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 minutes away from the world-renowned attractions of Orlando. Known for its rich history, diverse culture, and stunning natural beauty, Kissimmee offers a unique blend of urban amenities and small-town charm, making it an ideal place to call home.

Kissimmee boasts a variety of recreational opportunities, from the picturesque Lake Tohopekaliga, where you can enjoy fishing and boating, to the lush parks and nature trails that invite you to explore the great outdoors. The city's bustling downtown area is filled with delightful shops, restaurants, and entertainment options, ensuring there's always something to do.

For those seeking a home in this enchanting region, Kissimmee offers an impressive selection of properties under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking for a vacation home, you’ll find a diverse array of options, including charming single-family homes, modern townhouses, and spacious condos. Many of these homes feature desirable amenities such as open floor plans, updated kitchens, and beautiful outdoor spaces, perfect for enjoying the Florida sunshine.

With its affordable housing market and proximity to major attractions like Walt Disney World and Universal Studios, Kissimmee is not just a place to live; it’s a lifestyle. Embrace the magic of Florida living and discover your dream home in Kissimmee today! Your perfect oasis awaits in this enchanting city, where adventure and comfort blend seamlessly.

Newest Kissimmee Homes under $500,000

135 Oaxaca Lane, Kissimmee

135 Oaxaca Lane, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Bvl Unit 3 SubDv. ⋅ 34743 Zip Code

Discover your new sanctuary in this comfortable 3-bedroom, 2-bathroom home, offering 1,631 square feet of well-appointed living space. Perfectly designed for comfort and convenience, this residence features a spacious fenced yard, ideal for outdoor activities and gatherings. The master suite is a true highlight, showcasing a beautiful stall shower. Enjoy easy-to-maintain laminate floors in all bedrooms for style and durability. The kitchen offers ample cabinet space for all your storage needs. The fully enclosed Florida room has heat and air conditioning. Additional features include ceiling fans in every room for year-round comfort and a 1-car garage. The Seller will replace the roof before closing. The home is conveniently located near shopping, restaurants, transportation, and expressways.

135 Oaxaca Lane, Kissimmee

2502 Crown Ridge Circle, Kissimmee

2502 Crown Ridge Circle, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Remington Prcl H Ph 1 SubDv. ⋅ 34744 Zip Code

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

2963 Sera Bella Way, Kissimmee

2963 Sera Bella Way, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Sera Bella SubDv. ⋅ 34744 Zip Code

A 3-bed single family residence in Sera Bella with water views, a private entrance in-law suite, and potential 4th bedroom flexibility is hard to find in Kissimmee. This 2-story home offers 2,416 heated square feet, 2.5 baths, a 2-car garage, pond views with fountains and lights, and access to Sera Bella community amenities. This beautifully maintained home in Kissimmee’s 34744 area delivers the space, layout, and location buyers want. The inviting exterior features a brick paver driveway, covered entry, landscaped curb appeal, sidewalks, and an attached 2-car garage. Inside, the bright floor plan offers ceramic tile flooring, formal dining, a spacious living room, and a comfortable family room that flows naturally into the kitchen. The kitchen features granite counters, stainless steel appliances, a center island, closet pantry, stone counters, and generous workspace for everyday meals or entertaining. One of the home’s most valuable features is the attached in-law suite with a kitchenette, studio layout, and private entrance, creating added flexibility for guests, extended stay needs, a work-from-home setup, or a private retreat. Upstairs, the primary suite offers tray ceilings, a walk-in closet, dual sinks, granite counters, a garden bath, and a separate shower. Two additional bedrooms, an upstairs laundry room, and a spacious loft complete the second floor. The loft has excellent potential to become a 4th bedroom, with an existing built-in area intended for a closet. The covered, enclosed, screened rear porch overlooks the pond, where fountains and evening lights create a peaceful backdrop for relaxing or entertaining. Convenient to Lake Nona, Medical City, shopping, dining, major roads, Orlando International Airport, and Central Florida attractions.

2963 Sera Bella Way, Kissimmee

1516 Kelby Road, Kissimmee

1516 Kelby Road, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Shenandoah SubDv. ⋅ 34744 Zip Code

Welcome to 1516 Kelby Road in Kissimmee! This 3-bedroom, 1.5-bathroom single-family home offers approximately 1,321 square feet of living space on a 5,227-square-foot lot in the established Shenandoah community. The home features a functional layout, central air conditioning, ceiling fans and a combination of carpet, tile and laminate flooring. The property also offers a converted garage for additional flexible space and a paved road for convenient access. With no HOA, this home provides added flexibility for its next owner. Conveniently located near US-192, major roadways, shopping, dining and everyday conveniences. Schedule your showing today!

