. ⋅ 34746 Zip Code

GREAT LOCATION IN 34746;OFF OF NORTH PLEASANT HILL RD AT OAK POINTE *****NO HOA******. POOL PROPERTY IN A HALF ACRE LOT*** IS EVERYBODY DREAM HOME****. 4 BEDROOMS AND TWO BATHROOMS WITH A 2 CAR GARAGE AND A LOG DRIVEWAY ON A HUGE HALF ACRE FENCED AND CLEAN LOT. CALL YOUR REALTOR, YOU WANT AN APPOINTMENT ASAP. THIS PROPERTY COUNTS WITH A POOL WITH SCREEN ENCLOSURE PORCH, PICNIC AREA AND EXTERNAL BBQ KITCHEN AREA UNDER A SHADE PROVIDING TREE. INSIDE KITCHEN WITH SOLID GRANITE COUNTERS, STAINLESS STEEL APPLIANCES INCLUDED, LARGE LIVING AND DINING AREAS AND MORE TO SEE. YOU GOT TO SEE IT TO BE ABLE TO MAKE DECISIONS BEFORE IS GONE. SPACIOUS ROOMS AND PRIVACY IN A REAL GOOD FLOOR PLAN. SEE PHOTOS ATTACHED. Bonus 1: Solar Panels produce electricity for you and surplus to sell for credits. They will be paid off at closing therefore No electricity payments. YOUR family SAVES more than other alternatives. BONUS 2: Whole house water filtration system for your clean water; will convey with your purchase at listing price.

4030 Santa Barbara Road, Kissimmee

1200 Wahneta Drive, Kissimmee

1200 Wahneta Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Poinciana Nbrhd 02 West Village 07 SubDv. ⋅ 34759 Zip Code

Virtually Staged. Welcome to this move-in-ready Maronda Homes Oak “E” model, ideally situated on a premium corner lot in Poinciana Villages. Offering additional yard space, enhanced privacy, no directly front-facing neighbors, and an oversized driveway, this thoughtfully designed 3-bedroom, 2-bath home combines comfort, style, and functionality. The bright, open-concept layout is ideal for everyday living and entertaining. The kitchen features Azul Platino granite countertops, rich Chatham Umber cabinetry, stainless steel appliances, a spacious center island, and ample storage. Ceramic tile flows throughout the main living areas, while the bedrooms feature upgraded carpet padding for added comfort. Additional features include cordless blinds, irrigation and security systems, an extended 10-by-20-foot patio slab, and a spacious 2-car garage. Enjoy the amenities of Poinciana Villages without a second HOA fee or annual CDD assessments. Conveniently located near shopping, dining, parks, schools, hospitals, and major roadways, with easy access to Orlando-area attractions and Disney approximately 30 minutes away. A structural warranty provides additional peace of mind. This property is also available through the EEP (Earned Equity Program), offering a potential rent-to-own path to homeownership for qualified applicants. Program eligibility, terms, conditions, and approval requirements apply. Schedule your private showing today!

1200 Wahneta Drive, Kissimmee

7660 Whisper Way Unit 202, Kissimmee

7660 Whisper Way Unit 202, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square Condo Ph 4 SubDv. ⋅ 34747 Zip Code

Fully furnished, 3 bedroom, 3 bath, condominium in Reunion Resort. Short term rentals are allowed. This property is perfect for investors, or vacation home owners. Reunion Resort is one of the most highly amenitized resorts in Orlando. It has 3 signature golf courses, a waterpark, tennis, and pickleball courts, multiple pools, clubhouse, and mutiple restaurants. The condo has an open floor plan with kitchen, dining, and living area combined. Each bedroom has it's own full bathroom. It also has a large balcony overlooking a wooded area for lots of privacy. The condo has fresh paint, new appliances, new faucets, new rugs, and a renovated master bathroom. It also has a Reunion membership that is negotiable. The building it is in has an elevator. Reunion Resort is a guard gated community just a few miles from Walt Disny World. Come see this gem of a property.

7660 Whisper Way Unit 202, Kissimmee

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