1516 Kelby Road, Kissimmee

261 Autumn Lane Unit 5, Kissimmee

261 Autumn Lane Unit 5, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Autumn Lane Twnhms Condo SubDv. ⋅ 34743 Zip Code

SPACIOUS 3-BEDROOM, 3-FULL-BATH CONDO WITH ASSIGNED PARKING IN KISSIMMEE! Welcome to 261 Autumn Lane #5, offering 1,504 square feet of living space, three bedrooms, three full bathrooms, two private en-suite bedrooms, assigned parking, and major recent improvements including a 2025 ROOF and updated A/C from 2022. Built in 2007, this two-story condo offers a flexible layout with something buyers don't find in every 3-bedroom property: two bedrooms feature their own private full bathrooms. The additional privacy creates excellent flexibility for guests, multi-generational living, a home office setup, or households looking for more separation and personal space. Two major updates are already in place, including a NEW ROOF completed in 2025 and an updated A/C system from 2022, giving buyers added confidence when considering some of the home's major components. LOCATION is another major advantage. Situated in the Buenaventura Lakes area of Kissimmee, this Central Florida condo offers convenient access to Orlando International Airport, shopping, grocery stores, restaurants, everyday services, and major roadways connecting Kissimmee and the greater Orlando area. Nearby shopping and grocery options include ALDI, Walmart Neighborhood Market, and additional retail and dining options throughout the Osceola Parkway and Buenaventura Lakes area. If you've been searching for a 3-bedroom condo in Kissimmee with THREE FULL BATHROOMS, multiple en-suite bedrooms, assigned parking, generous living space, recent major updates, and convenient access to Orlando, 261 Autumn Lane #5 deserves a closer look. Schedule your private showing today.

261 Autumn Lane Unit 5, Kissimmee

651 Elderwood Court, Kissimmee

651 Elderwood Court, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Bvl Unit 7 3rd Add SubDv. ⋅ 34743 Zip Code

The property at 651 Elderwood Ct, Kissimmee, FL 34743 is a single-family home built in 1983, featuring 4 bedrooms and 3 bathrooms within a 1,812 sq ft layout. Situated in the Buena Ventura Lakes neighborhood, it offers convenient access to major highways like the Florida Turnpike and SR 417, facilitating easy commutes to Orlando International Airport, Walt Disney World, Universal Studios, and SeaWorld. Boggy Creek elementary & Parkway middle school are only minutes away from the property. This property also has a screened in Pool. Roof was recently replaced.

651 Elderwood Court, Kissimmee

1437 Tawny Ridge Road, Kissimmee

1437 Tawny Ridge Road, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Kindred Ph 1fa SubDv. ⋅ 34744 Zip Code

SOLAR PANELS TO BE PAID OFF AT CLOSING BY SELLER + WHOLE-HOUSE WATER FILTRATION SYSTEM INCLUDED! Welcome to this spacious 4-bedroom, 2-bath single-story home in the desirable Kindred community. Designed for comfortable everyday living, the home features a bright open-concept floor plan, tile flooring throughout the main living areas, and a modern kitchen with stainless steel appliances, ample cabinetry, and generous space for cooking, gathering, and entertaining. A major added benefit: the solar panel system will be paid off by the seller at closing, allowing the buyer to enjoy the system without assuming the seller's solar loan. The home also includes a whole-house water filtration system. Property is currently listed for both sale and lease. Seller intends to proceed with whichever transaction is secured first. Please contact listing agent for current availability prior to submitting an proposal. Step outside to a fully fenced backyard offering privacy and plenty of space to relax, entertain, or enjoy the Florida lifestyle. Kindred offers resort-style amenities including community pools, fitness center, clubhouse, tennis and pickleball courts, playgrounds, dog park, and scenic walking trails. Conveniently located with easy access to the Florida Turnpike, Orlando International Airport, Lake Nona, shopping, dining, schools, major employment areas, and Central Florida attractions. A wonderful combination of space, energy-conscious features, outdoor privacy, and resort-style community living—ready for its next owner!

1437 Tawny Ridge Road, Kissimmee

1512 Fernmeadow Street, Kissimmee

1512 Fernmeadow Street, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code

Welcome to 1512 Fernmeadow Street in the desirable Kindred community. This nearly new DR Horton Jemison floorplan features an open layout with a bright great room, stainless steel appliances, an oversized walk-in pantry, and smart home features. The private primary suite offers an ensuite bath with double vanity and walk-in closet, while two additional bedrooms provide space for guests, an office, or flexible living. Kindred offers resort-style amenities including pools, clubhouses, a fitness center, playgrounds, sports fields, a dog park, picnic areas, and walking and biking trails. Conveniently located near US-192 and Florida’s Turnpike, with easy access to NeoCity, Lake Nona, Orlando International Airport, Disney, shopping, dining, and downtown Kissimmee. Enjoy low-maintenance living with great amenities and convenient access to everything Central Florida has to offer.

1512 Fernmeadow Street, Kissimmee

125 Pansy Court, Kissimmee

125 Pansy Court, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Bvl Unit 2 SubDv. ⋅ 34743 Zip Code

LOCATION, LOCATION, LOCATION! Beautifully updated 4-bedroom, 3-full-bath home with over 2,100 sq. ft. and THREE PRIMARY SUITES! Enjoy NO HOA, NO CDD, and NO FLOOD ZONE, with space for RV or boat parking, subject to local regulations. Conveniently located near Lake Nona, Orlando International Airport, and Walt Disney World. This spacious home has been extensively updated, including a new roof (2023), remodeled kitchen (2022) with stainless-steel appliances, new A/C (2025), new water heater 2026, water softener, front windows, garage door (2023), gutters, and updated bathroom sinks and primary bathtub (2023). The interior was freshly painted in January 2026. Enjoy additional outdoor storage with a new shed and a new vinyl backyard fence (2025), a second kitchen in the florida room. The versatile three-primary-suite layout is ideal for a large family, multi-generational living, guests, or those seeking additional private spaces. Furniture is available for separate purchase. With major updates already completed and a highly convenient Central Florida location, this home is ready for its next owner. Schedule your showing today!

125 Pansy Court, Kissimmee

1733 Felicity Lane, Kissimmee

1733 Felicity Lane, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 1 SubDv. ⋅ 34744 Zip Code

Welcome to 1733 Felicity Ln, a beautifully designed single-story Mattamy Homes residence located on a desirable corner lot in Tohoqua, one of Kissimmee’s sought-after master-planned communities. With approximately 2,740 total building sq ft, this home combines space, flexibility, energy-conscious features, and an excellent Central Florida location. The thoughtfully designed floor plan features 4 bedrooms and 3 full bathrooms, including a private guest suite configuration with its own full bath—an excellent option for overnight guests, multigenerational living, a private workspace, or added everyday flexibility. The open-concept kitchen, dining, and gathering areas create a natural flow for daily living and entertaining, while the extended screened lanai expands the living experience outdoors. A welcoming covered front porch and the additional privacy and presence of a corner lot further enhance the home’s appeal. Additional features include a solar energy system and whole-house water filtration system, adding practical value for buyers looking for efficiency-focused home features. The spacious layout, guest suite, outdoor living area, and corner-lot setting also make this property attractive to buyers and investors seeking a versatile single-family home in the growing Kissimmee–St. Cloud corridor. Tohoqua residents enjoy resort-style community amenities including a zero-entry pool, clubhouse, fitness center, playground, lighted tennis courts, basketball court, sidewalks, outdoor gathering areas, and an extensive network of walking and biking trails. The community also provides convenient access to Florida’s Turnpike, shopping, dining, NeoCity, Lake Nona, Orlando International Airport, and the many employment, recreation, and entertainment destinations throughout Central Florida. **The property has an existing mortgage that may be assumable by a qualified buyer, subject to lender approval, underwriting, existing loan terms, and all applicable requirements..** Discover the combination of space, location, lifestyle, and flexibility that makes 1733 Felicity Ln stand out. Schedule your private showing today and see how this home can fit your next chapter.

1733 Felicity Lane, Kissimmee

1112 Ocean Street, Kissimmee

1112 Ocean Street, Kissimmee

6 Beds ⋅ 4 Baths ⋅ Kissimmee Heights SubDv. ⋅ 34744 Zip Code

Exceptional Investment Opportunity! NO HOA! This turnkey investment offers immediate cash flow with excellent long-term appreciation potential. Both units are occupied by the great tenants; they stay there more than 5 years and would like to stay longer. 2 bedroom (the garage was upgraded to the 3rd bed) 2 bath, ceramic tile through the whole house with easy maintenance,2024 new roof…An outstanding opportunity to add a well-maintained, income-generating asset to your investment portfolio, offering stable rental income, a prime location, and excellent potential for future value appreciation in one of Florida's fastest-growing real estate markets.

1112 Ocean Street, Kissimmee

1852 Summer Serenity Drive, Kissimmee

1852 Summer Serenity Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 4a SubDv. ⋅ 34744 Zip Code

Short Sale. Welcome home to this 3 bedroom, 2.5 bathroom home located in the desirable Tohoqua community in Kissimmee! Offering a functional two story layout, beautiful pond views, and comfortable living spaces, this home is designed for both everyday living and entertaining. The main level features tile flooring throughout the living areas and an open, welcoming layout. The kitchen is equipped with granite countertops, stainless steel appliances, ample cabinet space, and a large pantry for additional storage. A convenient half bathroom is located downstairs for guests. Sliding glass doors extend the living space outdoors to a covered paver patio overlooking the pond, creating a relaxing spot to unwind and enjoy the peaceful water views. Upstairs, a landing at the top of the stairs provides additional space along with a convenient storage closet. All three bedrooms are located on the second floor, including the spacious primary suite featuring a walk in closet and an en suite bathroom with a dual sink vanity and stand up shower. The two additional bedrooms share the hall bathroom, which features a large vanity and tub/shower combination. An indoor laundry room with a utility sink is also conveniently located upstairs near the bedrooms. Additional features include a two car garage and a Rain Bird irrigation system. Located in the sought after Tohoqua community with convenient access to shopping, dining, schools, major roadways, and all that the Kissimmee area has to offer. Schedule your private showing today!

1852 Summer Serenity Drive, Kissimmee

Start Your Search